5957-75-5

Usage

Uses

Used in Pharmaceutical Industry:
DELTA-8-THC is used as an active constituent in the development of medications for various medical conditions. Its agonist activity at CB1 and CB2 receptors makes it a promising candidate for treating a range of disorders, including chronic pain, anxiety, and nausea.
Used in Antiemetic Applications:
DELTA-8-THC is used as an antiemetic agent to help alleviate nausea and vomiting, particularly in patients undergoing chemotherapy or radiation treatments. Its ability to interact with cannabinoid receptors in the brain helps to reduce the severity and frequency of these symptoms.
Used in Appetite Stimulation:
DELTA-8-THC is used as an appetite stimulant to help increase food intake in patients with conditions that cause a loss of appetite, such as cancer, AIDS, or anorexia. By stimulating the CB1 receptors in the brain, it can help improve overall nutrition and quality of life for these individuals.
Used in Research and Development:
DELTA-8-THC is used as a research compound for studying the effects of cannabinoids on the human body. Its unique properties and interactions with cannabinoid receptors make it an important tool in understanding the potential therapeutic applications of cannabis and its derivatives.
Used in Controlled Substances:
DELTA-8-THC is classified as a controlled substance due to its hallucinogenic properties. Its use is regulated and restricted in many countries, with specific guidelines and laws governing its production, distribution, and consumption. This classification helps to ensure the safe and responsible use of DELTA-8-THC in medical and research settings.

InChI:InChI=1/C21H30O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h9,12-13,16-17,22H,5-8,10-11H2,1-4H3/t16-,17-/m1/s1

Upstream product

• 88510-95-6 (6aR,9S,10aR)-9α-bromo-6a,10a-trans-hexahydrocannabinol 
• 20053-58-1 (1S,2S,3R,6R)-(+)-trans-car-2-ene epoxide 
• 500-66-3 Olivetol 
• 781642-49-7 5-pentyl-1,3-benzenediol/β-cyclodextrin complex 
• 119678-39-6 (3S,4R)-1-p-menthene-3,8-diyl carbonate 
• 13956-29-1 CBD 
• 13956-30-4 (-)-5'-methyl-4-pentyl-2'-(prop-1-en-2-yl)-1',2',3',4'-tetrahydro-[1,1'-biphenyl]-2,6-diol 
• 23978-85-0 tetrahydrocannabinolic acid 
• 936-91-4 3-carene epoxide 
• 1686-20-0 p‐mentha‐1,5‐dien‐8‐ol 

Downstream Products

• 132213-91-3 (-)-1-O-(biphenylylmethyl)-Δ⁸-tetrahydrocannabinol 
• 1451-20-3 (-)-O-methyl-Δ⁸-tetrahydrocannabinol 
• 876625-59-1 3'-hydroxy-Δ8-tetrahydrocannabinol 
• 37936-81-5 7beta-Hydroxy-D₈-tetrahydrocannabinol 
• 28646-40-4 11-hydroxy-Δ8-tetrahydrocannabinol 
• 33886-04-3 1'-hydroxy-Δ8-tetrahydrocannabinol 
• 27179-28-8 (+/-)-delta7-Tetrahydrocannabinol 
• 27179-29-9 (-)-1-O-methyl-Δ^9,11-tetrahydrocannabinol 
• 132213-87-7 (-)-1-O-(4-aminobutyl)-Δ⁸-tetrahydrocannabinol 
• 132213-93-5 (-)-1-O-(biphenylylmethyl)-Δ^9,11-tetrahydrocannabinol 
• 1972-08-3 dronabinol 

Relevant academic research and scientific papers

MASS PRODUCTION AND APPLICATION OF DELTA 8 THC

A process of converting cannabidiol (CBD) to Δ8-tetrahydrocannabinol (Δ8-THC) or Δ9-tetrahydrocannabinol (Δ9-THC) can enable mass production of Δ8-THC and/or Δ9-THC, achieve greater yields and higher purity in comparison to previously reported processes while eliminating the use of organic solvent. The resultant hemp-derived Δ8-THC can be mixed with and absorbed by natural extracts, including tea extract, starch, sugar, lecithin, and other emulsifiers. Δ8-THC used in edible, topical and vaping products such as powdered Δ8-THC food ingredients, tablets or pills, suppositories, and vape formulations are disclosed. Further described are beverages and baked goods utilizing or incorporating the tablets or powdered Δ8-THC to create edible products containing an emulsified, tasteless, and odorless dose of Δ8-THC. The disclosure also describes a rectal suppository designed to provide improved comfort of use. A Δ8-THC liquid composition can be use in an electronic cigarette smoking device for pulmonary administration of Δ8-THC, which results in more effective absorption.

METHODS FOR CONVERTING CBD TO TETRAHYDROCANNABINOLS

This disclosure provides a method for converting CBD to a tetrahydrocannabinol featuring the use of cheap and non-toxic aluminum isopropoxide as a catalyst. The method comprises (a) providing a reaction mixture comprising a catalyst in an organic solvent, wherein the catalyst comprises aluminum isopropoxide; (b) adding a reagent comprising CBD to the reaction mixture; (c) mixing the reaction mixture and allowing a reaction for converting CBD to a tetrahydrocannabinol to occur for a predetermine period of time; (d) removing the catalyst by filtration upon the completion of the reaction; (e) removing the organic solvent; and (f) eluting the tetrahydrocannabinol from the organic phase.

METHODS FOR PREPARING CANNABINOIDS AND RELATED INSTRUMENTS

Methods and instrumentation for converting cannabidiol (CBD) and CBD-like compounds to other naturally-occurring or synthetic cannabinoids, such as THC, CBN and/or CBC, which processes may be solvent-free, Generally, the conversion of CBD is carried out in the presence of a Lewis acid, an oxidant or both, which may be present in catalytic amounts. A reaction may be a two-phase reaction with the Lewis acid present on a support material in a column or similar chamber through which CBD passes and is converted to the cannabinoids. The reactions allow direction of relative yields of certain cannabinoid products by altering the identity of the acid reagent.

Conversion of cannabidiol or delta-9 tetrahydrocannabinolic acid to delta-9 tetrahydrocannabinol and delta-8 tetrahydrocannabinol in nontoxic heterogeneous mixtures

A solvent-free method for converting CBD or delta-9 THC-A to delta-9 THC and delta-8 THC includes adding CBD to a reaction vessel, streaming an inert gas through the reaction vessel, heating the CBD while stirring to melt the CBD, stirring the melting CBD, adding concentrated hydrochloric acid as a catalyst to the melting CBD while stirring, increasing the temperature over time to a temperature not to exceed the boiling point of reactants and products in the reaction vessel, holding the reaction vessel at a temperature less than the boiling point temperature for the reactants and products in the reaction vessel for an amount of time to allow the complete conversion of the CBD, and bubbling an inert gas into the reaction products to remove free ions of hydrogen and chloride. The CBD can be replaced in whole or in part by delta-9 THC-A as the reactant.

NOVEL METHODS AND RELATED TOOLS FOR CBD CONVERSION TO THC

The present invention is directed to methods of producing THC from CBD utilizing non-harsh methodology and resulting in substantially increased yields, as well as devices built upon these novel methods. The methods and devices are material efficient, and in certain embodiments, solvent-free. In particular, in certain embodiments, these methods and related devices are suitable for commercial production of THC from CBD. Furthermore, in certain embodiments, the present invention provides methods of producing THC from CBD in manner that affords tunability to select the ratio of THC -8 to THC-9.

IMPROVED METHODS FOR CONVERTING CANNABIDIOL INTO DELTA9-TETRAHYDROCANNABINOL UNDER NEAT OR APROTIC REACTION CONDITIONS

Disclosed herein is a method for converting cannabidiol (CBD) into a composition comprising Δ9-tetrahydrocannabinol ( Δ9-THC) and Δ8-tetrahydrocannabinol ( Δ8-THC) in which the composition has a Δ9-ΤΗΟ: Δ8-ΤΗΟ ratio of greater than 1.0:1.0. The method comprises contacting the CBD with a Lewis-acidic heterogeneous reagent under reaction conditions comprising: (i) an aprotic-solvent system; (ii) a reaction temperature that is less than a threshold reaction temperature for the Lewis-acidic heterogeneous reagent and the aprotic-solvent system; and (ill) a reaction time that is less than a threshold reaction time for the Lewis-acidic heterogeneous reagent, the aprotic-solvent system, and the reaction temperature. Methods for converting CBD into a composition comprising Δ9-THC and Δ8-THC in which the composition has a Δ9-THC: Δ8-THC ratio of greater than 1.0:1.0 under neat reaction conditions are also provided.

IMPROVED METHODS FOR CANNABINOID ISOMERIZATION

Disclosed herein is a method for converting a first cannabinoid into a composition comprising a second cannabinoid and a third cannabinoid, in which the second cannabinoid and the third cannabinoid are each isomers of the first cannabinoid. The composition has a second cannabinoid:third cannabinoid ratio of greater than 1.0:1.0. The method comprises contacting the first cannabinoid with a Lewis-acidic heterogeneous reagent under reaction conditions comprising: (i) a protic-solvent environment, an aprotic-solvent environment, or a solvent-free environment; (ii) a reaction temperature that is within a target reaction-temperature range for the Lewis- acidic heterogeneous reagent and the solvent/solvent free environment; and (iii) a reaction time that is within a target reaction-time range for the Lewis-acidic heterogeneous reagent, the solvent/solvent-free environment, and the reaction temperature.

IMPROVED METHODS FOR CONVERTING CANNABIDIOL INTO DELTA9-TETRAHYDROCANNABINOL UNDER PROTIC REACTION CONDITIONS

Disclosed herein is a method for converting cannabidiol (CBD) into a composition comprising Δ9-tetrahydrocannabinol (Δ9-THC) and Δ8-tetrahydrocannabinol (Δ8-THC) in which the composition has a Δ9-ΤΗC:Δ8-ΤΗC ratio of greater than 1.0:1.0. The method comprises contacting the CBD with a Lewis-acidic heterogeneous reagent under reaction conditions comprising: (i) a protic-solvent system; (ii) a reaction temperature that is less than a threshold reaction temperature for the Lewis-acidic heterogeneous reagent and the protic-solvent system; and (ill) a reaction time that is less than a threshold reaction time for the Lewis-acidic heterogeneous reagent, the protic-solvent system, and the reaction temperature.

IMPROVED METHODS FOR CONVERTING CANNABIDIOL INTO DELTA 8-TETRAHYDROCANNABINOL

Disclosed herein a method for converting (cannabidiol) CBD into a composition comprising Δ8-tetrahydrocannabinol (A8-THC) and Δ9-tetrahydrocannabinol (Δ9-THC), in which the composition has a Δ8-THC:Δ9-THC ratio that is greater than 1.0:1.0. The method comprises contacting the CBD with a Lewis-acidic heterogeneous reagent under protic, aprotic, or neat reaction conditions comprising: (i) a reaction temperature that is greater than a threshold reaction temperature for the Lewis-acidic heterogeneous reagent and the solvent system; and (ii) a reaction time that is greater than a threshold reaction time for the Lewis-acidic heterogeneous reagent, the solvent system, and the reaction temperature.

Cannabidiol as the Substrate in Acid-Catalyzed Intramolecular Cyclization

The chemical reactivity of cannabidiol is based on its ability to undergo intramolecular cyclization driven by the addition of a phenolic group to one of its two double bonds. The main products of this cyclization are Δ9-THC (trans-Δ-9-tetrahydrocannabinol) and Δ8-THC (trans-Δ-8-tetrahydrocannabinol). These two cannabinoids are isomers, and the first one is a frequently investigated psychoactive compound and pharmaceutical agent. The isomers Δ8-iso-THC (trans-Δ-8-iso-tetrahydrocannabinol) and Δ4(8)-iso-THC (trans-Δ-4,8-iso-tetrahydrocannabinol) have been identified as additional products of intramolecular cyclization. The use of Lewis and protic acids in different solvents has been studied to investigate the possible modulation of the reactivity of CBD (cannabidiol). The complete NMR spectroscopic characterizations of the four isomers are reported. High-performance liquid chromatography analysis and 1H NMR spectra of the reaction mixture were used to assess the percentage ratio of the compounds formed.