34675-49-5

Usage

Uses

Used in Drug Testing:
(+/-)-11-HYDROXY-DELTA9-THC is used as a biomarker for [detecting recent cannabis use] in drug tests. Its presence in the body indicates that the individual has consumed cannabis, as it is a metabolite of THC and remains in the system for a longer duration than THC itself.
Used in Pharmaceutical Research:
(+/-)-11-HYDROXY-DELTA9-THC is used as a research compound for [studying the effects and potential therapeutic applications of cannabinoids]. Its psychoactive properties and potency make it a valuable subject for investigating the mechanisms of action and potential benefits of cannabis-based treatments.
Used in Toxicology Studies:
(+/-)-11-HYDROXY-DELTA9-THC is used as a toxicological indicator for [assessing the impact of cannabis consumption on health and safety]. Understanding the effects of this potent metabolite can help in determining the risks associated with cannabis use and guiding regulations and public health policies.

Upstream product

• 500-66-3 Olivetol 
• 67119-86-2 (4R)-1-(1,3-dithianyl)-4-(2-(2-hydroxypropanyl))-2-cyclohexen-1-ol 
• 61597-37-3 4-(1-hydroxy-1-methylethyl)-1-methoxy-1,4-cyclohexadiene 
• 6616-69-9 11-nor-9-keto-6a,10a-cis-HHC 
• 6616-69-9 dl-6aα,7,10,10aα-Tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-9(8H)-on 
• 83889-49-0 9-β-bromo-11-oxo-6a,10a-trans-HHC 
• 72390-08-0 Acetic acid (6aR,10aR)-6,6-dimethyl-9-methylsulfanylmethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-yl ester 
• 72377-99-2 trans-11-(methylthio)-Δ⁹-tetrahydrocannabinol 
• 72378-05-3 C₂₅H₃₇O₃S⁽¹⁺⁾*BF₄^(1-) 
• 72377-96-9 6-methyl-1-methylthiohept-5-en-2-one 
• 72377-98-1 6-methyl-1-methylthiohept-5-en-2-one 
• 74596-83-1 6-methylhept-5-en-2-one N,N-dimethylhydrazone 
• 80113-04-8 (+/-)-1-(1,3-dithianyl)-4-(1-hydroxy-1-methylethyl)cyclohex-2-enol 
• 104841-04-5 2-(2-Methoxy-4-trimethylsilanyloxy-cyclohex-3-enyl)-propan-2-ol 

Relevant academic research and scientific papers

A terpenic synthon for Δ1-cannabinoids

The reversal of the reactivity (i.e., umpolung) of carbonyl compounds when masked as dithioacetals has been shown to be of use for the elaboration of organic molecules. We have applied this principle to the synthesis of metabolites of Δ1--tetrahydrocannabinol (THC, 1) by preparing the novel cis- and trans-terpenes 7 and 8, which contain the dithiane masking group, and condensing them with olivetol under acid catalysis.

Synthesis of Racemic and Optically Active Δ9-Tetrahydrocannabinol (THC) Metabolites

The preparation of racemic and optically active Δ9-THC metabolites is described from synthon 13.Racemic synthon 13 is prepared in four steps (46percent) from Danishefsky's diene.Optically active synthon 13 is prepared from perillaldehyde via the enone 22 in six steps (23percent yield).Alternatively, nopinone can be converted to 13 in three steps (50percent yield) via a cyclobutane ring cleavage.The acid-catalyzed condensation of 13 with olivetol (6a) and subsequent conversion to 11-hydroxy and 9-carboxyl Δ9-THC metabolites 2a and 4a is described, as well as the preparation of 1',1'-dimethylheptyl THC analogues 2b, 3b, and 4 b from 5-(1',1'-dimethylheptyl)resorcinol (6c).

The synthesis of some 11-substituted tetrahydrocannabinol metabolites

9-Bromo-11-oxo-hexahydrocannabinol (5) was prepared from the ketocannabinoid 3b via the epoxysulfone 4.The dehydrobromination of the bromoaldehyde 5 could be controlled to give either the thermodinamically more stable Δ8-aldehyde 2c, or the Δ9-aldehyde 1c by an intramolecularly assisted elimination.Reduction of the unsaturated aldehydes gave the allylic alcohol metabolites 2a and 1a, respectively.

Synthesis of (±)-11-hydroxy-Δ9-6a,10a-trans-tetrahydrocannabinol and other 11-substituted Δ9-tetrahydrocannabinoids

11-Substituted Δ9-tetrahydorcannabinoids, including the racemate of the biologically important 11-hydroxy-Δ9-6a,10a-trans-tetrahydrocannabinol and the corresponding 11-mercapto analogue, are synthesized via condensation of olivetol with the terpenoid synthon 3 prepared from 6-methylhept-5-en-2-one.