155-09-9

Basic information

• Product Name: tranylcypromine
• Synonyms: Cyclopropanamine, 2-phenyl-, (1R,2S)-rel-;Tranylcypromine (base and/or unspecified salts);dl-Tranylcypromine;SKF-385;Transamine【thymoleptic】;C07155;(RS)-TranylcyproMine;rac-trans-TranylcyproMine
• CAS NO: 155-09-9
• Molecular Formula: C₉H₁₁N
• Molecular Weight: 133.193
• EINECS: 205-841-9
• Mol File: 155-09-9.mol
• Article Data: 23

Chemical Properties

• Melting Point: 28 °C
• Boiling Point: bp1.5-1.6 79-80°
• Flash Point: 90.8°C
• Appearance: /
• Density: 1.065g/cm³
• Vapor Pressure: 0.127mmHg at 25°C
• Refractive Index: 1.584
• PKA: 8.24±0.10(Predicted)
• CAS DataBase Reference: tranylcypromine(CAS DataBase Reference)
• NIST Chemistry Reference: tranylcypromine(155-09-9)
• EPA Substance Registry System: tranylcypromine(155-09-9)

Safety Data

• Hazardous Substances Data: 155-09-9(Hazardous Substances Data)

Usage

Description

Tranylcypromine, also known as Parnate, is a synthetic monoamine oxidase inhibitor (MAOI) that was first synthesized in the 1950s. It is a potent and non-selective inhibitor of both MAO-A and MAO-B enzymes, which are responsible for the breakdown of various neurotransmitters, including serotonin, norepinephrine, and dopamine. Tranylcypromine has been used in the treatment of various psychiatric disorders, particularly depression and anxiety, due to its ability to increase the levels of these neurotransmitters in the brain.

Uses

Used in Pharmaceutical Industry:
Tranylcypromine is used as an antidepressant for the treatment of major depressive disorder and atypical depression. It works by inhibiting the activity of monoamine oxidase enzymes, leading to an increase in the levels of neurotransmitters such as serotonin, norepinephrine, and dopamine in the brain. This results in an improvement in mood and a reduction in depressive symptoms.
Used in Research Applications:
Tranylcypromine is used as a research tool in neuroscience and pharmacology to study the role of monoamine oxidase enzymes in the regulation of neurotransmitter levels and their involvement in various psychiatric and neurological disorders. It is also used to investigate the mechanisms of action of other drugs that target these enzymes.
Used in Combination Therapy:
Tranylcypromine is used in combination with other medications, such as selective serotonin reuptake inhibitors (SSRIs) or tricyclic antidepressants (TCAs), to enhance their therapeutic effects in patients with treatment-resistant depression or anxiety disorders. The combination of tranylcypromine with these medications can help to achieve better control of symptoms and improve the overall response to treatment.
Used in Veterinary Medicine:
Tranylcypromine is also used in veterinary medicine for the treatment of behavioral disorders and anxiety in animals, such as dogs and cats. It can help to alleviate symptoms of separation anxiety, noise phobia, and other anxiety-related conditions in pets.

Originator

Parnate,SKF,UK,1960

Manufacturing Process

A solution containing 167 grams of stabilized styrene and 183 grams of ethyl diazoacetate is cooled to 0°C and dropped into 83.5 grams of styrene with stirring, in a dry nitrogen atmosphere, at 125° to 135°C. This produced the ester ethyl 2-phenylcyclopropanecarboxylate. A solution of the above ester (207.8 grams) and 64.5 grams of sodium hydroxide in 80 cc of water and 600 cc of ethanol is refluxed for 9 hours. The carboxylic acid of 2-phenylcyclopropane is liberated with 200 cc of concentrated hydrochloric acid. The 2-phenylcyclopropanecarboxylic acid contains 3 to 4 parts of the trans isomer to 1 part of the cis isomer. The acid is recrystallized from hot water. The pure trans isomer comes out as crystalline material (solid) while the cis isomer stays in solution. A solution of 4.62 grams of 2-phenylcyclopropanecarboxylic acid in 15 cc of dry benzene is refluxed with 4 cc of thionyl chloride for 5 hours, the volatile liquids are removed and the residue once more distilled with benzene. Fractionation of the residue yields the carbonyl chloride of 2- phenylcyclopropane. A mixture of 15 grams of technical sodium azide and 50 cc of dry toluene is stirred and warmed and a solution of 10 grams of 2- phenylcyclopropanecarbonyl chloride in 50 cc of dry toluene is added slowly. Inorganic salts are filtered and washed well with dry benzene and the solvents are removed under reduced pressure. The RCON3 compound produced undergoes the Curtius rearrangement to RNCO + N2. The residual isocyanate is a clear red oil of characteristic odor. It is cooled to 10°C and treated cautiously with 100 cc of 35% hydrochloric acid whereupon RNCO + H2O gives RNH2 + CO2.After most of the evolution of carbon dioxide has subsided the mixture is refluxed for 13 hours, the cooled solution is diluted with 75 cc of water and extracted with three 50 cc portions of ether. The acid solution is evaporated under reduced pressure with occasional additions of toluene to reduce foaming. The almost dry residue is cooled to 0°C and made strongly alkaline with a 50% potassium hydroxide solution. The amine is extracted into several portions of ether, dried over potassium hydroxide, the solvent removed, and the base fractioned. Reaction of the base with a half-molar quantity of sulfuric acid gives the sulfate.

Therapeutic Function

Psychostimulant

World Health Organization (WHO)

Tranylcypromine, a monoamine oxidase inhibitor (MAOI), was introduced in 1961 for the treatment of depressive illness. By 1964 its use had been associated with transient hypertensive crises and other adverse effects when taken together with certain cheeses and other foods containing tyramine. This led to the withdrawal of the drug in several countries and the suspension of marketing on a worldwide basis by the major manufacturer pending review of these adverse reactions. Subsequently, in response to requests from the medical profession, tranylcypromine was resubmitted for registration with appropriate warnings in the product information and it is now marketed in more than 30 countries.

InChI:InChI=1/C9H11N/c10-9-6-8(9)7-4-2-1-3-5-7/h1-5,8-9H,6,10H2/t8?,9-/m1/s1

Upstream product

• 185256-47-7 (-)-(1R,2S)-trans (2-phenyl-cyclopropyl)carbaminic acid tert-butyl ester 
• 1444-65-1 (RS)-2-phenylcyclohexanone 
• 93-92-5 1-phenylethyl acetate 
• 141-78-6 ethyl acetate 
• 874341-82-9 [(1S,2R)-2-nitrocyclopropyl]benzene 
• 874341-58-9 methyl (1R,2S)-1-nitro-2-phenylcyclopropanecarboxylate 
• 100-42-5 styrene 
• 23020-15-7 (1S,2S)-2-phenylcyclopropane-1-carboxylic acid 
• 97-71-2 ethyl (S,S)-2-phenylcyclopropane-1-carboxylate 
• 3471-10-1 (1R,2R)-trans-2-phenyl-1-cyclopropanecarboxylic acid 
• 97-71-2 (1R,2R)-2-phenyl-cyclopropanecarboxylic acid ethyl ester 
• 946-39-4 ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate 
• 1036637-32-7 methyl (1S,2R)-1-nitro-2-phenylcyclopropanecarboxylate 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 

Downstream Products

• 14177-80-1 trans-N,N-dimethyl-2-phenylcyclopropan-1-amine 
• 22783-18-2 (+/-)-benzaldehyde-(trans-2-phenyl-cyclopropylimine) 
• 50584-02-6 (+/-)-trans-2-benzamino-1-phenyl-cyclopropane 
• 50584-02-6 (+/-)-cis-2-benzamino-1-phenyl-cyclopropane 
• 21793-78-2 2,2'-(trans-2-phenyl-cyclopropylazanediyl)-bis-ethanol 
• 62398-17-8 (trans-2-isocyano-cyclopropyl)-benzene 
• 13140-87-9 trans-(2-Phenylcyclopropyl)-harnstoff 
• 32752-08-2 1,1'-(trans-2-phenyl-cyclopropylazanediyl)-bis-propan-2-ol 
• 137596-57-7 ((1S,2R)-2-Phenyl-cyclopropyl)-[(E)-3-phenyl-prop-2-en-(E)-ylidene]-amine 
• 103477-53-8 (-)-ethyl 2-(2,4-dichloro-5-fluorobenzoyl)-3-<<(1'R,2'S)-2'-phenylcyclopropyl>amino>acrylate 
• 14371-10-9 (E)-3-phenylpropenal 
• 137596-57-7 ((1S,2R)-2-Phenyl-cyclopropyl)-[(E)-3-phenyl-prop-2-en-(Z)-ylidene]-amine 
• 95-62-5 (1R,2S)-1-amino-2-phenylcyclopropane 
• 3721-28-6 (1S,2R)-tranylcypromine 

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CYCLOPROPYLAMINE COMPOUND AS LSD1 INHIBITOR AND USE THEREOF

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