Pirandamine
{{Short description|Chemical compound}}
{{Drugbox
| IUPAC_name = N,N-dimethyl-2-(1-methyl-4,9-dihydro-3H-indeno[2,3-c]pyran-1-yl)ethanamine
| image = Pirandamine.png
| image_class = skin-invert-image
| tradename =
| pregnancy_category =
| legal_status = Uncontrolled
| routes_of_administration = Oral
| bioavailability =
| metabolism =
| elimination_half-life =
| excretion =
| CAS_number = 42408-79-7
| CAS_number_Ref = {{cascite|correct|CAS}}
| ATC_prefix = none
| ATC_suffix =
| PubChem = 431429
| ChemSpiderID = 381558
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = WC6V8L1Z13
| C=17 | H=23 | N=1 | O=1
| smiles = CC1(C2=C(CCO1)C3=CC=CC=C3C2)CCN(C)C
| StdInChI = 1S/C17H23NO/c1-17(9-10-18(2)3)16-12-13-6-4-5-7-14(13)15(16)8-11-19-17/h4-7H,8-12H2,1-3H3
| StdInChIKey = AMJPIGOYWBNJLP-UHFFFAOYSA-N
}}
Pirandamine (AY-23,713) is a tricyclic derivative which acts as a selective serotonin reuptake inhibitor (SSRI).{{cite journal | vauthors = Pugsley T, Lippmann W | title = Effects of tandamine and pirandamine, new potential antidepressants, on the brain uptake of norepinephrine and 5-hydroxytryptamine and related activities | journal = Psychopharmacology | volume = 47 | issue = 1 | pages = 33–41 |date=May 1976 | pmid = 1085452 | doi = 10.1007/BF00428698| s2cid = 8354739 }}{{cite journal | vauthors = Lippmann W, Pugsley TA | title = Pirandamine, a relatively selective 5-hydroxytryptamine uptake inhibitor | journal = Pharmacological Research Communications | volume = 8 | issue = 4 | pages = 387–405 |date=August 1976 | pmid = 1088377 | doi = 10.1016/0031-6989(76)90039-4}}{{cite journal | vauthors = Lippmann W, Seethaler K | title = Effects of tandamine and pirandamine, selective blockers of biogenic amine uptake mechanisms, on gastric acid secretion and ulcer formation in the rat | journal = Life Sciences | volume = 20 | issue = 8 | pages = 1393–400 |date=April 1977 | pmid = 853871 | doi = 10.1016/0024-3205(77)90367-8}} It was investigated in the 1970s as a potential antidepressant but clinical development was not commenced and it was never marketed. Pirandamine is structurally related to tandamine, which, in contrast, is a selective norepinephrine reuptake inhibitor.
Synthesis
Pirandamine can be synthesized starting from 1-indanone.I. Jirkovsky, L. G. Humber and R. Noureldin,Eur. J. Med. Chem., 11, 571 (1976). The Reformatsky reaction between 1-indanone (1) and ethyl 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 with lithium aluminum hydride (LiAlH4) gives 1-(2-hydroxyethyl)-2,3-dihydroinden-1-ol (3). Acid-catalyzed dehydration then leads to indene-3-ethanol (4). Acid-catalyzed condensation with ethyl acetoacetate then gives (5). The saponification of the ester then gives the corresponding acid. The reaction of this with ethyl chloroformate gives a mixed anhydride, and further reaction of this with dimethylamine then leads to the amide (6). Reduction with lithium aluminium hydride completes the synthesis of pirandamine (7).
See also
References
{{Reflist|2}}
{{Antidepressants}}
{{Anxiolytics}}
{{Monoamine reuptake inhibitors}}
{{Tricyclics}}