[go: up one dir, main page]
More Web Proxy on the site http://driver.im/

WO2024113046A1 - Vaporizable cannabinoid compositions - Google Patents

Vaporizable cannabinoid compositions Download PDF

Info

Publication number
WO2024113046A1
WO2024113046A1 PCT/CA2023/051581 CA2023051581W WO2024113046A1 WO 2024113046 A1 WO2024113046 A1 WO 2024113046A1 CA 2023051581 W CA2023051581 W CA 2023051581W WO 2024113046 A1 WO2024113046 A1 WO 2024113046A1
Authority
WO
WIPO (PCT)
Prior art keywords
liquid composition
mixture
thc
terpenes
cannabinoids
Prior art date
Application number
PCT/CA2023/051581
Other languages
French (fr)
Inventor
Max Fraser
Original Assignee
Zest Cannabis Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Zest Cannabis Inc. filed Critical Zest Cannabis Inc.
Priority to CA3233434A priority Critical patent/CA3233434A1/en
Publication of WO2024113046A1 publication Critical patent/WO2024113046A1/en

Links

Classifications

    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/10—Chemical features of tobacco products or tobacco substitutes
    • A24B15/16—Chemical features of tobacco products or tobacco substitutes of tobacco substitutes
    • A24B15/167—Chemical features of tobacco products or tobacco substitutes of tobacco substitutes in liquid or vaporisable form, e.g. liquid compositions for electronic cigarettes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/658—Medicinal preparations containing organic active ingredients o-phenolic cannabinoids, e.g. cannabidiol, cannabigerolic acid, cannabichromene or tetrahydrocannabinol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/348—Cannabaceae
    • A61K36/3482—Cannabis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/02—Inorganic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/007—Pulmonary tract; Aromatherapy
    • A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
    • A61K9/0078—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy for inhalation via a nebulizer such as a jet nebulizer, ultrasonic nebulizer, e.g. in the form of aqueous drug solutions or dispersions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/08—Solutions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans

Definitions

  • the present application pertains to the field of vaporizable cannabinoid compositions. More particularly, the present application relates to liquid compositions for an electronic vaporizer containing cannabinoids and terpenes, methods for preparing such compositions, and cartridges comprising such compositions.
  • Cannabis is a genus of flowering plants that has been used by humans for various purposes, such as medicines, ritual, recreation and textiles.
  • the flowers of the cannabis plant include glandular trichomes, in which phytocannabinoids are produced.
  • THC tetrahydrocannabinolic acid
  • THC tetrahydrocannabinolic acid
  • users may use in order to get a “high” when the cannabis flower is smoked, but has also been shown to be useful for other purposes, such as an appetite stimulant for people with AIDS and an anti emetic for people undergoing chemotherapy (see e.g., product monographs for dronabinol approved by the FDA).
  • the cannabis plant In addition to phytocannabinoids, the cannabis plant also produces terpenes and terpenoids (collectively referred to herein as “terpenes” unless context dictates otherwise).
  • Terpenes are organic compounds produced in a variety of plants, many of which are consumed in human diets and/or used in perfumes. They contribute to the aromas and flavors of different cannabis cultivars. The terpenes found in cannabis share a precursor with phytocannabinoids.
  • an alternative to tobacco cigarettes is an electronic vaporization devices (a “vape” or an “e-cigarette”).
  • the active inhalable ingredient (“All”) is nicotine.
  • Electronic vaporization devices vaporize a liquid composition containing Alls (such as nicotine) into a “vapor” in order to permit inhalation by the user. These vapors are often produced at temperatures such that the formation of potentially harmful by-products is reduced as compared to a conventionally combusted analog.
  • a liquid composition for an electronic vaporizer comprising: (a) at least about 90 wt% of a mixture of one or more cannabinoids, the mixture of one or more cannabinoids comprising at least about 85 wt% tetrahydrocannabinol (THC) and at least about 0.1 wt% tetrahydrocannabinolic acid (THCA); and
  • a cannabis distillate oil comprising at least about 50 wt% THC
  • liquid composition comprises from about 50 wt% to about 60 wt% of the THC oil, from about 35 wt% to about 45 wt% of the cannabis distillate oil, and from about 3 wt% to about 7 wt% of a mixture of the one or more terpenes.
  • liquid composition for an electronic vaporization device prepared by the methods described herein.
  • a cartridge configured to operatively couple with an electronic vaporizer comprising the liquid compositions described herein.
  • THC oil of high purity also known as a “liquid diamond”
  • THCA liquid diamond
  • the combination of a “liquid diamond” THC oil and a cannabis distillate oil has the advantage of minimizing levels of minor cannabinoids and maximizing THC content, resulting in increased psychoactive potency of the composition, without raising the viscosity of the composition to an unusable level, i.e., one that results in an elevated cartridge failure rate when vaped.
  • the presence of about 3 wt% to about 7 wt% terpenes is sufficient to impart desirable flavour and simultaneously maintain the viscosity of the predominantly THC-containing composition at a level suitable for use in vape cartridges without the addition of a carrier or cutting agent. Higher levels of terpenes may lead to an undesirably overpowering taste in the vaporizable composition.
  • transitional terms “comprising”, “including”, “having”, “containing”, “involving”, and the like are to be understood as being inclusive or open-ended (i.e., to mean including but not limited to), and they do not exclude unrecited elements, materials or method steps. Only the transitional phrases “consisting of’ and “consisting essentially of’, respectively, are closed or semi -closed transitional phrases with respect to claims and exemplary embodiment paragraphs herein. The transitional phrase “consisting of’ excludes any element, step, or ingredient which is not specifically recited. The transitional phrase “consisting essentially of’ limits the scope to the specified elements, materials or steps and to those that do not materially affect the basic character! stic(s) of the invention disclosed and/or claimed herein.
  • any numerical value inherently contains certain errors necessarily resulting from the standard deviation found in the respective testing measurements.
  • the term “about” generally means within 10%, 5%, 1%, or 0.5% of a given value or range.
  • the term “about” means within an acceptable standard error of the mean when considered by one of ordinary skill in the art.
  • the numerical parameters set forth in the present disclosure and attached claims are approximations that can vary as desired. At the very least, each numerical parameter should at least be construed in light of the number of reported significant digits and by applying ordinary rounding techniques.
  • a reference to “A and/or B”, when used in conjunction with open-ended language such as “comprising” can refer, in one embodiment, to A only (optionally including elements other than B); in another embodiment, to B only (optionally including elements other than A); in yet another embodiment, to both A and B (optionally including other elements); etc.
  • the compounds described herein may contain one or more chiral centers and/or double bonds and therefore, may exist as stereoisomers, such as double-bond isomers (i.e., geometric isomers such as E and Z), enantiomers or diastereomers.
  • stereoisomers such as double-bond isomers (i.e., geometric isomers such as E and Z), enantiomers or diastereomers.
  • the present disclosure includes each of the isolated stereoisomeric forms (such as the enantiomerically pure isomers, the E and Z isomers, and other alternatives for stereoisomers) as well as mixtures of stereoisomers in varying degrees of chiral purity or percentage of E and Z, including racemic mixtures, mixtures of diastereomers, and mixtures of E and Z isomers.
  • the compounds described herein encompass all possible enantiomers and stereoisomers thereof including the stereoisomerically pure form (e.g., geometrically pure, enantiomerically pure or diastereomerically pure) and enantiomeric and stereoisomeric mixtures.
  • Enantiomeric and stereoisomeric mixtures can be resolved into their component enantiomers or stereoisomers using separation techniques or chiral synthesis techniques well known to the skilled artisan.
  • the present disclosure includes each of the isolated stereoisomeric forms as well as mixtures of stereoisomers in varying degrees of chiral purity, including racemic mixtures. It also encompasses the various diastereomers.
  • tautomer is generally understood to refer to isomers that change into one another with great ease so that they can exist together in equilibrium; the equilibrium may strongly favor one of the tautomers, depending on stability considerations.
  • ketone and enol are two tautomeric forms of one compound.
  • liquid composition for an electronic vaporizer comprising:
  • a liquid composition provided herein has a viscosity of from about 3500 cP to about 8000 cP when measured at room temperature. In some embodiments, a liquid composition provided herein has a viscosity of about 3500 cP, about 4000 cP, about 4500 cP, about 5000 cP, about 5500 cP, about 6000 cP, about 6500 cP, about 7000 cP, about 7500 cP, or about 8000 cP when measured at room temperature. In some embodiments, a liquid composition provided herein has a viscosity of about 6000 cP when measured at room temperature.
  • the liquid composition less than about 0.1 wt%, less than about 0.05 wt%, less than about 0.02 wt%, or less than about 0.01 wt% of a mixture of one or more cutting agents.
  • a cutting agent is a substance added as a diluent to a liquid composition that does not contribute to the potency or flavour of the composition.
  • the liquid composition comprises less than about 0.1 wt% of a mixture of one or more cutting agents. In some embodiments, the liquid composition comprises less than about 0.01 wt% of a mixture of one or more cutting agents.
  • cannabinoid is generally understood to include any chemical compound that acts upon a cannabinoid receptor.
  • Cannabinoids may include endocannabinoids (produced naturally by humans and animals), phytocannabinoids (found in cannabis and some other plants), and synthetic cannabinoids (manufactured artificially).
  • phytocannabinoids include, but are not limited to, cannabigerolic acid (CBGA), cannabigerol (CBG), cannabigerol monomethylether (CBGM), cannabigerovarin (CBGV), cannabichromene (CBC), cannabichromevarin (CBCV), cannabidiol (CBD), cannabidiolic acid (CBD A), cannabidiol monomethylether (CBDM), cannabidiol-C4 (CBD- C4), cannabidivarin (CBDV), cannabidivarinic acid (CBDVA), cannabidiorcol (CBD-C1), tetrahydrocannabinol -C4 (THC-C4), tetrahydrocannabivarin (THCV), tetrahydrocannabivarinic acid (THCVA), tetrahydrocannabiorcol (THC-C1), cannabicycl
  • a phytocannabinoid may be in an acid form or a non-acid form, the latter also being referred to as the decarboxylated form since the non-acid form can be generated by decarboxylating the acid form.
  • Examples of synthetic cannabinoids include, but are not limited to, naphthoylindoles, naphthylmethylindoles, naphthoylpyrroles, naphthylmethylindenes, phenylacetylindoles, cyclohexylphenols, tetramethylcyclopropylindoles, adamantoylindoles, indazole carboxamides, and quinolinyl esters.
  • the cannabinoid is tetrahydrocannabinol (THC).
  • THC is only psychoactive in its decarboxylated state.
  • the carboxylic acid form (THCA) is nonpsychoactive.
  • tetrahydrocannabinol or “THC” are generally understood to refer to one or more of the following compounds, and, unless a particular other stereoisomer or stereoisomers are specified, includes the compound delta-9-tetrahydrocannabinol (A 9 -THC).
  • the cannabinoid is cannabidiol (CBD).
  • CBD cannabidiol
  • CBD cannabidiol
  • a liquid composition provided herein may further comprise a terpene or terpenoid.
  • terpene is generally understood to include any organic compound derived biosynthetically from units of isoprene (although the term sometimes refers to only isoprene-derived hydrocarbons), and the term “terpenoid” generally refers to a chemically modified terpene (e.g., by oxidation).
  • terpene refers to both terpene hydrocarbons and terpenoids. Terpenes may be classified in various ways, such as by how many isoprene units they contain.
  • suitable terpenes may include monoterpenes, sesquiterpenes, or triterpenes. At least some terpenes are expected to interact with, and potentiate the activity of, cannabinoids, resulting in what is known as the entourage effect.
  • Examples of terpenes known to be extractable from cannabis include aromadendrene, bergamottin, bergamotol, bisabol ene, borneol, 3 -carene, caryophyllene, eucalyptol, p-cymene, dihydrojasmone, elemene, farnesene, fenchol, fenchone, geranyl acetate, guaiol, humulene, isopulegol, limonene, linalool, menthone, menthol, menthofuran, myrcene, neryl acetate, neomenthyl acetate, ocimene, perillyl alcohol, phellandrene, pinene, pulegone, sabinene, sabinene hydrate, terpinene, terpineol, terpinen-4-ol,
  • terpenes include nerolidol, phytol, geraniol, nerol, alpha- bisabolol, thymol, genipin, astragaloside, asiaticoside, camphene, camphor, beta-amyrin, thujone, citronellol, cycloartenol, caryophyllene oxide, cedrene, cedrol, isoborneol, isopulegol, valencene, and derivatives thereof. Further examples of terpenes are discussed in US Patent Application Pub. No. US2016/0250270.
  • each of the one or more terpenes is a cannabis-derived terpene, i.e., a terpene extracted from a cannabis plant.
  • a liquid composition may have cannabinoids and cannabis-derived terpenes present in specific ratios, which cooperate to provide an entourage effect when vaped.
  • none of the one or more terpenes is a cannabis-derived terpene.
  • Terpenes may be botanically derived, i.e., extracted from sources other than the cannabis plant, and mixed with cannabinoids in ratios that mimic those present in specific cannabis strains, or in ratios different from those found in naturally occurring cannabis to provide novel flavours.
  • the one or more terpenes comprises at least one cannabis- derived terpene and at least one non-cannabis-derived terpene.
  • Said compositions may provide a combination of the beneficial effects associated with the use of cannabis-derived terpenes or botanically derived terpenes on their own.
  • a method for preparing a liquid composition for an electronic vaporization device comprising: (a) thermally decarboxylating THCA in crystalline form to obtain a THC oil; and
  • a cannabis distillate oil comprising at least about 50 wt% THC
  • liquid composition comprises from about 50 wt% to about 60 wt% of the THC oil, from about 35 wt% to about 45 wt% of the cannabis distillate oil, and from about 3 wt% to about 7 wt% of a mixture of the one or more terpenes.
  • Crystalline THCA or THCA “diamonds” may be obtained from fresh, dried, or frozen cannabis plant material, e.g., by crystallization of a supersaturated cannabis extract or “sauce”. Thermal decarboxylation of THCA may be performed at temperatures of about 100 °C or above, e.g., from about 110 °C to about 120 °C, to yield a THC oil of high purity.
  • the THC oil comprises at least about 85 wt%, at least about 86 wt%, at least about 87 wt%, at least about 88 wt%, or at least about 89 wt%, at least about 90 wt%, at least about 91 wt%, at least about 92 wt%, at least about 93 wt%, at least about 94 wt%, at least about 95 wt%, at least about 96 wt%, at least about 97 wt%, at least about 98 wt%, or at least about 99 wt% THC.
  • the THC oil comprises at least about 85 wt% THC.
  • the THC oil comprises at least about 90 wt% THC.
  • the THC oil comprises at least about 95 wt% THC.
  • the cannabis distillate oil may be obtained from fresh, dried, or frozen cannabis plant material by any of several distillation methods, such as short-path distillation or wiped film distillation.
  • the cannabis distillate oil comprises at least about 55 wt%, at least about 60 wt%, at least about 65 wt%, at least about 70 wt%, at least about 75 wt%, at least about 80 wt%, at least about 85 wt%, at least about 90 wt%, at least about 95 wt%, at least about 98 wt%, or at least about 99 wt% THC.
  • the cannabis distillate oil comprises about 65 wt% to about 85 wt% THC.
  • the cannabis distillate oil comprises about 75 wt% THC.
  • the liquid composition comprises from about 50 wt% to about 55 wt% of the THC oil, or from about 55 wt% to about 60 wt% of the THC oil. In some embodiments, the liquid composition comprises about 50 wt%, about 51 wt%, about 52 wt%, about 53 wt%, about 54 wt%, about 55 wt%, about 56 wt%, about 57 wt%, about 58 wt%, about 59 wt%, or about 60 wt% of the THC oil.
  • the liquid composition comprises from about 35 wt% to about 40 wt% of the cannabis distillate oil, or from about 40 wt% to about 45 wt% of the cannabis distillate oil. In some embodiments, the liquid composition comprises about 35 wt%, about 36 wt%, about 37 wt%, about 38 wt%, about 39 wt%, about 40 wt%, about 41 wt%, about 42 wt%, about 43 wt%, about 44 wt%, or about 45 wt% of the cannabis distillate oil.
  • the present application further provides a cartridge configured to operatively couple with an electronic vaporizer comprising the liquid composition as described herein.
  • the cartridge further comprises a cartridge body defining, at least in part, a reservoir configured to contain the liquid composition as described herein; a vaporizing assembly positioned within the cartridge body in fluid communication with the reservoir, the vaporizing assembly configured to vaporize the liquid composition; and a mouthpiece coupled to a proximal end region of the cartridge body.
  • a liquid composition for an electronic vaporizer comprising:
  • a method for preparing a liquid composition for an electronic vaporization device comprising:
  • a cannabis distillate oil comprising at least about 50 wt% THC
  • liquid composition comprises from about 50 wt% to about 60 wt% of the THC oil, from about 35 wt% to about 45 wt% of the cannabis distillate oil, and from about 3 wt% to about 7 wt% of a mixture of the one or more terpenes.
  • the cannabis distillate oil comprises at least about 55 wt%, at least about 60 wt%, at least about 65 wt%, at least about 70 wt%, at least about 75 wt%, at least about 80 wt%, at least about 85 wt%, at least about 90 wt%, at least about 95 wt%, at least about 98 wt%, or at least about 99 wt% THC.
  • liquid composition comprises from about 50 wt% to about 55 wt% of the THC oil, or from about 55 wt% to about 60 wt% of the THC oil.
  • liquid composition comprises about 50 wt%, about 51 wt%, about 52 wt%, about 53 wt%, about 54 wt%, about 55 wt%, about 56 wt%, about 57 wt%, about 58 wt%, about 59 wt%, or about 60 wt% of the THC oil.
  • liquid composition comprises from about 35 wt% to about 40 wt% of the cannabis distillate oil, or from about 40 wt% to about 45 wt% of the cannabis distillate oil.
  • liquid composition comprises about 35 wt%, about 36 wt%, about 37 wt%, about 38 wt%, about 39 wt%, about 40 wt%, about 41 wt%, about 42 wt%, about 43 wt%, about 44 wt%, or about 45 wt% of the cannabis distillate oil.
  • a liquid composition for an electronic vaporization device prepared by the method of any one of paragraphs 2-8.
  • liquid composition of paragraph 8 wherein the liquid composition comprises at least about 90 wt% of a mixture of one or more cannabinoids, the mixture of one or more cannabinoids comprising at least about 85 wt% tetrahydrocannabinol (THC) and at least about 0.1 wt% tetrahydrocannabinolic acid (THCA).
  • THC tetrahydrocannabinol
  • THCA tetrahydrocannabinolic acid
  • liquid composition of any one of paragraphs 1 and 9-16, wherein the mixture of one or more cannabinoids comprises at least about 86 wt%, at least about 87 wt%, at least about 88 wt%, at least about 89 wt%, at least about 90 wt%, at least about 91 wt%, at least about 92 wt%, at least about 93 wt%, at least about 94 wt%, at least about 95 wt%, at least about 96 wt%, at least about 97 wt%, at least about 98 wt%, or at least about 99 wt% THC.
  • the mixture of one or more cannabinoids comprises at least about 0.2 wt%, at least about 0.3 wt%, at least about 0.4 wt%, at least about 0.5 wt%, at least about 0.6 wt%, at least about 0.8 wt%, at least about 1.0 wt%, at least about 1.5 wt%, at least about 2.0 wt%, at least about 2.5 wt%, at least about 3.0 wt%, at least about 3.5 wt%, at least about 4.0 wt%, at least about 4.5 wt%, or at least about 5.0 wt% THC A.
  • the one or more cannabinoids further comprises cannabigerolic acid (CBGA), cannabigerol (CBG), cannabigerol monomethylether (CBGM), cannabigerovarin (CBGV), cannabichromene (CBC), cannabichromevarin (CBCV), cannabidiol (CBD), cannabidiolic acid (CBDA), cannabidiol monomethylether (CBDM), cannabidiol-C4 (CBD-C4), cannabidivarin (CBDV), cannabidivarinic acid (CBDVA), cannabidiorcol (CBD-C1), tetrahydrocannabinol-C4 (THC- C4), tetrahydrocannabivarin (THCV), tetrahydrocannabivarinic acid (THCVA), tetrahydrocannabiorcol (THC)
  • a cartridge configured to operatively couple with an electronic vaporizer comprising the liquid composition of any one of paragraphs 1 and 9-28.
  • the cartridge of paragraph 29, further comprising: a cartridge body defining, at least in part, a reservoir configured to contain the liquid composition of any one of paragraphs 1 and 9-28; a vaporizing assembly positioned within the cartridge body in fluid communication with the reservoir, the vaporizing assembly configured to vaporize the liquid composition; and a mouthpiece coupled to a proximal end region of the cartridge body.
  • Crystalline THCA was heated to 110-120 °C to effect decarboxylation, yielding a THC oil of at least 90% purity.
  • This THC oil was blended at -100 °C with a commercial THC distillate oil containing 65-85 wt% THC and commercially available botanical terpenes in a 50:45:5 ratio to obtain a vaporizable composition (Composition A) with a viscosity of about 6000 cP.
  • Composition B A more viscous comparative vaporizable composition was obtained by blending the THCA-derived THC oil with commercially available botanical terpenes in a 95:5 ratio.
  • compositions were loaded into commercial CCELL cartridges.
  • the cartridges containing Composition B had a failure rate of 5-15%.
  • the cartridges containing Composition A had a failure rate of less than 5%.
  • This example shows that a potent, high-THC composition with viscosity suitable for use in cartridges for electronic vaporization can be obtained by the combination of THCA- derived THC oil, THC distillate oil, and botanical terpenes, and is superior to the combination of THCA-derived THC oil and botanical terpenes without THC distillate oil.

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medical Informatics (AREA)
  • Pulmonology (AREA)
  • Dispersion Chemistry (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Biotechnology (AREA)
  • Botany (AREA)
  • Otolaryngology (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Inorganic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pyrane Compounds (AREA)

Abstract

The present application provides liquid compositions for an electronic vaporizer comprising: (a) at least about 90 wt% of a mixture of one or more cannabinoids, the mixture of one or more cannabinoids comprising at least about 85 wt% tetrahydrocannabinol (THC) and at least about 0.1 wt% tetrahydrocannabinolic acid (THCA); and (b) from about 3 wt% to about 7 wt% of a mixture of one or more terpenes. Also provided are methods for preparing a liquid composition for an electronic vaporization device comprising: (a) thermally decarboxylating THCA in crystalline form to obtain a THC oil; and (b) mixing the THC oil with (i) a cannabis distillate oil comprising at least about 50 wt% THC, and (ii) one or more terpenes; and liquid compositions prepared by said methods. Also provided are cartridges configured to operatively couple with an electronic vaporizer comprising said liquid compositions.

Description

VAPORIZABLE CANNABINOID COMPOSITIONS
CROSS-REFERENCE TO RELATED APPLICATION
[0001] This application claims the benefit of U.S. Provisional Patent Application Serial No. 63/428180 filed on November 28, 2022. The contents of the aforementioned application are incorporated by reference herein.
FIELD
[0002] The present application pertains to the field of vaporizable cannabinoid compositions. More particularly, the present application relates to liquid compositions for an electronic vaporizer containing cannabinoids and terpenes, methods for preparing such compositions, and cartridges comprising such compositions.
BACKGROUND
[0003] Cannabis is a genus of flowering plants that has been used by humans for various purposes, such as medicines, ritual, recreation and textiles. The flowers of the cannabis plant include glandular trichomes, in which phytocannabinoids are produced.
[0004] Over 100 phytocannabinoids produced by the cannabis plant have been identified to date. A notable phytocannabinoid is tetrahydrocannabinolic acid (THCA), which when decarboxylated, is transformed into tetrahydrocannabinol (THC). THC is a psychoactive substance that users may use in order to get a “high” when the cannabis flower is smoked, but has also been shown to be useful for other purposes, such as an appetite stimulant for people with AIDS and an anti emetic for people undergoing chemotherapy (see e.g., product monographs for dronabinol approved by the FDA).
[0005] In addition to phytocannabinoids, the cannabis plant also produces terpenes and terpenoids (collectively referred to herein as “terpenes” unless context dictates otherwise). Terpenes are organic compounds produced in a variety of plants, many of which are consumed in human diets and/or used in perfumes. They contribute to the aromas and flavors of different cannabis cultivars. The terpenes found in cannabis share a precursor with phytocannabinoids.
[0006] Currently, the most common method of utilizing cannabis is through inhalation of combusted dried cannabis flower. However, reactions occurring during the combustion of the dried flower can result in the formation of undesirable by-products. By-products can include formaldehyde, acetaldehyde, acrolein and other potentially carcinogenic compounds.
[0007] In other combusted plant products, such as tobacco products, some users have switched from traditional combustion cigarettes to alternative delivery mechanisms in an effort to reduce their exposure to such compounds. For example, an alternative to tobacco cigarettes is an electronic vaporization devices (a “vape” or an “e-cigarette”). In tobacco, the active inhalable ingredient (“All”) is nicotine. Electronic vaporization devices vaporize a liquid composition containing Alls (such as nicotine) into a “vapor” in order to permit inhalation by the user. These vapors are often produced at temperatures such that the formation of potentially harmful by-products is reduced as compared to a conventionally combusted analog.
[0008] However, it has been found that conventional liquid compositions containing cannabinoids require the presence of carrier oils, also known as cutting agents or diluents, to achieve a viscosity compatible with cartridges used in electronic vaporization devices. These carriers may not be desirable for inhalation and may cause adverse health effects. Moreover, conventional vaporizable liquid compositions generally contain no more than 85-87 wt% THC, limiting the potency of the compositions. The presence of minor cannabinoids and carriers also dilutes the taste provided by terpenes which are also present in conventional liquid compositions.
[0009] There is a need for improved liquid compositions containing cannabinoids for use in electronic vaporization devices.
SUMMARY OF THE INVENTION
[0010] In one aspect, there is provided a liquid composition for an electronic vaporizer comprising: (a) at least about 90 wt% of a mixture of one or more cannabinoids, the mixture of one or more cannabinoids comprising at least about 85 wt% tetrahydrocannabinol (THC) and at least about 0.1 wt% tetrahydrocannabinolic acid (THCA); and
(b) from about 3 wt% to about 7 wt% of a mixture of one or more terpenes.
[0011] In another aspect, there is provided a method for preparing a liquid composition for an electronic vaporization device comprising:
(a) thermally decarboxylating THCA in crystalline form to obtain a THC oil; and
(b) mixing the THC oil with
(i) a cannabis distillate oil comprising at least about 50 wt% THC, and
(ii) one or more terpenes, wherein the liquid composition comprises from about 50 wt% to about 60 wt% of the THC oil, from about 35 wt% to about 45 wt% of the cannabis distillate oil, and from about 3 wt% to about 7 wt% of a mixture of the one or more terpenes.
[0012] In another aspect, there is provided a liquid composition for an electronic vaporization device prepared by the methods described herein.
[0013] In another aspect, there is provided a cartridge configured to operatively couple with an electronic vaporizer comprising the liquid compositions described herein.
DETAILED DESCRIPTION
[0014] The present inventors have developed vaporizable liquid compositions that maximize psychoactive potency (from high THC content) and flavour (from terpenes). A THC oil of high purity (at least 85 wt% THC), also known as a “liquid diamond”, may be obtained by decarboxylation of THCA in crystalline form (so-called THCA “diamonds”). Surprisingly, it has been discovered that by combining about 50 wt% to about 60 wt% of such a THC oil with about 35 wt% to about 45 wt% of a cannabis distillate oil high in THC, and from about 3 wt% to about 7 wt% of a mixture of the one or more terpenes, the inventors have obtained a vaporizable composition of superior potency and flavour compared to conventional vaporizable compositions. The combination of a “liquid diamond” THC oil and a cannabis distillate oil has the advantage of minimizing levels of minor cannabinoids and maximizing THC content, resulting in increased psychoactive potency of the composition, without raising the viscosity of the composition to an unusable level, i.e., one that results in an elevated cartridge failure rate when vaped. Moreover, the presence of about 3 wt% to about 7 wt% terpenes is sufficient to impart desirable flavour and simultaneously maintain the viscosity of the predominantly THC-containing composition at a level suitable for use in vape cartridges without the addition of a carrier or cutting agent. Higher levels of terpenes may lead to an undesirably overpowering taste in the vaporizable composition.
Definitions
[0015] Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.
[0016] As used in the specification and claims, the singular forms “a”, “an” and “the” include plural references unless the context clearly dictates otherwise.
[0017] As used herein, whether in the specification or the appended claims, the transitional terms “comprising”, “including”, “having”, “containing”, “involving”, and the like are to be understood as being inclusive or open-ended (i.e., to mean including but not limited to), and they do not exclude unrecited elements, materials or method steps. Only the transitional phrases “consisting of’ and “consisting essentially of’, respectively, are closed or semi -closed transitional phrases with respect to claims and exemplary embodiment paragraphs herein. The transitional phrase “consisting of’ excludes any element, step, or ingredient which is not specifically recited. The transitional phrase “consisting essentially of’ limits the scope to the specified elements, materials or steps and to those that do not materially affect the basic character! stic(s) of the invention disclosed and/or claimed herein.
[0018] It is to be understood that any numerical value inherently contains certain errors necessarily resulting from the standard deviation found in the respective testing measurements. Also, as used herein, the term “about” generally means within 10%, 5%, 1%, or 0.5% of a given value or range. Alternatively, the term “about” means within an acceptable standard error of the mean when considered by one of ordinary skill in the art. Unless indicated to the contrary, the numerical parameters set forth in the present disclosure and attached claims are approximations that can vary as desired. At the very least, each numerical parameter should at least be construed in light of the number of reported significant digits and by applying ordinary rounding techniques.
[0019] The phrase “and/or,” as used herein in the specification and in the claims, should be understood to mean “either or both” of the elements so conjoined, i.e., elements that are conjunctively present in some cases and disjunctively present in other cases. Multiple elements listed with “and/or” should be construed in the same fashion, i.e., “one or more” of the elements so conjoined. Other elements may optionally be present other than the elements specifically identified by the “and/or” clause, whether related or unrelated to those elements specifically identified. Thus, as a non-limiting example, a reference to “A and/or B”, when used in conjunction with open-ended language such as “comprising” can refer, in one embodiment, to A only (optionally including elements other than B); in another embodiment, to B only (optionally including elements other than A); in yet another embodiment, to both A and B (optionally including other elements); etc.
[0020] As used herein in the specification and in the claims, "or" should be understood to encompass the same meaning as "and/or" as defined above. For example, when separating items in a list, "or" or "and/or" shall be interpreted as being inclusive, i.e., the inclusion of at least one, but also including more than one, of a number or list of elements, and, optionally, additional unlisted items.
[0021] The compounds described herein may contain one or more chiral centers and/or double bonds and therefore, may exist as stereoisomers, such as double-bond isomers (i.e., geometric isomers such as E and Z), enantiomers or diastereomers. The present disclosure includes each of the isolated stereoisomeric forms (such as the enantiomerically pure isomers, the E and Z isomers, and other alternatives for stereoisomers) as well as mixtures of stereoisomers in varying degrees of chiral purity or percentage of E and Z, including racemic mixtures, mixtures of diastereomers, and mixtures of E and Z isomers.
[0022] Accordingly, the compounds described herein encompass all possible enantiomers and stereoisomers thereof including the stereoisomerically pure form (e.g., geometrically pure, enantiomerically pure or diastereomerically pure) and enantiomeric and stereoisomeric mixtures. Enantiomeric and stereoisomeric mixtures can be resolved into their component enantiomers or stereoisomers using separation techniques or chiral synthesis techniques well known to the skilled artisan. The present disclosure includes each of the isolated stereoisomeric forms as well as mixtures of stereoisomers in varying degrees of chiral purity, including racemic mixtures. It also encompasses the various diastereomers.
[0023] When the chemical name does not specify the isomeric form of the compound, it denotes any one of the possible isomeric forms or mixtures of those isomeric forms of the compound. The compounds may also exist in several tautomeric forms. Accordingly, the compounds depicted herein encompass all possible tautomeric forms thereof.
[0024] The term "tautomer" is generally understood to refer to isomers that change into one another with great ease so that they can exist together in equilibrium; the equilibrium may strongly favor one of the tautomers, depending on stability considerations. For example, ketone and enol are two tautomeric forms of one compound.
Liquid compositions and their components
[0025] In one aspect, there is provided a liquid composition for an electronic vaporizer comprising:
(a) at least about 90 wt% of a mixture of one or more cannabinoids, the mixture of one or more cannabinoids comprising at least about 85 wt% tetrahydrocannabinol (THC) and at least about 0.1 wt% tetrahydrocannabinolic acid (THCA); and
(b) from about 3 wt% to about 7 wt% of a mixture of one or more terpenes. [0026] All weight percentages of components in liquid compositions provided herein refer to the ratio of the weight of a component to the weight of the entire liquid composition as a whole.
[0027] In some embodiments, a liquid composition provided herein has a viscosity of from about 3500 cP to about 8000 cP when measured at room temperature. In some embodiments, a liquid composition provided herein has a viscosity of about 3500 cP, about 4000 cP, about 4500 cP, about 5000 cP, about 5500 cP, about 6000 cP, about 6500 cP, about 7000 cP, about 7500 cP, or about 8000 cP when measured at room temperature. In some embodiments, a liquid composition provided herein has a viscosity of about 6000 cP when measured at room temperature.
[0028] In some embodiments, the liquid composition less than about 0.1 wt%, less than about 0.05 wt%, less than about 0.02 wt%, or less than about 0.01 wt% of a mixture of one or more cutting agents. As used herein, a cutting agent is a substance added as a diluent to a liquid composition that does not contribute to the potency or flavour of the composition. In some embodiments, the liquid composition comprises less than about 0.1 wt% of a mixture of one or more cutting agents. In some embodiments, the liquid composition comprises less than about 0.01 wt% of a mixture of one or more cutting agents.
Cannabinoids
[0029] As used herein, the term “cannabinoid” is generally understood to include any chemical compound that acts upon a cannabinoid receptor. Cannabinoids may include endocannabinoids (produced naturally by humans and animals), phytocannabinoids (found in cannabis and some other plants), and synthetic cannabinoids (manufactured artificially).
[0030] Examples of phytocannabinoids include, but are not limited to, cannabigerolic acid (CBGA), cannabigerol (CBG), cannabigerol monomethylether (CBGM), cannabigerovarin (CBGV), cannabichromene (CBC), cannabichromevarin (CBCV), cannabidiol (CBD), cannabidiolic acid (CBD A), cannabidiol monomethylether (CBDM), cannabidiol-C4 (CBD- C4), cannabidivarin (CBDV), cannabidivarinic acid (CBDVA), cannabidiorcol (CBD-C1), tetrahydrocannabinol -C4 (THC-C4), tetrahydrocannabivarin (THCV), tetrahydrocannabivarinic acid (THCVA), tetrahydrocannabiorcol (THC-C1), cannabicyclol (CBL), cannabicyclovarin (CBLV), cannabielsoin (CBE), cannabinol (CBN), cannabinolic acid (CBNA), cannabinol methylether (CBNM), cannabinol-C4 (CBN-C4), cannabivarin (CBV), cannabinol-C2 (CBN-C2), cannabiorcol (CBN-C1), cannabinodiol (CBND), cannabinodivarin (CBVD), cannabitriol (CBT), cannabitriolvarin (CBTV), ethoxy- cannabitriolvarin (CBTVE), dehydrocannabifuran (DCBF), cannabifuran (CBF), cannabichromanon (CBCN), cannabicitran (CBT), cannabiripsol (CBR), trihydroxytetrahydrocannabinol (triOH-THC), cannabinol propyl variant (CBNV), and derivatives thereof. Further examples of cannabinoids are discussed in PCT Patent Application Pub. No. WO2017/190249 and US Patent Application Pub. No. US2014/0271940.
[0031] A phytocannabinoid may be in an acid form or a non-acid form, the latter also being referred to as the decarboxylated form since the non-acid form can be generated by decarboxylating the acid form.
[0032] Examples of synthetic cannabinoids include, but are not limited to, naphthoylindoles, naphthylmethylindoles, naphthoylpyrroles, naphthylmethylindenes, phenylacetylindoles, cyclohexylphenols, tetramethylcyclopropylindoles, adamantoylindoles, indazole carboxamides, and quinolinyl esters.
[0033] In some embodiments, the cannabinoid is tetrahydrocannabinol (THC). THC is only psychoactive in its decarboxylated state. The carboxylic acid form (THCA) is nonpsychoactive. The terms "tetrahydrocannabinol" or "THC" are generally understood to refer to one or more of the following compounds, and, unless a particular other stereoisomer or stereoisomers are specified, includes the compound delta-9-tetrahydrocannabinol (A9-THC). These compounds are: (1) A6a’10a-tetrahydrocannabinol (7,8,9,10-tetrahydro-6,6,9-trimethyl-3- pentyl-6H-dibenzo[b,d]pyran-l-ol); (2) A6a(7)-tetrahydrocannabinol (9R,10aR)-8,9,l 0,10a- tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-l-ol; (3) A7-tetrahydrocannabinol ((6aR,9R,10aR)-6a,9,10,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-l-ol); (4) A8-tetrahydrocannabinol ((6aR, 10aR)-6a,7, 10,10a-tetrahydro-6,6,9-trimethyl-3 -pentyl- 6Hdibenzo[b,d]pyran-l-ol); (5) A6a’10a-tetrahydrocannabinol (7,8,9,10-tetrahydro-6,6,9- trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-l-ol); (6) A10-tetrahydrocannabinol (6a,7,8,9- tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-l-ol); (7) A9(11)- tetrahydrocannabinol (6a,7,8,9-tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-l- ol); (6) A10-tetrahydrocannabinol ((6aR,10aR)-6a,7,8,9,10,10a-hexahydro-6,6-dimethyl-9- methylene-3-pentyl-6H-dibenzo[b,d]pyran-l-ol); and (7) A9-tetrahydrocannabinol ((6aR,10aR)-6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-l-ol).
[0034] In some embodiments, the cannabinoid is cannabidiol (CBD). The terms "cannabidiol" or "CBD" are generally understood to refer to one or more of the following compounds, and, unless a particular other stereoisomer or stereoisomers are specified, includes the compound A2-cannabidiol. These compounds are: (1) A5-cannabidiol (2-(6- isopropenyl-3-methyl-5-cyclohexen-l-yl)-5-pentyl-l,3-benzenediol); (2) A4-cannabidiol (2- (6-isopropenyl-3-methyl-4-cyclohexen-l-yl)-5-pentyl-l,3-benzenediol); (3) A3-cannabidiol (2-(6-isopropenyl-3-methyl-3-cyclohexen-l-yl)-5-pentyl-l,3-benzenediol); (4) A3,7- cannabidiol (2-(6-isopropenyl-3-methylenecyclohex-l-yl)-5-pentyl-l,3-benzenediol); (5) A2- cannabidiol (2-(6-isopropenyl-3-methyl-2-cyclohexen-l-yl)-5-pentyl-l,3-benzenediol); (6) A^cannabidiol (2-(6-isopropenyl-3-methyl-l-cyclohexen-l-yl)-5-pentyl-l,3-benzenediol); and (7) A6-cannabidiol (2-(6-isopropenyl-3-methyl-6-cyclohexen-l-yl)-5-pentyl-l,3-benzenediol).
Terpenes
[0035] In some embodiments, a liquid composition provided herein may further comprise a terpene or terpenoid. The term “terpene” is generally understood to include any organic compound derived biosynthetically from units of isoprene (although the term sometimes refers to only isoprene-derived hydrocarbons), and the term “terpenoid” generally refers to a chemically modified terpene (e.g., by oxidation). As used herein, unless the context clearly dictates otherwise, the term “terpene” refers to both terpene hydrocarbons and terpenoids. Terpenes may be classified in various ways, such as by how many isoprene units they contain. For example, suitable terpenes may include monoterpenes, sesquiterpenes, or triterpenes. At least some terpenes are expected to interact with, and potentiate the activity of, cannabinoids, resulting in what is known as the entourage effect. [0036] Examples of terpenes known to be extractable from cannabis include aromadendrene, bergamottin, bergamotol, bisabol ene, borneol, 3 -carene, caryophyllene, eucalyptol, p-cymene, dihydrojasmone, elemene, farnesene, fenchol, fenchone, geranyl acetate, guaiol, humulene, isopulegol, limonene, linalool, menthone, menthol, menthofuran, myrcene, neryl acetate, neomenthyl acetate, ocimene, perillyl alcohol, phellandrene, pinene, pulegone, sabinene, sabinene hydrate, terpinene, terpineol, terpinen-4-ol, terpinolene, and derivatives thereof.
[0037] Additional examples of terpenes include nerolidol, phytol, geraniol, nerol, alpha- bisabolol, thymol, genipin, astragaloside, asiaticoside, camphene, camphor, beta-amyrin, thujone, citronellol, cycloartenol, caryophyllene oxide, cedrene, cedrol, isoborneol, isopulegol, valencene, and derivatives thereof. Further examples of terpenes are discussed in US Patent Application Pub. No. US2016/0250270.
[0038] In some embodiments, each of the one or more terpenes is a cannabis-derived terpene, i.e., a terpene extracted from a cannabis plant. A liquid composition may have cannabinoids and cannabis-derived terpenes present in specific ratios, which cooperate to provide an entourage effect when vaped.
[0039] In some embodiments, none of the one or more terpenes is a cannabis-derived terpene. Terpenes may be botanically derived, i.e., extracted from sources other than the cannabis plant, and mixed with cannabinoids in ratios that mimic those present in specific cannabis strains, or in ratios different from those found in naturally occurring cannabis to provide novel flavours.
[0040] In some embodiments, the one or more terpenes comprises at least one cannabis- derived terpene and at least one non-cannabis-derived terpene. Said compositions may provide a combination of the beneficial effects associated with the use of cannabis-derived terpenes or botanically derived terpenes on their own.
Methods
[0041] In another aspect, there is provided a method for preparing a liquid composition for an electronic vaporization device comprising: (a) thermally decarboxylating THCA in crystalline form to obtain a THC oil; and
(b) mixing the THC oil with
(i) a cannabis distillate oil comprising at least about 50 wt% THC, and
(ii) one or more terpenes, wherein the liquid composition comprises from about 50 wt% to about 60 wt% of the THC oil, from about 35 wt% to about 45 wt% of the cannabis distillate oil, and from about 3 wt% to about 7 wt% of a mixture of the one or more terpenes.
[0042] Crystalline THCA or THCA “diamonds” may be obtained from fresh, dried, or frozen cannabis plant material, e.g., by crystallization of a supersaturated cannabis extract or “sauce”. Thermal decarboxylation of THCA may be performed at temperatures of about 100 °C or above, e.g., from about 110 °C to about 120 °C, to yield a THC oil of high purity. In some embodiments, the THC oil comprises at least about 85 wt%, at least about 86 wt%, at least about 87 wt%, at least about 88 wt%, or at least about 89 wt%, at least about 90 wt%, at least about 91 wt%, at least about 92 wt%, at least about 93 wt%, at least about 94 wt%, at least about 95 wt%, at least about 96 wt%, at least about 97 wt%, at least about 98 wt%, or at least about 99 wt% THC. In some embodiments, the THC oil comprises at least about 85 wt% THC. In some embodiments, the THC oil comprises at least about 90 wt% THC. In some embodiments, the THC oil comprises at least about 95 wt% THC.
[0043] The cannabis distillate oil may be obtained from fresh, dried, or frozen cannabis plant material by any of several distillation methods, such as short-path distillation or wiped film distillation.
[0044] In some embodiments, the cannabis distillate oil comprises at least about 55 wt%, at least about 60 wt%, at least about 65 wt%, at least about 70 wt%, at least about 75 wt%, at least about 80 wt%, at least about 85 wt%, at least about 90 wt%, at least about 95 wt%, at least about 98 wt%, or at least about 99 wt% THC. In some embodiments, the cannabis distillate oil comprises about 65 wt% to about 85 wt% THC. In some embodiments, the cannabis distillate oil comprises about 75 wt% THC. [0045] In some embodiments, the liquid composition comprises from about 50 wt% to about 55 wt% of the THC oil, or from about 55 wt% to about 60 wt% of the THC oil. In some embodiments, the liquid composition comprises about 50 wt%, about 51 wt%, about 52 wt%, about 53 wt%, about 54 wt%, about 55 wt%, about 56 wt%, about 57 wt%, about 58 wt%, about 59 wt%, or about 60 wt% of the THC oil.
[0046] In some embodiments, the liquid composition comprises from about 35 wt% to about 40 wt% of the cannabis distillate oil, or from about 40 wt% to about 45 wt% of the cannabis distillate oil. In some embodiments, the liquid composition comprises about 35 wt%, about 36 wt%, about 37 wt%, about 38 wt%, about 39 wt%, about 40 wt%, about 41 wt%, about 42 wt%, about 43 wt%, about 44 wt%, or about 45 wt% of the cannabis distillate oil.
Cartridges
[0047] The present application further provides a cartridge configured to operatively couple with an electronic vaporizer comprising the liquid composition as described herein.
[0048] In some embodiments, the cartridge further comprises a cartridge body defining, at least in part, a reservoir configured to contain the liquid composition as described herein; a vaporizing assembly positioned within the cartridge body in fluid communication with the reservoir, the vaporizing assembly configured to vaporize the liquid composition; and a mouthpiece coupled to a proximal end region of the cartridge body.
Embodiments
[0049] Particular embodiments of the invention include, without limitation, the following:
1. A liquid composition for an electronic vaporizer comprising:
(a) at least about 90 wt% of a mixture of one or more cannabinoids, the mixture of one or more cannabinoids comprising at least about 85 wt% tetrahydrocannabinol (THC) and at least about 0.1 wt% tetrahydrocannabinolic acid (THCA); and
(b) from about 3 wt% to about 7 wt% of a mixture of one or more terpenes.
2. A method for preparing a liquid composition for an electronic vaporization device comprising:
(a) thermally decarboxylating THCA in crystalline form to obtain a THC oil; and (b) mixing the THC oil with
(i) a cannabis distillate oil comprising at least about 50 wt% THC, and
(ii) one or more terpenes, wherein the liquid composition comprises from about 50 wt% to about 60 wt% of the THC oil, from about 35 wt% to about 45 wt% of the cannabis distillate oil, and from about 3 wt% to about 7 wt% of a mixture of the one or more terpenes.
3. The method of paragraph 2, wherein the cannabis distillate oil comprises at least about 55 wt%, at least about 60 wt%, at least about 65 wt%, at least about 70 wt%, at least about 75 wt%, at least about 80 wt%, at least about 85 wt%, at least about 90 wt%, at least about 95 wt%, at least about 98 wt%, or at least about 99 wt% THC.
4. The method of paragraph 2 or 3, wherein the liquid composition comprises from about 50 wt% to about 55 wt% of the THC oil, or from about 55 wt% to about 60 wt% of the THC oil.
5. The method of paragraph 2 or 3, wherein the liquid composition comprises about 50 wt%, about 51 wt%, about 52 wt%, about 53 wt%, about 54 wt%, about 55 wt%, about 56 wt%, about 57 wt%, about 58 wt%, about 59 wt%, or about 60 wt% of the THC oil.
6. The method of any one of paragraphs 2-5, wherein the liquid composition comprises from about 35 wt% to about 40 wt% of the cannabis distillate oil, or from about 40 wt% to about 45 wt% of the cannabis distillate oil.
7. The method of any one of paragraphs 2-5, wherein the liquid composition comprises about 35 wt%, about 36 wt%, about 37 wt%, about 38 wt%, about 39 wt%, about 40 wt%, about 41 wt%, about 42 wt%, about 43 wt%, about 44 wt%, or about 45 wt% of the cannabis distillate oil.
8. A liquid composition for an electronic vaporization device prepared by the method of any one of paragraphs 2-8.
9. The liquid composition of paragraph 8, wherein the liquid composition comprises at least about 90 wt% of a mixture of one or more cannabinoids, the mixture of one or more cannabinoids comprising at least about 85 wt% tetrahydrocannabinol (THC) and at least about 0.1 wt% tetrahydrocannabinolic acid (THCA).
10. The liquid composition of paragraph 1 or 9, comprising at least about 91 wt%, at least about 92 wt%, or at least about 93 wt% of the mixture of one or more cannabinoids. 11. The liquid composition of any one of paragraphs 1 and 9-10, comprising from about 3 wt% to about 5 wt%, from about 4 wt% to about 6 wt%, or from about 5 wt% to about 7 wt% of the mixture of one or more terpenes.
12. The liquid composition of paragraph 1 or 9, comprising:
(a) about 93 wt% of the mixture of one or more cannabinoids; and
(b) about 7 wt% of the mixture of one or more terpenes.
13. The liquid composition of paragraph 1 or 9, comprising:
(a) about 94 wt% of the mixture of one or more cannabinoids; and
(b) about 6 wt% of the mixture of one or more terpenes.
14. The liquid composition of paragraph 1 or 9, comprising:
(a) about 95 wt% of the mixture of one or more cannabinoids; and
(b) about 5 wt% of the mixture of one or more terpenes.
15. The liquid composition of paragraph 1 or 9, comprising:
(a) about 96 wt% of the mixture of one or more cannabinoids; and
(b) about 4 wt% of the mixture of one or more terpenes.
16. The liquid composition of paragraph 1 or 9, comprising:
(a) about 97 wt% of the mixture of one or more cannabinoids; and
(b) about 3 wt% of the mixture of one or more terpenes.
17. The liquid composition of any one of paragraphs 1 and 9-16, wherein the mixture of one or more cannabinoids comprises at least about 86 wt%, at least about 87 wt%, at least about 88 wt%, at least about 89 wt%, at least about 90 wt%, at least about 91 wt%, at least about 92 wt%, at least about 93 wt%, at least about 94 wt%, at least about 95 wt%, at least about 96 wt%, at least about 97 wt%, at least about 98 wt%, or at least about 99 wt% THC.
18. The liquid composition of any one of paragraphs 1 and 9-17, wherein the mixture of one or more cannabinoids comprises at least about 0.2 wt%, at least about 0.3 wt%, at least about 0.4 wt%, at least about 0.5 wt%, at least about 0.6 wt%, at least about 0.8 wt%, at least about 1.0 wt%, at least about 1.5 wt%, at least about 2.0 wt%, at least about 2.5 wt%, at least about 3.0 wt%, at least about 3.5 wt%, at least about 4.0 wt%, at least about 4.5 wt%, or at least about 5.0 wt% THC A.
19. The liquid composition of any one of paragraphs 1 and 9-18, wherein the one or more cannabinoids further comprises cannabigerolic acid (CBGA), cannabigerol (CBG), cannabigerol monomethylether (CBGM), cannabigerovarin (CBGV), cannabichromene (CBC), cannabichromevarin (CBCV), cannabidiol (CBD), cannabidiolic acid (CBDA), cannabidiol monomethylether (CBDM), cannabidiol-C4 (CBD-C4), cannabidivarin (CBDV), cannabidivarinic acid (CBDVA), cannabidiorcol (CBD-C1), tetrahydrocannabinol-C4 (THC- C4), tetrahydrocannabivarin (THCV), tetrahydrocannabivarinic acid (THCVA), tetrahydrocannabiorcol (THC-C1), cannabicyclol (CBL), cannabicyclovarin (CBLV), cannabielsoin (CBE), cannabinol (CBN), cannabinolic acid (CBNA), cannabinol methylether (CBNM), cannabinol-C4 (CBN-C4), cannabivarin (CBV), cannabinol-C2 (CBN-C2), cannabiorcol (CBN-C1), cannabinodiol (CBND), cannabinodivarin (CBVD), cannabitriol (CBT), cannabitriolvarin (CBTV), ethoxy-cannabitriolvarin (CBTVE), dehydrocannabifuran (DCBF), cannabifuran (CBF), cannabichromanon (CBCN), cannabicitran (CBT), cannabiripsol (CBR), trihydroxytetrahydrocannabinol (triOH-THC), cannabinol propyl variant (CBNV), or any combination thereof.
20. The liquid composition of any one of paragraphs 1 and 9-19, wherein the one or more terpenes comprises aromadendrene, bergamottin, bergamotol, bisabolene, borneol, 3-carene, caryophyllene, eucalyptol, p-cymene, dihydrojasmone, elemene, farnesene, fenchol, fenchone, geranyl acetate, guaiol, humulene, isopulegol, limonene, linalool, menthone, menthol, menthofuran, myrcene, neryl acetate, neomenthyl acetate, ocimene, perillyl alcohol, phellandrene, pinene, pulegone, sabinene, sabinene hydrate, terpinene, terpineol, terpinen-4- ol, terpinolene, nerolidol, phytol, geraniol, nerol, alpha-bisabolol, thymol, genipin, astragaloside, asiaticoside, camphene, camphor, beta-amyrin, thujone, citronellol, cycloartenol, caryophyllene oxide, cedrene, cedrol, isoborneol, isopulegol, valencene, or any combination thereof.
21. The liquid composition of any one of paragraphs 1 and 9-20, wherein each of the one or more terpenes is a cannabis-derived terpene.
22. The liquid composition of any one of paragraphs 1 and 9-20, wherein none of the one or more terpenes is a cannabis-derived terpene.
23. The liquid composition of any one of paragraphs 1 and 9-20, wherein the one or more terpenes comprises at least one cannabis-derived terpene and at least one non-cannabis- derived terpene. 24. The liquid composition of any one of paragraphs 1 and 9-23, wherein the liquid composition comprises less than about 0.1 wt% of a mixture of one or more cutting agents.
25. The liquid composition of any one of paragraphs 1 and 9-24, wherein the liquid composition comprises less than about 0.05 wt%, less than about 0.02 wt%, or less than about 0.01 wt% of the mixture of one or more cutting agents.
26. The liquid composition of paragraph 24 or 25, wherein the one or more cutting agents comprises glycerin, propylene glycol, a polyethylene glycol, vitamin E, a vitamin E derivative, a medium-chain triglyceride, or any combination thereof.
27. The liquid composition of any one of paragraphs 1 and 9-26, wherein the viscosity of the liquid composition is from about 3500 cP to about 8000 cP.
28. The liquid composition of any one of paragraphs 1 and 9-26, wherein the viscosity of the liquid composition is about 6000 cP.
29. A cartridge configured to operatively couple with an electronic vaporizer comprising the liquid composition of any one of paragraphs 1 and 9-28.
30. The cartridge of paragraph 29, further comprising: a cartridge body defining, at least in part, a reservoir configured to contain the liquid composition of any one of paragraphs 1 and 9-28; a vaporizing assembly positioned within the cartridge body in fluid communication with the reservoir, the vaporizing assembly configured to vaporize the liquid composition; and a mouthpiece coupled to a proximal end region of the cartridge body.
[0050] To gain a better understanding of the invention described herein, the following examples are set forth. It should be understood that these examples are for illustrative purposes only. Therefore, they should not limit the scope of this invention in any way.
EXAMPLE
[0051] Crystalline THCA was heated to 110-120 °C to effect decarboxylation, yielding a THC oil of at least 90% purity. This THC oil was blended at -100 °C with a commercial THC distillate oil containing 65-85 wt% THC and commercially available botanical terpenes in a 50:45:5 ratio to obtain a vaporizable composition (Composition A) with a viscosity of about 6000 cP. [0052] A more viscous comparative vaporizable composition (Composition B) was obtained by blending the THCA-derived THC oil with commercially available botanical terpenes in a 95:5 ratio.
[0053] Both compositions were loaded into commercial CCELL cartridges. When used in electronic vaporization devices, the cartridges containing Composition B had a failure rate of 5-15%. In contrast, the cartridges containing Composition A had a failure rate of less than 5%.
[0054] This example shows that a potent, high-THC composition with viscosity suitable for use in cartridges for electronic vaporization can be obtained by the combination of THCA- derived THC oil, THC distillate oil, and botanical terpenes, and is superior to the combination of THCA-derived THC oil and botanical terpenes without THC distillate oil.
[0055] All publications, patents and patent applications mentioned in this Specification are indicative of the level of skill of those skilled in the art to which this invention pertains and are herein incorporated by reference to the same extent as if each individual publication, patent, or patent applications was specifically and individually indicated to be incorporated by reference.
[0056] Although the foregoing invention has been described in some detail by way of illustration and example for purposes of clarity of understanding, it is readily apparent to those of ordinary skill in the art in light of the teachings of this invention that certain changes and modifications may be made thereto without departing from the scope of the appended claims.

Claims

1. A liquid composition for an electronic vaporizer comprising:
(a) at least about 90 wt% of a mixture of one or more cannabinoids, the mixture of one or more cannabinoids comprising at least about 85 wt% tetrahydrocannabinol (THC) and at least about 0.1 wt% tetrahydrocannabinolic acid (THCA); and
(b) from about 3 wt% to about 7 wt% of a mixture of one or more terpenes.
2. A method for preparing a liquid composition for an electronic vaporization device comprising:
(a) thermally decarboxylating THCA in crystalline form to obtain a THC oil; and
(b) mixing the THC oil with
(i) a cannabis distillate oil comprising at least about 50 wt% THC, and
(ii) one or more terpenes, wherein the liquid composition comprises from about 50 wt% to about 60 wt% of the THC oil, from about 35 wt% to about 45 wt% of the cannabis distillate oil, and from about 3 wt% to about 7 wt% of a mixture of the one or more terpenes.
3. The method of claim 2, wherein the cannabis distillate oil comprises at least about 55 wt%, at least about 60 wt%, at least about 65 wt%, at least about 70 wt%, at least about 75 wt%, at least about 80 wt%, at least about 85 wt%, at least about 90 wt%, at least about 95 wt%, at least about 98 wt%, or at least about 99 wt% THC.
4. The method of claim 2 or 3, wherein the liquid composition comprises from about 50 wt% to about 55 wt% of the THC oil, or from about 55 wt% to about 60 wt% of the THC oil.
5. The method of claim 2 or 3, wherein the liquid composition comprises about 50 wt%, about 51 wt%, about 52 wt%, about 53 wt%, about 54 wt%, about 55 wt%, about 56 wt%, about 57 wt%, about 58 wt%, about 59 wt%, or about 60 wt% of the THC oil.
6. The method of any one of claims 2-5, wherein the liquid composition comprises from about 35 wt% to about 40 wt% of the cannabis distillate oil, or from about 40 wt% to about 45 wt% of the cannabis distillate oil.
7. The method of any one of claims 2-5, wherein the liquid composition comprises about 35 wt%, about 36 wt%, about 37 wt%, about 38 wt%, about 39 wt%, about 40 wt%, about 41 wt%, about 42 wt%, about 43 wt%, about 44 wt%, or about 45 wt% of the cannabis distillate oil.
8. A liquid composition for an electronic vaporization device prepared by the method of any one of claims 2-8.
9. The liquid composition of claim 8, wherein the liquid composition comprises at least about 90 wt% of a mixture of one or more cannabinoids, the mixture of one or more cannabinoids comprising at least about 85 wt% tetrahydrocannabinol (THC) and at least about 0.1 wt% tetrahydrocannabinolic acid (THCA).
10. The liquid composition of claim 1 or 9, comprising at least about 91 wt%, at least about 92 wt%, or at least about 93 wt% of the mixture of one or more cannabinoids.
11. The liquid composition of any one of claims 1 and 9-10, comprising from about 3 wt% to about 5 wt%, from about 4 wt% to about 6 wt%, or from about 5 wt% to about 7 wt% of the mixture of one or more terpenes.
12. The liquid composition of claim 1 or 9, comprising:
(a) about 93 wt% of the mixture of one or more cannabinoids; and
(b) about 7 wt% of the mixture of one or more terpenes.
13. The liquid composition of claim 1 or 9, comprising:
(a) about 94 wt% of the mixture of one or more cannabinoids; and
(b) about 6 wt% of the mixture of one or more terpenes.
14. The liquid composition of claim 1 or 9, comprising:
(a) about 95 wt% of the mixture of one or more cannabinoids; and
(b) about 5 wt% of the mixture of one or more terpenes.
15. The liquid composition of claim 1 or 9, comprising:
(a) about 96 wt% of the mixture of one or more cannabinoids; and
(b) about 4 wt% of the mixture of one or more terpenes.
16. The liquid composition of claim 1 or 9, comprising:
(a) about 97 wt% of the mixture of one or more cannabinoids; and
(b) about 3 wt% of the mixture of one or more terpenes.
17. The liquid composition of any one of claims 1 and 9-16, wherein the mixture of one or more cannabinoids comprises at least about 86 wt%, at least about 87 wt%, at least about 88 wt%, at least about 89 wt%, at least about 90 wt%, at least about 91 wt%, at least about 92 wt%, at least about 93 wt%, at least about 94 wt%, at least about 95 wt%, at least about 96 wt%, at least about 97 wt%, at least about 98 wt%, or at least about 99 wt% THC.
18. The liquid composition of any one of claims 1 and 9-17, wherein the mixture of one or more cannabinoids comprises at least about 0.2 wt%, at least about 0.3 wt%, at least about 0.4 wt%, at least about 0.5 wt%, at least about 0.6 wt%, at least about 0.8 wt%, at least about 1.0 wt%, at least about 1.5 wt%, at least about 2.0 wt%, at least about 2.5 wt%, at least about 3.0 wt%, at least about 3.5 wt%, at least about 4.0 wt%, at least about 4.5 wt%, or at least about
5.0 wt% THC A.
19. The liquid composition of any one of claims 1 and 9-18, wherein the one or more cannabinoids further comprises cannabigerolic acid (CBGA), cannabigerol (CBG), cannabigerol monomethylether (CBGM), cannabigerovarin (CBGV), cannabichromene (CBC), cannabichromevarin (CBCV), cannabidiol (CBD), cannabidiolic acid (CBDA), cannabidiol monomethylether (CBDM), cannabidiol-C4 (CBD-C4), cannabidivarin (CBDV), cannabidivarinic acid (CBDVA), cannabidiorcol (CBD-C1), tetrahydrocannabinol-C4 (THC- C4), tetrahydrocannabivarin (THCV), tetrahydrocannabivarinic acid (THCVA), tetrahydrocannabiorcol (THC-C1), cannabicyclol (CBL), cannabicyclovarin (CBLV), cannabielsoin (CBE), cannabinol (CBN), cannabinolic acid (CBNA), cannabinol methylether (CBNM), cannabinol-C4 (CBN-C4), cannabivarin (CBV), cannabinol-C2 (CBN-C2), cannabiorcol (CBN-C1), cannabinodiol (CBND), cannabinodivarin (CBVD), cannabitriol (CBT), cannabitriolvarin (CBTV), ethoxy-cannabitriolvarin (CBTVE), dehydrocannabifuran (DCBF), cannabifuran (CBF), cannabichromanon (CBCN), cannabicitran (CBT), cannabiripsol (CBR), trihydroxytetrahydrocannabinol (triOH-THC), cannabinol propyl variant (CBNV), or any combination thereof.
20. The liquid composition of any one of claims 1 and 9-19, wherein the one or more terpenes comprises aromadendrene, bergamottin, bergamotol, bisabolene, borneol, 3-carene, caryophyllene, p-cymene, dihydrojasmone, elemene, eucalyptol, famesene, fenchol, fenchone, geranyl acetate, guaiol, humulene, isopulegol, limonene, linalool, menthone, menthol, menthofuran, myrcene, neryl acetate, neomenthyl acetate, ocimene, perillyl alcohol, phellandrene, pinene, pulegone, sabinene, sabinene hydrate, terpinene, terpineol, terpinen-4- ol, terpinolene, nerolidol, phytol, geraniol, nerol, alpha-bisabolol, thymol, genipin, astragaloside, asiaticoside, camphene, camphor, beta-amyrin, thujone, citronellol, cycloartenol, caryophyllene oxide, cedrene, cedrol, isoborneol, isopulegol, valencene, or any combination thereof.
21. The liquid composition of any one of claims 1 and 9-20, wherein each of the one or more terpenes is a cannabis-derived terpene.
22. The liquid composition of any one of claims 1 and 9-20, wherein none of the one or more terpenes is a cannabis-derived terpene.
23. The liquid composition of any one of claims 1 and 9-20, wherein the one or more terpenes comprises at least one cannabis-derived terpene and at least one non-cannabis- derived terpene.
24. The liquid composition of any one of claims 1 and 9-23, wherein the liquid composition comprises less than about 0.1 wt% of a mixture of one or more cutting agents.
25. The liquid composition of any one of claims 1 and 9-24, wherein the liquid composition comprises less than about 0.05 wt%, less than about 0.02 wt%, or less than about 0.01 wt% of the mixture of one or more cutting agents.
26. The liquid composition of claim 24 or 25, wherein the one or more cutting agents comprises glycerin, propylene glycol, a polyethylene glycol, vitamin E, a vitamin E derivative, a medium-chain triglyceride, or any combination thereof.
27. The liquid composition of any one of claims 1 and 9-26, wherein the viscosity of the liquid composition is from about 3500 cP to about 8000 cP.
28. The liquid composition of any one of claims 1 and 9-26, wherein the viscosity of the liquid composition is about 6000 cP.
29. A cartridge configured to operatively couple with an electronic vaporizer comprising the liquid composition of any one of claims 1 and 9-28.
30. The cartridge of claim 29, further comprising: a cartridge body defining, at least in part, a reservoir configured to contain the liquid composition of any one of claims 1 and 9-28; a vaporizing assembly positioned within the cartridge body in fluid communication with the reservoir, the vaporizing assembly configured to vaporize the liquid composition; and a mouthpiece coupled to a proximal end region of the cartridge body.
PCT/CA2023/051581 2022-11-28 2023-11-27 Vaporizable cannabinoid compositions WO2024113046A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA3233434A CA3233434A1 (en) 2022-11-28 2023-11-27 Vaporizable cannabinoid compositions

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US202263428180P 2022-11-28 2022-11-28
US63/428,180 2022-11-28

Publications (1)

Publication Number Publication Date
WO2024113046A1 true WO2024113046A1 (en) 2024-06-06

Family

ID=91322684

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CA2023/051581 WO2024113046A1 (en) 2022-11-28 2023-11-27 Vaporizable cannabinoid compositions

Country Status (1)

Country Link
WO (1) WO2024113046A1 (en)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2408979A (en) * 2002-09-10 2005-06-15 Sankio Chemical Co Ltd Process for producing arylamine
WO2020093170A1 (en) * 2018-11-09 2020-05-14 Cronos Group Inc. Liquid composition for an electronic vapor device
WO2020097726A1 (en) * 2018-11-13 2020-05-22 Hexo Operations Inc. Method of manufacturing vape oil including a cannabinoid for use in a vape device
US20210220323A1 (en) * 2015-02-27 2021-07-22 Canopy Growth Corporation Compositions comprising combinations of purified cannabinoids, with at least one flavonoid, terpene or mineral
US20220031845A1 (en) * 2019-04-18 2022-02-03 Kanabo Research Ltd. Diluents for compositions of cannabinoids and uses thereof
WO2023212170A1 (en) * 2022-04-29 2023-11-02 Abstrax Tech Inc. Endogenous stabilization of cannabinoids

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2408979A (en) * 2002-09-10 2005-06-15 Sankio Chemical Co Ltd Process for producing arylamine
US20210220323A1 (en) * 2015-02-27 2021-07-22 Canopy Growth Corporation Compositions comprising combinations of purified cannabinoids, with at least one flavonoid, terpene or mineral
WO2020093170A1 (en) * 2018-11-09 2020-05-14 Cronos Group Inc. Liquid composition for an electronic vapor device
WO2020097726A1 (en) * 2018-11-13 2020-05-22 Hexo Operations Inc. Method of manufacturing vape oil including a cannabinoid for use in a vape device
US20220031845A1 (en) * 2019-04-18 2022-02-03 Kanabo Research Ltd. Diluents for compositions of cannabinoids and uses thereof
WO2023212170A1 (en) * 2022-04-29 2023-11-02 Abstrax Tech Inc. Endogenous stabilization of cannabinoids

Similar Documents

Publication Publication Date Title
US10821147B2 (en) Printable cannabinoid and terpene compositions
US20210220323A1 (en) Compositions comprising combinations of purified cannabinoids, with at least one flavonoid, terpene or mineral
AU2018101357A4 (en) Composition and method for treating autism
US20180344790A1 (en) Enhanced smokable therapeutic cannabis product and method for making same
US20170367386A1 (en) Terpene flavoring compositions
US20220323403A1 (en) Cannabis tablet formulations and compositions and methods of making the same
CN110177543A (en) Water-soluble composition comprising purifying cannboid
US20210038666A1 (en) Printable cannabinoid and terpene compositions
US20190275268A1 (en) Multi-use cartridge for ingestion of cannabis-based products
US20180344786A1 (en) System and method enhanced cannabiniod effect delivery
CA3054690A1 (en) Compositions purposefully selected comprising purified cannabinoids and/or purified terpenes
US20210392943A1 (en) Liquid composition for an electronic vapor device
FR3062303A1 (en) VAPORIZABLE LIQUID FORMULATION COMPRISING AT LEAST ONE DIOL AND AT LEAST ONE CANNABINOID COMPOUND
US20200297025A1 (en) Method of manufacturing vape oil including a cannabinoid for use in a vape device
US11346051B2 (en) Aromatized and flavored paper products
WO2024113046A1 (en) Vaporizable cannabinoid compositions
CA3233434A1 (en) Vaporizable cannabinoid compositions
EP3817735A1 (en) Cannabinoid composition and method for treating ptsd and/or anxiety
US20190321306A1 (en) Cannabis-based therapeutic product for treatment of chronic pain
US20230346810A1 (en) Endogenous stabilization of cannabinoids
WO2019171170A1 (en) Device and method for administering an active ingredient
US20200094003A1 (en) Multi-use cartridge for ingestion of cannabis-based products
WO2021179087A1 (en) Terpene-enhanced compositions and uses thereof

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 23895620

Country of ref document: EP

Kind code of ref document: A1