Iproniazid

Iproniazid

Systematic (IUPAC) name
N'-isopropylisonicotinohydrazide
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy category	?
Legal status	?
Routes of administration	?
Pharmacokinetic data
Bioavailability	?
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Identifiers
CAS Number	54-92-2 Y
ATC code	N06AF05 (WHO)
PubChem	CID: 3748
DrugBank	DB04818 Y
ChemSpider	3617 Y
UNII	D892HFI3XA Y
KEGG	D02579 Y
ChEMBL	CHEMBL92401 Y
Chemical data
Formula	C9H13N3O
Molecular mass	179.219 g/mol
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) Y Key:NYMGNSNKLVNMIA-UHFFFAOYSA-N Y
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Iproniazid (Marsilid, Rivivol, Euphozid, Iprazid, Ipronid, Ipronin) is a non-selective, irreversible monoamine oxidase inhibitor (MAOI) of the hydrazine class. It was discontinued in most of the world in the 1960s, but remained in use in France up until fairly recently.

Iproniazid was originally developed for the treatment of tuberculosis, but in 1952, its antidepressant properties were discovered when researchers noted that patients given isoniazid became inappropriately happy. Subsequently N-isopropyl addition led to development as an antidepressant and was approved for use in 1958. It was withdrawn a few years later in 1961 due to a high incidence of hepatitis, and was replaced by less hepatotoxic drugs such as phenelzine and isocarboxazid.

Although iproniazid was one of the first antidepressants ever marketed, amphetamine (marketed as Benzedrine from 1935, for "mild depression", amid other indications) predates it; and frankincense has been marketed traditionally for millennia for, among other things, altering mood, although it was not until 2012 that one of the components of its smoke was found to have antidepressant effects in mice.

See also

• Hydrazine (antidepressant)
• Nialamide