95-62-5

Basic information

• Product Name: TRANYLCYPROMINE
• Synonyms: TRANYLCYPROMINE;AURORA KA-7804;TRANS-2-PHENYLCYCLOPROPYLAMINE HYDROCHLO RIDE (TRANYLCYPROMINE HCL);TRANS-1-AMINO-2-PHENYLCYCLOPROPANE;TRANS-LAMINO-2-PHENYLCYCLOPROPANE;rel-2β*-Phenylcyclopropane-1α*-amine;(1R,2S)-2-phenylcyclopropan-1-amine;[(1R,2S)-2-phenylcyclopropyl]amine
• CAS NO: 95-62-5
• Molecular Formula: C₉H₁₁N
• Molecular Weight: 133.19
• Mol File: 95-62-5.mol
• Article Data: 20

Chemical Properties

• Melting Point: 162-169℃
• Appearance: /
• PKA: pKa 8.2 (Uncertain)
• CAS DataBase Reference: TRANYLCYPROMINE(CAS DataBase Reference)
• NIST Chemistry Reference: TRANYLCYPROMINE(95-62-5)
• EPA Substance Registry System: TRANYLCYPROMINE(95-62-5)

Safety Data

• Safety Statements: S24/25:Avoid contact with skin and eyes.
• Hazardous Substances Data: 95-62-5(Hazardous Substances Data)

Usage

Clinical Use

Tranylcypromine is a nonhydrazine, irreversible MAO inhibitor antidepressant agent that was designed as the cyclopropyl analogue of amphetamine. Instead of exhibiting amphetamine-like stimulation, its mechanism of action is nonselective, irreversible inhibition of MAO. Its onset of antidepressant action is more rapid than for phenelzine. Tranylcypromine is well absorbed following oral administration. Metabolism occurs via aromatic ring hydroxylation and N-acetylation. It is a competitive inhibitor of CYP2C19 and CYP2D6 and a noncompetitive inhibitor of CYP 2C9. Most metabolism studies suggest that tranylcypromine is not metabolized to amphetamine contrary to debate. Maximal MAO inhibition, however, occurs within 5 to 10 days. The GI absorption of the tranylcypromine shows interindividual variation and may be biphasic in some individuals, achieving an initial peak within approximately 1 hour and a secondary peak within 2 to 3 hours. It has been suggested that this apparent biphasic absorption in some individuals may represent different absorption rates. Following discontinuance of tranylcypromine, the drug is excreted within 24 hours. On withdrawal of tranylcypromine, MAO activity is recovered in 3 to 5 days (possibly in up to 10 days). Concentrations of urinary tryptamine, an indicator of MAO-A inhibition return to normal, however, within 72 to 120 hours.

InChI:InChI=1/C9H11N/c10-9-6-8(9)7-4-2-1-3-5-7/h1-5,8-9H,6,10H2/t8-,9+/m0/s1

Upstream product

• 1444-65-1 (RS)-2-phenylcyclohexanone 
• 93-92-5 1-phenylethyl acetate 
• 939-89-9 (1S*,2R*)-2-phenylcyclopropane-1-carboxylic acid 
• 14561-40-1 (+/-)-cis-2-phenyl-cyclopropane-carboxylic acid-⁽¹⁾-hydrazide 
• 110659-58-0 (1R,2R)-1-hydroxymethyl-2-phenylcyclopropane 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 185256-47-7 (-)-(1R,2S)-trans (2-phenyl-cyclopropyl)carbaminic acid tert-butyl ester 
• 3471-10-1 (1R,2R)-trans-2-phenyl-1-cyclopropanecarboxylic acid 
• 874341-58-9 methyl (1R,2S)-1-nitro-2-phenylcyclopropanecarboxylate 
• 874341-82-9 [(1S,2R)-2-nitrocyclopropyl]benzene 
• 155-09-9 trans-2-phenylcyclopropylamine 
• 141-78-6 ethyl acetate 
• 100-42-5 styrene 
• 1036637-32-7 methyl (1S,2R)-1-nitro-2-phenylcyclopropanecarboxylate 

Downstream Products

• 1351165-22-4 C₂₁H₂₂Cl₂N₄O₂ 
• 1351165-63-3 C₂₁H₂₂Cl₂N₄O₂ 
• 1211400-41-7 (8aS)-N-(2,3-dichlorophenyl)-1,3-dioxo-2-[(1R,2S)-2-phenylcyclopropyl]hexahydroimidazo[1,5-a]pyrazine-7(1H)-carboxamide 
• 1351165-31-5 C₂₂H₂₅N₃O₃ 
• 1211400-32-6 (8aR)-N-(2,3-dichlorophenyl)-1,3-dioxo-2-[(1R,2S)-2-phenylcyclopropyl]hexahydroimidazo[1,5-a]pyrazine-7(1H)-carboxamide 
• 1351165-18-8 C₂₂H₂₅N₃O₃ 
• 50584-02-6 trans-2-Benzamido-1-phenyl-cyclopropan 
• 1521265-14-4 (2S,3S,4S)-4-fluoro-3-methoxy-2-((1R,2S)-2-phenyl-cyclopropylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

CYCLOPROPYLAMINE COMPOUND AS LSD1 INHIBITOR AND USE THEREOF

Provided is a cyclopropylamine compound as lysine-specific demethylase 1 (LSD1) inhibitor, and a use thereof in preparation of drug for treating diseases associated with LSD1. The cyclopropylamine compound is a compound represented by formula (I), an isomer thereof, and a pharmaceutically acceptable salt thereof.

Gram-Scale Synthesis of Chiral Cyclopropane-Containing Drugs and Drug Precursors with Engineered Myoglobin Catalysts Featuring Complementary Stereoselectivity

Engineered hemoproteins have recently emerged as promising systems for promoting asymmetric cyclopropanations, but variants featuring predictable, complementary stereoselectivity in these reactions have remained elusive. In this study, a rationally driven strategy was implemented and applied to engineer myoglobin variants capable of providing access to 1-carboxy-2-aryl-cyclopropanes with high trans-(1R,2R) selectivity and catalytic activity. The stereoselectivity of these cyclopropanation biocatalysts complements that of trans-(1S,2S)-selective variants developed here and previously. In combination with whole-cell biotransformations, these stereocomplementary biocatalysts enabled the multigram synthesis of the chiral cyclopropane core of four drugs (Tranylcypromine, Tasimelteon, Ticagrelor, and a TRPV1 inhibitor) in high yield and with excellent diastereo- and enantioselectivity (98–99.9% de; 96–99.9% ee). These biocatalytic strategies outperform currently available methods to produce these drugs.

COMPLEMENT PATHWAY MODULATORS AND USES THEREOF

The present invention provides a compound of formula I: (I) a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.