{"ATC Code":"N06AF03","Abbreviation":"","Aliases":["2-Phenylethylhydrazine","Phenethylhydrazine","Hydrazine, (2-phenylethyl)-","Fenelzyne","Fenelzyna","β-Phenylethylhydrazine","Phenelzinum","Fenelzin","Fenelzina","2-Phenethylhydrazine"],"Biological Half-Life":"After administration phenelzine presents a very short half-life of 11.6 hours in humans.","Boiling Point":"74 °C","CAS":"51-71-8","ChEBI":"CHEBI:8060","ChEMBL":"CHEMBL1089","ChemicalClasses":["phenethylamine"],"Chirality":"achiral","Classes":["Monoamine oxidase inhibitor"],"Color/Form":"Liquid","Decomposition":"When heated to decomposition material emits toxic fumes of /sulfur oxides and nitrogen oxides/.","Drug Classes":"Breast Feeding; Lactation; Antidepressive Agents; Monoamine Oxidase Inhibitors","Drug Indication":"Phenelzine is indicated for the treatment of nonendogenous, neurotic or atypical depression for patients that do not tolerate other forms of therapy.   Atypical depression has a high prevalence rate, starts in early life, tends to last longer, is more likely to occur in people with bipolar disorder, has a high comorbidity with anxiety disorder and carries more risk of suicidal behavior. It is important to specify the atypical feature to predict the clinical course of depression and hence generate the best treatment and service. The featuring symptoms of the atypical feature include mood reactivity, two or more of this symptoms: 1) increased appetite, 2) increased sleep, 3) leaden paralysis and 4) interpersonal rejection sensitivity and should not have melancholic or catatonic features of depression.  Neurotic depression is a depression of an emotionally unstable person. It is a secondary condition to major personality disorder, neuroses and drug use disorders. Likewise, a primary depression with a family history of depression spectrum disease would fit in this category.  A nonendogenous depression is characterized by a disturbance in mood and general outlook. The physical symptoms tend to be less severe and it often occurs in response to stressful life events that keep occurring over a large period of time generating a continuous stress in the daily living.","Drug Warnings":"/BOXED WARNING/ Suicidality and Antidepressant Drugs: Antidepressants increased the risk compared to placebo of suicidal thinking and behavior (suicidality) in children, adolescents, and young adults in short-term studies of major depressive disorder (MDD) and other psychiatric disorders. Anyone considering the use of Nardil or any other antidepressant in a child, adolescent, or young adult must balance this risk with the clinical need. Short-term studies did not show an increase in the risk of suicidality with antidepressants compared to placebo in adults beyond age 24; there was a reduction in risk with antidepressants compared to placebo in adults aged 65 and older. Depression and certain other psychiatric disorders are themselves associated with increases in the risk of suicide. Patients of all ages who are started on antidepressant therapy should be monitored appropriately and observed closely for clinical worsening, suicidality, or unusual changes in behavior. Families and caregivers should be advised of the need for close observation and communication with the prescriber. Nardil is not approved for use in pediatric patients.","DrugClasses":["antidepressant","depressant"],"DurationOfAction":"","EINECS":"200-117-9","EliminationHalfLife":"11.6 hours","Erowid Experience Reports":[],"European Community (EC) Number":"200-117-9","FDA Pharmacological Classification":"O408N561GF","FullSalts":["Phenelzine sulfate"],"HMDB ID":"HMDB0014918","HeavyAtomCount":10,"Human Drugs":"Antidepressants -\u003e Monoamine oxidase inhibitors (MAOI)","IUPACName":"2-phenylethylhydrazine","InChI":"InChI=1S/C8H12N2/c9-10-7-6-8-4-2-1-3-5-8/h1-5,10H,6-7,9H2","InChIKey":"RMUCZJUITONUFY-UHFFFAOYSA-N","MeSH Pharmacological Classification":"Mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions. Several MONOAMINE OXIDASE INHIBITORS are useful as antidepressants apparently as a long-term consequence of their modulation of catecholamine levels. The tricyclic compounds useful as antidepressive agents (ANTIDEPRESSIVE AGENTS, TRICYCLIC) also appear to act through brain catecholamine systems. A third group (ANTIDEPRESSIVE AGENTS, SECOND-GENERATION) is a diverse group of drugs including some that act specifically on serotonergic systems. (See all compounds classified as Antidepressive Agents.)","Melting Point":"157-161ºC","MolecularFormula":"C\u003csub\u003e8\u003c/sub\u003eH\u003csub\u003e12\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003e","MolecularWeight":"136.19 g/mol","Pharmacodynamics":"The elimination of monoamine oxidase by phenelzine results in the elevation of brain amines such as 2-phenylethylamine which is a metabolite of phenelzine. These amines have then marked effects on the uptake and release of catecholamines and serotonin in nerve endings. Phenelzine is shown to elevate brain levels of the gamma-aminobutyric acid (GABA) and alanine (ALA) as well as to inhibit the activity of the transaminases that normally metabolize these amino acids. In preclinical studies, it has been shown to be neuroprotective in cerebral ischemia.","Physical Description":"Solid","PrevSalts":["sulfate"],"PubChemId":3675,"Record Description":["Phenelzine is a primary amine.","Phenelzine, with the formula β-phenylethylhydrazine, is a monoamine oxidase inhibiting antidepressant that is effective in the treatment of panic disorder and social anxiety disorder. It was developed by Parke Davis and originally FDA approved on June 9th, 1961. It is currently approved under prescription by the name of Nardil.","Phenelzine is a Monoamine Oxidase Inhibitor. The mechanism of action of phenelzine is as a Monoamine Oxidase Inhibitor.","Phenelzine is a monoamine oxidase inhibitor (MAO inhibitor) used in therapy of moderate-to-severe depression. Phenelzine therapy is associated with rare instances of clinically apparent acute liver injury.","PHENELZINE is a small molecule drug with a maximum clinical trial phase of IV (across all indications) that was first approved in 1961 and is indicated for major depressive disorder and has 2 investigational indications. This drug has a black box warning from the FDA.","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.","One of the MONOAMINE OXIDASE INHIBITORS used to treat DEPRESSION; PHOBIC DISORDERS; and PANIC.","See also: Phenelzine Sulfate (has salt form).","Phenelzine is a primary amine.","LiverTox|CNS|Antidepressant|MAO inhibitor"],"RefCount":4,"References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Phenelzine","Name":"Phenelzine","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q1747559","Name":"Phenelzine","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/drugs/DB00780","Name":"Phenelzine","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/3675","Name":"Phenelzine","Sub":false}]},{"Name":"ChEMBL","Urls":[{"Link":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1089","Name":"Phenelzine","Sub":false}]},{"Name":"ChEBI","Urls":[{"Link":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8060","Name":"Phenelzine","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=51-71-8","Name":"Phenelzine","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0014918","Name":"Phenelzine","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/C07430","Name":"Phenelzine","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/O408N561GF","Name":"Phenelzine","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID2041094","Name":"Phenelzine","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 3675, Phenelzine. Accessed June 28, 2025. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/3675\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/3675\u003c/a\u003e","U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. Phenelzine. UNII: O408N561GF. Global Substance Registration System. Accessed June 28, 2025. \u003ca href=https://gsrs.ncats.nih.gov/ginas/app/beta/substances/O408N561GF\u003ehttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/O408N561GF\u003c/a\u003e","Anvisa. RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial. Diário Oficial da União. March 31, 2023. Accessed June 28, 2025. \u003ca href=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992\u003ehttps://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992\u003c/a\u003e"],"SMILES":"C1=CC=C(C=C1)CCNN","Salts":["sulfate"],"SaltsAcidCount":[1],"SaltsAmineCount":[1],"SaltsUNII":["2681D7P965"],"Scheduling":[{"gov":"Australia","ref":[],"schedule":"S4 substance"},{"gov":"Brazil","ref":["3"],"schedule":"C1 substance"},{"gov":"United States","ref":[],"schedule":"prescription only substance"}],"Solubility":"1.11e+01 g/L","StoreUNII":["O408N561GF"],"StructureBase64":"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Effects":null,"Therapeutic Uses":"Antidepressive Agents, Monoamine Oxidase Inhibitors","Title":"Phenelzine","UNII":"O408N561GF","Wikidata":"Q1747559","Wikipedia":"Phenelzine","XLogP":1.2}