JWH-133

Chemistry

Also known as

• 259869-55-1
• JWH 133
• JWH133
• JW 133
• (6AR,10AR)-3-(1,1-DIMETHYLBUTYL)-6A,7,10,10A-TETRAHYDRO-6,6,9-TRIMETHYL-6H-DIBENZO[B,D]PYRAN
• 1,1-dimethylbutyl-1-deoxy-Delta(9)-THC
• TDG8048RDA
• (6aR,10aR)-6,6,9-trimethyl-3-(2-methylpentan-2-yl)-6a,7,10,10a-tetrahydrobenzo[c]chromene

Stereoisomers

2 distinct stereoisomers are registered for this structure.

• Jwh 133 this area CID 6918505
• (6aS,10aS)-6,6,9-trimethyl-3-(2-methylpentan-2-yl)-6a,7,10,10a-tetrahydrobenzo[c]chromene CID 124309017
• 3-(1,1-Dimethylbutyl)-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-6h-dibenzo[b,d]pyran mixture CID 4373102

Attribution

• JW

  John W. Huffman — first synthesis, 1999

  3-(1',1'-Dimethylbutyl)-1-deoxy-Δ8-THC, from Huffman, Liddle, Yu, Aung, Abood, Wiley and Martin (Bioorg. Med. Chem. 7:2905–2914, 1999) — the paper is titled after this exact structure. Ki 3.4 nM at CB2 against 677 nM at CB1, roughly 200-fold CB2 selectivity. Widely used in laboratories as a CB2-selective probe and, unlike the naphthoylindoles, essentially absent from the recreational market.

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