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 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 & 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
Organometallic formation between 5-chlorodibenzosuberene [18506-04-2] (1) and butyl lithium, is proceeded by a dry ice quench to give the acid, PC12515652 (2). Halogenation with thionyl chloride and Schotten-Baumann reaction with ammonia gives the amide, and hence citenamide (3).
References
- ^ Wilhelm, M., Schmidt, P. (January 1969). "Synthese und Eigenschaften von 1-Aminoalkyl-dibenzo[ b , e ]bicyclo[2.2.2]octadienen". Helvetica Chimica Acta. 52 (6): 1385–1395. doi:10.1002/hlca.19690520602. PMID 5820776.
- ^ Davis, M. A., Winthrop, S. O., Thomas, R. A., Herr, F., Charest, M.-P., 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.
- ^ Leonard Frederick & Gagneux Andre, US3287409 (1966 to Novartis Corp); CA, 66, 37702
- ^ 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 A. 134 (2): 299–305. doi:10.1016/S0021-9673(00)88526-X. PMID 858759.