TRANYLCYPROMINE

Base Information

• Chemical Name: TRANYLCYPROMINE
• CAS No.: 95-62-5
• Molecular Formula: C₉H₁₁N
• Molecular Weight: 133.193
• Mol file: 95-62-5.mol

Synonyms:TRANS-2-PHENYLCYCLOPROPYLAMINE;CAS No.:155-09-9(Deleted CAS No.: 95-62-5);trans-(-)-2-Phenylcyclopropanamine;(-)-Tranylcypromine Hydrochloride;TRANS-2-PHENYLCYCLOPROPYLAMINE HYDROCHLORIDE;

Chemical Property of TRANYLCYPROMINE

Chemical Property:

• PKA: pKa 8.2 (Uncertain)
• PSA: 26.02000
• LogP: 2.20150

Purity/Quality:

99%, ^*data from raw suppliers

(1R,2S)-2-PHENYLCYCLOPROPAN-1-AMINE 95.00% ^*data from reagent suppliers

Safty Information:

• Safety Statements: S24/25:Avoid contact with skin and eyes.

MSDS Files:

SDS file from LookChem

Useful:

• 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.

Technology Process of TRANYLCYPROMINE

There total 40 articles about TRANYLCYPROMINE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

C17H23NO2 → (1R,2S)-1-amino-2-phenylcyclopropane (95-62-5,155-09-9,3721-26-4,3721-28-6,13531-35-6,24873-95-8,69684-88-4,69684-89-5,54-97-7)

Guidance literature:

With trifluoroacetic acid; In 1,4-dioxane; water; for 21h;

DOI:10.1055/s-2008-1072786

Reference yield: 79.0%

(RS)-2-phenylcyclohexanone (1444-65-1) + 1-phenylethyl acetate (93-92-5,50373-55-2) → (1R,2S)-1-amino-2-phenylcyclopropane (95-62-5,155-09-9,3721-26-4,3721-28-6,13531-35-6,24873-95-8,69684-88-4,69684-89-5,54-97-7) + (+)-(1S,2R)-2-Phenylcyclohexanamine (37982-23-3) + (1R,2S)-N-(2-phenylcyclohexyl)acetamide (312611-48-6) + cis-1-amino-2-phenylcyclohexane (1011-11-6,17293-45-7,22147-09-7,37982-23-3,37982-28-8,37982-29-9,40960-61-0,46175-82-0,69743-67-5)

Guidance literature:

(RS)-2-phenylcyclohexanone; With ammonium formate; palladium on activated charcoal; In methanol; water; at 20 ℃;

1-phenylethyl acetate; With Novozyme 435 immobilized on polyacrylamide;

DOI:10.1016/j.tetasy.2005.07.033

Reference yield: 68.0%

(-)-(1R,2S)-trans (2-phenyl-cyclopropyl)carbaminic acid tert-butyl ester (185256-47-7,847644-86-4) → (1R,2S)-1-amino-2-phenylcyclopropane (95-62-5,155-09-9,3721-26-4,3721-28-6,13531-35-6,24873-95-8,69684-88-4,69684-89-5,54-97-7)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 40 ℃; for 0.5h;

DOI:10.1016/S0957-4166(96)00457-0

upstream raw materials:

trans-2-phenylcyclopropylamine

(-)-(1R,2S)-trans (2-phenyl-cyclopropyl)carbaminic acid tert-butyl ester

(RS)-2-phenylcyclohexanone

1-phenylethyl acetate

Downstream raw materials:

C₂₁H₂₂Cl₂N₄O₂

C₂₁H₂₂Cl₂N₄O₂

(8aS)-N-(2,3-dichlorophenyl)-1,3-dioxo-2-[(1R,2S)-2-phenylcyclopropyl]hexahydroimidazo[1,5-a]pyrazine-7(1H)-carboxamide

C₂₂H₂₅N₃O₃

Refernces

• 1、 -. "SALT OF LSD1 INHIBITOR AND A POLYMORPH THEREOF". Paragraph 0038-0040. . Retrieved 2021/10/15.
• 2、 -. "KDM1A INHIBITORS FOR THE TREATMENT OF DISEASE". Paragraph 0258. . Retrieved 2014/10/18.