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<compound>
  <id type="integer">2923</id>
  <title>T3D2881</title>
  <common-name>Tranylcypromine</common-name>
  <description>Tranylcypromine is an exogenous organic compound with the formula C9H11N and an average molecular weight of 133.19 g/mol. It exists as a solid at room temperature. Tranylcypromine belongs to the amines, a subclass of organonitrogen compounds within the organic compounds.

This compound is found in antidepressants, as well as in other smoking requisites and pipe accessories within household cleaning and consumer products. The recorded route of exposure is oral. Tranylcypromine irreversibly inhibits monoamine oxidase (MAO), specifically targeting amine oxidase [flavin-containing] A (MAOA) and amine oxidase [flavin-containing] B (MAOB). Other protein targets include the D(2) dopamine receptor (DRD2) and the 5-hydroxytryptamine receptor 2A (HTR2A).

Within neurons, MAO appears to regulate the levels of monoamines released upon synaptic firing. Because depression is associated with low levels of monoamines, the inhibition of MAO serves to ease depressive symptoms. Consequently, tranylcypromine is effective in the treatment of major depression, atypical depression, and dysthymic disorder. Additionally, it is useful in the treatment of phobic and panic disorders.</description>
  <cas>155-09-9</cas>
  <pubchem-id>441233</pubchem-id>
  <chemical-formula>C9H11N</chemical-formula>
  <weight>133.089150</weight>
  <appearance>White powder.</appearance>
  <melting-point>79-80°C at 1.50E+00 mm Hg</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>4.86E+004 mg/L</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Interindividual variability in absorption. May be biphasic in some individuals. Peak plasma concentrations occur in one hour following oral administration with a secondary peak occurring within 2-3 hours. Biphasic absorption may represent different rates of absorption of the stereoisomers of the drug, though additional studies are required to confirm this. </route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Tranylcypromine irreversibly and nonselectively inhibits monoamine oxidase (MAO). Within neurons, MAO appears to regulate the levels of monoamines released upon synaptic firing. Since depression is associated with low levels of monoamines, the inhibition of MAO serves to ease depressive symptoms, as this results in an increase in the concentrations of these amines within the CNS.</mechanism-of-toxicity>
  <metabolism>Hepatic.Half Life: 1.5-3.2 hours in patients with normal renal and hepatic function</metabolism>
  <toxicity></toxicity>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Primarily indicated for the treatment of clinical depression. It is generally used to remedy various types of mood and anxiety disorders, typically after a last resort only after conventional antidepressants have been tried without success. It also has some off-label uses, such as in the treatment of post-traumatic stress disorder (PTSD). [Wikipedia]</use-source>
  <min-risk-level nil="true"/>
  <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]</health-effects>
  <symptoms>In overdosage, some patients exhibit insomnia, restlessness and anxiety, progressing in severe cases to agitation, mental confusion and incoherence. Hypotension, dizziness, weakness and drowsiness may occur, progressing in severe cases to extreme dizziness and shock. A few patients have displayed hypertension with severe headache and other symptoms. Rare instances have been reported in which hypertension was accompanied by twitching or myoclonic fibrillation of skeletal muscles with hyperpyrexia, sometimes progressing to generalized rigidity and coma.</symptoms>
  <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)</treatment>
  <created-at type="dateTime">2009-07-21T20:27:35Z</created-at>
  <updated-at type="dateTime">2026-05-14T16:47:55Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Tranylcypromine</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C07155</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id></chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Tranylcypromine</stitch-id>
  <drugbank-id>DB00752</drugbank-id>
  <pdb-id>GJZ</pdb-id>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>N[C@@H]1CC1C1=CC=CC=C1</moldb-smiles>
  <moldb-formula>C9H11N</moldb-formula>
  <moldb-inchi>InChI=1S/C9H11N/c10-9-6-8(9)7-4-2-1-3-5-7/h1-5,8-9H,6,10H2/t8?,9-/m1/s1</moldb-inchi>
  <moldb-inchikey>AELCINSCMGFISI-YGPZHTELSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">133.1903</moldb-average-mass>
  <moldb-mono-mass type="decimal">133.089149357</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>1.58</logp>
  <hmdb-id>HMDB14890</hmdb-id>
  <chembl-id>CHEMBL1179</chembl-id>
  <chemspider-id>390008</chemspider-id>
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  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference></synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002265</chemdb-id>
  <dsstox-id>DTXSID2023694</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00008974</susdat-id>
  <iupac>2-phenylcyclopropan-1-amine</iupac>
  <moldb-polar-surface-area>26.02</moldb-polar-surface-area>
  <moldb-refractivity>41.696600000000004</moldb-refractivity>
  <moldb-polarizability>15.334201185763868</moldb-polarizability>
  <moldb-rotatable-bond-count>1</moldb-rotatable-bond-count>
  <moldb-acceptor-count>1</moldb-acceptor-count>
  <moldb-donor-count>1</moldb-donor-count>
  <moldb-pka-strongest-acidic nil="true"/>
  <moldb-pka-strongest-basic>9.622454981560159</moldb-pka-strongest-basic>
  <moldb-physiological-charge>1</moldb-physiological-charge>
  <moldb-number-of-rings>2</moldb-number-of-rings>
  <moldb-alogps-logp>1.50</moldb-alogps-logp>
  <moldb-alogps-logs>-1.95</moldb-alogps-logs>
  <moldb-alogps-solubility>1.49e+00 g/l</moldb-alogps-solubility>
  <kingdom>Organic compounds</kingdom>
  <superklass>Organic nitrogen compounds</superklass>
  <klass>Organonitrogen compounds</klass>
  <subklass>Amines</subklass>
  <paper-count type="integer">2370</paper-count>
  <sync-id>CED0004725</sync-id>
  <structure-inchikey>AELCINSCMGFISI-YGPZHTELSA-N</structure-inchikey>
  <structure-fingerprint>4000000000000000100000000000000000000000000000000000000000000000000000000000000000000000000000000000000000002000000000000000000000000020000000000000000000000100000000000000000800000000000000000001000000900000000000020000001000880000000000000000000080000000000000000000000000000000000000000000000000000000000000000000001000000000000000000000200000000000000000000800000000040000000000000000000000000000000000000000000</structure-fingerprint>
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  <structure-indexed-at type="dateTime">2026-09-19T04:00:38Z</structure-indexed-at>
</compound>
