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 ;
	(verify)

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.^[3] Along with tranylcypromine and isocarboxazid, phenelzine is one of the few non-selective and irreversible MAOIs still in widespread clinical use.^[4]

Synthesis of phenelzine was first described by Emil Votoček and Otakar Leminger in 1932.^[5]^[6]

^ "Phenelzine (Nardil) Use During Pregnancy". Drugs.com. 3 March 2020. Retrieved 11 July 2020.
^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.
^ "Phenelzine". MedlinePlus Drug Information. U.S. National Library of Medicine. Retrieved 27 October 2023.
^ Sidhu G, Marwaha R (2023). "Phenelzine". StatPearls. Treasure Island (FL): StatPearls Publishing. PMID 32119395. Retrieved 23 November 2023.
^ Budavari S, O'Neil, Smith A, Heckelman PE, Kinneary JF (1996). "Phenelzine". The Merck Index (12th ed.). Whitehouse Station: Merck & Co. 7181.
^ Votoček E, Leminger O (1932). "Sur la β-phenoéthylhydrazine" [On the [preparation and properties of] β-phenoethylhydrazine]. Collection of Czechoslovak Chemical Communications (in French). 4: 271–281. doi:10.1135/cccc19320271.