AM251

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AM251
Systematic (IUPAC) name
1-(2,4-dichlorophenyl)-5-(4-iodophenyl]])-4-methyl- N-(1-piperidyl)pyrazole-3-carboxamide
Identifiers
CAS number	?
ATC code	?
PubChem	2125
Chemical data
Formula	C₂₂H₂₁Cl₂I N₄O
Mol. mass	555.238 g/mol
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status
Routes	?

AM251 is a CB1 cannabinoid receptor antagonist. AM251 is structurally very close to SR 141716A (rimonabant), which both are biarylpyrazole cannabinoid receptor antagonists. In AM251 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 7.5 nM compound to SR 141716A, which has a Ki value of 11.5 nM. However AM251 is about two-fold more selective for the CB1 receptor when compared to SR 141716A.^[1]

References

↑ Lan, R., Liu, Q., Fan, P., et al. Structure-activity relationships of pyrazole derivatives as cannabinoid receptor antagonists. J Med Chem 42 769-776 (1999). PubMed: 10052983

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Cannabinoids

Plant cannabinoids

CBD • CBDV • CBN • CBG • CBV • CBL • THC • THC-C4 • THCV

Cannabinoid metabolites

11-Hydroxy-THC • 11-nor-9-Carboxy-THC

Endogenous cannabinoids

Arachidonoyl ethanolamide (Anandamide or AEA) • 2-Arachidonoylglycerol (2-AG) • 2-Arachidonyl glyceryl ether (noladin ether) • Virodhamine • N-arachidonoyl-dopamine (NADA)

Synthetic cannabinoid agonists

Classical cannabinoids (Dibenzopyrans)	A-41988 • Ajulemic acid • AM-087 • AM-411 • AM-855 • AM-905 • AM-906 • AM-919 • AM-938 • AM-4030 • AMG-1 • AMG-3 • AMG-36 • AMG-41 • Dexanabinol (HU-211) • DMHP • Dronabinol • HU-210 • JWH-051 • JWH-133 • JWH-139 • L-759,633 • L-759,656 • Levonantradol • Nabilone • Nabitan • O-806 • O-823 • O-1057 • O-1125 • O-1238 • O-2545 • Parahexyl • THC-O-acetate • THC-O-phosphate
Nonclassical cannabinoids	CP 47,497 • CP 55,244 • CP 55,940 • HU-308 • 2-Isopropyl-5-methyl-1-(2,6-dihydroxy-4-nonylphenyl)cyclohex-1-ene
Aminoalkylindoles	AM-630 • AM-1241 • JWH-015 • JWH-018 • JWH-073 • JWH-081 • JWH-200 • L-768,242 • Pravadoline • WIN 55,212-2
Aminoalkylpyrroles	JWH-030 • JWH-147 • JWH-307
Eicosanoids	AM-883 • Arachidonyl-2'-chloroethylamide • Arachidonylcyclopropylamide • Methanandamide • O-585 • O-689 • O-1812 • O-1860 • O-1861
Others	BAY 38-7271 • BAY 59-3074 • JWH-171 • O-2220