GJZ

(1R,2S)-2-phenylcyclopropanamine

Created: 2010-04-01
Last modified:  2011-06-04

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Chemical Details

Formal Charge0
Atom Count21
Chiral Atom Count2
Bond Count22
Aromatic Bond Count6
2D diagram of GJZ

Chemical Component Summary

Name(1R,2S)-2-phenylcyclopropanamine
Systematic Name (OpenEye OEToolkits)(1R,2S)-2-phenylcyclopropan-1-amine
FormulaC9 H11 N
Molecular Weight133.19
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs12.01c1cccc(c1)C2CC2N
SMILESCACTVS3.370N[CH]1C[CH]1c2ccccc2
SMILESOpenEye OEToolkits1.7.0c1ccc(cc1)C2CC2N
Canonical SMILESCACTVS3.370 N[C@@H]1C[C@H]1c2ccccc2
Canonical SMILESOpenEye OEToolkits1.7.0 c1ccc(cc1)[C@@H]2C[C@H]2N
InChIInChI1.03 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
InChIKeyInChI1.03 AELCINSCMGFISI-DTWKUNHWSA-N

Drug Info: DrugBank

DrugBank IDDB00752 
NameTranylcypromine
Groups
  • approved
  • investigational
DescriptionA 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).
Synonyms
  • Tranilcipromina
  • trans-2-phenylcyclopropylamine
  • Tranylcypromin
  • Racemic Tranylcypromine
  • trans-DL-2-Phenylcyclopropylamine
Brand Names
  • M-tranylcypromine
  • Parnate
  • Tranylcypromine
  • Tranylcypromine Sulfate
IndicationFor the treatment of major depressive episode without melancholia.
Categories
  • Agents that produce hypertension
  • Agents that reduce seizure threshold
  • Amines
  • Anti-Anxiety Agents
  • Antidepressive Agents
ATC-CodeN06AF04
CAS number155-09-9

Drug Targets

NameTarget SequencePharmacological ActionActions
Amine oxidase [flavin-containing] BMSNKCDVVVVGGGISGMAAAKLLHDSGLNVVVLEARDRVGGRTYTLRNQK...unknowninhibitor
Amine oxidase [flavin-containing] AMENQEKASIAGHMFDVVVIGGGISGLSAAKLLTEYGVSVLVLEARDRVGG...unknowninhibitor
Cytochrome P450 2D6MGLEALVPLAVIVAIFLLLVDLMHRRQRWAARYPPGPLPLPGLGNLLHVD...unknowninhibitor
Cytochrome P450 2C9MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...unknowninhibitor
Cytochrome P450 2C19MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDV...unknowninhibitor
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL1179
PubChem 19493
ChEMBL CHEMBL1179
ChEBI CHEBI:94631, CHEBI:131510