Ciclopramine

Ciclopramine is a tetracyclic antidepressant (TeCA) that was never marketed.[1][2]

Ciclopramine
Clinical data
ATC code
  • None
Legal status
Legal status
  • Not marketed
Identifiers
IUPAC name
  • N-Methyl-2,3,7,8-tetrahydro-1H-quino[1,8-ab][1]benzazepin-3-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC18H20N2
Molar mass264.372 g·mol−1
3D model (JSmol)
SMILES
  • c14c2c(ccc1)C(NC)CCN2c3ccccc3CC4

The structure is best compared to desipramine, where the sidechain has been abridged to the tricyclic dibenzazepine ring.

Synthesis
Patent:[3]

The reaction of 3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propionic acid, CID:22390899 (1) with lewis acid in a mixture of acetic anhydride and acetic acid led to the characteristic Haworth cyclization reaction to give 1,2,7,8-tetrahydro-3H-quino[1,8-ab][1]benzazepin-3-one, CID:21853518 (2). The condensation with methylamine gives a Schiff-base; the reduction to the secondary amine compound completed the synthesis of ciclopramine (3).

References
  1. Triggle DJ (1997). Dictionary of pharmacological agents. London: Chapman & Hall. ISBN 0-412-46630-9.
  2. Saletu B (1982). "Pharmaco-EEG profiles of typical and atypical antidepressants". Advances in Biochemical Psychopharmacology. 32: 257–68. PMID 7090895.
  3. DE2004818 idem G Hackmack & H Menge, U.S. Patent 3,830,818 (1974 to Takeda GmbH)
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