{"ATC Code":"N - Nervous system","Abbreviation":[],"Adverse Effects":"Common adverse effects of tranylcypromine include dry mouth, headaches, diarrhea, urinary hesitancy, insomnia, agitation, anxiety, nausea, and sexual dysfunction. Postural hypotension, sometimes leading to syncope, is another common adverse effect that warrants special attention for older patients on this medication. This adverse effect is dose-related and may require splitting the dose into 3 to 4 doses daily. More serious side effects include hepatotoxicity, seizures, and induction of mania. Additionally, in the United States, there is a black-box warning stating that this medication may lead to the activation of suicidal ideation and behavior in children, adolescents, and young adults aged 18 to 24 with major depressive disorder and other psychiatric disorders.","Aliases":["Tranylcypromine","tranylcypromine","Transamine","Racemic Tranylcypromine","SKF 385","Jatrosom","Parnitene","Tranilcipromina","Tranylcyprominum","Cyclopropanamine, 2-phenyl-, trans-(+-)-","Cyclopropylamine, 2-phenyl-, trans-(+-)-","Tranylcypromin","trans 2 Phenylcyclopropylamine","RefChem:56146","3-12-00-02797","N06AF04","205-841-9","3E3V44J4Z9","54-97-7","2-Phenylcyclopropanamine","2-phenylcyclopropylamine","2-Phenylcyclopropane-1-amine","Parnate","trans-2-Phenylcyclopropylamine","trans-DL-2-Phenylcyclopropylamine"],"Biological Half-Life":"1.5-3.2 hours in patients with normal renal and hepatic function","Boiling Point":"79-80 °C @ 1.5-1.6 mm Hg","CAS":"155-09-9","ChEBI":"CHEBI:9652","ChEMBL":"CHEMBL313833","ChemicalClasses":["phenylcyclopropylamine"],"Chirality":"racemic","Classes":["Monoamine oxidase inhibitor"],"Color/Form":"Liquid","Drug Classes":"Breast Feeding; Lactation; Antidepressive Agents; Monoamine Oxidase Inhibitors","Drug Indication":"For the treatment of major depressive episode without melancholia.","Drug Warnings":"MAJORITY OF SMALL NUMBER OF DEATHS...OCCURRED AFTER DOSES OF OVER 350 MG; PT HAVE SURVIVED AFTER INGESTION OF THIS AMT, HOWEVER. DEPENDENCE ON TRANYLCYPROMINE HAS BEEN REPORTED OCCASIONALLY. /SULFATE/","EliminationHalfLife":"2.5 hours","Esters":[],"European Community (EC) Number":"205-841-9","FDA Pharmacological Classification":"3E3V44J4Z9","Formating":[],"HMDB ID":"HMDB0243563","Health Effects":"Rare cases have been reported of hypertensive crisis, serotonin syndrome, myoclonus, hyperpyrexia, psychosis, and delirium, some of which progressed to coma. Additionally, in sensitive individuals or at extreme dosages, hypotension may lead to shock. [Wikipedia]","HeavyAtomCount":10,"Human Drugs":"Breast Feeding; Lactation; Antidepressive Agents; Monoamine Oxidase Inhibitors","IUPACName":"2-phenylcyclopropan-1-amine","InChI":"InChI=1S/C9H11N/c10-9-6-8(9)7-4-2-1-3-5-7/h1-5,8-9H,6,10H2","InChIKey":"AELCINSCMGFISI-UHFFFAOYSA-N","Interactions":"HEXOBARBITAL SLEEPING TIME IS PROLONGED BY PARNATE, INDICATING ITS ABILITY TO POTENTIATE OTHER DRUGS PRESUMABLY BY INTERFERING WITH THEIR DETOXIFICATION. /PARNATE/","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.","Melting Point":"79-80 °C at 1.50E+00 mm Hg","MolecularFormula":"C\u003csub\u003e9\u003c/sub\u003eH\u003csub\u003e11\u003c/sub\u003eN","MolecularWeight":"133.19 g/mol","Pharmacodynamics":"Tranylcypromine belongs to a class of antidepressants called monoamine oxidase inhibitors (MAOIs). Tranylcypromine is a non-hydrazine monoamine oxidase inhibitor with a rapid onset of activity. MAO is an enzyme that catalyzes the oxidative deamination of a number of amines, including serotonin, norepinephrine, epinephrine, and dopamine. Two isoforms of MAO, A and B, are found in the body. MAO-A is mainly found within cells located in the periphery and catalyzes the breakdown of serotonin, norepinephrine, epinephrine, dopamine and tyramine. MAO-B acts on phenylethylamine, norepinephrine, epinephrine, dopamine and tyramine, is localized extracellularly and is found predominantly in the brain. While the mechanism of MAOIs is still unclear, it is thought that they act by increasing free serotonin and norepinephrine concentrations and/or by altering the concentrations of other amines in the CNS. It has been postulated that depression is caused by low levels of serotonin and/or norepinephrine and that increasing serotonergic and norepinephrinergic neurotransmission results in relief of depressive symptoms. MAO A inhibition is thought to be more relevant to antidepressant activity than MAO B inhibition. Selective MAO B inhibitors, such as selegiline, have no antidepressant effects.","PubChemId":5530,"RefCount":3,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Tranylcypromine","Name":"Tranylcypromine","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q100423358","Name":"Tranylcypromine","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/drugs/DB00752","Name":"Tranylcypromine","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/5530","Name":"Tranylcypromine","Sub":false}]},{"Name":"ChEMBL","Urls":[{"Link":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL313833","Name":"Tranylcypromine","Sub":false}]},{"Name":"ChEBI","Urls":[{"Link":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9652","Name":"Tranylcypromine","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=155-09-9","Name":"Tranylcypromine","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0243563","Name":"Tranylcypromine","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/C07155","Name":"Tranylcypromine","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID2023694","Name":"Tranylcypromine","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 5530, Tranylcypromine. Accessed October 9, 2025. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/5530\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/5530\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 October 9, 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":"C1C(C1N)C2=CC=CC=C2","SaltData":[],"Salts":[],"Scheduling":[{"gov":"Australia","ref":[],"schedule":"S4 substance"},{"gov":"Brazil","ref":["2"],"schedule":"C1 substance"},{"gov":"Canada","ref":[],"schedule":"prescription only substance"},{"gov":"United Kingdom","ref":[],"schedule":"prescription only substance"},{"gov":"United States","ref":[],"schedule":"prescription only substance"}],"Solubility":"Sol in water /Sulfate/","Stability/Shelf Life":"STABLE IN LIGHT, HEAT \u0026 IN AIR /SULFATE/","StereoisomerData":[{"Aliases":null,"PubChemId":null,"SMILES":"N[C@@H]1C[C@H]1C1=CC=CC=C1","Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 78.347 45.747\"\u003e\u003crect 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class=\"hi\"/\u003e\u003c/g\u003e\u003c/g\u003e\u003c/svg\u003e","Title":"(1R,2S)-Tranylcypromine","UNII":null}],"StereoisomerType":"diastereomer","Stereoisomers":["(1S,2R)-Tranylcypromine","(1R,2R)-Tranylcypromine","(1S,2S)-Tranylcypromine","(1R,2S)-Tranylcypromine"],"Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 78.347 45.747\"\u003e\u003crect width=\"100%\" height=\"100%\" fill=\"#fff\"/\u003e\u003cdesc\u003eGenerated by the Chemistry Development Kit (http://github.com/cdk)\u003c/desc\u003e\u003cg fill=\"#3050f8\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".7\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h79v46H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath d=\"m48.234 1.038-7.618 13.2M40.616 14.238l15.231.002M48.234 1.038l7.613 13.202M55.847 14.24l10.036 5.798M40.616 14.238l-13.191 7.615\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m27.43 37.093-.005-15.24M24.991 35.686l-.004-12.425\"/\u003e\u003c/g\u003e\u003cpath d=\"m27.43 37.093-13.191 7.616\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m1.043 37.085 13.196 7.624M3.481 35.677l10.758 6.216\"/\u003e\u003c/g\u003e\u003cpath d=\"m1.043 37.085-.005-15.24\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"M14.229 14.229 1.038 21.845M14.229 17.045 3.477 23.252\"/\u003e\u003c/g\u003e\u003cpath d=\"m27.425 21.853-13.196-7.624\" class=\"bond\"/\u003e\u003cg stroke=\"none\" class=\"atom\"\u003e\u003cpath d=\"M70.976 24.31h-.72l-2.619-4.066h-.03l.03.595q.024.357.024.732v2.739h-.566v-4.9h.714l2.608 4.054h.03l-.018-.327-.024-.476q-.006-.262-.006-.482V19.41h.577zM75.283 24.31h-.619v-2.286h-2.513v2.286h-.613v-4.9h.613v2.072h2.513V19.41h.619zM77.787 25.799h-1.943v-.3l.772-.778q.221-.222.371-.393.154-.175.233-.34.078-.168.078-.364 0-.243-.146-.368-.143-.129-.372-.129-.214 0-.378.075-.161.075-.329.208l-.193-.243q.172-.147.393-.247.225-.1.507-.1.411 0 .65.207.24.208.24.576 0 .228-.097.432-.093.2-.264.396-.168.197-.393.418l-.614.604v.018h1.485z\"/\u003e\u003c/g\u003e\u003cpath stroke=\"#3050f8\" d=\"m65.883 20.038-5.018-2.899\" class=\"hi\"/\u003e\u003c/g\u003e\u003c/g\u003e\u003c/svg\u003e","Subjective Effects":null,"Therapeutic Uses":"Antidepressive Agents; Monoamine Oxidase Inhibitors; Anti-Anxiety Agents","Title":"Tranylcypromine","Treatment":"Treatment should normally consist of general supportive measures, close observation of vital signs and steps to counteract specific symptoms as they occur, since MAO inhibition may persist. External cooling is recommended if hyperpyrexia occurs. Barbiturates have been reported to help relieve myoclonic reactions, but frequency of administration should be controlled carefully because Tranylcypromine may prolong barbiturate activity. When hypotension requires treatment, the standard measures for managing circulatory shock should be initiated. If pressor agents are used, the rate of infusion should be regulated by careful observation of the patient because an exaggerated pressor response sometimes occurs in the presence of MAO inhibition. (L1712)","Wikidata":"Q100423358","Wikipedia":"Tranylcypromine","XLogP":1.5}