59652-70-9

Basic information

• Product Name: 3',11-dihydroxy-delta(9)-tetrahydrocannabinol
• Synonyms: 3',11-dihydroxy-delta(9)-tetrahydrocannabinol
• CAS NO: 59652-70-9
• Molecular Formula: C₂₁H₃₀O₄
• Molecular Weight: 346.4605
• Mol File: 59652-70-9.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 482.5°C at 760 mmHg
• Flash Point: 245.6°C
• Appearance: /
• Density: 1.131g/cm³
• Vapor Pressure: 4.03E-10mmHg at 25°C
• Refractive Index: 1.556
• CAS DataBase Reference: 3',11-dihydroxy-delta(9)-tetrahydrocannabinol(CAS DataBase Reference)
• NIST Chemistry Reference: 3',11-dihydroxy-delta(9)-tetrahydrocannabinol(59652-70-9)
• EPA Substance Registry System: 3',11-dihydroxy-delta(9)-tetrahydrocannabinol(59652-70-9)

Safety Data

• Hazardous Substances Data: 59652-70-9(Hazardous Substances Data)

Usage

General Description

3',11-dihydroxy-delta(9)-tetrahydrocannabinol is a chemical compound found in the marijuana plant and is one of the active compounds responsible for its psychoactive effects. It is a derivative of delta-9-tetrahydrocannabinol (THC), the main psychoactive component of cannabis. 3',11-dihydroxy-delta(9)-tetrahydrocannabinol has been shown to have a high affinity for the cannabinoid receptors in the brain, leading to its potent psychoactive effects. The compound is also known to have anti-inflammatory and analgesic properties, making it a subject of interest in medicinal research for its potential therapeutic applications in the treatment of pain and inflammation. However, its psychoactive properties also make it a controlled substance in many jurisdictions.

InChI:InChI=1/C21H30O4/c1-4-15(23)7-5-13-10-18(24)20-16-9-14(12-22)6-8-17(16)21(2,3)25-19(20)11-13/h9-11,15-17,22-24H,4-8,12H2,1-3H3

Upstream product

• 83333-23-7 (+/-)-3'-acetoxy-11-oxo-Δ⁹-tetrahydrocannabinol trimethylene dithiacetal 1-acetate 
• 80113-04-8 (+/-)-1-(1,3-dithianyl)-4-(1-hydroxy-1-methylethyl)cyclohex-2-enol 
• 83333-22-6 Acetic acid (6aR,10aR)-3-(3-acetoxy-pentyl)-9-formyl-6,6-dimethyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-yl ester 

Relevant articles and documents

3'-Hydroxy- and (±)-3',11-dihydroxy-Δ9-tetrahydrocannabinol: Biologically active metabolites of Δ9-tetrahydrocannabinol

Synthesis of 3'-Hydroxy- (7) and (±)-3',11-dihydroxy-Δ9-tetrahydrocannabinol (11), metabolites of Δ9-THC, is described. Condensation of the monoterpene (±)-cis-p-menth-2-ene-1,8-diol (1) and (±)-3'-acetoxyolivetol (2) in the presence of fused ZnCl2 in CH2Cl2 gave a mixture from which the Δ9-THC derivative 3, containing small amounts of the Δ8 isomer 4, was isolated after column chromatography. This mixture was separated as their diacetates 5 and 6 by high-pressure liquid chromatography. Alkaline hydrolysis (5% KOH in MeOH) of 5 furnished the metabolite 7. Condensation of (±)-8 with 2 in the presence of p-toluenesulfonic acid gave 9a, which was acetylated to 9b. Treatment with HgO/BF3.Et2O in wet THF gave the aldehyde 10. Reduction with LiAlH4 furnished the metabolite 11. These metabolites were compared with Δ9-THC for their ability to depress spontaneous activity and rectal temperature in mice and for their effects on overt behavior in dogs. 3'-Hydroxy-Δ9-THC was also compared to Δ9-THC in the mouse sympatomatology test and cardiovascular system in dogs. The metabolites produced pharmacological effects similar to those of Δ9-THC in all tests. 3'-Hydroxy-Δ9-THC was 2-3 times more effective than Δ9-THC in the behavioral tests, whereas (±)-3',11-dihydroxy-Δ9-THC was approximately 3 times less active than Δ9-THC.