Citenamide
(Redirected from Draft:Citenamide)
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| Other names | 5H-Dibenzo[a,d]cycloheptene-5-carboxamide, Cytenamide, AY-15,613. |
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| Formula | C16H13NO |
| Molar mass | 235.286 g·mol−1 |
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Citenamide is a tricyclic chemical agent that is very similar in character to and most closely resembles carbamazepine (Tegretol), which a non-addictive anticonvulsant agent used to treat epileptic seizures, schizophrenia, phantom limb pain and alcoholism. Citenamide contains an amide functional group whereas carbamazepine contains a urea. Citenamide is an old drug and there is little pharmacological data surrounding its use in medicine.[1][2][3][4]
Synthesis
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Organometallic formation between 5-chlorodibenzosuberene [18506-04-2] (1) and butyl lithium, is proceeded by a dry ice quench to give the acid, PC12515652[5] (2). Halogenation with thionyl chloride and Schotten-Baumann reaction with ammonia gives the amide, and hence citenamide (3).
References
[edit]- ^ Wilhelm M, Schmidt P (January 1969). "[Synthesis and properties of 1-aminoalkyl-dibenzo(b,e)bicyclo(2,2,2) octadienes]". Helvetica Chimica Acta. 52 (6): 1385–1395. doi:10.1002/hlca.19690520602. PMID 5820776.
- ^ Davis MA, Winthrop SO, Thomas RA, Herr F, Charest MP, Gaudry R (January 1964). "Anticonvulsants. I. Dibenzo[a,d]cycloheptadiene-5-carboxamide and Related Compounds". Journal of Medicinal Chemistry. 7 (1): 88–94. doi:10.1021/jm00331a019. PMID 14186033.
- ^ US 3287409, Leonard F, Gagneux A, issued 1966, assigned to Novartis Corp
- ^ Frigerio A, Lanzoni J, Pantarotto C, Rossi E, Rovei V, Zanol M (April 1977). "Epoxide-diol metabolic pathway of cytenamide in the rat". Journal of Chromatography. 134 (2): 299–305. doi:10.1016/S0021-9673(00)88526-X. PMID 858759.
- ^ "5H-dibenzo[a,d]cycloheptene-5-carboxylic acid". PubChem. U.S. National Library of Medicine.