Ciclopramine: Difference between revisions
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{{Short description|Tetracyclic antidepressant}} |
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{{Distinguish|cyclopamine}} |
{{Distinguish|cyclopamine}} |
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'''Ciclopramine''' is a [[tetracyclic antidepressant]] (TeCA) that was never marketed.<ref name=" |
'''Ciclopramine''' is a [[tetracyclic antidepressant]] (TeCA) that was never marketed.<ref name="Triggle1997">{{cite book | vauthors = Triggle DJ, Ganellin CR | url = https://books.google.com/books?id=A0THacd46ZsC | oclc = 223303192 | title = Dictionary of pharmacological agents | publisher = Chapman & Hall | location = London | year = 1997 | isbn = 9780412466304}}</ref><ref name="Saletu1982">{{cite journal | vauthors = Saletu B | title = Pharmaco-EEG profiles of typical and atypical antidepressants | journal = Advances in Biochemical Psychopharmacology | volume = 32 | pages = 257–268 | year = 1982 | pmid = 7090895 | url = https://pubmed.ncbi.nlm.nih.gov/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== |
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[[File:Ciclopramine synthesis.svg|thumb|center|400px|Patent:<ref>DE2004818 idem G Hackmack & H Menge, {{US patent|3830818}} (1974 to Takeda GmbH)</ref>]] |
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The reaction of 3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propionic acid, [https://pubchem.ncbi.nlm.nih.gov/compound/22390899 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, [https://pubchem.ncbi.nlm.nih.gov/compound/21853518 CID:21853518] ('''2'''). The condensation with methylamine gives a Schiff-base; the reduction to the secondary amine compound completed the synthesis of ''{{highlight|ciclopramine}}'' ('''3'''). |
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== References == |
== References == |
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Latest revision as of 20:51, 20 March 2023
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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]
References[edit]
- ^ Triggle DJ, Ganellin CR (1997). Dictionary of pharmacological agents. London: Chapman & Hall. ISBN 9780412466304. OCLC 223303192.
- ^ Saletu B (1982). "Pharmaco-EEG profiles of typical and atypical antidepressants". Advances in Biochemical Psychopharmacology. 32: 257–268. PMID 7090895.
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