Cutamesine

Base Information

• Chemical Name: Cutamesine
• CAS No.: 165377-43-5
• Molecular Formula: C23H32N2O2
• Molecular Weight: 368.519
• UNII: 9J7A4144BX
• DSSTox Substance ID: DTXSID50167935
• Nikkaji Number: J750.911A
• Wikipedia: Cutamesine
• Wikidata: Q6589967
• NCI Thesaurus Code: C83642
• Pharos Ligand ID: 64RZNVTBPYJ3
• Metabolomics Workbench ID: 149861
• ChEMBL ID: CHEMBL408867
• Mol file: 165377-43-5.mol

Synonyms:(11C)SA4503;1-(3,4-dimethoxyphenethyl)-4-(3-phenylpropyl)piperazine dihydrochloride;cutamesine;SA 4503;SA-4503;SA4503

Chemical Property of Cutamesine

Chemical Property:

• Boiling Point: 499.2±45.0 °C(Predicted)
• PKA: 7.61±0.10(Predicted)
• PSA: 24.94000
• Density: 1.053±0.06 g/cm3(Predicted)
• LogP: 3.37250
• Storage Temp.: 2-8°C
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 9
• Exact Mass: 368.246378268
• Heavy Atom Count: 27
• Complexity: 392

Purity/Quality:

97% ^*data from raw suppliers

SA4503 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)CCN2CCN(CC2)CCCC3=CC=CC=C3)OC
• Recent ClinicalTrials: Study to Evaluate Safety, PK, PD, Immunogenicity & Antitumor Activity of MSC-1 in Patients With Adv Solid Tumors
• Recent EU Clinical Trials: A Randomized, Double-Blind, Placebo-Controlled, Ascending Dose, Phase IIa Study of Safety and Motor Function Restoration in Subjects Treated with SA4503 following Acute Ischemic Stroke

Technology Process of Cutamesine

There total 9 articles about Cutamesine 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: 89.0%

1-(3-phenylpropyl)piperazine (55455-92-0) + 3,4-dimethoxyphenethyl bromide (40173-90-8) → 1-(3,4-dimethoxyphenethyl)-4-(3-phenylpropyl)piperazine (165377-43-5)

Guidance literature:

With potassium carbonate; potassium iodide; In acetonitrile; at 95 ℃; for 4h;

DOI:10.1021/jm301734g

Reference yield:

cinnamamide (621-79-4,22031-64-7) → 1-(3,4-dimethoxyphenethyl)-4-(3-phenylpropyl)piperazine (165377-43-5)

Guidance literature:

Multi-step reaction with 2 steps

1: LiAlH₄ / tetrahydrofuran / 5 h

2: NaI, K₂CO₃ / dimethylformamide / 13 h / 60 °C

With lithium aluminium tetrahydride; potassium carbonate; sodium iodide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(97)00093-X

Reference yield:

Cutamesine dihydrochloride (165377-44-6) → 1-(3,4-dimethoxyphenethyl)-4-(3-phenylpropyl)piperazine (165377-43-5)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water;

upstream raw materials:

3-Phenylpropan-1-amine

cinnamamide

N,N-bis(2-hydroxyethyl)-2-<(3,4-dimethoxy)phenyl>ethylamine

cinnamoyl chloride

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