Propizepine
Clinical data | |
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Trade names | Depressin, Vagran |
Routes of administration | Oral |
ATC code |
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Legal status | |
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Identifiers | |
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ECHA InfoCard | 100.030.629 |
Chemical and physical data | |
Formula | C17H20N4O |
Molar mass | 296.374 g·mol−1 |
Propizepine (brand names Depressin, Vagran) is a tricyclic antidepressant (TCA) used in France for the treatment of depression which was introduced in the 1970s.[1][2][3][4]
Synthesis
Condensation of 2-chloronicotinic acid (2) with o-phenylenediamine (1) leads directly to the tricyclic lactam (3) Although the reaction involves amide formation and nucleophilic aromatic displacement of chlorine, the order of these steps is not known. Alkylation of the anion obtained by treatment if 3 with the 1-chloro-2-dimethylaminopropane (4) affords the antidepressant compound propizepine (5).
The last step in this sequence there is considerable evidence that such alkylations often proceed via the
What this intends to say is that even if the chloroamine used is actually 1-dimethylamino-2-chloro-propane, although could still be a mixture of products one still gets predominantly the same reaction product as above and not the "iso" product.
References
- ISBN 3-88763-075-0.
- ISBN 0-412-46630-9.
- )
- PMID 996559.
- ^ Hoffman C, Faure A (1966). "Réactions de l'acide chloro-2-nicotinique". Bull. Soc. Chim. Fr. 7: 2316.
- ^ NL 6600065, issued 1966, assigned to Labs. U.P.S.A.