A-836,339

A-836,339
Legal status
Legal status
Identifiers
IUPAC name
  • N-[3-(2-methoxyethyl)-4,5-dimethyl-1,3-thiazol-2-ylidene]-2,2,3,3-tetramethylcyclopropane-1-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC16H26N2O2S
Molar mass310.46 g·mol−1
3D model (JSmol)
SMILES
  • Cc1c(sc(=NC(=O)C2C(C2(C)C)(C)C)n1CCOC)C
InChI
  • InChI=1S/C16H26N2O2S/c1-10-11(2)21-14(18(10)8-9-20-7)17-13(19)12-15(3,4)16(12,5)6/h12H,8-9H2,1-7H3 checkY
  • Key:JKGIMVBQKSRTGX-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

A-836,339 is a drug developed by Abbott Laboratories that acts as a potent cannabinoid receptor full agonist. It is selective for CB2, with Ki values of 0.64 nM at CB2 vs 270 nM at the psychoactive CB1 receptor, but while it exhibits selective analgesic, anti-inflammatory and anti-hyperalgesic effects at low doses,[1] its high efficacy at both targets results in typical cannabis-like effects appearing at higher doses, despite its low binding affinity for CB1.[2] In 2012 A-836,339 was detected via X-ray crystallography in a "dubious product" sold in Japan, though the product was described as a white powder, not herbal incense, it was suggested to be for human consumption.[3]

References

  1. ↑ McGaraughty S, Chu KL, Dart MJ, Yao BB, Meyer MD (February 2009). "A CB(2) receptor agonist, A-836339, modulates wide dynamic range neuronal activity in neuropathic rats: contributions of spinal and peripheral CB(2) receptors". Neuroscience. 158 (4): 1652–61. doi:10.1016/j.neuroscience.2008.11.015. PMID 19063946. S2CID 207244894.
  2. ↑ Yao BB, Hsieh G, Daza AV, Fan Y, Grayson GK, Garrison TR, et al. (January 2009). "Characterization of a cannabinoid CB2 receptor-selective agonist, A-836339 [2,2,3,3-tetramethyl-cyclopropanecarboxylic acid [3-(2-methoxy-ethyl)-4,5-dimethyl-3H-thiazol-(2Z)-ylidene]-amide], using in vitro pharmacological assays, in vivo pain models, and pharmacological magnetic resonance imaging". The Journal of Pharmacology and Experimental Therapeutics. 328 (1): 141–51. doi:10.1124/jpet.108.145011. PMID 18931146. S2CID 46602629.
  3. ↑ Uemura N, Fukaya H, Kanai C, Yoshida M, Nakajima JI, Takahashi M, et al. (2013). "Identification of a synthetic cannabinoid A-836339 as a novel compound found in a product". Forensic Toxicology. 32: 45–50. doi:10.1007/s11419-013-0201-x. S2CID 24846364.
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