Parnate

Base Information

• Chemical Name: Parnate
• CAS No.: 155-09-9
• Deprecated CAS: 95-62-5
• Molecular Formula: C9H11 N
• Molecular Weight: 133.193
• Hs Code.: 2921499090
• European Community (EC) Number: 205-841-9
• UNII: 3E3V44J4Z9
• DSSTox Substance ID: DTXSID2023694,DTXSID201015773
• Nikkaji Number: J9.122G
• Wikipedia: Tranylcypromine
• Wikidata: Q100429273
• NCI Thesaurus Code: C61979
• RXCUI: 10734
• Pharos Ligand ID: LM1GZFVJ9TM4
• ChEMBL ID: CHEMBL1179
• Mol file: 155-09-9.mol

Synonyms:Jatrosom;Parnate;Sulfate, Tranylcypromine;trans 2 Phenylcyclopropylamine;trans-2-Phenylcyclopropylamine;Transamine;Tranylcypromine;Tranylcypromine Sulfate

Chemical Property of Parnate

Chemical Property:

• Vapor Pressure: 0.127mmHg at 25°C
• Melting Point: 28 °C
• Boiling Point: 218.3°C at 760 mmHg
• PKA: 8.24±0.10(Predicted)
• Flash Point: 90.8°C
• PSA: 26.02000
• Density: 1.065g/cm³
• LogP: 2.20150
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 133.089149355
• Heavy Atom Count: 10
• Complexity: 116

Purity/Quality:

97% ^*data from raw suppliers

(1R,2S)-rel-2-Phenylcyclopropanamine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antidepressant Agents
• Canonical SMILES: C1C(C1N)C2=CC=CC=C2
• Isomeric SMILES: C1[C@H]([C@@H]1N)C2=CC=CC=C2
• Recent ClinicalTrials: Study of TCP-ATRA for Adult Patients With AML and MDS
• Recent EU Clinical Trials: Phase I/II pilot trial of ATRA (Tretinoin) and TCP (Tranylcypromine) in patients with relapsed or refractory acute myeloid leukemia (AML) when no intensive treatment is possible
• General Description: Tranylcypromine is a trans-2-phenylcyclopropylamine derivative that serves as a foundational structure for developing central 5-hydroxytryptamine (5-HT) receptor agonists. The study highlights that specific modifications, such as hydroxy substituents at the 2- or 3-position of the phenyl ring and N,N-dialkylation (e.g., diethyl or di-n-propyl groups), enhance 5-HT receptor activity, while 4-hydroxy or 3,4-dihydroxy substitutions render tranylcypromines inactive. These findings underscore the structural specificity required for receptor agonism, with tranylcypromine derivatives offering potential as targeted serotonergic agents.

Technology Process of Parnate

There total 50 articles about Parnate 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:

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

(RS)-2-phenylcyclohexanone

1-phenylethyl acetate

ethyl acetate

Downstream raw materials:

(-)-ethyl 2-(2,4-dichloro-5-fluorobenzoyl)-3-<<(1'R,2'S)-2'-phenylcyclopropyl>amino>acrylate

N⁶-[(1R,2S)-2-phenyl-1-cyclopropyl]adenosine

(-)-7-chloro-6-fluoro-1-<(1'R,2'S)-2'-phenylcyclopropyl>-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

(-)-7-chloro-6-fluoro-1-<(1'R,2'S)-2'-phenylcyclopropyl>-1,4-dihydro-3-ethoxycarbonyl-4-oxoquinoline

Refernces

N,N-dialkylated monophenolic trans-2-phenylcyclopropylamines: Novel central 5-hydroxytryptamine receptor agonists

10.1021/jm00396a014

This research aimed to synthesize and test N,N-dialkylated monophenolic derivatives of trans-2-phenylcyclopropylamine for their activity as central 5-hydroxytryptamine (5-HT) and dopamine (DA) receptor agonists. The study found that a hydroxy substituent in the 2- or 3-position of the phenyl ring was necessary for 5-HT-receptor stimulation, with N,N-diethyl or N,N-di-n-propyl substitution yielding the most potent 5-HT-receptor agonists. Notably, the 4-hydroxy and 3,4-dihydroxy derivatives were inactive at central DA and 5-HT receptors. The compounds were synthesized using various chemical reactions, including cyclopropanation, Curtius rearrangement, and reductive methylation, with starting materials such as methyl trans-cinnamates and ethyl diazoacetate.