PHENELZINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H12N2
Molecular Weight	136.1943
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NNCCC1=CC=CC=C1

InChI

InChIKey=RMUCZJUITONUFY-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C8H12N2
Molecular Weight	136.1943
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.drugbank.ca/drugs/DB00780
Curator's Comment: Description was created based on several sources, including https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/011909s038lbl.pdf

Phenelzine is an irreversible non-selective inhibitor of monoamine oxidase. 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. Phenelzine is used for the treatment of major depressive disorder. Has also been used with some success in the management of bulimia nervosa.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Monoamine oxidase A 52 Target ID: CHEMBL1951 Sources: http://www.drugbank.ca/drugs/DB00780	Inhibitor 8504
Monoamine oxidase B 75 Target ID: CHEMBL2039 Sources: http://www.drugbank.ca/drugs/DB00780	Inhibitor 8504
Monoamine oxidase B 75 Target ID: CHEMBL2993 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11591508	Inhibitor 8504	76.3 nM [IC50]
Monoamine oxidase A 52 Target ID: CHEMBL3358 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11591508	Inhibitor 8504	30.0 nM [IC50]
Cytochrome P450 2C19 51 Target ID: CHEMBL3622 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16669850	Inhibitor 8504
Cytochrome P450 3A 22 Target ID: CHEMBL2364675 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16669850	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Depression 240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/011909s038lbl.pdf	Primary		Approved 8583	Nardil Approved Use Nardil is used for: Treating depression in patients who do not respond well to other medicines. Launch Date 1961

C_max

Value	Dose	Co-administered	Analyte	Population
19.8 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/011909s038lbl.pdf	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:		PHENELZINE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN
10.14 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/27085800	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:		PHENELZINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
384.2 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/27085800	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:		PHENELZINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
11.6 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/011909s038lbl.pdf	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:		PHENELZINE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN
9.75 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/27085800	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:		PHENELZINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
750 mg single, oral Overdose Dose: 750 mg Route: oral Route: single Dose: 750 mg Sources: https://pubmed.ncbi.nlm.nih.gov/14489944	unhealthy, 20 Health Status: unhealthy Age Group: 20 Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/14489944	Disc. AE: Weakness, Lethargy... AEs leading to discontinuation/dose reduction: Weakness Lethargy Dizziness Gait abnormal NOS Restlessness Grand mal seizure Hyperreflexia Coma Depression central nervous system Sources: https://pubmed.ncbi.nlm.nih.gov/14489944
2760 mg single, oral Overdose Dose: 2760 mg Route: oral Route: single Dose: 2760 mg Sources: https://pubmed.ncbi.nlm.nih.gov/17823790	unhealthy, 23 Health Status: unhealthy Age Group: 23 Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/17823790	Disc. AE: Depressed level of consciousness, Seizures... AEs leading to discontinuation/dose reduction: Depressed level of consciousness Seizures Tachycardia Acute myocarditis (grade 5) Sources: https://pubmed.ncbi.nlm.nih.gov/17823790
225 mg single, oral Overdose Dose: 225 mg Route: oral Route: single Dose: 225 mg Sources: https://pubmed.ncbi.nlm.nih.gov/6391305	unhealthy, 26 Health Status: unhealthy Age Group: 26 Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/6391305	Disc. AE: Muscular tone excessive, Hyperthermia... AEs leading to discontinuation/dose reduction: Muscular tone excessive Hyperthermia (severe) Coma Cardiovascular collapse Acute renal failure Hemolysis Rhabdomyolysis Disseminated intravascular coagulation Sources: https://pubmed.ncbi.nlm.nih.gov/6391305
90 mg 1 times / day multiple, oral Recommended Dose: 90 mg, 1 times / day Route: oral Route: multiple Dose: 90 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/011909s038lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/011909s038lbl.pdf	Disc. AE: Suicidal ideation... AEs leading to discontinuation/dose reduction: Suicidal ideation Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/011909s038lbl.pdf
90 mg 1 times / day multiple, oral Recommended Dose: 90 mg, 1 times / day Route: oral Route: multiple Dose: 90 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/011909s038lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/011909s038lbl.pdf	Disc. AE: Crisis hypertensive... AEs leading to discontinuation/dose reduction: Crisis hypertensive Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/011909s038lbl.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C8 1057 CYP1A2 2153 CYP2C19 2057 CYP3A 227 CYP3A5 136 CYP3A7 7 CYP2A6 879 CYP2E1 1060 P-gp 1741 BSEP 550 OATP1B1 1079 OATP1B3 961

Drug as perpetrator

Target	Modality	Activity
CYP2A6 911	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEwODkifX0%3D	no [IC50 >10 uM]
CYP2E1 1146	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEwODkifX0%3D	no [IC50 >10 uM]
P-gp 1932	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16997908/	no
BSEP 554	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22961681/	unlikely [IC50 >897.2 uM]
CYP2C8 1117	inhibitor 4027 Sources: https://go.drugbank.com/drugs/DB00780\| https://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=biology&ligandId=7266	yes [Ki 1.2 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16669850/\| https://pubmed.ncbi.nlm.nih.gov/22931300/	yes
CYP2C19 2141	inhibitor 4027 Sources: https://go.drugbank.com/drugs/DB00780\| https://pubmed.ncbi.nlm.nih.gov/16669850/, https://pubmed.ncbi.nlm.nih.gov/22931300/	yes
CYP2C9 2497	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16669850/\| https://pubmed.ncbi.nlm.nih.gov/22931300/	yes
CYP2D6 2546	inhibitor 4027 Sources: https://go.drugbank.com/drugs/DB00780\| https://pubmed.ncbi.nlm.nih.gov/16669850/, https://pubmed.ncbi.nlm.nih.gov/22931300/	yes
CYP3A 317	inhibitor 4027 Sources: https://go.drugbank.com/drugs/DB00780\| https://pubmed.ncbi.nlm.nih.gov/16669850/	yes
CYP3A4 2633	inhibitor 4027 Sources: https://go.drugbank.com/drugs/DB00780\| https://pubmed.ncbi.nlm.nih.gov/22931300/	yes
CYP3A5 201	inhibitor 4027 Sources: https://go.drugbank.com/drugs/DB00780 \| https://pubmed.ncbi.nlm.nih.gov/16669850/	yes
CYP3A7 22	inhibitor 4027 Sources: https://go.drugbank.com/drugs/DB00780 \| https://pubmed.ncbi.nlm.nih.gov/16669850/	yes
OATP1B1 1095	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23571415/	yes
OATP1B3 970	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23571415/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTA4OSJ9fQ%3D%3D

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B3-036093	http://www.3bsc.com/index/pro_info.php?id=58125
AA Blocks	AA00I926	https://www.aablocks.com/goods/Goods/detail?id=AA00I926
abcr GmbH	AB200546	http://www.abcr.com/shop/en/AB200546
AHH Chemical co.,ltd	MT-20901	http://www.ahhchemical.com/product/MT-20901.html
AK Scientific, Inc. (AKSCI)	4752AE	http://www.aksci.com/item_detail.php?cat=4752AE
Alfa Chemistry	51-71-8	https://www.alfa-chemistry.com/phenelzine-cas-51-71-8-item-168473.htm
Alichem	250001552	http://www.alichem.com/en/products/51-71-8.html
Ambinter	Amb1117029	http://www.ambinter.com/reference/1117029
Angel Pharmatech	AG199778	http://www.angelpharmatech.com/51-71-8.html
Angene	AGN-PC-0JK6MF	http://www.angenechemical.com/productshow/AGN-PC-0JK6MF.html
Aurora Fine Chemicals LLC	A00.215.116	http://online.aurorafinechemicals.com/info?ID=A00.215.116
BLD Pharm	BD44517	http://www.bldpharm.com/products/51-71-8.html
Capot Chemical	16246	http://www.capotchem.com/en/16246.htm
Capot Chemical	PubChem16246	http://www.capotchem.com/en/16246.htm
Chem Scene	CS-4532	http://www.chemscene.com/51-71-8.html
ChemMol	49417192	http://www.chemmol.com/chemmol/49417192.html
CSNpharm	CSN16899	https://www.csnpharm.com/products/phenelzine.html
Debye Scientific	DB-052010	http://www.debyesci.com/cas_51-71-8.html
Finetech	FT-0631225	http://www.finetechnology-ind.com/prod/detail/pub/51-71-8.html
Hairui	HR100277	http://www.hairuichem.com/en/product/51-71-8.html
iChemical	EBD46347	http://www.ichemical.com/products/51-71-8.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
Lab Network	LN00126164	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00126164
Matrix Scientific	20638	https://www.matrixscientific.com/020638.html
mcule	MCULE-2911295500	https://mcule.com/MCULE-2911295500/
MedChem Express	HY-B1018	https://www.medchemexpress.com/Phenelzine.html
MuseChem	I003863	https://www.musechem.com/product/I003863.html
OChem	4816	http://www.ocheminc.com/index.php?act=psearch&pid=047P825
Sigma-Aldrich	CDS021446_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/cds021446?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S017495	http://www.sinfoobiotech.com/product/1020893
Smolecule	S568415	https://www.smolecule.com/products/s568415
THE BioTek	bt-315150	https://www.thebiotek.com/product/others/bt-315150

PubMed

Title	Date	PubMed
Antidepressant therapy in tinnitus.	2007-04	16973315
Successful use of phenelzine in treatment-resistant panic disorder.	2007-02	17335337
Serotonin syndrome from the interaction of cyclobenzaprine with other serotoninergic drugs.	2006-12	17122225
Rapid identification of P-glycoprotein substrates and inhibitors.	2006-12	16997908
Aldehyde load in ischemia-reperfusion brain injury: neuroprotection by neutralization of reactive aldehydes with phenelzine.	2006-11-29	17026969
Increased nicotine self-administration following prenatal exposure in female rats.	2006-11	17196243
Modeling anxiety-like states: pharmacological characterization of the chick separation stress paradigm.	2006-11	17021390
Sustained effects of phenelzine and tranylcypromine on orthostatic challenge in antidepressant-refractory depression.	2006-10	16974207
Antidepressants and inflammatory bowel disease: a systematic review.	2006-09-20	16984660
Monoamine oxidase inhibitors allow locomotor and rewarding responses to nicotine.	2006-08	16395299
13C magnetic resonance spectroscopy studies of alterations in glutamate neurotransmission.	2006-05-15	16199016
Tamoxifen protect against hydroxyl radical generation induced by phenelzine in rat striatum.	2006-05-01	16500014
An evaluation of potential mechanism-based inactivation of human drug metabolizing cytochromes P450 by monoamine oxidase inhibitors, including isoniazid.	2006-05	16669850
Transdermal selegiline: the new generation of monoamine oxidase inhibitors.	2006-05	16641841
Leading the way: advances in the diagnosis, treatment, and management of neuropsychiatric illnesses.	2006-05	16641838
Use of antidepressant medications in relation to the incidence of breast cancer.	2006-04-10	16523201
Effects of monoamine oxidase inhibitors on cocaine discrimination in rats.	2006-03	16495723
Quetiapine for insomnia associated with refractory depression exacerbated by phenelzine.	2006-03	16478812
Treatment of depression with atypical features: a meta-analytic approach.	2006-01-30	16321446
The effect of antidepressants on glucose homeostasis and insulin sensitivity: synthesis and mechanisms.	2006-01	16370964
Traumatic stress: effects on the brain.	2006	17290802
Pharmacotherapy of social anxiety disorder: what does the evidence tell us?	2006	17092192
Antidepressants reverse corticosterone-mediated decrease in brain-derived neurotrophic factor expression: differential regulation of specific exons by antidepressants and corticosterone.	2006	16500030
Cytochrome p450 enzymes mechanism based inhibitors: common sub-structures and reactivity.	2005-10	16248836
A selective test for antidepressant treatments using rats bred for stress-induced reduction of motor activity in the swim test.	2005-10	16047194
Screening antidepressants in the chick separation-stress paradigm.	2005-08	15778882
A microarray study of MPP+-treated PC12 Cells: Mechanisms of toxicity (MOT) analysis using bioinformatics tools.	2005-07-15	16026605
Inhibition of monoamine oxidase-A activity in rat brain by synthetic hydrazines: structure-activity relationship (SAR).	2005-06	16119198
Remission rates with 3 consecutive antidepressant trials: effectiveness for depressed outpatients.	2005-06	15960558
Shy-Drager syndrome: multisystem atrophy with comorbid depression.	2005-03-16	15765825
Chronic treatment with the monoamine oxidase inhibitor phenelzine increases hypothalamic-pituitary-adrenocortical activity in male C57BL/6 mice: relevance to atypical depression.	2005-03	15564336
Validity of sudden gains in acute phase treatment of depression.	2005-02	15709845
Brainstem levels of transcription factor AP-2 in rat are changed after treatment with phenelzine, but not with citalopram.	2005-01-21	15663788
Contribution of sleep research to the development of new antidepressants.	2005	16416706
Sleep and psychiatry.	2005	16416705
Neuroendocrine predictors of the evolution of depression.	2005	16156385
In vivo evidence for reduced cortical glutamate-glutamine cycling in rats treated with the antidepressant/antipanic drug phenelzine.	2005	16154287
Herb-drug interactions: a literature review.	2005	15916450
Social anxiety disorder : current treatment recommendations.	2005	15907150
Mechanism-based inactivation of human cytochrome P4502C8 by drugs in vitro.	2004-12	15304522
[Neurobiology and pharmacotherapy of social phobia].	2004-11-13	15538306
Efficacy and tolerability of tranylcypromine versus phenelzine: a double-blind study in antidepressant-refractory depressed inpatients.	2004-11	15554763
Effect of antidepressants on GABA(B) receptor function and subunit expression in rat hippocampus.	2004-10-15	15451391
Monoamine oxidase inhibitors, their structural analogues, and neuroprotection.	2004-09	15462176
Modafinil augmentation of phenelzine for residual fatigue in dysthymia.	2004-09	15337670
Efficacy of quality criteria to identify potentially harmful information: a cross-sectional survey of complementary and alternative medicine web sites.	2004-06-29	15249270
Hypericum perforatum L (St John's wort) preferentially increases extracellular dopamine levels in the rat prefrontal cortex.	2004-06	15148244
Phenylethylidenehydrazine, a novel GABA-transaminase inhibitor, reduces epileptiform activity in rat hippocampal slices.	2004	15207360
Depression after cyproheptadine: MAO treatment.	1992-06-01	1525285
Phenelzine associated peripheral neuropathy--clinical and electrophysiologic findings.	1991-06	1659356

Patents

Sample Use Guides

In Vivo Use Guide

Initial dose: The usual starting dose of NARDIL is one tablet (15 mg) three times a day. Early phase treatment: Dosage should be increased to at least 60 mg per day at a fairly rapid pace consistent with patient tolerance. It may be necessary to increase dosage up to 90 mg per day to obtain sufficient MAO inhibition. Many patients do not show a clinical response until treatment at 60 mg has been continued for at least 4 weeks.

Route of Administration: Oral

In Vitro Use Guide

20 uM of Phenelzine inactivated all human liver microsomal CYP (CYP1A2, CYP2C9, CYP2C19, CYP2D6 and CYP3A) but were most potent toward CYP3A and CYP2C19

Substance Class	Chemical Created by `admin` on `Wed Apr 02 07:05:54 GMT 2025` Edited by `admin` on `Wed Apr 02 07:05:54 GMT 2025`
Record UNII	O408N561GF
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PHENELZINE

Official Name

English

PHENELZINE [MI]

Preferred Name

English

PHENETHYLHYDRAZINE

Systematic Name

English

HYDRAZINE, (2-PHENYLETHYL)-

Systematic Name

English

PHENELZINE [VANDF]

Common Name

English

Phenelzine [WHO-DD]

Common Name

English

phenelzine [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C667