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<compound>
  <id type="integer">2801</id>
  <title>T3D2759</title>
  <common-name>Protriptyline</common-name>
  <description>Protriptyline belongs to the dibenzocycloheptenes, a class of benzenoids within the organic compounds. This exogenous compound has the formula C19H21N and an average molecular weight of 263.38 g/mol. At room temperature, it exists as a solid.

Protriptyline is used as an antidepressant and is associated with oral exposure. It is found in antidepressants, food preservation, and various household cleaning and consumer products, including tobacco smoke filters, other smoking requisites, and non-electric simulated smoking devices. It is also recorded in electrical and electronic equipment, such as radio transmission systems, antennas, and electrically stimulated smoking devices.

The compound acts by decreasing the reuptake of norepinephrine and serotonin (5-HT). Its recorded protein targets include the sodium-dependent noradrenaline transporter (SLC6A2), the sodium-dependent serotonin transporter (SLC6A4), the sodium-dependent dopamine transporter (SLC6A3), and the adenosine receptor A3 (ADORA3).</description>
  <cas>438-60-8</cas>
  <pubchem-id>4976</pubchem-id>
  <chemical-formula>C19H21N</chemical-formula>
  <weight>263.167400</weight>
  <appearance>White powder.</appearance>
  <melting-point>169-171°C (Protriptyline HCl)</melting-point>
  <boiling-point></boiling-point>
  <density nil="true"/>
  <solubility>1.04 mg/L</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Oral</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Protriptyline acts by decreasing the reuptake of norepinephrine and serotonin (5-HT).</mechanism-of-toxicity>
  <metabolism>Route of Elimination: Cumulative urinary excretion during 16 days accounted for approximately 50% of the drug. The fecal route of excretion did not seem to be important.</metabolism>
  <toxicity></toxicity>
  <lethaldose></lethaldose>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>For the treatment of depression.</use-source>
  <min-risk-level></min-risk-level>
  <health-effects>Protriptyline shares side effects common to all tricyclic antidepressants. The most frequent of these are dry mouth, constipation, urinary retention, increased heart rate, sedation, irritability, dizziness, decreased coordination, anxiety, blood disorders, confusion, decreased libido, dizziness, flushing, headache, impotence, insomnia, low blood pressure, nightmares, rapid or irregular heartbeat, rash, seizures, sensitivity to sunlight, stomach and intestinal problems. Other more complicated side effects include; chest pain or heavy feeling, pain spreading to the arm or shoulder, nausea, sweating, general ill feeling; sudden numbness or weakness, especially on one side of the body; sudden headache, confusion, problems with vision, speech, or balance; hallucinations, or seizure (convulsions); easy bruising or bleeding, unusual weakness; restless muscle movements in your eyes, tongue, jaw, or neck; urinating less than usual or not at all; extreme thirst with headache, nausea, vomiting, and weakness; or feeling light-headed or fainting. Deaths may occur from overdosage with this class of drugs. Multiple drug ingestion (including alcohol) is common in deliberate tricyclic antidepressant overdose. (Wikipedia)</health-effects>
  <symptoms>Withdrawal symptoms include gastrointestinal disturbances, anxiety, and insomnia. </symptoms>
  <treatment>Dry mouth, if severe to the point of causing difficulty speaking or swallowing, may be managed by dosage reduction or temporary discontinuation of the drug. Patients may also chew sugarless gum or suck on sugarless candy in order to increase the flow of saliva. Some artificial saliva products may give temporary relief. Men with prostate enlargement who take protriptyline may be especially likely to have problems with urinary retention. Symptoms include having difficulty starting a urine flow and more difficulty than usual passing urine. In most cases, urinary retention is managed with dose reduction or by switching to another type of antidepressant. In extreme cases, patients may require treatment with bethanechol, a drug that reverses this particular side effect. As management of overdose is complex and changing, it is recommended that the physician contact a poison control center for current information on treatment. Signs and symptoms of toxicity develop rapidly after tricyclic antidepressant overdose, therefore, hospital monitoring is required as soon as possible. (Wikipedia)</treatment>
  <created-at type="dateTime">2009-07-21T20:26:40Z</created-at>
  <updated-at type="dateTime">2026-05-14T16:36:02Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Protriptyline</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C07408</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>8597</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id></ctd-id>
  <stitch-id>Protriptyline</stitch-id>
  <drugbank-id>DB00344</drugbank-id>
  <pdb-id></pdb-id>
  <actor-id></actor-id>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>CNCCCC1C2=CC=CC=C2C=CC2=CC=CC=C12</moldb-smiles>
  <moldb-formula>C19H21N</moldb-formula>
  <moldb-inchi>InChI=1S/C19H21N/c1-20-14-6-11-19-17-9-4-2-7-15(17)12-13-16-8-3-5-10-18(16)19/h2-5,7-10,12-13,19-20H,6,11,14H2,1H3</moldb-inchi>
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  <moldb-average-mass type="decimal">263.3767</moldb-average-mass>
  <moldb-mono-mass type="decimal">263.167399677</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>4.7</logp>
  <hmdb-id>HMDB14488</hmdb-id>
  <chembl-id>CHEMBL668</chembl-id>
  <chemspider-id>4805</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>CHEM002178</chemdb-id>
  <dsstox-id>DTXSID0023535</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00009004</susdat-id>
  <iupac>methyl(3-{tricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,9,11,13-heptaen-2-yl}propyl)amine</iupac>
  <moldb-polar-surface-area>12.03</moldb-polar-surface-area>
  <moldb-refractivity>87.30340000000004</moldb-refractivity>
  <moldb-polarizability>31.60441131093086</moldb-polarizability>
  <moldb-rotatable-bond-count>4</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>10.54323028083324</moldb-pka-strongest-basic>
  <moldb-physiological-charge>1</moldb-physiological-charge>
  <moldb-number-of-rings>3</moldb-number-of-rings>
  <moldb-alogps-logp>4.65</moldb-alogps-logp>
  <moldb-alogps-logs>-6.06</moldb-alogps-logs>
  <moldb-alogps-solubility>2.31e-04 g/l</moldb-alogps-solubility>
  <kingdom>Organic compounds</kingdom>
  <superklass>Benzenoids</superklass>
  <klass>Dibenzocycloheptenes</klass>
  <subklass nil="true"/>
  <paper-count type="integer">421</paper-count>
  <sync-id>CED0008061</sync-id>
  <structure-inchikey>BWPIARFWQZKAIA-UHFFFAOYSA-N</structure-inchikey>
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  <structure-indexed-at type="dateTime">2026-09-19T04:00:33Z</structure-indexed-at>
</compound>
