Chemistry:JWH-138

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Short description: Chemical compound
JWH-138
JWH-138 structure.png
Identifiers
CAS Number
PubChem CID
Chemical and physical data
FormulaC24H36O2
Molar mass356.550 g·mol−1
3D model (JSmol)

JWH-138 (THC-Octyl, Δ8-THC-C8) is a synthetic cannabinoid first synthesised by John W. Huffman, with a Ki 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]

Isomers

Δ3-THC-C8
Δ9-THC-C8 (Tetrahydrocannabioctyl), CAS# 2552798-63-5

The Δ36a(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 THCO, which may cause confusion with THC-O-acetate which is commonly known as THC-O.

See also

References

  1. "Manipulation of the tetrahydrocannabinol side chain delineates agonists, partial agonists, and antagonists". The Journal of Pharmacology and Experimental Therapeutics 290 (3): 1065–1079. September 1999. PMID 10454479. 
  2. https://pubs.acs.org/doi/abs/10.1021/ja01255a061
  3. "Tetrahydrocannabinol Homologs with Marihuana Activity. IX.". Journal of the American Chemical Society 63 (7): 1971–1973. July 1941. doi:10.1021/ja01852a052. 
  4. Abdur-Rashid, Kamaluddin; Wenli Jia & Kareem Abdur-Rashid, "Catalytic cannabinoid processes and precursors", WO patent application 2020232545, published 2020-11-26, assigned to Kare Chemical Technologies Inc..
  5. Senate Bill 23-271, General Assembly, State of Colorado