Citenamide

Anticonvulsant From Wikipedia, the free encyclopedia

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]

Other names5H-Dibenzo[a,d]cycloheptene-5-carboxamide, Cytenamide, AY-15,613.
CAS Number
Quick facts Clinical data, Other names ...
Citenamide
Clinical data
Other names5H-Dibenzo[a,d]cycloheptene-5-carboxamide, Cytenamide, AY-15,613.
Identifiers
  • tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,9,11,13-heptaene-2-carboxamide
CAS Number
PubChem CID
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KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC16H13NO
Molar mass235.286 g·mol−1
3D model (JSmol)
  • C1=CC=C2C(C3=CC=CC=C3C=CC2=C1)C(=O)N
  • 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
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Synthesis

Citenamide 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

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