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    Tranylcypromine molecular structure

    Tranylcypromine Stats & Data

    Tcp 2-pcpa Parnate Skf-385
    Chemical Class Amphetamine
    Psychoactive Class Stimulant
    Half-Life 1.5–3.2 hours (plasma); functional MAO inhibition persists ~10–21 days after last dose

    Pharmacology

    DrugBank
    State Solid Vd 1.1-5.7 L/kg Metabolism Hepatic.

    Description

    A propylamine formed from the cyclization of the side chain of amphetamine. This monoamine oxidase inhibitor is effective in the treatment of major depression, dysthymic disorder, and atypical depression. It also is useful in panic and phobic disorders (From AMA Drug Evaluations Annual, 1994, p311). Tranylcypromine is a racemate comprising equal amounts of (1R,2S)- and (1S,2R)-2-phenylcyclopropan-1-amine with the chiral centers both located on the cylopropane ring. An irreversible monoamine oxidase inhibitor that is used as an antidepressant (INN tranylcypromine).

    Mechanism of Action

    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.

    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.

    Absorption

    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.

    Toxicity

    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.

    Indication

    For the treatment of major depressive episode without melancholia.

    Half-life

    1.5-3.2 hours in patients with normal renal and hepatic function

    Effect Profile

    Curated + 2 Reports
    Stimulant 4.9

    Moderate stimulation, euphoria, and anxiety/jitters

    Stimulation / Energy×3
    7
    Euphoria / Mood Lift×2
    7
    Focus / Productivity×2
    0
    Anxiety / Jitters×1
    6

    Tolerance & Pharmacokinetics

    drugs.wiki
    Half-Life
    1.5–3.2 hours (plasma); functional MAO inhibition persists ~10–21 days after last dose
    Addiction Potential
    Low for classical substance use disorder; misuse uncommon. However, abrupt discontinuation can precipitate withdrawal-like symptoms (e.g., agitation, insomnia, delirium) and clinical relapse; taper medically.

    Experience Report Analysis

    Erowid
    2 Reports
    2015–2019 Date Range
    1 With Age Data

    Demographics

    Gender Distribution

    Age Distribution

    Reports Over Time

    Real-World Dose Distribution

    62K Doses

    From 5 individual dose entries

    Form / Preparation

    Most common forms and preparations reported

    Harm Reduction

    drugs.wiki

    Irreversible MAOI: although the parent drug’s plasma half-life is ~1.5–3.2 hours, enzyme inhibition persists until new MAO is synthesized, so interaction risks remain for at least 14 days after stopping (and often 10–21 days). Maintain a 14‑day washout when switching to or from serotonergic antidepressants; extend to 5 weeks after fluoxetine due to its long half-life. Hypertensive crisis (“cheese reaction”) can occur from dietary tyramine or sympathomimetic drugs; earliest sign is often a severe occipital headache, and can progress to chest pain, palpitations, shortness of breath, confusion, and seizures — seek emergency care immediately. Serotonin syndrome risk is high if combined with serotonergic medicines (e.g., SSRIs/SNRIs, clomipramine, MDMA, tramadol, DXM, linezolid, methylene blue); symptoms include agitation, hyperreflexia, clonus, fever, diaphoresis, diarrhea — urgent evaluation is required. Avoid OTC cold/cough products that contain dextromethorphan or decongestants (pseudoephedrine, phenylephrine); many carry a label warning against use within 14 days of an MAOI. Follow a low‑tyramine diet throughout therapy and for 2 weeks after stopping; avoid aged cheeses, cured/fermented meats, soy sauce/miso/yeast extracts, fava beans, and tap/draft beers; packaged spirits in modest amounts still require caution for hypotension/CNS effects. For planned surgery or dental procedures, inform anesthesia providers; some agents (e.g., meperidine, serotonergic antiemetics) are contraindicated, and perioperative plans may need adjustment. Tranylcypromine has a stimulant-like profile and can cause insomnia and orthostatic hypotension; dosing earlier in the day and dividing doses may reduce insomnia and BP swings. Rare hepatotoxicity has been reported; baseline and periodic liver function and blood pressure monitoring are prudent in clinical use. Carry an MAOI alert card/bracelet listing key contraindications (meperidine, DXM, serotonergic antidepressants, sympathomimetics) so emergency staff can avoid dangerous drugs.

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