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Tranylcypromine information


Tranylcypromine
(1S,2R)-(−)-tranylcypromine (top),
(1R,2S)-(+)-tranylcypromine (bottom)
Clinical data
Trade namesParnate, many generics[1]
Other namestrans-2-phenylcyclopropylamine
AHFS/Drugs.comMonograph
MedlinePlusa682088
Pregnancy
category
  • AU: B2
Routes of
administration
Oral
ATC code
  • N06AF04 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • BR: Class C1 (Other controlled substances)[3]
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: WARNING[2]Rx-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability50%[4]
MetabolismLiver[5][6]
Elimination half-life2.5 hours[4]
ExcretionUrine, Feces[4]
Identifiers
IUPAC name
  • (±)-trans-2-phenylcyclopropan-1-amine
    or
    rel-(1R,2S)-2-phenylcyclopropan-1-amine
CAS Number
  • 155-09-9 checkY
PubChem CID
  • 19493
DrugBank
  • DB00752 checkY
ChemSpider
  • 18369 checkY
UNII
  • 3E3V44J4Z9
KEGG
  • D08625 ☒N
ChEBI
  • CHEBI:9652 ☒N
ChEMBL
  • ChEMBL1179 ☒N
ECHA InfoCard100.005.312 Edit this at Wikidata
Chemical and physical data
FormulaC9H11N
Molar mass133.194 g·mol−1
3D model (JSmol)
  • Interactive image
ChiralityRacemic mixture
SMILES
  • c1cccc(c1)[C@@H]2C[C@H]2N
InChI
  • InChI=1S/C9H11N/c10-9-6-8(9)7-4-2-1-3-5-7/h1-5,8-9H,6,10H2/t8-,9+/m0/s1 checkY
  • Key:AELCINSCMGFISI-DTWKUNHWSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Tranylcypromine, sold under the brand name Parnate among others,[1] is a monoamine oxidase inhibitor (MAOI).[4][7] More specifically, tranylcypromine acts as nonselective and irreversible inhibitor of the enzyme monoamine oxidase (MAO).[4][7] It is used as an antidepressant and anxiolytic agent in the clinical treatment of mood and anxiety disorders, respectively.

Tranylcypromine is a cyclopropylamine formed pro forma from the cyclization of amphetamine's side chain; therefore, it is classified as a substituted amphetamine.

  1. ^ a b Drugs.com International brands for Tranylcypromine. Page accessed April 17, 2016
  2. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
  3. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  4. ^ a b c d e Williams DA (2007). "Antidepressants". In Foye WO, Lemke TL, Williams DA (eds.). Foye's Principles of Medicinal Chemistry. Hagerstwon, USA: Lippincott Williams & Wilkins. pp. 590–1. ISBN 978-0-7817-6879-5.
  5. ^ "Tranylcypromine". www.drugbank.ca. Retrieved 2019-12-06.
  6. ^ Baker GB, Urichuk LJ, McKenna KF, Kennedy SH (June 1999). "Metabolism of monoamine oxidase inhibitors". Cellular and Molecular Neurobiology. 19 (3): 411–26. doi:10.1023/a:1006901900106. PMID 10319194. S2CID 21380176.
  7. ^ a b Baldessarini RJ (2005). "17. Drug therapy of depression and anxiety disorders". In Brunton LL, Lazo JS, Parker KL (eds.). Goodman & Gilman's The Pharmacological Basis of Therapeutics. New York: McGraw-Hill. ISBN 978-0-07-142280-2.

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