ContaminantDB: Phenelzine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (11)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:38 UTC

Update Date

2026-05-14 16:48:41 UTC

Accession Number

CHEM002272

Identification

Common Name

Phenelzine

Class

Small Molecule

Description

Phenelzine is only found in individuals that have used or taken this drug. It is an irreversible non-selective inhibitor of monoamine oxidase. May be used to treat major depressive disorder.Although the exact mechanism of action has not been determined, it appears that the irreversible, nonselective inhibition of MAO by phenelzine relieves depressive symptoms by causing an increase in the levels of serotonin, norepinephrine, and dopamine in the neuron.

Contaminant Sources

HMDB Contaminants - Urine
IARC Carcinogens Group 3
T3DB toxins

Contaminant Type

Amine
Antidepressant
Antidepressive Agent
Drug
Human Neurotoxin
Hydrazine
Metabolite
Monoamine Oxidase Inhibitor
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Nardil	HMDB
2 Phenethylhydrazine	HMDB
2-Phenethylhydrazine	HMDB
Nardelzine	HMDB
beta Phenylethylhydrazine	HMDB
Phenelzine sulfate	HMDB
Parke davis brand OF phenelzine sulfate	HMDB
Phenethylhydrazine	HMDB
beta-Phenylethylhydrazine	HMDB
Fenelzin	HMDB
Pfizer brand OF phenelzine sulfate	HMDB
Sulfate, phenelzine	HMDB
United drug brand OF phenelzine sulfate	HMDB
Warner chilcott brand OF phenelzine sulfate	HMDB

Chemical Formula

C₈H₁₂N₂

Average Molecular Mass

136.194 g/mol

Monoisotopic Mass

136.100 g/mol

CAS Registry Number

51-71-8

IUPAC Name

(2-phenylethyl)hydrazine

Traditional Name

phenelzine

SMILES

NNCCC1=CC=CC=C1

InChI Identifier

InChI=1S/C8H12N2/c9-10-7-6-8-4-2-1-3-5-8/h1-5,10H,6-7,9H2

InChI Key

RMUCZJUITONUFY-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Not Available

Direct Parent

Benzene and substituted derivatives

Alternative Parents

Substituents

Monocyclic benzene moiety
Alkylhydrazine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Hydrazine derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

primary amine (CHEBI:8060 )
a small molecule (CPD-13895 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	< 25°C
Boiling Point	74°C at 1.00E-01 mm Hg
Solubility	29.1 g/L

Predicted Properties

Property	Value	Source
Water Solubility	11.1 g/L	ALOGPS
logP	1.2	ALOGPS
logP	1.2	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Basic)	5.55	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	38.05 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	54.26 m³·mol⁻¹	ChemAxon
Polarizability	15.8 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4l-9800000000-fec970db2245559d8531	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4l-9800000000-fec970db2245559d8531	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0007-9200000000-b2c57d1368223a96c523	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-01t9-0592000000-92a48c620c961fdb430f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0a4i-0900000000-cf09dbe619ab21f16ce0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0a4i-2900000000-fcb3587623714354e760	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-6c9dda205486ea199582	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-1900000000-d6caecbd05b28ce80778	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9200000000-e6be767f746d7eec77ba	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-1900000000-97c518b056fc3f0c5992	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-4900000000-6d2d5af23910f83be107	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0kx3-9600000000-9577503e15a41993941b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-5ca1a374df7ceed01896	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-3900000000-9f4b820ee530441e453f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004l-9100000000-40882216bbd046d0ab4e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-e9776c924504e8fd7ea8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052f-6900000000-27086fbc61d9efcf4d5a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9100000000-f3ed866d0f02ae18d439	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-9000000000-833e467e14c48ae4f6b3	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Readily absorbed after oral administration.

Mechanism of Toxicity

Although the exact mechanism of action has not been determined, it appears that the irreversible, nonselective inhibition of MAO by phenelzine relieves depressive symptoms by causing an increase in the levels of serotonin, norepinephrine, and dopamine in the neuron.

Metabolism

Hepatic. Acetylation of phenelzine appears to be a minor metabolic pathway. Beta-phenylethylamine is a metabolite of phenelzine, and there is indirect evidence that phenelzine may also be ring-hydroxylated and N-methylated. Route of Elimination: NARDIL® is extensively metabolized, primarily by oxidation via monoamine oxidase. Half Life: 1.2-11.6 hours following single dose administration. Multiple-dose pharmacokinetics have not been studied.

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

3, not classifiable as to its carcinogenicity to humans. (3)

Uses/Sources

For the treatment of major depressive disorder. Has also been used with some success in the management of bulimia nervosa.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Symptoms of overdose include drowsiness, dizziness, faintness, irritability, hyperactivity, agitation, severe headache, hallucinations, trismus, opisthotonos, convulsions and coma, rapid and irregular pulse, hypertension, hypotension and vascular collapse, precordial pain, respiratory depression and failure, hyperpyrexia, diaphoresis, and cool, clammy skin.

Treatment

Intensive symptomatic and supportive treatment may be required. Induction of emesis or gastric lavage with instillation of charcoal slurry may be helpful in early poisoning, provided the airway has been protected against aspiration. Signs and symptoms of central nervous system stimulation, including convulsions, should be treated with diazepam, given slowly intravenously. Phenothiazine derivatives and central nervous system stimulants should be avoided. Hypotension and vascular collapse should be treated with intravenous fluids and, if necessary, blood pressure titration with an intravenous infusion of dilute pressor agent. It should be noted that adrenergic agents may produce a markedly increased pressor response. Respiration should be supported by appropriate measures, including management of the airway, use of supplemental oxygen, and mechanical ventilatory assistance, as required. Body temperature should be monitored closely. Intensive management of hyperpyrexia may be required. Maintenance of fluid and electrolyte balance is essential. (5)

Concentrations

Not Available

External Links

DrugBank ID

DB00780

HMDB ID

HMDB0014918

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID