A-836,339

From Wikipedia, the free encyclopedia
Jump to: navigation, search
A-836,339
A-836339 structure.png
Systematic (IUPAC) name
N-[3-(2-methoxyethyl)-4,5-dimethyl-1,3-thiazol-2-ylidene]-2,2,3,3-tetramethylcyclopropane-1-carboxamide
Clinical data
Legal status
?
Identifiers
CAS number 959746-77-1 N
ATC code ?
PubChem CID 17754357
ChemSpider 26286892 YesY
Chemical data
Formula C16H26N2O2S 
Mol. mass 310.454 g/mol
 N (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 0.64nM at CB2 vs 270nM 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[edit]

  1. ^ McGaraughty, S., et al. (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): 1652–1661. doi:10.1016/j.neuroscience.2008.11.015. PMID 19063946.   edit
  2. ^ Yao, B., et al. (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): 141–151. doi:10.1124/jpet.108.145011. PMID 18931146.   edit
  3. ^ Uemura, N.; Fukaya, H. (2013). "Identification of a synthetic cannabinoid A-836339 as a novel compound found in a product". Forensic Toxicology.