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| Routes of administration | Oral |
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| Formula | C17H23NO |
| Molar mass | 257.377 g·mol−1 |
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Pirandamine (AY-23,713) is atricyclicderivative which acts as aselective serotonin reuptake inhibitor (SSRI).[1][2][3] It was investigated in the 1970s as a potentialantidepressant but clinical development was not commenced and it was never marketed.[1] Pirandamine isstructurally related totandamine, which, in contrast, is a selectivenorepinephrine reuptake inhibitor.[1][3]
Pirandamine can be synthesized starting from1-indanone.[4] TheReformatsky reaction between 1-indanone (1) andethyl bromoacetate in the presence of zinc gives ethyl 2-(1-hydroxy-2,3-dihydroinden-1-yl)acetate (2). The reduction of the ester with ester withlithium aluminum hydride (LiAlH4) gives 1-(2-hydroxyethyl)-2,3-dihydroinden-1-ol (3). Acid-catalyzeddehydration then leads to indene-3-ethanol (4). Acid-catalyzedcondensation withethyl acetoacetate then gives (5). Thesaponification of the ester then gives the corresponding acid. The reaction of this withethyl chloroformate gives a mixed anhydride, and further reaction of this withdimethylamine then leads to the amide (6). Reduction with lithium aluminium hydride completes the synthesis of pirandamine (7).
