Traxoprodil

Base Information

• Chemical Name: Traxoprodil
• CAS No.: 134234-12-1
• Molecular Formula: C20H25NO3
• Molecular Weight: 327.4174
• European Community (EC) Number: 694-572-4
• UNII: UTC046R5HM
• DSSTox Substance ID: DTXSID90158605
• Nikkaji Number: J668.731H
• Wikipedia: Traxoprodil
• Wikidata: Q7836470
• NCI Thesaurus Code: C87769
• Pharos Ligand ID: 35HCWRYZTKMT
• ChEMBL ID: CHEMBL17350
• Mol file: 134234-12-1.mol

Synonyms:1-(4-hydroxyphenyl)-2-(4-hydroxy-4-phenylpiperidino)-1-propanol;CP 101,606;CP-101,606;CP-101606;CP101,606;traxoprodil;traxoprodil mesylate

Chemical Property of Traxoprodil

Chemical Property:

• Vapor Pressure: 2.98E-12mmHg at 25°C
• Boiling Point: 534.4°Cat760mmHg
• PKA: 9.99±0.26(Predicted)
• Flash Point: 290.3°C
• PSA: 63.93000
• Density: 1.228g/cm³
• LogP: 2.73560
• Storage Temp.: 2-8°C
• Solubility.: DMSO: ≥35mg/mL
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 327.18344366
• Heavy Atom Count: 24
• Complexity: 380

Purity/Quality:

97% ^*data from raw suppliers

Traxoprodil ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T,N
• Statements: 25-36-50
• Safety Statements: 26-45-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(C1=CC=C(C=C1)O)O)N2CCC(CC2)(C3=CC=CC=C3)O
• Isomeric SMILES: C[C@@H]([C@H](C1=CC=C(C=C1)O)O)N2CCC(CC2)(C3=CC=CC=C3)O
• Uses: Traxoprodil (CP101,606) is a potent and selective NMDA antagonist and protect hippocampal neurons with an IC50 of 10 nM. CP-101,606 has been used as a N-methyl-D-aspartate (NMDA)?receptor antagonist to study its role in recovery of spinal cord injuries.

Technology Process of Traxoprodil

There total 22 articles about Traxoprodil 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: 65.0%

threo-1-<4-<(triisopropylsilyl)oxy>phenyl>-2-(4-hydroxy-4-phenylpiperidino)-1-propanol → (+/-)-Traxoprodil (134234-12-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.75h;

DOI:10.1021/jm00016a017

Reference yield:

4-hydroxy-4-phenylpiperidin (40807-61-2) → (+)-(1S,2S)-1-(4-hydroxy-phenyl)-2-(4-hydroxy-4-phenylpiperidino-1-yl)-1-propanol (134234-12-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 78 percent / Et₃N / ethanol / 16 h / Heating

2: 69 percent / NaBH₄ / ethanol / 24 h

3: 65 percent / Bu₄NF / tetrahydrofuran / 0.75 h

With sodium tetrahydroborate; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; ethanol;

DOI:10.1021/jm00016a017

Reference yield:

4-hydroxy-4-phenylpiperidin (40807-61-2) → Traxoprodil (134234-12-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 78 percent / Et₃N / ethanol / 16 h / Heating

2: 69 percent / NaBH₄ / ethanol / 24 h

3: 65 percent / Bu₄NF / tetrahydrofuran / 0.75 h

With sodium tetrahydroborate; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; ethanol;

DOI:10.1021/jm00016a017

upstream raw materials:

4-hydroxy-4-phenylpiperidin

1-(4-{[tris(1-methylethyl)silyl]oxy}phenyl)propan-1-one

4-(triisopropylsilyloxy)-alpha-bromopropiophenone

1-<4-<(triisopropylsilyl)oxy>phenyl>-2-(4-hydroxy-4-phenylpiperidino)-1-propanone

Refernces

• 1、 -. "NMDA NR2B antagonists for treatment". . . Retrieved 2008/06/13.
• 2、 -. "Pharmaceutical combinations for the treatment of stroke and traumatic brain injury". . . Retrieved 2008/06/13.