A-796,260

A-796,260
Legal status
Legal status	UK: Class B;
Identifiers
	IUPAC name [1-(2-morpholin-4-ylethyl)-1H-indol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone;
CAS Number	895155-26-7 ;
PubChem CID	11584525;
ChemSpider	9759290 ;
UNII	5N69DXA53Z;
ChEMBL	ChEMBL262865 ;
CompTox Dashboard (EPA)	DTXSID801010107 ;
ECHA InfoCard	100.233.198
Chemical and physical data
Formula	C22H30N2O2
Molar mass	354.494 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C4COCCN4CCn(c3ccccc13)cc1C(=O)C2C(C)(C)C2(C)C;
	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 ; Key:ZCFHOMLAFTWDFM-UHFFFAOYSA-N ;
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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-tetramethyl cyclopropyl methanone 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]

Legal Status

As of October 2015 A-796,260 is a controlled substance in China.^[3]

References

^ Frost JM, Dart MJ, Tietje KR, Garrison TR, Grayson GK, Daza AV, et al. (January 2010). "Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB(2) cannabinoid receptor activity". Journal of Medicinal Chemistry. 53 (1): 295–315. doi:10.1021/jm901214q. PMID 19921781.
^ Yao BB, Hsieh GC, Frost JM, Fan Y, Garrison TR, Daza AV, et al. (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.
^ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.

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[1] Frost JM, Dart MJ, Tietje KR, Garrison TR, Grayson GK, Daza AV, et al. (January 2010). "Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB(2) cannabinoid receptor activity". Journal of Medicinal Chemistry. 53 (1): 295–315. doi:10.1021/jm901214q. PMID 19921781.

[pmid17994110-2] Yao BB, Hsieh GC, Frost JM, Fan Y, Garrison TR, Daza AV, et al. (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.

[3] "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.

[1]

[2]

[3]

Legal status

Legal status	UK: Class B
Identifiers
IUPAC name [1-(2-morpholin-4-ylethyl)-1H-indol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone
CAS Number	895155-26-7^N
PubChem CID	11584525
ChemSpider	9759290^Y
UNII	5N69DXA53Z
ChEMBL	ChEMBL262865^Y
CompTox Dashboard (EPA)	DTXSID801010107
ECHA InfoCard	100.233.198
Chemical and physical data
Formula	C₂₂H₃₀N₂O₂
Molar mass	354.494 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C4COCCN4CCn(c3ccccc13)cc1C(=O)C2C(C)(C)C2(C)C
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
^NY (what is this?) (verify)

A-796,260

Legal Status

See also

References