A-836,339

A-836,339

Systematic (IUPAC) name
N-[3-(2-methoxyethyl)-4,5-dimethyl-1,3-thiazol-2-ylidene]-2,2,3,3-tetramethylcyclopropane-1-carboxamide
Clinical data
Pregnancy cat.	?
Legal status	?
Identifiers
CAS number	959746-77-1 Y
ATC code	?
PubChem	CID 17754357
ChemSpider	26286892 Y
Chemical data
Formula	C16H26N2O2S
Mol. mass	310.454 g/mol
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 Y Key:JKGIMVBQKSRTGX-UHFFFAOYSA-N Y
Y (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 K_i 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]

See also

• A-796,260
• CBS-0550
• SER-601

References

1. ^ McGaraughty, S.; Chu, K.; Dart, M.; Yao, B.; Meyer, M. (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.; Hsieh, G.; Daza, A.; Fan, Y.; Grayson, G.; Garrison, T.; El Kouhen, O.; Hooker, 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

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