(1R,2S)-2-phenylcyclopropan-1-amine

• ChemBase ID: 2391
• Molecular Formular: C9H11N
• Molecular Mass: 133.19034
• Monoisotopic Mass: 133.08914936
• SMILES: N[C@@H]1C[C@H]1c1ccccc1
• Canonical SMILES: N[C@@H]1C[C@H]1c1ccccc1
• 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
• InChIKey: AELCINSCMGFISI-DTWKUNHWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S)-2-phenylcyclopropan-1-amine
• IUPAC Traditional name: tranylcypromine
• Brand Name: Parnate
• Synonyms: Trans-2-Phenylcyclopropylamine; Transamine; Tranylcypromine

Database IDs

• CAS Number: 155-09-9
• PubChem SID: 160965842; 46506494
• PubChem CID: 11861988; 19493
• ATC CODE: N06AF04
• CHEMBL: 1179
• Chemspider ID: 18369
• DrugBank ID: DB00752
• Unique Ingredient Identifier: 3E3V44J4Z9
• Wikipedia Title: Tranylcypromine
• Medline Plus: a682088

CALCULATED PROPERTIES

JChem

• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): -1.6602782
• LogD (pH = 7.4): -0.82371813
• Log P: 1.3388824
• Molar Refractivity: 41.6966 cm^3
• Polarizability: 16.617031 Å^3
• Polar Surface Area: 26.02 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.64
• LOG S: -4.21
• Solubility (Water): 1.04e-02 g/l

PROPERTIES

Pharmacology Properties

• Admin Routes: Oral
• Bioavailability: 50%
• Excretion: Urine, Feces
• Half Life: 2.5 hours
• Metabolism: Liver (by enzymes CYP2A6, CYP2C19, CYP2D6, MAO_A, and MAO_B)
• Legal Status: Rx-only
• Pregnancy Category: C

DETAILS

DrugBank - DB02665

• Drug Groups: experimental
• 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)