Citenamide

Citenamide

Clinical data
Other names	5H-Dibenzo[a,d]cycloheptene-5-carboxamide, Cytenamide, AY-15,613.
Identifiers
IUPAC name tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,9,11,13-heptaene-2-carboxamide
CAS Number	10423-37-7
PubChem CID	25255
ChemSpider	23588
UNII	17NZ10DWW0
KEGG	D03527
ChEMBL	ChEMBL2104133
CompTox Dashboard (EPA)	DTXSID00146356
Chemical and physical data
Formula	C16H13NO
Molar mass	235.286 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1=CC=C2C(C3=CC=CC=C3C=CC2=C1)C(=O)N
InChI InChI=1S/C16H13NO/c17-16(18)15-13-7-3-1-5-11(13)9-10-12-6-2-4-8-14(12)15/h1-10,15H,(H2,17,18) Key:HXQAPLNYYFQSFU-UHFFFAOYSA-N

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

Citenamide 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

1. 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.
2. 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.
3. US 3287409,Leonard F, Gagneux A,issued 1966, assigned to Novartis Corp 
4. 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.
5. "5H-dibenzo[a,d]cycloheptene-5-carboxylic acid". PubChem. U.S. National Library of Medicine.