Ciclopramine: Difference between revisions
Content deleted Content added
No edit summary Tag: Reverted |
reduced size of graphic so that it doesn't overwhelm the rest of the article Tag: Reverted |
||
| Line 35: | Line 35: | ||
The structure is best compared to [[desipramine]], where the sidechain has been abridged to the tricyclic [[dibenzazepine]] ring. |
The structure is best compared to [[desipramine]], where the sidechain has been abridged to the tricyclic [[dibenzazepine]] ring. |
||
==Synthesis== |
==Synthesis== |
||
[[File:Ciclopramine synthesis.svg|thumb|center| |
[[File:Ciclopramine synthesis.svg|thumb|center|400px|Patent:<ref>DE2004818 idem G Hackmack & H Menge, {{US patent|3830818}} (1974 to Takeda GmbH)</ref>]] |
||
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'''). |
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'''). |
||
Revision as of 16:38, 18 October 2022
 | |
| Clinical data | |
|---|---|
| ATC code |
|
| Legal status | |
| Legal status |
|
| Identifiers | |
| |
| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| UNII | |
| ChEMBL | |
| CompTox Dashboard (EPA) | |
| Chemical and physical data | |
| Formula | C18H20N2 |
| Molar mass | 264.372 g·mol−1 |
| 3D model (JSmol) | |
| |
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)
 | This drug article relating to the nervous system is a stub. You can help Wikipedia by expanding it. |