Pirandamine

Not to be confused with Prindamine.

Pirandamine

Systematic (IUPAC) name
N,N-dimethyl-2-(1-methyl-4,9-dihydro-3H-indeno[2,3-c]pyran-1-yl)ethanamine
Clinical data
Legal status	Uncontrolled
Routes of administration	Oral
Identifiers
CAS Number	57932-12-4
ATC code	none
PubChem	CID: 431429
ChemSpider	381558
UNII	WC6V8L1Z13 Y
Chemical data
Formula	C17H23NO
Molecular mass	257.37 g/mol
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

Pirandamine (AY-23,713) is a tricyclic derivative which acts as a selective serotonin reuptake inhibitor (SSRI). 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 synthesis:

Condesation of 1-indanone (1) with ethyl bromoacetate and zinc addords Reformatsky reaction product 2; then reduction with LiAlH4 gives diol 3. Dehydration with H2SO4 gives the indene ethanol 4. Acid catalyzed condensation of 4 with ethyl acetoacetate then gives the fused tetrahydropyran derivative 5 (no doubt by a scheme quite analogous to prodolic acid). The ester is then saponified to the corresponding acid, which is then converted to the dimethylamide (6). Reduction with LiAlH4 completes the synthesis of the antidepressant agent pirandamine (7).

See also

• Tandamine
• Prindamine (21489-22-5) This interesting chemical is exactly the same as talopram but for the oxygen atom that is replaced by a methine group.