Pirandamine
Source: Wikipedia, the free encyclopedia.
Chemical compound
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Routes of administration | Oral |
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Pirandamine (AY-23,713) is a
derivative which acts as a selective serotonin reuptake inhibitor (SSRI).[1][2][3] It was investigated in the 1970s as a potential antidepressant but clinical development was not commenced and it was never marketed.[1] Pirandamine is structurally related to tandamine, which, in contrast, is a selective norepinephrine reuptake inhibitor.[1][3]
Synthesis
The
1-indanone [83-33-0] (1) and ethyl bromoacetate [105-36-2] in the presence of zinc gives ethyl 2-(1-hydroxy-2,3-dihydroinden-1-yl)acetate [1620-02-6] (2). The reduction of the ester with ester with LiAlH4 gives 1-(2-hydroxyethyl)-2,3-dihydroinden-1-ol, CID:130147665 (3). Acid catalyzed dehydration then leads to indene-3-ethanol [57931-97-2] (4'). Acid catalyzed condensation with ethyl acetoacetate [141-97-9] then gives CID:53692067
(5) The saponification of the ester to the corresponding acid [52001-26-0]. The reaction of this with ethyl chloroformate would give a mixed anhydride, and further reaction of this with dimethylamine then led to the amide [52001-28-2] (6). Reduction with lithium aluminium hydride completes the synthesis of pirandamine (7).
See also
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SNRIs Tooltip Serotonin–norepinephrine reuptake inhibitors | ||
NRIs Tooltip Norepinephrine reuptake inhibitors | ||
NDRIs Tooltip Norepinephrine–dopamine reuptake inhibitors | ||
NaSSAs Tooltip Noradrenergic and specific serotonergic antidepressants | ||
SARIs Tooltip Serotonin antagonist and reuptake inhibitors | ||
SMS Tooltip Serotonin modulator and stimulators | ||
Others |
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TCAs Tooltip Tricyclic antidepressants |
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TeCAs Tooltip Tetracyclic antidepressants | ||
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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Antidepressants (Tricyclic antidepressants (TCAs)) |
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Antihistamines |
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Antipsychotics |
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