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AM-251 is an inverse agonist at the CB1 cannabinoid receptor. AM-251 is structurally very close to SR141716A (rimonabant); both are biarylpyrazole cannabinoid receptor antagonists. In AM-251 the p-chloro group attached to the phenyl substituent at C-5 of the pyrazole ring is replaced with a p-iodo group. The resulting compound exhibits slightly better binding affinity for the CB1 receptor (with a Ki value of 7.5nM) than SR141716A, which has a Ki value of 11.5nM, AM-251 is, however, about two-fold more selective for the CB1 receptor when compared to SR141716A. Like SR141716A, it is additionally a μ-opioid receptor antagonist.
|CompTox Dashboard (EPA)|
|Chemical and physical data|
|Molar mass||555.238 g/mol g·mol−1|
|3D model (JSmol)|
- Lan, R; Liu, Q; Fan, P; Lin, S; Fernando, SR; McCallion, D; Pertwee, R; Makriyannis, A. "Structure-activity relationships of pyrazole derivatives as cannabinoid receptor antagonists". J Med Chem. 42: 769–76. doi:10.1021/jm980363y. PMID 10052983.
- Seely, KA; Brents, LK; Franks, LN; Rajasekaran, M; Zimmerman, SM; Fantegrossi, WE; Prather, PL (2012). "AM-251 and rimonabant act as direct antagonists at mu-opioid receptors: implications for opioid/cannabinoid interaction studies". Neuropharmacology. 63: 905–15. doi:10.1016/j.neuropharm.2012.06.046. PMC 3408547. PMID 22771770.
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