Phenelzine

Phenelzine
Clinical data
Trade names	Nardil, others
Other names	2-Phenylethylhydrazine; β-Phenylethylhydrazine; Phenethylhydrazine; Phenylethylhydrazine; Phenylethylamine hydrazide; Phenethylamine hydrazide; β-Hydrazinoethylbenzene; Fenelzine; 1-(2-Phenylethyl)hydrazine
AHFS/Drugs.com	Monograph
MedlinePlus	a682089
License data	US DailyMed: Phenelzine;
Pregnancy; category	AU: B3;
Routes of; administration	By mouth
Drug class	Monoamine oxidase inhibitor; Antidepressant
ATC code	N06AF03 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C1 (Other controlled substances); US: ℞-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Metabolism	Liver
Elimination half-life	11.6 hours
Excretion	Urine
Identifiers
	IUPAC name 2-phenylethylhydrazine;
CAS Number	51-71-8 ;
PubChem CID	3675;
IUPHAR/BPS	7266;
DrugBank	DB00780 ;
ChemSpider	3547 ;
UNII	O408N561GF;
KEGG	D08349 ;
ChEMBL	ChEMBL1089 ;
CompTox Dashboard (EPA)	DTXSID2041094 ;
ECHA InfoCard	100.000.108
Chemical and physical data
Formula	C8H12N2
Molar mass	136.198 g·mol−1
3D model (JSmol)	Interactive image;
Boiling point	74 °C (165 °F)
	SMILES N(N)CCc1ccccc1;
	InChI InChI=1S/C8H12N2/c9-10-7-6-8-4-2-1-3-5-8/h1-5,10H,6-7,9H2 ; Key:RMUCZJUITONUFY-UHFFFAOYSA-N ;
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Phenelzine, sold under the brand name Nardil among others, is a non-selective and irreversible monoamine oxidase inhibitor (MAOI) of the hydrazine family which is primarily used as an antidepressant and anxiolytic to treat depression and anxiety. Along with tranylcypromine and isocarboxazid, phenelzine is one of the few non-selective and irreversible MAOIs still in widespread clinical use.

Synthesis of phenelzine was first described by Emil Votoček and Otakar Leminger in 1932.