Alpidem

• CAT Number: R008875
• CAS Number: 82626-01-5
• Molecular Formula: C21H23Cl2N3O
• Molecular Weight: 404.335
• Purity: ≥95%
• Storage: Store at -20°C
• IUPAC Name: 2-[6-chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl]-N,N-dipropylacetamide
• InChI: InChI=1S/C21H23Cl2N3O/c1-3-11-25(12-4-2)20(27)13-18-21(15-5-7-16(22)8-6-15)24-19-10-9-17(23)14-26(18)19/h5-10,14H,3-4,11-13H2,1-2H3
• InChIKey: JRTIDHTUMYMPRU-UHFFFAOYSA-N
• SMILES: CCCN(CCC)C(=O)CC1=C(N=C2N1C=C(C=C2)Cl)C3=CC=C(C=C3)Cl

Alpidem is an anxiolytic drug from the imidazopyridine family, related to the more well known sleeping medication zolpidem. Unlike zolpidem however, alpidem does not produce sedative effects at normal doses, and is instead used specifically for the treatment of anxiety. It was approved for marketing in France in 1991 and was withdrawn fin 1994 and is not approved for marketing anywhere in the world. Alpidem has nanomolar binding affinity for both the central benzodiazepine receptor (CBR) and the peripheral benzodiazepine receptor (PBR) (translocator protein 18 kDa) (PBR (Ki ) 0.5-7 nM) and CBR (Ki ) 1-28 nM, respectively).

Reference

1:Synthesis of imidazopyridines from the Morita-Baylis-Hillman acetates of nitroalkenes and convenient access to Alpidem and Zolpidem. Nair DK, Mobin SM, Namboothiri IN.Org Lett. 2012 Sep 7;14(17):4580-3. doi: 10.1021/ol3020418. Epub 2012 Aug 24. PMID: 22920993 2:General and efficient copper-catalyzed three-component coupling reaction towards imidazoheterocycles: one-pot synthesis of alpidem and zolpidem. Chernyak N, Gevorgyan V.Angew Chem Int Ed Engl. 2010 Apr 1;49(15):2743-6. doi: 10.1002/anie.200907291. No abstract available. PMID: 20213787 Free PMC Article3:Synthesis and structure-activity relationship studies in peripheral benzodiazepine receptor ligands related to alpidem. Cappelli A, Giuliani G, Valenti S, Anzini M, Vomero S, Giorgi G, Sogliano C, Maciocco E, Biggio G, Concas A.Bioorg Med Chem. 2008 Mar 15;16(6):3428-37. doi: 10.1016/j.bmc.2007.06.044. Epub 2007 Jun 27. PMID: 18294852 4:Alpidem analogues containing a GABA or glycine moiety as new anticonvulsant agents. Trapani G, Latrofa A, Franco M, Carrieri A, Cellamare S, Serra M, Sanna E, Biggio G, Liso G.Eur J Pharm Sci. 2003 Mar;18(3-4):231-40. PMID: 12659934 5:Toxicity of alpidem, a peripheral benzodiazepine receptor ligand, but not zolpidem, in rat hepatocytes: role of mitochondrial permeability transition and metabolic activation. Berson A, Descatoire V, Sutton A, Fau D, Maulny B, Vadrot N, Feldmann G, Berthon B, Tordjmann T, Pessayre D.J Pharmacol Exp Ther. 2001 Nov;299(2):793-800. PMID: 11602696 Free Article6:Anticonflict effect of alpidem as compared with the benzodiazepine alprazolam in rats. Hascoët M, Bourin M.Pharmacol Biochem Behav. 1997 Feb;56(2):317-24. PMID: 9050091 7:Molecular basis of peripheral vs central benzodiazepine receptor selectivity in a new class of peripheral benzodiazepine receptor ligands related to alpidem. Anzini M, Cappelli A, Vomero S, Giorgi G, Langer T, Bruni G, Romeo MR, Basile AS.J Med Chem. 1996 Oct 11;39(21):4275-84. PMID: 8863805 8:A randomized, double-blind study of alpidem vs placebo in the prevention and treatment of benzodiazepine withdrawal syndrome. Cassano G, Petracca A, Borghi C, Chiroli S, Didoni G, Garreau M.Eur Psychiatry. 1996;11(2):93-9. doi: 10.1016/0924-9338(96)84786-9. PMID: 19698430 9:[Subfulminant hepatitis caused by alpidem and treated by liver transplantation]. Ausset P, Malavialle P, Vallet A, Miremont G, Le Bail B, Dumas F, Saric J, Winnock S.Gastroenterol Clin Biol. 1995 Feb;19(2):222-3. French. No abstract available. PMID: 7750714 10:Comparison of the efficacy, safety and withdrawal of alpidem and alprazolam in anxious patients. Frattola L, Garreau M, Piolti R, Bassi S, Albizzati MG, Borghi C, Morselli PL.Br J Psychiatry. 1994 Jul;165(1):94-100. PMID: 7802852