Chemistry:JWH-138

From HandWiki

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 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 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. Both Δ8 and Δ9 (C8)-THC have been sold as designer drugs, first identified in Denmark in August 2024.[6]

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. "Tetrahydrocannabinol Homologs and Analogs with Marihuana Activity. XIII1". Journal of the American Chemical Society 64 (3): 694–697. 1942. doi: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 K, Jia W, Abdur-Rashid K, "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. https://leg.colorado.gov/sites/default/files/documents/2023A/bills/2023a_271_rev.pdf. 
  6. European Drug Report 2025: Trends and Developments