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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==Synthesis== |
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[[File:Ciclopramine synthesis.svg|thumb|center|700px|Ciclopramine synthesis:<ref>{{Cite patent|DE|2004818}}, (1971); CA, 75, 118245k eidem {{US patent|3830818}}</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'''). Condensation with methylamine obviously gives a Schiff-base. The reduction of this to the secondary amine compound completed the synthesis of {{highlight|ciclopramine}}'' ('''3'''). |
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== References == |
== References == |
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{{Reflist}} |
{{Reflist}} |
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Revision as of 12:26, 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]
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). Condensation with methylamine obviously gives a Schiff-base. The reduction of this 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.
- ^ DE 2004818, (1971); CA, 75, 118245k eidem U.S. patent 3,830,818
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