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    Chemistry

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    Also known as: Tranylcypromine sulfate, 13492-01-8, Tranylcypromine sulfate (usp), Chebi:9653, D00826
    Molecular Formula
    C18H24N2O4S
    Molecular Weight
    364.5  g/mol
    InChI Key
    BKPRVQDIOGQWTG-VYIKEJMZSA-N
    Tranylcypromine Sulfate
    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)
    1 2D Structure

    Tranylcypromine Sulfate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (1R)-2-phenylcyclopropan-1-amine;sulfuric acid
    2.1.2 InChI
    InChI=1S/2C9H11N.H2O4S/c2*10-9-6-8(9)7-4-2-1-3-5-7;1-5(2,3)4/h2*1-5,8-9H,6,10H2;(H2,1,2,3,4)/t2*8?,9-;/m11./s1
    2.1.3 InChI Key
    BKPRVQDIOGQWTG-VYIKEJMZSA-N
    2.1.4 Canonical SMILES
    C1C(C1N)C2=CC=CC=C2.C1C(C1N)C2=CC=CC=C2.OS(=O)(=O)O
    2.1.5 Isomeric SMILES
    C1[C@H](C1C2=CC=CC=C2)N.C1[C@H](C1C2=CC=CC=C2)N.OS(=O)(=O)O
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. Jatrosom

    2. Parnate

    3. Sulfate, Tranylcypromine

    4. Trans 2 Phenylcyclopropylamine

    5. Trans-2-phenylcyclopropylamine

    6. Transamine

    7. Tranylcypromine

    8. Tranylcypromine Sulfate

    2.2.2 Depositor-Supplied Synonyms

    1. Tranylcypromine Sulfate

    2. 13492-01-8

    3. Tranylcypromine Sulfate (usp)

    4. Chebi:9653

    5. D00826

    2.3 Create Date
    2008-02-08
    3 Chemical and Physical Properties
    Molecular Weight 364.5 g/mol
    Molecular Formula C18H24N2O4S
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count2
    Exact Mass364.14567842 g/mol
    Monoisotopic Mass364.14567842 g/mol
    Topological Polar Surface Area135 Ų
    Heavy Atom Count25
    Formal Charge0
    Complexity197
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count2
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count3
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Anti-Anxiety Agents

    Agents that alleviate ANXIETY, tension, and ANXIETY DISORDERS, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions. ADRENERGIC BETA-ANTAGONISTS are commonly used in the symptomatic treatment of anxiety but are not included here. (See all compounds classified as Anti-Anxiety Agents.)

    Antidepressive Agents

    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.)

    Monoamine Oxidase Inhibitors

    A chemically heterogeneous group of drugs that have in common the ability to block oxidative deamination of naturally occurring monoamines. (From Gilman, et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed, p414) (See all compounds classified as Monoamine Oxidase Inhibitors.)

    4.2 FDA Pharmacological Classification
    4.2.1 Pharmacological Classes
    Monoamine Oxidase Inhibitors [MoA]; Monoamine Oxidase Inhibitor [EPC]

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