Alpidem
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MedKoo CAT#: 326870

CAS#: 82626-01-5

Description: 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 It was approved for marketing in France in 1991 and was withdrawn fin 1994 and is not approved for marketing anywhere in the world.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).


Chemical Structure

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Alpidem
CAS# 82626-01-5

Theoretical Analysis

MedKoo Cat#: 326870
Name: Alpidem
CAS#: 82626-01-5
Chemical Formula: C21H23Cl2N3O
Exact Mass: 403.1218
Molecular Weight: 404.335
Elemental Analysis: C, 62.38; H, 5.73; Cl, 17.53; N, 10.39; O, 3.96

Price and Availability

Size Price Availability Quantity
5.0mg USD 225.0 2 Weeks
25.0mg USD 800.0 2 Weeks
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Synonym: Alpidem, brand name: Ananxyl.

IUPAC/Chemical Name: 2-(6-chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-N,N-dipropylacetamide

InChi Key: JRTIDHTUMYMPRU-UHFFFAOYSA-N

InChi Code: 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

SMILES Code: O=C(N(CCC)CCC)CC1=C(C2=CC=C(Cl)C=C2)N=C3C=CC(Cl)=CN31

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Certificate of Analysis:

Safety Data Sheet (SDS):

Preparing Stock Solutions

The following data is based on the product molecular weight 404.335 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Nair DK, Mobin SM, Namboothiri IN. Synthesis of imidazopyridines from the Morita-Baylis-Hillman acetates of nitroalkenes and convenient access to Alpidem and Zolpidem. Org Lett. 2012 Sep 7;14(17):4580-3. doi: 10.1021/ol3020418. Epub 2012 Aug 24. PubMed PMID: 22920993.

2: Chernyak N, Gevorgyan V. General and efficient copper-catalyzed three-component coupling reaction towards imidazoheterocycles: one-pot synthesis of alpidem and zolpidem. Angew Chem Int Ed Engl. 2010 Apr 1;49(15):2743-6. doi: 10.1002/anie.200907291. PubMed PMID: 20213787; PubMed Central PMCID: PMC3516864.

3: Cappelli A, Giuliani G, Valenti S, Anzini M, Vomero S, Giorgi G, Sogliano C, Maciocco E, Biggio G, Concas A. Synthesis and structure-activity relationship studies in peripheral benzodiazepine receptor ligands related to alpidem. Bioorg Med Chem. 2008 Mar 15;16(6):3428-37. doi: 10.1016/j.bmc.2007.06.044. Epub 2007 Jun 27. PubMed PMID: 18294852.

4: Trapani G, Latrofa A, Franco M, Carrieri A, Cellamare S, Serra M, Sanna E, Biggio G, Liso G. Alpidem analogues containing a GABA or glycine moiety as new anticonvulsant agents. Eur J Pharm Sci. 2003 Mar;18(3-4):231-40. PubMed PMID: 12659934.

5: Berson A, Descatoire V, Sutton A, Fau D, Maulny B, Vadrot N, Feldmann G, Berthon B, Tordjmann T, Pessayre D. Toxicity of alpidem, a peripheral benzodiazepine receptor ligand, but not zolpidem, in rat hepatocytes: role of mitochondrial permeability transition and metabolic activation. J Pharmacol Exp Ther. 2001 Nov;299(2):793-800. PubMed PMID: 11602696.

6: Hascoët M, Bourin M. Anticonflict effect of alpidem as compared with the benzodiazepine alprazolam in rats. Pharmacol Biochem Behav. 1997 Feb;56(2):317-24. PubMed PMID: 9050091.

7: Anzini M, Cappelli A, Vomero S, Giorgi G, Langer T, Bruni G, Romeo MR, Basile AS. Molecular basis of peripheral vs central benzodiazepine receptor selectivity in a new class of peripheral benzodiazepine receptor ligands related to alpidem. J Med Chem. 1996 Oct 11;39(21):4275-84. PubMed PMID: 8863805.

8: Cassano G, Petracca A, Borghi C, Chiroli S, Didoni G, Garreau M. A randomized, double-blind study of alpidem vs placebo in the prevention and treatment of benzodiazepine withdrawal syndrome. Eur Psychiatry. 1996;11(2):93-9. doi: 10.1016/0924-9338(96)84786-9. PubMed PMID: 19698430.

9: Ausset P, Malavialle P, Vallet A, Miremont G, Le Bail B, Dumas F, Saric J, Winnock S. [Subfulminant hepatitis caused by alpidem and treated by liver transplantation]. Gastroenterol Clin Biol. 1995 Feb;19(2):222-3. French. PubMed PMID: 7750714.

10: Frattola L, Garreau M, Piolti R, Bassi S, Albizzati MG, Borghi C, Morselli PL. Comparison of the efficacy, safety and withdrawal of alpidem and alprazolam in anxious patients. Br J Psychiatry. 1994 Jul;165(1):94-100. PubMed PMID: 7802852.

11: Flaminio L, Ripamonti M, Ascalone V. Determination of alpidem, an imidazopyridine anxiolytic, and its metabolites by column-switching high-performance liquid chromatography with fluorescence detection. J Chromatogr A. 1994 May 13;668(2):403-11. PubMed PMID: 7913366.

12: Bisserbe JC, Boulenger JP. Paradoxical acute anxiety exacerbation with alpidem in a panic disorder patient. J Psychopharmacol. 1994 Jan;8(3):189-90. doi: 10.1177/026988119400800310. PubMed PMID: 22298589.

13: Prat B, Weiss AM, Glikmanas M. [A new case of hepatitis after alpidem monotherapy]. Gastroenterol Clin Biol. 1994;18(10):903-4. French. PubMed PMID: 7875405.

14: Sanger DJ, Zivkovic B. Discriminative stimulus effects of alpidem, a new imidazopyridine anxiolytic. Psychopharmacology (Berl). 1994 Jan;113(3-4):395-403. PubMed PMID: 7862851.

15: Baty V, Denis B, Goudot C, Bas V, Renkes P, Bigard MA, Boissel P, Gaucher P. [Hepatitis induced by alpidem (Ananxyl). Four cases, one of them fatal]. Gastroenterol Clin Biol. 1994;18(12):1129-31. French. PubMed PMID: 7750686.

16: Gaillard Y, Gay-Montchamp JP, Ollagnier M. Simultaneous screening and quantitation of alpidem, zolpidem, buspirone and benzodiazepines by dual-channel gas chromatography using electron-capture and nitrogen-phosphorus detection after solid-phase extraction. J Chromatogr. 1993 Dec 22;622(2):197-208. PubMed PMID: 7908670.

17: Perrault G, Morel E, Sanger DJ, Zivkovic B. Repeated treatment with alpidem, a new anxiolytic, does not induce tolerance or physical dependence. Neuropharmacology. 1993 Sep;32(9):855-63. PubMed PMID: 7901790.

18: Tracqui A, Kintz P, Mangin P. High-performance liquid chromatographic assay with diode-array detection for toxicological screening of zopiclone, zolpidem, suriclone and alpidem in human plasma. J Chromatogr. 1993 Jun 23;616(1):95-103. PubMed PMID: 8104192.

19: Schneier FR, Carrasco JL, Hollander E, Campeas R, Fallon B, Saoud JB, Feerick J, Liebowitz MR. Alpidem in the treatment of panic disorder. J Clin Psychopharmacol. 1993 Apr;13(2):150-3. PubMed PMID: 8096527.

20: Benavides J, Peny B, Ruano D, Vitorica J, Scatton B. Comparative autoradiographic distribution of central omega (benzodiazepine) modulatory site subtypes with high, intermediate and low affinity for zolpidem and alpidem. Brain Res. 1993 Feb 26;604(1-2):240-50. PubMed PMID: 8096157.

Alpidem

5.0mg / USD 225.0