Pirandamine information

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 ;
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;

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]

^ ^a ^b ^c Pugsley T, Lippmann W (May 1976). "Effects of tandamine and pirandamine, new potential antidepressants, on the brain uptake of norepinephrine and 5-hydroxytryptamine and related activities". Psychopharmacology. 47 (1): 33–41. doi:10.1007/BF00428698. PMID 1085452. S2CID 8354739.
^ Lippmann W, Pugsley TA (August 1976). "Pirandamine, a relatively selective 5-hydroxytryptamine uptake inhibitor". Pharmacological Research Communications. 8 (4): 387–405. doi:10.1016/0031-6989(76)90039-4. PMID 1088377.
^ ^a ^b Lippmann W, Seethaler K (April 1977). "Effects of tandamine and pirandamine, selective blockers of biogenic amine uptake mechanisms, on gastric acid secretion and ulcer formation in the rat". Life Sciences. 20 (8): 1393–400. doi:10.1016/0024-3205(77)90367-8. PMID 853871.

[pmid1085452-1] Pugsley T, Lippmann W (May 1976). "Effects of tandamine and pirandamine, new potential antidepressants, on the brain uptake of norepinephrine and 5-hydroxytryptamine and related activities". Psychopharmacology. 47 (1): 33–41. doi:10.1007/BF00428698. PMID 1085452. S2CID 8354739.

[pmid1088377-2] Lippmann W, Pugsley TA (August 1976). "Pirandamine, a relatively selective 5-hydroxytryptamine uptake inhibitor". Pharmacological Research Communications. 8 (4): 387–405. doi:10.1016/0031-6989(76)90039-4. PMID 1088377.

[pmid853871-3] Lippmann W, Seethaler K (April 1977). "Effects of tandamine and pirandamine, selective blockers of biogenic amine uptake mechanisms, on gastric acid secretion and ulcer formation in the rat". Life Sciences. 20 (8): 1393–400. doi:10.1016/0024-3205(77)90367-8. PMID 853871.

Pirandamine information

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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