Chemistry:Citenamide
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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
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
- ↑ "[Synthesis and properties of 1-aminoalkyl-dibenzo(b,e)bicyclo(2,2,2) octadienes]". Helvetica Chimica Acta 52 (6): 1385–1395. January 1969. doi:10.1002/hlca.19690520602. PMID 5820776.
- ↑ "Anticonvulsants. I. Dibenzo[a,d]cycloheptadiene-5-carboxamide and Related Compounds". Journal of Medicinal Chemistry 7 (1): 88–94. January 1964. doi:10.1021/jm00331a019. PMID 14186033.
- ↑ Leonard F, Gagneux A, US patent 3287409, issued 1966
- ↑ "Epoxide-diol metabolic pathway of cytenamide in the rat". Journal of Chromatography 134 (2): 299–305. April 1977. doi:10.1016/S0021-9673(00)88526-X. PMID 858759.
- ↑ "5H-dibenzo[a,dcycloheptene-5-carboxylic acid"]. PubChem. U.S. National Library of Medicine. https://pubchem.ncbi.nlm.nih.gov/compound/12515652.
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