Ciclopramine: Difference between revisions
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'''Ciclopramine''' is a [[tetracyclic antidepressant]] (TeCA) that was never marketed.<ref name="isbn0-412-46630-9">{{cite book | first = David J. | last = Triggle | name-list-style = vanc | title = Dictionary of pharmacological agents | publisher = Chapman & Hall | location = London | year = 1997 | isbn = 0-412-46630-9 }}</ref><ref name="pmid7090895">{{cite journal | vauthors = Saletu B | title = Pharmaco-EEG profiles of typical and atypical antidepressants | journal = Advances in Biochemical Psychopharmacology | volume = 32 | pages = 257–68 | year = 1982 | pmid = 7090895 }}</ref> |
'''Ciclopramine''' is a [[tetracyclic antidepressant]] (TeCA) that was never marketed.<ref name="isbn0-412-46630-9">{{cite book | first = David J. | last = Triggle | name-list-style = vanc | title = Dictionary of pharmacological agents | publisher = Chapman & Hall | location = London | year = 1997 | isbn = 0-412-46630-9 }}</ref><ref name="pmid7090895">{{cite journal | vauthors = Saletu B | title = Pharmaco-EEG profiles of typical and atypical antidepressants | journal = Advances in Biochemical Psychopharmacology | volume = 32 | pages = 257–68 | year = 1982 | pmid = 7090895 }}</ref> |
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The structure is best compared to [[desipramine]], where the sidechain has been abridged to the tricyclic [[dibenzazepine]] ring. |
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==Synthesis== |
==Synthesis== |
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[[File:Ciclopramine synthesis.svg|thumb|center|700px|Patent:<ref>DE2004818 idem G Hackmack & H Menge, {{US patent|3830818}} (1974 to Takeda GmbH)</ref>]] |
[[File:Ciclopramine synthesis.svg|thumb|center|700px|Patent:<ref>DE2004818 idem G Hackmack & H Menge, {{US patent|3830818}} (1974 to Takeda GmbH)</ref>]] |
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Revision as of 12:31, 18 October 2022
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| Formula | C18H20N2 |
| Molar mass | 264.372 g·mol−1 |
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Ciclopramine is a tetracyclic antidepressant (TeCA) that was never marketed.[1][2]
The structure is best compared to desipramine, where the sidechain has been abridged to the tricyclic dibenzazepine ring.
Synthesis
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
- ^ Triggle DJ (1997). Dictionary of pharmacological agents. London: Chapman & Hall. ISBN 0-412-46630-9.
- ^ Saletu B (1982). "Pharmaco-EEG profiles of typical and atypical antidepressants". Advances in Biochemical Psychopharmacology. 32: 257–68. PMID 7090895.
- ^ DE2004818 idem G Hackmack & H Menge, U.S. patent 3,830,818 (1974 to Takeda GmbH)
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