A-836,339

A-836,339
Legal status
Legal status	CA: Schedule II;
Identifiers
	IUPAC name N-[3-(2-methoxyethyl)-4,5-dimethyl-1,3-thiazol-2-ylidene]-2,2,3,3-tetramethylcyclopropane-1-carboxamide;
CAS Number	959746-77-1 ;
PubChem CID	17754357;
ChemSpider	26286892 ;
UNII	Z6Y1J258EG;
CompTox Dashboard (EPA)	DTXSID601010006 ;
Chemical and physical data
Formula	C16H26N2O2S
Molar mass	310.46 g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:JKGIMVBQKSRTGX-UHFFFAOYSA-N ;
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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 0.64 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

^ 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.
^ 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.
^ 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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[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.

[Uemura-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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Legal status

Legal status	CA: Schedule II
Identifiers
IUPAC name N-[3-(2-methoxyethyl)-4,5-dimethyl-1,3-thiazol-2-ylidene]-2,2,3,3-tetramethylcyclopropane-1-carboxamide
CAS Number	959746-77-1^N
PubChem CID	17754357
ChemSpider	26286892^Y
UNII	Z6Y1J258EG
CompTox Dashboard (EPA)	DTXSID601010006
Chemical and physical data
Formula	C₁₆H₂₆N₂O₂S
Molar mass	310.46 g·mol⁻¹
3D model (JSmol)	Interactive image
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^Y Key:JKGIMVBQKSRTGX-UHFFFAOYSA-N^Y
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