Iproniazid

Iproniazid
Clinical data
Trade names	Marsilid, others
AHFS/Drugs.com	International Drug Names
ATC code	N06AF05 (WHO) ;
Pharmacokinetic data
Bioavailability	1
Identifiers
	IUPAC name N-isopropylisonicotinohydrazide;
CAS Number	54-92-2 ;
PubChem CID	3748;
DrugBank	DB04818 ;
ChemSpider	3617 ;
UNII	D892HFI3XA;
KEGG	D02579 ;
ChEMBL	ChEMBL92401 ;
CompTox Dashboard (EPA)	DTXSID5023168 ;
ECHA InfoCard	100.000.199
Chemical and physical data
Formula	C9H13N3O
Molar mass	179.223 g·mol−1
3D model (JSmol)	Interactive image;
Density	1.084 g/cm3
Boiling point	265.9 °C (510.6 °F)
	SMILES O=C(NNC(C)C)c1ccncc1;
	InChI InChI=1S/C9H13N3O/c1-7(2)11-12-9(13)8-3-5-10-6-4-8/h3-7,11H,1-2H3,(H,12,13) ; Key:NYMGNSNKLVNMIA-UHFFFAOYSA-N ;
	(verify)

Iproniazid (Marsilid, Rivivol, Euphozid, Iprazid, Ipronid, Ipronin) is a non-selective, irreversible monoamine oxidase inhibitor (MAOI) of the hydrazine class.^[1]^[2] It is a xenobiotic that was originally designed to treat tuberculosis, but was later most prominently used as an antidepressant drug. However, it was withdrawn from the market because of its hepatotoxicity.^[3]^[4] The medical use of iproniazid was discontinued in most of the world in the 1960s, but remained in use in France until its discontinuation in 2015.

^ Maxwell RA, Eckhardt SB (1990). "Iproniazid". Drug Discovery. Humana Press. pp. 143–154. ISBN 9780896031807.
^ Fagervall I, Ross SB (April 1986). "Inhibition of monoamine oxidase in monoaminergic neurones in the rat brain by irreversible inhibitors". Biochemical Pharmacology. 35 (8): 1381–1387. doi:10.1016/0006-2952(86)90285-6. PMID 2870717.
^ Timbrell J (2008). Taylor & Francis Group. pp. 324–326. doi:10.3109/9781420007084. ISBN 978-0-8493-7302-2.
^ Henn F, Sartorius N, Helmchen H, Lauter H, eds. (2013-11-11). Contemporary Psychiatry. Springer Science & Business Media. p. 109. ISBN 9783642595196.

[bookDrug_discovery-1] Maxwell RA, Eckhardt SB (1990). "Iproniazid". Drug Discovery. Humana Press. pp. 143–154. ISBN 9780896031807.

[pmid2870717-2] Fagervall I, Ross SB (April 1986). "Inhibition of monoamine oxidase in monoaminergic neurones in the rat brain by irreversible inhibitors". Biochemical Pharmacology. 35 (8): 1381–1387. doi:10.1016/0006-2952(86)90285-6. PMID 2870717.

[Timbrell_2008-3] Timbrell J (2008). Taylor & Francis Group. pp. 324–326. doi:10.3109/9781420007084. ISBN 978-0-8493-7302-2.

[Henn_2013-4] Henn F, Sartorius N, Helmchen H, Lauter H, eds. (2013-11-11). Contemporary Psychiatry. Springer Science & Business Media. p. 109. ISBN 9783642595196.

[1]

[2]

[3]

[4]