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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]

API Reference Price

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29-Dec-2021
05-Oct-2024
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