THC Science

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;

JWH-138 (THC-Octyl, Δ⁸-THC-C8) is a synthetic cannabinoid first synthesised by John W. Huffman, with a K_i of 8.5nM at the CB₁ cannabinoid receptor.^[1]

Isomers

The Δ³/Δ^6a(10a) isomer was synthesised in 1941, but was found to be slightly less active than Δ³-THC itself.^[2] The alternate isomer Δ⁹-THC-C8 has also been synthesised,^[3] but has not been identified as a natural product.

References

^ 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.
^ 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.
^ WO 2020232545, Kamaluddin AR, Wenli J. Kareem AR, published 26 November 2020, assigned to Kare Chemical Tech Inc, Canada.

[pmid10454479-1] 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, 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.

[3] WO 2020232545, Kamaluddin AR, Wenli J. Kareem AR, published 26 November 2020, assigned to Kare Chemical Tech Inc, Canada.

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THC Science

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Revision as of 11:34, 23 January 2023

Isomers

See also

References

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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