6469-58-5

Usage

Classification

Synthetic cannabinoid

Receptor Interaction

Potent agonist of the CB1 receptor

Structural Relation

Related to the natural cannabinoid THC (found in marijuana)

Potency

Significantly more potent than THC

Potential Medical Uses

Treatment for pain, inflammation, and neurodegenerative diseases

Research Use

Understanding how cannabinoids interact with the endocannabinoid system in the body

Legal Status

Schedule I controlled substance in the United States due to its potential for abuse and lack of accepted medical use.

Upstream product

• 122700-13-4 1-Methoxy-3-pentyl-6,6a,7,8-tetrahydro-6,6-dimethyl-9H-dibenzopyran-9-one 
• 122722-23-0 4-(2,6-Bis(methoxymethoxy)-4-pentylphenyl)-6,6-dimethylbicyclo<3.1.1>hept-3-en-2-one 
• 94450-80-3 1,3-Bis(methoxymethoxy)-5-pentylbenzene 
• 500-66-3 Olivetol 
• 80393-04-0 1-oxymethylenemethoxy-3-methoxy-5-pentylbenzene 
• 41408-15-5 olivetol monomethyl ether 
• 122700-18-9 1-(2,6-Dimethoxy-4-pentyl-phenyl)-6-(1-methoxy-1-methyl-ethyl)-cyclohex-2-enol 
• 67895-00-5 (2,6-dimethoxy-4-pentylphenyl)lithium 
• 122700-14-5 4-(2-Methoxy-4-pentyl-6-(methoxymethoxy)phenyl)-6,6-dimethylbicyclo<3.1.1>hept-3-en-2-one 
• 122700-20-3 4-(2-Methoxy-4-pentyl-6-(methoxymethoxy)phenyl)-6,6-dimethylbicyclo<3.1.1>hept-3-en-2-one 
• 122700-11-2 6-(1-Methoxy-1-methylethyl)-2-cyclohexen-1-one 
• 122700-12-3 3-(2,6-Dimethoxy-4-pentyl-phenyl)-4-(1-methoxy-1-methyl-ethyl)-cyclohex-2-enone 

Downstream Products

• 95543-73-0 (+/-)-7-nor-oxo-Δ²-tetrahydrocannabinol tosylhydrazone 
• 104874-50-2 (+/-)-11-Nor-9-carboxy-Δ⁹-tetrahydrocannabinol 

Relevant academic research and scientific papers

Immunoassay for tetrahydrocannabinol metabolites

Novel cannabinol derivatives are provided which can be used in improved immunoassays for the detection in blood or urine samples of cannabinol metabolites.

Synthesis of (+/-)-11-Nor-9-carboxy-Δ9-tetrahydrocannabinol: New Synthetic Approaches to Cannabinoids

A completely regioselective synthesis of (+/-)-11-nor-9-carboxy-Δ9-tetrahydrocannabinol (1), a principal human metabolite of Δ9-tetrahydrocannabinol (2), has been carried out in seven steps and 14percent overall yield from apoverbene (9) and the bis-MOM ether of olivetol.Condensation of 9 with the aryllithium derived from the bis-MOM ether of olivetol gives an unstable tertiary allylic alcohol that undergoes oxidative rearrangement to give enone 42.Reaction of 42 with acid results in hydrolysis of the MOM ethers and cyclization to benzopyranone 21.Conversion to MOM ether 39 followed by Li/NH3 reduction and trapping of the enolate with N-phenyltriflimide gives vinyl triflate 40 plus the isomer with a cis ring fusion.Palladium-catalyzed carboxylation, hydrolysis of the MOM ether, and separation from cis acid 41 gives pure 1.Model experiments employing unsubstituted resorcinol derivatives that lead to ester 27 are described, as are a number of alternative approaches to acid 1.