Pirandamine

Pirandamine (AY-23,713) is a tricyclic 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]

Pirandamine

Clinical data
Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: uncontrolled
Identifiers
IUPAC name N,N-dimethyl-2-(1-methyl-4,9-dihydro-3H-indeno[2,3-c]pyran-1-yl)ethanamine
CAS Number	42408-79-7 Y
PubChem CID	431429
ChemSpider	381558
UNII	WC6V8L1Z13
CompTox Dashboard (EPA)	DTXSID10866093
Chemical and physical data
Formula	C17H23NO
Molar mass	257.377 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC1(C2=C(CCO1)C3=CC=CC=C3C2)CCN(C)C
InChI InChI=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 Key:AMJPIGOYWBNJLP-UHFFFAOYSA-N

Synthesis

Pirandamine can be synthesized starting from 1-indanone.^[4] 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).

Pirandamine synthesis

See also

• Tandamine