A-796,260

A-796,260

Systematic (IUPAC) name
1-(2-morpholin-4-ylethyl)-1H-indol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone
Clinical data
Pregnancy cat.	?
Legal status	?
Identifiers
CAS number	895155-26-7 Y[SciFinder]
ATC code	?
PubChem	CID 11584525
ChemSpider	9759290 Y
ChEMBL	CHEMBL262865 Y
Chemical data
Formula	C22H30N2O2
Mol. mass	354.485 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C22H30N2O2/c1-21(2)20(22(21,3)4)19(25)17-15-24(18-8-6-5-7-16(17)18)10-9-23-11-13-26-14-12-23/h5-8,15,20H,9-14H2,1-4H3 Y Key:ZCFHOMLAFTWDFM-UHFFFAOYSA-N Y
N (what is this?)  (verify)

A-796,260 is a drug developed by Abbott Laboratories that acts as a potent and selective cannabinoid CB₂ receptor agonist. Replacing the aromatic 3-benzoyl or 3-naphthoyl group found in most indole derived cannabinoids with the 3-tetramethylcyclopropylmethanone group, imparts significant selectivity for CB₂, and A-796,260 was found to be a highly selective CB₂ agonist with little affinity for CB₁, having a CB₂ K_i of 4.6 nM vs 945 nM at CB₁.^[1] It has potent analgesic and anti-inflammatory actions in animal models, being especially effective in models of neuropathic pain, but without producing cannabis-like behavioral effects.^[2]

See also

• A-834,735
• A-836,339
• JWH-200
• (1-Pentylindol-3-yl)-(2,2,3,3-tetramethylcyclopropyl)methanone

References

1. ^ Frost, J. M.; Dart, M. J.; Tietje, K. R.; Garrison, T. R.; Grayson, G. K.; Daza, A. V.; El-Kouhen, O. F.; Yao, B. B. et al (2010). "Indol-3-ylcycloalkyl Ketones: Effects of N1 Substituted Indole Side Chain Variations on CB2 Cannabinoid Receptor Activity". Journal of Medicinal Chemistry 53 (1): 295. doi:10.1021/jm901214q. PMID 19921781.  edit
2. ^ Yao BB, Hsieh GC, Frost JM, Fan Y, Garrison TR, Daza AV, Grayson GK, Zhu CZ, Pai M, Chandran P, Salyers AK, Wensink EJ, Honore P, Sullivan JP, Dart MJ, Meyer MD (January 2008). "In vitro and in vivo characterization of A-796260: a selective cannabinoid CB2 receptor agonist exhibiting analgesic activity in rodent pain models". British Journal of Pharmacology 153 (2): 390–401. doi:10.1038/sj.bjp.0707568. PMC 2219533. PMID 17994110. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2219533. 

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