WO2017180948A1 - Cannabinoid and caffeine emulsifications - Google Patents
Cannabinoid and caffeine emulsifications Download PDFInfo
- Publication number
- WO2017180948A1 WO2017180948A1 PCT/US2017/027543 US2017027543W WO2017180948A1 WO 2017180948 A1 WO2017180948 A1 WO 2017180948A1 US 2017027543 W US2017027543 W US 2017027543W WO 2017180948 A1 WO2017180948 A1 WO 2017180948A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- oil
- emulsification
- cannabis
- caffeine
- cannabinoid
- Prior art date
- Legal status (The legal status 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 status listed.)
- Ceased
Links
Classifications
-
- 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
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
- A61K9/0056—Mouth soluble or dispersible forms; Suckable, eatable, chewable coherent forms; Forms rapidly disintegrating in the mouth; Lozenges; Lollipops; Bite capsules; Baked products; Baits or other oral forms for animals
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
- A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
- A23D7/005—Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by ingredients other than fatty acid triglycerides
- A23D7/0053—Compositions other than spreads
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G1/00—Cocoa; Cocoa products, e.g. chocolate; Substitutes therefor
- A23G1/30—Cocoa products, e.g. chocolate; Substitutes therefor
- A23G1/32—Cocoa products, e.g. chocolate; Substitutes therefor characterised by the composition containing organic or inorganic compounds
- A23G1/48—Cocoa products, e.g. chocolate; Substitutes therefor characterised by the composition containing organic or inorganic compounds containing plants or parts thereof, e.g. fruits, seeds or extracts
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/30—Artificial sweetening agents
- A23L27/33—Artificial sweetening agents containing sugars or derivatives
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/80—Emulsions
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
- A61K31/522—Purines, e.g. adenine having oxo groups directly attached to the heterocyclic ring, e.g. hypoxanthine, guanine, acyclovir
-
- 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)
-
- 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
-
- 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
-
- 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
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
-
- 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
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
- A61K47/40—Cyclodextrins; Derivatives thereof
-
- 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
- A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
-
- 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
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
Definitions
- the present invention relates to cannabinoid and caffeine emulsifi cations that are bio-available, fast action and highly metabolizable.
- Cannabinoids are chemical compounds found in the cannabis plant that interact with receptors in the brain and body to create various effects Herbal cannabis contains over 400 compounds including over 100 cannabinoids, which are aryl- substituted meroterpenes unique to the plant genus Cannabis. The pharmacology of most of the cannabinoids is largely unknown but the most potent psychoactive agent, ⁇ 9 -tetrahydrocannabinol ( - 9 -THC, or THC), has been isolated, synthesized and much studied due to its abundance and psychoactive attributes. Other plant cannabinoids include ⁇ 8 -THC, cannabinol and cannabidiol (CBD). These and other cannabinoids have additive, synergistic or antagonistic effects with THC and may modify its actions when herbal cannabis is smoked.
- cannabinoids are chemical compounds found in the cannabis plant that interact with receptors in the brain and body to create various effects
- Herbal cannabis contains over 400 compounds including over 100 cannabinoids,
- cannabinoids include tetrahydrocannabinol (THC), cannabidiol (CBD) and cannabinol (CBN). These structures are shown below in Figure 1 . All cannabinoids derive from cannabigerol-type compounds and differ mainly in the way this precursor is cyclized. The classical cannabinoids are derived from their respective 2-carboxylic acids (2-COOH) by decarboxylation (catalyzed by heat, light, or alkaline conditions).
- THC isolation came from an Israeli chemist by the name of Raphael Mechoulam. In 1964, Mechoulam isolated and synthesized THC from Lebanese hashish, marking the beginning of cannabis research that would lead to the discovery of many other cannabinoids, cannabinoid receptors throughout the body, and "endocannabinoids" - the THC-like compounds the human body naturally produces to maintain stability and health.
- CBD and THC levels tend to vary among different plants. Marijuana grown for recreational purposes often contains more THC than CBD. However, by using selective breeding techniques, cannabis breeders can create varieties with high levels of CBD and next to zero levels of THC.
- THC Humans and many other animals have receptor systems that THC binds to, and therefore can also reap the benefits of cannabinoids for both health and enjoyment.
- the endocannabinoid system (or "ECS"), is a group of specialized signaling chemicals, their receptors, and the metabolic enzymes that produce and break them down. These endocannabinoid chemical signals act on some of the same brain and immune cell receptors (CB1 and CB2) that plant cannabinoids like CBD and THC act on.
- CBD cannabinoids like CBD and THC act on.
- THC works by binding to cannabinoid receptors concentrated in the brain and central nervous system to produce psychoactive effects.
- the main difference between THC and CBD, both of which are very popular cannabinoids, is in their psychoactive effects. THC elicits strong cerebral euphoria, while CBD lacks psychoactive effects altogether. This basically comes down to the fact that THC activates CB1 receptors in the human brain while CBD does not
- CBD canabinoids
- THC canabinoids
- CBD's subtle effects are primarily felt in pain, inflammation, and anxiety relief, as well as other medicinal benefits.
- CBD also does not have any adverse side effects that may occur with consumption of THC.
- CBD also does not cause a high. While this makes CBD a significant advantage as a medicine, since health professionals prefer treatments with minimal side effects.
- CBD also appears to counteract the sleep-inducing effects of THC, which may explain why some strains of cannabis are known to increase alertness.
- CBD also acts to reduce the intoxicating effects of THC, such as memory impairment and paranoia.
- THC has a wide range of short-term effects which may or may not be experienced depending on the individual and their body chemistry.
- Some positive short-term effects of THC include: elation, relaxation, sedation, pain relief, energy, hunger, drowsiness, slowed perception of time and laughter.
- THC Trigger Traumatic Stress Disorder
- neuropathic and chronic pain insomnia
- nausea inflammation, arthritis, migraines, Cancer, Crohn's disease
- fibromyalgia Alzheimer's disease
- Glaucoma Glaucoma
- ADHD Attention deficit hyperactivity disorder
- sleep apnea sleep apnea and appetite loss.
- THC Decarboxylation of the THC occurs with heating and is the key to enjoying THC, whether it is consumed by smoking or ingesting.
- cannabis In its raw form, cannabis is non- psychoactive, with its primary cannabinoid being THCA.
- THCA cannabinoid
- the THCA is converted to THC.
- the invention method provides an advantageous alternative to smoking cannabis by providing a water-soluble cannabinoid composition for oral ingestion that is bioavailable, highly metabolizable and fast acting.
- THC As an aromatic terpenoid, THC has a very low solubility in water, but good solubility in most organic solvents, specifically lipids and alcohols.
- the problem with edible cannabis products is they take a varied amount of time to take effect due to the liver's varied ability to process the THC molecule. Depending on liver function at the time, between 2-6% of the THC is able to be metabolized. This process makes it so the THC is absorbed in the esophagus and soft tissues, making it faster acting and more highly metabolizable.
- U.S. Patent No. 8,906,429 to Kolsky discloses lozenges made with THC, coconut oil, sugar and other ingredients. However, there is no use of emulsifiers, which is the main component that makes the cannabis oil hydrophilic and soluble in water.
- the purpose of the invention is to provide a cannabinoid emulsification to create cannabis oil infused products for medical and recreational use that are bioavailable, fast acting and highly metabolized, with consistent results that take place in a consistent amount of time.
- the purpose of the invention is to provide a method to make cannabis oil water soluble using a combination of emulsifiers and variations in time and temperature of the reaction steps.
- the process results in a cannabinoid emulsification which can be used in a variety of edible products providing fast acting, bioavailability and highly metabolizable delivery of the cannabis oil.
- Another purpose of the invention is to provide a line of cannabis oil and caffeine edible products that share a base of coconut water infused with coconut fat and to sell the products to wholesale distributors for retail sale in legal dispensaries.
- Another purpose of the invention is to provide a line of cannabis oil and caffeine infused sugars and elixirs that share a base of coconut water infused with coconut fat and to sell the products to wholesale distributors for retail sale in legal dispensaries. More specifically a purpose of the invention is to use the water soluble cannabinoid emulsification to treat Post Traumatic Stress Disorder, neuropathic and chronic pain, insomnia, nausea, inflammation, arthritis, migranes, Cancer, Crohn's disease, fibromyalgia, Alzheimer's disease, Multiple sclerosis, Glaucoma, Attention deficit hyperactivity disorder ( "ADHD”), sleep apnea and appetite loss.
- DHD Attention deficit hyperactivity disorder
- Yet another purpose of the invention emulsification is to treat pain, inflammation, and anxiety relief.
- the emulsification can be combined with chocolate and/or liquor to create edible products.
- compositions can be used to produce other edible products at home or professionally with predictable results, including being fast-acting, and highly metabolizable, which are referred to herein as supercharged. This lets consumers know that the invention products have markedly different results than other products.
- These compositions can be marketed in many forms, both in retail and wholesale manufacturing, as well as aiding companies with quality products to use for research and development
- a cannabinoid emulsification made of at least one emulsifying agent; an aqueous vehicle; a base oil; cannabis oil; and caffeine.
- the resulting cannabinoid emulsification is bio-available, highly metabolizable and fast acting when ingested by the user..
- the aqueous vehicle is selected from the group consisting of coconut water, fruit juice, milk and water.
- the aqueous vehicle is in the range of 60% to 99.9% of the emulsification.
- the preferred vehicle is coconut water.
- the base oil is selected from the group consisting of vegetable glycerine, almond oil, avocado oil, canola oil, coconut oil, corn oil, cottonseed oil, grapeseed oil, hazelnut oil, olive oil, extra virgin olive oil, palm oil, peanut oil, palm seed oil, pumpkin seed oil, safflower oil, sesame oil, soy oil, sunflower oil, vegetable oil and walnut oil and any oil high in saturated fats.
- the base oil is preferably in the range of 0.1 % to 40% of the emulsification.
- the cannabis oil is selected from the group consisting of tetrahydrocanniabinol (THC), cannabidiol (CBD) and other cannabinoid oils isolated from the marijuana plant.
- the emulsifying agent is in the range of 0.15% and 2% of the total volume of the emulsification and is selected from the group consisting of xantham gum, guar gum, cyclodextrin, lecithin, carrageen, monoglycerides, natural emulsifiers and organic emulsifiers that are safe for ingestion by humans.
- the emulsifying agent is a combination of at least two emulsifying agents.
- cyclodextrin is used in combination with at least one other emulsifying agent selected from the group consisting of xantham gum, guar gum, lecithin, carrageen, monoglycerides, natural emulsifiers and organic emulsifiers that are safe for ingestion by humans
- the cannabis oil in the emulsification is in the range of 5mg to 30 mg per 2 ounces of the emulsification.
- Caffeine is present in the emulsification in the range of 10 to 300mg per 2 ounces of the emulsification.
- the caffeine can be in anhydrous form.
- the base oil:aqueous vehicle ratio is between 1 to 10 grams of base oil per 2 ounces of the emulsification.
- the invention also provides a method for making cannabinoid emulsifications comprising the steps of heating a base oil, preferably coconut oil, to between 120 to 220 degrees F. Adding at least one emulsifying agent, caffeine and cannabis oil to an aqueous vehicle and adding to the heated coconut oil to create a mixture. Blending the mixture in a high speed machine, while holding the temperature between 120 to 220 degrees F to emulsify the mixture and then adding caffeine to the mixture.
- a base oil preferably coconut oil
- the emulsifying agents are added in an amount between 0.15% and 2% of the total volume of the mixture and are selected from the group consisting of xantham gum, guar gum, cyclodextrin, lecithin, carrageen, monoglycerides, natural emulsifiers and organic emulsifiers that are safe for ingestion by humans.
- the hot mixture is blended at high speed for between 30 seconds and 2 minutes.
- the resulting cannabinoid emulsification is bio-available, highly metabolizable and fast acting when ingested by the user.
- the invention provides a unique emulsified combination of cannabis oil, caffeine, and a base oil and aqueous vehicle, which are respectively, preferably coconut oil, and coconut water.
- coconut oil is one of the best sources of excellent fatty acids.
- Emulsified with coconut water, cannabis oil and caffeine provide a beneficial experience for people experiencing a variety of ailments: insomnia, muscle aches, anxiety, etc, or are in recovery from surgery, or in chemotherapy.
- the emulsification makes the cannabis oil molecules water soluble, by modification from its normal hydrophobic state into a hydrophilic ( "water-loving”), which makes the cannabis oil bioavialable, faster acting, and more highly metabolizable.
- Bioavailability refers to the degree to which food nutrients, in this invention - cannabis oil - are available for absorption and utilization in the body. Bioavailability typically applies to nutrients and drugs which pass through first-pass metabolism, i.e. orally consumed substances. Anything absorbed in the gut first passes through the liver before reaching the rest of the circulation, and both the gut and liver may metabolize it to some extent.
- Metabolizable refers to the process of changing food/substances into a form that can be used by your body. To process and use substances brought into your body by metabolism
- the cannabinoid emulsification of the invention is made of at least one emulsifying agent, an aqueous vehicle; a base oil; cannabis oil; and caffeine.
- Emulsions are produced by dispersing normally unmixable material into another by mixing, colloidal milling or homogenization.
- the surface-active qualities of emulsifiers of the invention make them effective emulsifying agents that reduce mixing time and maintain the stability of the dispersion.
- the emulsifying agent in the invention is present in the range of 0.15% to 2% of the composition.
- At least one emulsifying agent is used in the invention process which is selected from the group consisting of xanthan gum, guar gum, cyclodextrin, lecithin, carrageen, monogiycerides, natural emulsifiers and organic emulsifiers that are safe for ingestion by humans.
- the emulsifying agent is a combination of at least two different emulsifying agents.
- Cannabis oil including THC and CBD
- THC and CBD are not water-soluble, so it needs to be "trapped" in something with dual polarity - that is, a compound that reconciles the fact that water is polar and the cannaboid is not.
- the emulsifiers provide this.
- the THC Once trapped in the compound, the THC has new de facto properties, like the ability to dissolve in water, distribute itself evenly, and stay suspended in the solution. It also displays increased bioavailability: while the same amount of cannabis oil in an edible can take up to two hours to reach the bloodstream, the effects of water soluble cannabis oil dissolved in water can be felt more acutely, in as little as 10 minutes.
- cannaboids are soluble in fat. It is also known that only water soluble substances can pass the intestine membrane. Fat is itself not water soluble because it is like cannaboids, uncharged. Fat absorption into the membrane requires substances with a dipole character to build up vehicles which can connect at the outer surface with water (charged side) and at the inner surface with the fat and the THC (uncharged side).
- Xanthan gum which is also called xanthene, has the chemical formula C 13 H 10 O. Its molecular weight is 182.22 grams/mol.
- Figure 2 shows the chemical structure of xantham gum.
- xanthan gum is a substance made by fermenting bacteria with sugars It is an additive found in both foods and medicines. As a food additive, this substance is utilized either as a thickener or stabilizer. This compound has a variety of uses in medicine, such as in the treatment of diabetes, cholesterol and dry mouth, Specifically, xanthan gum is a polysaccharide secreted by the bacterium Xanthomonas campestris. It's known uses, prior to the invention, is as a food additive and rheology modifier,commonly used as a food thickening agent (in salad dressings, for example) and a stabilizer (in cosmetic products, for example, to prevent ingredients from separating).
- Figure 1 it is composed of pentasaccharide repeat units, comprising glucose, mannose, and glucuronic acid in the molar ratio 2:2: 1. It is produced by the fermentation of glucose, sucrose, or lactose. After a fermentation period, the polysaccharide is precipitated from a growth medium with isopropyl alcohol, dried, and ground into a fine powder. Later, it is added to a liquid medium to form the gum.
- pentasaccharide repeat units comprising glucose, mannose, and glucuronic acid in the molar ratio 2:2: 1. It is produced by the fermentation of glucose, sucrose, or lactose. After a fermentation period, the polysaccharide is precipitated from a growth medium with isopropyl alcohol, dried, and ground into a fine powder. Later, it is added to a liquid medium to form the gum.
- guar gum is a polysaccharide composed of the sugars galactose and mannose.
- Figure 3 show that the backbone is a linear chain of ⁇ 1 ,4-linked mannose residues to which galactose residues are 1 ,6-linked at every second mannose, formin short side-branches.
- guar gum In water, guar gum is nonionic and hydrocolloidal. It is not affected by ionic strength or pH, but will degrade at extreme pH and temperature (e.g. pH 3 at 50 °C). It remains stable in solution over pH range 5-7. Strong acids cause hydrolysis and loss of viscosity, and alkalies in strong concentration also tend to reduce viscosity. It is insoluble in most hydrocarbon solvents. The viscosity attained is dependent on time, temperature, concentration, pH, rate of agitation and practical size of the powdered gum used. The lower the temperature lower the rate at which viscosity increases and the lower the final viscosity. Above 80° the final viscosity is slightly reduced.
- the finer guar powders swells more rapidly than coarse powdered gum.
- Guar gum has almost eight times the water-thickening potency of cornstarch - only a very small quantity is needed for producing sufficient viscosity.
- it can be used in various multiphase formulations: as an emulsifier because it helps to prevent oil droplets from coalescing, and/or as a stabilizer because it helps to prevent solid particles from settling.
- Cyclodextrins are a group of structurally related natural products formed during bacterial digestion of cellulose. These cyclic oligosaccharides consist of (a-1 ,4)- linked a-D-glucopyranose units and contain a somewhat lipophilic central cavity and a hydrophilic outer surface. Due to the chair conformation of the glucopyranose units, the cyclodextrins are shaped like a truncated cone rather than perfect cylinders.
- the hydroxyl functions are orientated to the cone exterior with the primary hydroxyl groups of the sugar residues at the narrow edge of the cone and the secondary hydroxyl groups at the wider edge
- the central cavity is lined by the skeletal carbons and ethereal oxygens of the glucose residues, which gives it a lipophilic character.
- the polarity of the cavity has been estimated to be similar to that of an aqueous ethanolic solution.
- the natural ⁇ -, ⁇ - and ⁇ -cyclodextrin consist of six, seven, and eight glucopyranose units, respectively.
- the natural cyclodextrins, in particular PCD are of limited aqueous solubility meaning that complexes resulting from interaction of lipophiles with these cyclodextrin can be of limited solubility resulting in precipitation of solid cyclodextrin complexes from water and other aqueous systems.
- the aqueous solubility of the natural cyclodextrins is much lower than that of comparable acyclic saccharides. This is thought to be due to relatively strong intermolecular hydrogen bonding in the crystal state.
- Water-soluble cyclodextrin derivatives of commercial interest include the hydroxypropyl derivatives of PCD and yCD, the randomly methylated ⁇ -cyclodextrin (RMpCD), and sulfobutylether ⁇ -cyclodextrin sodium salt (SBEpCD).
- Figure 4 and Table 1 were taken from an article entitled "Cyclodextrins" (A. Magnusdottir, M. Masson and T. Loftsson, J. Incl. Phenom. Macroc. Chem.44, 213- 218, 2002).
- Cyclodextrins create highly concentrated and water-soluble granules. Cyclodextrins are circular structures of sugar molecules that are known to absorb other compounds into their center. They form inclusion complexes with poorly water- soluble compounds. Acting like a molecule magnet, cyclodextrins absorb other molecules and assume their properties. These molecules can absorb up to 60% of their weight in alcohol while remaining in powdered form. It isn't until you mix them with water that they dissolve.
- the emulsifying agent is a combination of at least two different emulsifying agents with at least one being cyclodextrin and the other emulsifying agent selected from the group consisting of xanthan gum, guar gum, lecithin, carrageen, monoglycerides, natural emulsifiers and organic emulsifiers that are safe for ingestion by humans.
- cyclodextrin is very expensive and some versions even cause unwanted side effects when ingested.
- a lesser amount of cyclodextrin is used in combination with other emulsifiers that are less costly to provide the same or better solubility results. This provides an economic solution to using a lesser amount of cyclodextrin with the benefits at lower cost
- Lecithins are used in the invention as emulsifiers. They are surface-active; simultaneous hydrophilic (water-loving) and hydrophobic (water-repelling) properties enable lecithins to make stable blends of materials that otherwise do not mix easily and tend to separate.
- Lecithin is a generic term to designate any group of yellow-brownish fatty substances occurring in animal and plant tissues, which are amphiphilic - they attract both water and fatty substances (and so are both hydrophilic and lipophilic). Lecithins are generally used for smoothing food textures, dissolving powders (emulsifying), homogenizing liquid mixtures, and repelling sticking materials. Lecithins are composed of phosphoric acid with choline, glycerol or other fatty acids usually glycolipids or triglyceride. Glycerophospholipids in lecithin include phosphatidylcholine, phosphatidylethanolamine, phosphatidylinositol, phosphatidylserine, and phosphatidic acid.
- Carrageens are a family of linear sulphated polysaccharides that are extracted from red edible seaweeds. They are widely used in the food industry, for their gelling, thickening, and stabilizing properties. Their main application is in dairy and meat products, due to their strong binding to food proteins. There are three main varieties of carrageenan, which differ in their degree of sulphation. Kappa-carrageenan has one sulphate group per disaccharide, lota-carrageenan has two, and Lambda- carrageenan has three.
- Monoglycerides are a class of glycerides which are composed of a molecule of glycerol linked to a fatty acid via an ester bond.
- glycerol contains both primary and secondary alcohol groups two different types of monoglycerides may be formed; 1 -monoacylglycerols where the fatty acid is attached to a primary alcohol, or a 2- monoacylglycerols where the fatty acid is attached to the secondary alcohol.
- Monoglycerides are primarily used as surfactants, usually in the form of emulsifiers. Together with diglycerides, monoglycerides are commonly added to commercial food products in small quantities which helps to prevent mixtures of oils and water from separating.
- the base oil is preferably in the range of 0.1 % to 40% of the emulsification.
- the base oil is preferably selected from the group consisting of vegetable glycerine, coconut oil and any oil high in saturated fats.
- Nut oils are also used in the invention process.
- the nut oils are selected from the group consisting of almond oil, avocado oil, canola oil, coconut oil, corn oil, cottonseed oil, grapeseed oil, hazelnut oil, olive oil, extra virgin olive oil, palm oil, peanut oil, palm seed oil, pumpkin seed oil, safflower oil, sesame oil, soy oil, sunflower oil, vegetable oil and walnut oil.
- the aqueous vehicle is selected from the group consisting of coconut water, fruit juice, milk and water.
- the aqueous vehicle is in the range of 60% to 99.9% of the emulsification.
- the preferred vehicle is coconut water.
- the base oil:aqueous vehicle ratio is between 1 to 10 grams of base oil per 2 ounces of the emulsification.
- the cannabis oil used in the invention is in a pure state. This is important sine the intended end use of the products of the invention are to be ingested by humans for medical or recreational use, where permitted.
- the cannabis oil used can be extracted from the marijuana plant by C02 extraction, water extraction, butane extraction and extraction methods that leave a zero testing for residuals. Representative structures of the cannabis oil are illustrated in Figure 1 .
- the cannabis oil used in the invention is selected from the group consisting of tetrahydrocanniabinol (THC), cannabidiol (CBD) and other cannabinoid oils isolated from the marijuana plant.
- THC tetrahydrocanniabinol
- CBD cannabidiol
- the cannabis oil in the emulsification is in the range of 5mg to 30 mg per 2 ounces of the emulsification.
- Caffeine is present in the emulsification in the range of 10 to 300mg per 2 ounces of the emulsification.
- the caffeine can be in anhydrous form.
- the method to produce the invention emulsifications include first heating a base oil, preferably, extra virgin organic coconut oil to between 120 to 220 degrees F. Pure extracted cannabis oil is added to the heated mixture. In a high speed blender (or similar machine) an aqueous vehicle, preferably coconut water, is added to the coconut fat (oil) to insure emulsification. While blending the heated mixture, adding at least one emulsifying agent in the amount of 0.15% and 2% of the total volume of finished product, to the heated oil to create a mixture. Percentages's used herein are on a dry weight basis and are based on the total volume of the finished product.
- the blender is run at high speed for between 30 seconds and 2 minutes before adding the anhydrous caffeine in amounts ranging from 10-300 mg.
- the caffeine can be added prior to adding the emulsifying agent or at the same time.
- the resulting cannabinoid emulsification is bio-available, highly metabolizable and fast acting when ingested by the user.
- the resulting emulsification is used to produce a line of THC and caffeine infused emulsifcations.
- the invention process makes the cannabis oil more bioavailable by making the oleo molecule water soluble. Thus, upon ingestion, making it fast acting, taking effect in as little as 15 minutes.
- cannabis oil in the range of 5 to 30 mg and different flavor profiles including lime, pomegranate, orange, lemon and others; and different serving sizes between 1 and 64 oz
- a cannabis infused chocolate is provided that is bioavailable and delivers fast acting effects of the cannabis when ingested.
- the method of making such includes use of 5 to 10 oz of a base oil of either vegetable glycerine or coconut oil.
- a high quality liquor such as cognac or whiskey can be added but is optional.
- the base oil liquid is heated to between 120 to 220°F.
- the cannabis oil extract is added equal to 1 10 to 1 120mg THC.
- the emulsifiers are added next, generally in the following amounts 0.5% lecithin, 0.15% xanthan gum, 0.1 % cyclodextrin.
- the emulsifiers can be used individually or in combination.
- the hot mixture is blended in a high speed blender or other machine, run on high speed for 2 minutes. The mixture is allowed to cool to room temperature.
- solid and liquid (MCT) is coconut oil that has medium chain triglyceride.
- Guar gum, lecithin, and cyclodextrin were tested as emulsifying agents and provided good results.
- xantham gum was the most effective and provided the best emulsification of the oil and water, at the lowest viscosity
- the method used to produce the invention emulsifications, included first heating extra virgin organic coconut oil to between 120 to 220 degrees F. C02 extracted cannabis oil is added.
- C02 extracted cannabis oil is added.
- coconut water is added to the coconut fat (oil) to insure emulsification.
- xantham gum powder is added in an amount between 0.15% and 0.45% of the total volume of finished product, %'s used herein are on a dry weight basis and are based on the total volume of the finished product.
- the blender is run at high speed for between 30 seconds and 2.
- the resulting emulsification is used to produce a variety of cannabis infused products.
- the invention process makes the THC more bioavailable by making the oleo molecule water soluble. Thus, upon ingestion, making it fast acting, taking effect in as little as 15 minutes.
- Cannabis infused products were prepared and tested in a random study group of 40 individuals.
- the products tested included cannabis infused sugar, a cannaboid/caffeine emulsification and a cannabis infused elixir and are summarized in the tables below.
- the products in Table 2 and 4 are the subject of a co-pending patent application by the same inventor entitled “Cannabis Infused Sweeteners and Elixirs.”; and the subject of a co-pending patent application by the same inventor entitled “Method of Making Cannabis Oil Hydrophilic Using Emulsifiers and Related Cannabinoid Compositions” is relevant to making these products, all of which is incorporated herein by reference.
- the cannabinoid and caffeine emulsifications of the invention provide a beneficial experience for people experiencing a variety of ailments: insomnia, muscle aches, anxiety, etc, or are in recovery from surgery, or in chemotherapy.
- the emulsifications makes the cannabis oil molecules hydrophilic, and thus water soluble, which makes the THC, bioavailable, faster acting, and more highly metabolizable.
- the water-soluble cannabis of the invention provides them a convenient, and smokeless, alternative to access the cannabinoids they need to alleviate their ailments.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Inorganic Chemistry (AREA)
- Nutrition Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Botany (AREA)
- Mycology (AREA)
- Microbiology (AREA)
- Medical Informatics (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Alternative & Traditional Medicine (AREA)
- Dispersion Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Physiology (AREA)
- Zoology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Medicinal Preparation (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15/565,136 US20180200315A1 (en) | 2016-04-15 | 2017-04-14 | Cannabinoid and caffeine emulsifications |
| US16/161,027 US10624844B2 (en) | 2016-04-15 | 2018-10-15 | Cannabinoid compositions comprising cannabis oil and methods of making thereof |
| US16/854,800 US20220087972A9 (en) | 2016-04-15 | 2020-04-21 | Cannabinoid Compositions |
| US18/375,846 US12194018B2 (en) | 2016-04-15 | 2023-10-02 | Cannabinoid compositions |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662323154P | 2016-04-15 | 2016-04-15 | |
| US62/323,154 | 2016-04-15 | ||
| US201662328975P | 2016-04-28 | 2016-04-28 | |
| US62/328,975 | 2016-04-28 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US2017/027549 Continuation-In-Part WO2017180953A1 (en) | 2016-04-15 | 2017-04-14 | Cannabis infused sweeteners and elixirs |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US16/161,027 Continuation-In-Part US10624844B2 (en) | 2016-04-15 | 2018-10-15 | Cannabinoid compositions comprising cannabis oil and methods of making thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2017180948A1 true WO2017180948A1 (en) | 2017-10-19 |
Family
ID=60041918
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US2017/027543 Ceased WO2017180948A1 (en) | 2016-04-15 | 2017-04-14 | Cannabinoid and caffeine emulsifications |
| PCT/US2017/027549 Ceased WO2017180953A1 (en) | 2016-04-15 | 2017-04-14 | Cannabis infused sweeteners and elixirs |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US2017/027549 Ceased WO2017180953A1 (en) | 2016-04-15 | 2017-04-14 | Cannabis infused sweeteners and elixirs |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US10617636B2 (enExample) |
| EP (1) | EP3442521A4 (enExample) |
| JP (1) | JP7053054B2 (enExample) |
| CA (1) | CA3021093A1 (enExample) |
| IL (1) | IL262350B2 (enExample) |
| WO (2) | WO2017180948A1 (enExample) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10617636B2 (en) | 2016-04-15 | 2020-04-14 | Sre Wellness, Inc. | Cannabis infused sweeteners and elixirs |
| US10624844B2 (en) | 2016-04-15 | 2020-04-21 | Sre Wellness, Inc. | Cannabinoid compositions comprising cannabis oil and methods of making thereof |
| US20200352191A1 (en) * | 2019-05-06 | 2020-11-12 | Karl Lonsbery | Edible formulations and uses thereof |
| WO2020232557A1 (en) * | 2019-05-23 | 2020-11-26 | Canopy Growth Corporation | Method of making cocoa butter-derived products containing cannabinoids |
| US20210393519A1 (en) * | 2020-06-19 | 2021-12-23 | NuRevelation, LLC | Cannabinoid syrup and methods for making and using same |
| US12194018B2 (en) | 2016-04-15 | 2025-01-14 | Sre Wellness, Inc. | Cannabinoid compositions |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019211771A1 (en) * | 2018-05-03 | 2019-11-07 | Radient Technologies Inc. | Water soluble and water dispersible formulations of cannabinoids |
| EP3820530A4 (en) * | 2018-07-10 | 2022-03-30 | Cardinal Advisory Limited | FORMULATION OF CANNABINOID COMPOUNDS |
| US10383819B1 (en) | 2018-07-23 | 2019-08-20 | Callitas Therapeutics, Inc. | Method to effect biphasic bioavailability of oral euphoric psychogenic cannabinoids |
| US10987391B2 (en) | 2018-08-02 | 2021-04-27 | Slate Podaima | Method of agglomerating cannabis extract with energizing consumables |
| US20210361574A1 (en) * | 2018-10-15 | 2021-11-25 | New Frontier Brewing Company, Llc | Nanoemulsion cannabis formulations and methods of making same |
| WO2020089913A1 (en) * | 2018-11-04 | 2020-05-07 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Cannabinoids-containing beverages |
| EP3894036A2 (en) * | 2018-12-11 | 2021-10-20 | NATURALIA INGREDIENTS S.r.l | Extraction method and composition obtained therefrom |
| CA3040547C (en) | 2019-04-17 | 2021-12-07 | Medcan Pharma A/S | Cannabinoid lozenge formulation |
| US20220323523A1 (en) * | 2019-08-26 | 2022-10-13 | Gianna Marie FILIPETTO | Method and apparatus for the infusion of cannabinoids into a shelf-stable food composition |
| US20210393540A1 (en) * | 2020-06-19 | 2021-12-23 | NuRevelation, LLC | Nanoparticle-encapsulated cannabinoids and methods for making and using same |
| CA3200579A1 (en) * | 2020-11-30 | 2022-06-02 | Mark James DYE | Stable composition comprising a honey and a cannabinoid |
| JP2024051530A (ja) * | 2022-09-30 | 2024-04-11 | 龍 石川 | 液体組成物 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6303662B1 (en) * | 1997-04-18 | 2001-10-16 | Taisho Pharmaceutical Co., Ltd. | Microemulsion |
| US6383513B1 (en) * | 1997-12-19 | 2002-05-07 | West Pharmaceutical Services Drug Delivery & Clinical Research Centre Limited | Compositions comprising cannabinoids |
| US20150105455A1 (en) * | 2013-10-16 | 2015-04-16 | William Bjorncrantz | Winterized crude cannabis extracts and methods of preparation and use |
Family Cites Families (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2301015B (en) | 1996-03-12 | 1997-04-23 | Nestle Sa | Soluble coffee beverage product |
| FI20020333A0 (fi) | 2002-02-20 | 2002-02-20 | Tomi Jaervinen | Metyloidun syklodekstriinin uudet kompleksit |
| FI113340B (fi) | 2002-02-20 | 2004-04-15 | Tomi Jaervinen | Uudet luonnon syklodekstriinin kompleksit |
| UA79281C2 (en) * | 2002-04-03 | 2007-06-11 | Solvay Pharm Bv | Stabilized composition comprising a natural cannabinoid compound and process for the preparation thereof |
| AU2003247496A1 (en) | 2002-06-06 | 2003-12-22 | Matthew Davis | Cardiac glycosides for treating muscle pain and spasm |
| TW200522944A (en) | 2003-12-23 | 2005-07-16 | Lilly Co Eli | CB1 modulator compounds |
| DK1903866T3 (en) | 2005-11-07 | 2016-07-25 | Murty Pharmaceuticals Inc | Improved release of tetrahydrocannabinol |
| US20140357708A1 (en) | 2005-11-07 | 2014-12-04 | Murty Pharmaceuticals, Inc. | Oral dosage form of tetrahydrocannabinol and a method of avoiding and/or suppressing hepatic first pass metabolism via targeted chylomicron/lipoprotein delivery |
| US20160184258A1 (en) | 2005-11-07 | 2016-06-30 | Murty Pharmaceuticals, Inc. | Oral gastrointestinal dosage form delivery system of cannabinoids and/or standardized marijuana extracts |
| CA2741862C (en) * | 2008-10-31 | 2017-10-17 | Mahmoud A. Elsohly | Compositions containing delta-9-thc-amino acid esters and process of preparation |
| WO2011006066A1 (en) | 2009-07-10 | 2011-01-13 | Ironwood Pharmaceuticals, Inc. | Cb receptor agonists |
| US20130178453A1 (en) | 2010-02-09 | 2013-07-11 | Ironwood Pharmaceuticals, Inc. | Cannabinoid Agonists |
| WO2011100324A1 (en) | 2010-02-09 | 2011-08-18 | Ironwood Pharmaceuticals Inc. | Cannabinoid receptor agonists |
| US20120043242A1 (en) | 2010-08-19 | 2012-02-23 | Andrew David Hospodor | Medicinal cannabis fatty foodstuff |
| US8808734B2 (en) | 2011-07-11 | 2014-08-19 | Full Spectrum Laboratories Limited | Cannabinoid formulations |
| WO2014159688A1 (en) | 2013-03-14 | 2014-10-02 | Sc Laboratories, Inc. | Bioactive concentrates and uses thereof |
| US20150057342A1 (en) | 2013-08-21 | 2015-02-26 | Cannabics Pharmaceuticals Inc | Compositions for combined immediate and sustained release of cannabinoids, methods of manufacture and use thereof |
| US20150182455A1 (en) * | 2013-10-21 | 2015-07-02 | HDDC Holdings, LLC | Cannabinoids alcohol mixtures, methods to make and use of the same |
| US8906429B1 (en) * | 2013-12-11 | 2014-12-09 | Jeffrey A. Kolsky | Medical cannabis lozenges and compositions thereof |
| US9259449B2 (en) | 2014-01-07 | 2016-02-16 | Joshua Michael Raderman | Method for modifying THC content in a lipid-based extract of cannabis |
| EP3164141B1 (en) | 2014-06-11 | 2020-11-11 | Poviva Corp. | Food and beverage compositions infused with lipophilic active agents and methods of use thereof |
| WO2016004121A1 (en) | 2014-07-01 | 2016-01-07 | MJAR Holdings, LLC | High cannabidiol cannabis strains |
| US10307397B2 (en) * | 2014-07-28 | 2019-06-04 | Concept Matrix Solutions | Oral dissolvable film that includes plant extract |
| WO2016022936A1 (en) * | 2014-08-07 | 2016-02-11 | Murty Pharmaceuticals, Inc. | An improved oral gastrointestinal dosage form delivery system of cannabinoids and/or standardized marijuana extracts |
| CA2859930A1 (en) | 2014-09-22 | 2016-03-22 | Antony Paul Hornby | A cannabis topical from heat treated cocount oil |
| MX395015B (es) | 2014-12-12 | 2025-03-24 | Ojai Energetics Pbc | Composiciones microencapsuladas de cannabinoides |
| EP3442521A4 (en) | 2016-04-15 | 2020-01-01 | SRE Wellness, Inc. | SWEETENERS AND ELIXIRS INFused WITH CANNABIS |
| US20180200315A1 (en) | 2016-04-15 | 2018-07-19 | Ronald Silver | Cannabinoid and caffeine emulsifications |
| CA3021095A1 (en) | 2016-04-15 | 2017-10-19 | Sre Wellness Inc. | Method of making cannabis oil hydrophiilic using emulsifiers and related cannabinoid compositions |
| US9987567B1 (en) | 2017-09-29 | 2018-06-05 | NextLeaf Solutions Ltd. | Cannabinoid extraction process and system |
| US10406453B2 (en) | 2017-09-29 | 2019-09-10 | NextLeaf Solutions Ltd. | Cannabinoid extraction process using brine |
| US10245525B1 (en) | 2017-11-10 | 2019-04-02 | NextLeaf Solutions Ltd. | Closed-loop multi-stage chilled filter system |
-
2017
- 2017-04-14 EP EP17783190.6A patent/EP3442521A4/en active Pending
- 2017-04-14 JP JP2019505135A patent/JP7053054B2/ja active Active
- 2017-04-14 WO PCT/US2017/027543 patent/WO2017180948A1/en not_active Ceased
- 2017-04-14 US US15/565,138 patent/US10617636B2/en active Active
- 2017-04-14 CA CA3021093A patent/CA3021093A1/en active Pending
- 2017-04-14 WO PCT/US2017/027549 patent/WO2017180953A1/en not_active Ceased
- 2017-04-14 IL IL262350A patent/IL262350B2/en unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6303662B1 (en) * | 1997-04-18 | 2001-10-16 | Taisho Pharmaceutical Co., Ltd. | Microemulsion |
| US6383513B1 (en) * | 1997-12-19 | 2002-05-07 | West Pharmaceutical Services Drug Delivery & Clinical Research Centre Limited | Compositions comprising cannabinoids |
| US20150105455A1 (en) * | 2013-10-16 | 2015-04-16 | William Bjorncrantz | Winterized crude cannabis extracts and methods of preparation and use |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10617636B2 (en) | 2016-04-15 | 2020-04-14 | Sre Wellness, Inc. | Cannabis infused sweeteners and elixirs |
| US10624844B2 (en) | 2016-04-15 | 2020-04-21 | Sre Wellness, Inc. | Cannabinoid compositions comprising cannabis oil and methods of making thereof |
| US12194018B2 (en) | 2016-04-15 | 2025-01-14 | Sre Wellness, Inc. | Cannabinoid compositions |
| US20200352191A1 (en) * | 2019-05-06 | 2020-11-12 | Karl Lonsbery | Edible formulations and uses thereof |
| WO2020232557A1 (en) * | 2019-05-23 | 2020-11-26 | Canopy Growth Corporation | Method of making cocoa butter-derived products containing cannabinoids |
| US20210393519A1 (en) * | 2020-06-19 | 2021-12-23 | NuRevelation, LLC | Cannabinoid syrup and methods for making and using same |
Also Published As
| Publication number | Publication date |
|---|---|
| US20180193392A1 (en) | 2018-07-12 |
| US10617636B2 (en) | 2020-04-14 |
| IL262350B2 (en) | 2025-01-01 |
| WO2017180953A1 (en) | 2017-10-19 |
| EP3442521A4 (en) | 2020-01-01 |
| EP3442521A1 (en) | 2019-02-20 |
| IL262350A (en) | 2018-11-29 |
| JP7053054B2 (ja) | 2022-04-12 |
| JP2019511579A (ja) | 2019-04-25 |
| CA3021093A1 (en) | 2017-10-19 |
| IL262350B1 (en) | 2024-09-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US10624844B2 (en) | Cannabinoid compositions comprising cannabis oil and methods of making thereof | |
| US10617636B2 (en) | Cannabis infused sweeteners and elixirs | |
| JP2019511579A5 (enExample) | ||
| US20180200315A1 (en) | Cannabinoid and caffeine emulsifications | |
| US20200170950A1 (en) | Compositions comprising a cannabinoid or a cannabis-derived compound, methods of making and use | |
| CN101801216B (zh) | 含有植物精油的纳米乳液和纳米颗粒及其制备方法 | |
| EP2986151B1 (en) | Substantially surfactant-free, submicron dispersions and food enhancement therewith | |
| EP3840764A1 (en) | Cannabis-infused product with enhanced cannabinoid profile user experience | |
| JPH03197502A (ja) | テンサイペクチンの製造方法並びにその可食物における利用物と利用方法 | |
| HK1202380A1 (en) | Emulsified food product composition | |
| WO1984002271A1 (en) | Readily-absorpable fatty acid emulsions | |
| US10531674B2 (en) | Compositions having an oil-in-water dispersion of submicron particles to enhance foods and beverages | |
| US12194018B2 (en) | Cannabinoid compositions | |
| JP2013519518A (ja) | 液体を充填したキトサン−アニオン性脂溶性界面活性剤カプセルの分散体 | |
| US20060105021A1 (en) | Cholesterol-reducing liquid | |
| JP2013519499A (ja) | 液体を充填したタンパク質−ホスファチジン酸カプセルの分散体 | |
| RU2734830C1 (ru) | Композиция для производства безалкогольного эмульсионного напитка | |
| JPH0779751A (ja) | 活性飲料の製造法 | |
| JPS59141510A (ja) | 乳化組成物 | |
| US20210401733A1 (en) | Skin crème | |
| JP2025528862A (ja) | カンナビノイドエマルジョンおよび複合体、ならびに関連する製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NENP | Non-entry into the national phase |
Ref country code: DE |
|
| 121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 17783187 Country of ref document: EP Kind code of ref document: A1 |
|
| 122 | Ep: pct application non-entry in european phase |
Ref document number: 17783187 Country of ref document: EP Kind code of ref document: A1 |