JWH-138

JWH-138 (THC-Octyl, Δ⁸-THC-C8) is a synthetic cannabinoid first synthesized by Roger Adams and studied heavily by John W. Huffman, with a K_i of 8.5nM at the CB₁ cannabinoid receptor.^[1] THC-Octyl and its hydrogenated analog HHC-Octyl was synthesized and studied by Roger Adams as early as 1942.^[2]

JWH-138

Identifiers
IUPAC name (6aR,10aR)-6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-octyl-6H-Dibenzo[b,d]pyran-1-ol
CAS Number	431041-39-3
PubChem CID	102024084
Chemical and physical data
Formula	C24H36O2
Molar mass	356.550 g·mol−1
3D model (JSmol)	Interactive image
SMILES OC1=C2[C@]3([C@](C(C)(C)OC2=CC(CCCCCCCC)=C1)(CCC(C)=C3)[H])[H]
InChI InChI=InChI=1S/C24H36O2/c1-5-6-7-8-9-10-11-18-15-21(25)23-19-14-17(2)12-13-20(19)24(3,4)26-22(23)16-18/h14-16,19-20,25H,5-13H2,1-4H3/t19-,20-/m1/s1 Key:SFWRRSGOJSILSQ-WOJBJXKFSA-N

Isomers

Δ³-THC-C8

Δ⁹-THC-C8 (tetrahydrocannabioctyl), CAS# 2552798-63-5

The Δ³/Δ^6a(10a) isomer was synthesised in 1941, but was found to be slightly less active than Δ³-THC itself.^[3] The alternate isomer Δ⁹-THC-C8 has also been synthesised,^[4] and both the Δ⁸ and Δ⁹ isomers are included within the definition of an "intoxicating cannabinoid" in Colorado under the name tetrahydrocannabioctyl,^[5] but it is unclear if it has been identified as a natural product. Tetrahydrocannabioctyl is sometimes referred to as THC-Octyl or THC-O, which may cause confusion with THC-O-acetate which is commonly known as THC-O on packaging for grey market vaping liquids sold for use in humans.

See also

• 1,2-Didehydro-3-oxo-THCO
• Cannabicyclohexanol
• Parahexyl
• Tetrahydrocannabihexol
• THCP

References

1. Martin BR, Jefferson R, Winckler R, Wiley JL, Huffman JW, Crocker PJ, et al. (September 1999). "Manipulation of the tetrahydrocannabinol side chain delineates agonists, partial agonists, and antagonists". The Journal of Pharmacology and Experimental Therapeutics. 290 (3): 1065–1079. PMID 10454479.
2. Adams R, Loewe S, Smith CM, McPhee WD (1942). "Tetrahydrocannabinol Homologs and Analogs with Marihuana Activity. XIII¹". Journal of the American Chemical Society. 64 (3): 694–697. doi:10.1021/ja01255a061.
3. Adams R, Loewe S, Jelinek C, Wolff H (July 1941). "Tetrahydrocannabinol Homologs with Marihuana Activity. IX". Journal of the American Chemical Society. 63 (7): 1971–1973. doi:10.1021/ja01852a052.
4. WO application 2020232545, Abdur-Rashid K, Jia W, Abdur-Rashid K, "Catalytic cannabinoid processes and precursors", published 2020-11-26, assigned to Kare Chemical Technologies Inc..
5. "Senate Bill 23-271" (PDF). General Assembly. State of Colorado.