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
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
DescriptionSources: http://www.drugbank.ca/drugs/DB00780Curator's Comment: Description was created based on several sources, including
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/011909s038lbl.pdf
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
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1951 Sources: http://www.drugbank.ca/drugs/DB00780 |
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Target ID: CHEMBL2039 Sources: http://www.drugbank.ca/drugs/DB00780 |
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Target ID: CHEMBL2993 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11591508 |
76.3 nM [IC50] | ||
Target ID: CHEMBL3358 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11591508 |
30.0 nM [IC50] | ||
Target ID: CHEMBL3622 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16669850 |
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Target ID: CHEMBL2364675 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16669850 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Nardil Approved UseNardil is used for:
Treating depression in patients who do not respond well to other medicines. Launch Date-2.70345601E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
19.8 ng/mL |
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 |
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 |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
11.6 h |
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 |
Doses
Dose | Population | Adverse events |
---|---|---|
750 mg single, oral Overdose |
unhealthy, 20 n = 1 Health Status: unhealthy Condition: Depression Age Group: 20 Sex: F Population Size: 1 Sources: |
Disc. AE: Weakness, Lethargy... AEs leading to discontinuation/dose reduction: Weakness Sources: Lethargy Dizziness Gait abnormal NOS Restlessness Grand mal seizure Hyperreflexia Coma Depression central nervous system |
2760 mg single, oral Overdose Dose: 2760 mg Route: oral Route: single Dose: 2760 mg Co-administed with:: olanzapine, p.o(50 mg; single) Sources: Page: p.1007 |
unhealthy, 23 n = 1 Health Status: unhealthy Condition: Depression Age Group: 23 Sex: F Population Size: 1 Sources: Page: p.1007 |
Disc. AE: Depressed level of consciousness, Seizures... AEs leading to discontinuation/dose reduction: Depressed level of consciousness Sources: Page: p.1007Seizures Tachycardia Acute myocarditis (grade 5) |
225 mg single, oral Overdose Dose: 225 mg Route: oral Route: single Dose: 225 mg Sources: Page: p.1137/99 |
unhealthy, 26 n = 1 Health Status: unhealthy Condition: Depression Age Group: 26 Sex: F Population Size: 1 Sources: Page: p.1137/99 |
Disc. AE: Muscular tone excessive, Hyperthermia... AEs leading to discontinuation/dose reduction: Muscular tone excessive Sources: Page: p.1137/99Hyperthermia (severe) Coma Cardiovascular collapse Acute renal failure Hemolysis Rhabdomyolysis Disseminated intravascular coagulation |
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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Depression Sources: Page: p.1 |
Disc. AE: Suicidal ideation... AEs leading to discontinuation/dose reduction: Suicidal ideation Sources: Page: p.1 |
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: Page: p.6 |
unhealthy Health Status: unhealthy Condition: Depression Sources: Page: p.6 |
Disc. AE: Crisis hypertensive... AEs leading to discontinuation/dose reduction: Crisis hypertensive Sources: Page: p.6 |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Coma | Disc. AE | 750 mg single, oral Overdose |
unhealthy, 20 n = 1 Health Status: unhealthy Condition: Depression Age Group: 20 Sex: F Population Size: 1 Sources: |
Depression central nervous system | Disc. AE | 750 mg single, oral Overdose |
unhealthy, 20 n = 1 Health Status: unhealthy Condition: Depression Age Group: 20 Sex: F Population Size: 1 Sources: |
Dizziness | Disc. AE | 750 mg single, oral Overdose |
unhealthy, 20 n = 1 Health Status: unhealthy Condition: Depression Age Group: 20 Sex: F Population Size: 1 Sources: |
Gait abnormal NOS | Disc. AE | 750 mg single, oral Overdose |
unhealthy, 20 n = 1 Health Status: unhealthy Condition: Depression Age Group: 20 Sex: F Population Size: 1 Sources: |
Grand mal seizure | Disc. AE | 750 mg single, oral Overdose |
unhealthy, 20 n = 1 Health Status: unhealthy Condition: Depression Age Group: 20 Sex: F Population Size: 1 Sources: |
Hyperreflexia | Disc. AE | 750 mg single, oral Overdose |
unhealthy, 20 n = 1 Health Status: unhealthy Condition: Depression Age Group: 20 Sex: F Population Size: 1 Sources: |
Lethargy | Disc. AE | 750 mg single, oral Overdose |
unhealthy, 20 n = 1 Health Status: unhealthy Condition: Depression Age Group: 20 Sex: F Population Size: 1 Sources: |
Restlessness | Disc. AE | 750 mg single, oral Overdose |
unhealthy, 20 n = 1 Health Status: unhealthy Condition: Depression Age Group: 20 Sex: F Population Size: 1 Sources: |
Weakness | Disc. AE | 750 mg single, oral Overdose |
unhealthy, 20 n = 1 Health Status: unhealthy Condition: Depression Age Group: 20 Sex: F Population Size: 1 Sources: |
Depressed level of consciousness | Disc. AE | 2760 mg single, oral Overdose Dose: 2760 mg Route: oral Route: single Dose: 2760 mg Co-administed with:: olanzapine, p.o(50 mg; single) Sources: Page: p.1007 |
unhealthy, 23 n = 1 Health Status: unhealthy Condition: Depression Age Group: 23 Sex: F Population Size: 1 Sources: Page: p.1007 |
Seizures | Disc. AE | 2760 mg single, oral Overdose Dose: 2760 mg Route: oral Route: single Dose: 2760 mg Co-administed with:: olanzapine, p.o(50 mg; single) Sources: Page: p.1007 |
unhealthy, 23 n = 1 Health Status: unhealthy Condition: Depression Age Group: 23 Sex: F Population Size: 1 Sources: Page: p.1007 |
Tachycardia | Disc. AE | 2760 mg single, oral Overdose Dose: 2760 mg Route: oral Route: single Dose: 2760 mg Co-administed with:: olanzapine, p.o(50 mg; single) Sources: Page: p.1007 |
unhealthy, 23 n = 1 Health Status: unhealthy Condition: Depression Age Group: 23 Sex: F Population Size: 1 Sources: Page: p.1007 |
Acute myocarditis | grade 5 Disc. AE |
2760 mg single, oral Overdose Dose: 2760 mg Route: oral Route: single Dose: 2760 mg Co-administed with:: olanzapine, p.o(50 mg; single) Sources: Page: p.1007 |
unhealthy, 23 n = 1 Health Status: unhealthy Condition: Depression Age Group: 23 Sex: F Population Size: 1 Sources: Page: p.1007 |
Acute renal failure | Disc. AE | 225 mg single, oral Overdose Dose: 225 mg Route: oral Route: single Dose: 225 mg Sources: Page: p.1137/99 |
unhealthy, 26 n = 1 Health Status: unhealthy Condition: Depression Age Group: 26 Sex: F Population Size: 1 Sources: Page: p.1137/99 |
Cardiovascular collapse | Disc. AE | 225 mg single, oral Overdose Dose: 225 mg Route: oral Route: single Dose: 225 mg Sources: Page: p.1137/99 |
unhealthy, 26 n = 1 Health Status: unhealthy Condition: Depression Age Group: 26 Sex: F Population Size: 1 Sources: Page: p.1137/99 |
Coma | Disc. AE | 225 mg single, oral Overdose Dose: 225 mg Route: oral Route: single Dose: 225 mg Sources: Page: p.1137/99 |
unhealthy, 26 n = 1 Health Status: unhealthy Condition: Depression Age Group: 26 Sex: F Population Size: 1 Sources: Page: p.1137/99 |
Disseminated intravascular coagulation | Disc. AE | 225 mg single, oral Overdose Dose: 225 mg Route: oral Route: single Dose: 225 mg Sources: Page: p.1137/99 |
unhealthy, 26 n = 1 Health Status: unhealthy Condition: Depression Age Group: 26 Sex: F Population Size: 1 Sources: Page: p.1137/99 |
Hemolysis | Disc. AE | 225 mg single, oral Overdose Dose: 225 mg Route: oral Route: single Dose: 225 mg Sources: Page: p.1137/99 |
unhealthy, 26 n = 1 Health Status: unhealthy Condition: Depression Age Group: 26 Sex: F Population Size: 1 Sources: Page: p.1137/99 |
Muscular tone excessive | Disc. AE | 225 mg single, oral Overdose Dose: 225 mg Route: oral Route: single Dose: 225 mg Sources: Page: p.1137/99 |
unhealthy, 26 n = 1 Health Status: unhealthy Condition: Depression Age Group: 26 Sex: F Population Size: 1 Sources: Page: p.1137/99 |
Rhabdomyolysis | Disc. AE | 225 mg single, oral Overdose Dose: 225 mg Route: oral Route: single Dose: 225 mg Sources: Page: p.1137/99 |
unhealthy, 26 n = 1 Health Status: unhealthy Condition: Depression Age Group: 26 Sex: F Population Size: 1 Sources: Page: p.1137/99 |
Hyperthermia | severe Disc. AE |
225 mg single, oral Overdose Dose: 225 mg Route: oral Route: single Dose: 225 mg Sources: Page: p.1137/99 |
unhealthy, 26 n = 1 Health Status: unhealthy Condition: Depression Age Group: 26 Sex: F Population Size: 1 Sources: Page: p.1137/99 |
Suicidal ideation | Disc. AE | 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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Depression Sources: Page: p.1 |
Crisis hypertensive | Disc. AE | 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: Page: p.6 |
unhealthy Health Status: unhealthy Condition: Depression Sources: Page: p.6 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no | ||||
unlikely [IC50 >897.2 uM] | ||||
yes [Ki 1.2 uM] | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Phenelzine associated peripheral neuropathy--clinical and electrophysiologic findings. | 1991 Jun |
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Depression after cyproheptadine: MAO treatment. | 1992 Jun 1 |
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Phenylethylidenehydrazine, a novel GABA-transaminase inhibitor, reduces epileptiform activity in rat hippocampal slices. | 2004 |
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Mechanism-based inactivation of human cytochrome P4502C8 by drugs in vitro. | 2004 Dec |
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[Neurobiology and pharmacotherapy of social phobia]. | 2004 Jul-Aug |
|
Hypericum perforatum L (St John's wort) preferentially increases extracellular dopamine levels in the rat prefrontal cortex. | 2004 Jun |
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Efficacy of quality criteria to identify potentially harmful information: a cross-sectional survey of complementary and alternative medicine web sites. | 2004 Jun 29 |
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Efficacy and tolerability of tranylcypromine versus phenelzine: a double-blind study in antidepressant-refractory depressed inpatients. | 2004 Nov |
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Effect of antidepressants on GABA(B) receptor function and subunit expression in rat hippocampus. | 2004 Oct 15 |
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Monoamine oxidase inhibitors, their structural analogues, and neuroprotection. | 2004 Sep |
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Modafinil augmentation of phenelzine for residual fatigue in dysthymia. | 2004 Sep |
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Contribution of sleep research to the development of new antidepressants. | 2005 |
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Sleep and psychiatry. | 2005 |
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Neuroendocrine predictors of the evolution of depression. | 2005 |
|
In vivo evidence for reduced cortical glutamate-glutamine cycling in rats treated with the antidepressant/antipanic drug phenelzine. | 2005 |
|
Herb-drug interactions: a literature review. | 2005 |
|
Social anxiety disorder : current treatment recommendations. | 2005 |
|
Screening antidepressants in the chick separation-stress paradigm. | 2005 Aug |
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Validity of sudden gains in acute phase treatment of depression. | 2005 Feb |
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Brainstem levels of transcription factor AP-2 in rat are changed after treatment with phenelzine, but not with citalopram. | 2005 Jan 21 |
|
Shy-Drager syndrome: multisystem atrophy with comorbid depression. | 2005 Jan-Feb |
|
A microarray study of MPP+-treated PC12 Cells: Mechanisms of toxicity (MOT) analysis using bioinformatics tools. | 2005 Jul 15 |
|
Inhibition of monoamine oxidase-A activity in rat brain by synthetic hydrazines: structure-activity relationship (SAR). | 2005 Jun |
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Remission rates with 3 consecutive antidepressant trials: effectiveness for depressed outpatients. | 2005 Jun |
|
Chronic treatment with the monoamine oxidase inhibitor phenelzine increases hypothalamic-pituitary-adrenocortical activity in male C57BL/6 mice: relevance to atypical depression. | 2005 Mar |
|
Cytochrome p450 enzymes mechanism based inhibitors: common sub-structures and reactivity. | 2005 Oct |
|
A selective test for antidepressant treatments using rats bred for stress-induced reduction of motor activity in the swim test. | 2005 Oct |
|
Traumatic stress: effects on the brain. | 2006 |
|
Pharmacotherapy of social anxiety disorder: what does the evidence tell us? | 2006 |
|
Antidepressants reverse corticosterone-mediated decrease in brain-derived neurotrophic factor expression: differential regulation of specific exons by antidepressants and corticosterone. | 2006 |
|
Use of antidepressant medications in relation to the incidence of breast cancer. | 2006 Apr 10 |
|
Monoamine oxidase inhibitors allow locomotor and rewarding responses to nicotine. | 2006 Aug |
|
Serotonin syndrome from the interaction of cyclobenzaprine with other serotoninergic drugs. | 2006 Dec |
|
Rapid identification of P-glycoprotein substrates and inhibitors. | 2006 Dec |
|
The effect of antidepressants on glucose homeostasis and insulin sensitivity: synthesis and mechanisms. | 2006 Jan |
|
Treatment of depression with atypical features: a meta-analytic approach. | 2006 Jan 30 |
|
Effects of monoamine oxidase inhibitors on cocaine discrimination in rats. | 2006 Mar |
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Quetiapine for insomnia associated with refractory depression exacerbated by phenelzine. | 2006 Mar |
|
An evaluation of potential mechanism-based inactivation of human drug metabolizing cytochromes P450 by monoamine oxidase inhibitors, including isoniazid. | 2006 May |
|
Transdermal selegiline: the new generation of monoamine oxidase inhibitors. | 2006 May |
|
Leading the way: advances in the diagnosis, treatment, and management of neuropsychiatric illnesses. | 2006 May |
|
Tamoxifen protect against hydroxyl radical generation induced by phenelzine in rat striatum. | 2006 May 1 |
|
13C magnetic resonance spectroscopy studies of alterations in glutamate neurotransmission. | 2006 May 15 |
|
Increased nicotine self-administration following prenatal exposure in female rats. | 2006 Nov |
|
Modeling anxiety-like states: pharmacological characterization of the chick separation stress paradigm. | 2006 Nov |
|
Aldehyde load in ischemia-reperfusion brain injury: neuroprotection by neutralization of reactive aldehydes with phenelzine. | 2006 Nov 29 |
|
Sustained effects of phenelzine and tranylcypromine on orthostatic challenge in antidepressant-refractory depression. | 2006 Oct |
|
Antidepressants and inflammatory bowel disease: a systematic review. | 2006 Sep 20 |
|
Antidepressant therapy in tinnitus. | 2007 Apr |
|
Successful use of phenelzine in treatment-resistant panic disorder. | 2007 Feb |
Sample Use Guides
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16669850
20 uM of Phenelzine inactivated all human liver microsomal CYP (CYP1A2, CYP2C9, CYP2C19, CYP2D6 and CYP3A) but were most potent toward CYP3A and CYP2C19
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C667
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NDF-RT |
N0000000184
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WHO-VATC |
QN06AF03
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NCI_THESAURUS |
C265
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WHO-ATC |
N06AF03
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LIVERTOX |
NBK548402
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NDF-RT |
N0000175744
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Code System | Code | Type | Description | ||
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8127
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PRIMARY | |||
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DTXSID2041094
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PRIMARY | |||
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8123
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PRIMARY | RxNorm | ||
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C61888
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PRIMARY | |||
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D010624
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PRIMARY | |||
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DB00780
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PRIMARY | |||
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2123
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PRIMARY | |||
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51-71-8
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PRIMARY | |||
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919
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PRIMARY | |||
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7266
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PRIMARY | |||
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Phenelzine
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PRIMARY | |||
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200-117-9
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PRIMARY | |||
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CHEMBL1089
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O408N561GF
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PRIMARY | |||
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PHENELZINE
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O408N561GF
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PRIMARY | |||
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M8605
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PRIMARY | Merck Index | ||
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SUB09757MIG
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3675
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PRIMARY |
ACTIVE MOIETY
METABOLITE (PARENT)
SALT/SOLVATE (PARENT)