64280-14-4

Usage

InChI:InChI=1/C21H28O4/c1-4-5-6-7-13-10-17(22)19-15-12-14(20(23)24)8-9-16(15)21(2,3)25-18(19)11-13/h10-12,15-16,22H,4-9H2,1-3H3,(H,23,24)

Upstream product

• 124-38-9 carbon dioxide 
• 949595-94-2 C₃₅H₅₂N₂O₄S 
• 123408-92-4 (6aR,10aR)-9-[1,3]Dithian-2-yl-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol 
• 138285-36-6 (-)-11-oxo-Δ⁹-tetrahydrocannabinol tert-butyldimethylsilyl ether 
• 52663-85-1 (6aR,10aR)-1-Hydroxy-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromene-9-carbaldehyde 
• 124588-22-3 [(6aR,10aR)-1-(tert-Butyl-dimethyl-silanyloxy)-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-9-yl]-methanol 
• 6616-69-9 dl-6aα,7,10,10aα-Tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-9(8H)-on 
• 52195-11-6 (-)-9-Nor-9-oxohexahydrocannabinol 
• 138285-38-8 (-)-11-nor-9-carboxy-Δ⁹-tetrahydrocannabinol tert-butyldimethylsilyl ether 
• 1972-08-3 dronabinol 

Downstream Products

• 848242-78-4 C₂₅H₃₁NO₆ 

Relevant academic research and scientific papers

A concise methodology for the synthesis of (-)-Δ9-tetrahydrocannabinol and (-)-Δ9-tetrahydrocannabivarin metabolites and their regiospecifically deuterated analogs

The availability of tetrahydrocannabinols (Δ9-THC), tetrahydrocannabivarins (Δ9-THCV), and their metabolites in both their undeuterated and deuterated forms is critical for the analysis of biological and toxicological samples. We report here a concise methodology for the syntheses of (-)-Δ9-THC and (-)-Δ9-THCV metabolites in significantly improved overall yields using commercially available starting materials. Our approach allowed us to obtain the key intermediates (6aR,10aR)-9-nor-9-oxo-hexahydrocannabinols in four steps from (+)-(1R)-nopinone. This was followed by an optimized Shapiro reaction to give the (-)-11-nor-9-carboxy-metabolites, which were converted to their respective (-)-11-hydroxy analogs. The synthetic sequence involves a minimum number of steps, avoids undesirable oxidative conditions, and incorporates the costly deuterated resorcinols near the end of the synthetic sequence. This methodology enabled us to synthesize eight regiospecifically deuterated (-)-Δ9-THC and (-)-Δ9-THCV metabolites in a preparative scale and high optical purity without deuterium scrambling or loss.

TETRAHYDROCANNABINOID ANTIGENS AND METHOD OF USE

The present invention is directed to Δ8-THC and Δ9-THC compounds useful for the covalent attachment to immunogenic molecules to form antigens for the preparation of specific binding molecules to Δ9-Tetrahydrocannabinol, Δ9-Tetrahydrocannabinoids, Δ8-Tetrahydrocannabinol, and Δ8-Tetrahydrocannabinoids, and their derivatives and metabolites. The present invention is directed to the compounds, their method of preparation, cell lines producing the specific binding molecules, methods of using the antigens to produce the specific binding molecules, and test devices containing the antigens, haptens, or specific binding molecules of the invention.

Studies on the synthesis of (-)-11-nor-9-carboxy-Δ9-tetrahydrocannabinol (THC) and related compounds: An improved oxidative procedure

A facile procedure is described whereby Δ9-THC aldehydes 4, as their tert-butyldimethylsilyl derivatives, are conveniently oxidized to the corresponding acids with sodium chlorite in the presence of a large excess of 2-methyl-2-butene without isomerization of the Δ9-double bond. Deprotection of the O-protecting group with tetrabutylammonium fluoride in tetrahydrofuran gave the acids 2 in an overall yield of ≥80%. A study of other oxidizing agents and protecting groups demonstrated that this is the procedure of choice for the preparation of 9-carboxy-Δ9-tetrahydrocannabinols.

Glucuronic acid conjugate of Δ1-tetrahydrocannabinol identified in the urine of man

A Δ1-tetrahydrocannabinol (Δ1-THC) metabolite has been identified as an O-glucuronide of Δ1-THC in the human urine after oral administration of Δ1-THC. The metabolite was present in small amounts and its identify was confirmed by comparison of its mass spectrum to that of a reference compound.