Tapentadol

Base Information

• Chemical Name: Tapentadol
• CAS No.: 175591-23-8
• Molecular Formula: C14H23NO
• Molecular Weight: 221.343
• Hs Code.: 2922299015
• UNII: H8A007M585
• DSSTox Substance ID: DTXSID30170003
• Nikkaji Number: J2.771.076J
• Wikipedia: Tapentadol
• Wikidata: Q414463
• NCI Thesaurus Code: C72139
• RXCUI: 787390
• Pharos Ligand ID: LFH5DAQJQJMG
• Metabolomics Workbench ID: 149676
• ChEMBL ID: CHEMBL1201776
• Mol file: 175591-23-8.mol

Synonyms:3-((1R,2R)-3-(dimethylamino)-1-ethyl-2-methylpropyl)phenol;Nucynta;tapentadol;tapentadol hydrochloride

 This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.

Chemical Property of Tapentadol

Chemical Property:

• Vapor Pressure: 0.000138mmHg at 25°C
• Refractive Index: 1.518
• Boiling Point: 323.493 °C at 760 mmHg
• PKA: 9.97±0.10(Predicted)
• Flash Point: 134.18 °C
• PSA: 23.47000
• Density: 0.97 g/cm³
• LogP: 3.08350
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 221.177964357
• Heavy Atom Count: 16
• Complexity: 193

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C1=CC(=CC=C1)O)C(C)CN(C)C
• Isomeric SMILES: CC[C@@H](C1=CC(=CC=C1)O)[C@@H](C)CN(C)C
• Recent ClinicalTrials: Tapentadol Versus Tramadol Analgesia Post Cardiac Surgery
• Recent EU Clinical Trials: Multicentre, randomized, open-label study to prove an additional
• Recent NIPH Clinical Trials: A quasi-randomized clinical trial of tapentadol versus oxycodone for initial control of moderate cancer-related pain
• Uses: Analgesic (μ-agonist).

Technology Process of Tapentadol

There total 103 articles about Tapentadol 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: 98.0%

(βR,γR)-γ-ethyl-N,N,β-trimethyl-3-methoxybenzenepropanamine (175591-22-7) → tapentadol (175591-23-8)

Guidance literature:

With hydrogen bromide; In water; at 100 - 110 ℃; for 3h;

Reference yield: 90.0%

(2R,3R)-(3-hydroxyphenyl)-2-methylpentanal + N,N-dimethylammonium chloride (506-59-2) → tapentadol (175591-23-8)

Guidance literature:

(2R,3R)-(3-hydroxyphenyl)-2-methylpentanal; N,N-dimethylammonium chloride; With triethylamine; In methanol; at 20 ℃; for 0.25h; Inert atmosphere;

With sodium tris(acetoxy)borohydride; In methanol; at 5 - 20 ℃; Reagent/catalyst; Temperature;

Reference yield: 90.0%

[1R,2R]-toluene-4-sulfonic acid 3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenyl ester (1369205-85-5) → tapentadol (175591-23-8)

Guidance literature:

[1R,2R]-toluene-4-sulfonic acid 3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenyl ester; With water; sodium hydroxide; In methanol; at 28 - 35 ℃; for 20h;

With hydrogenchloride; In water; at 5 - 10 ℃; pH=10 - 11; Product distribution / selectivity;

upstream raw materials:

2-(3-methoxybenzylidene)malononitrile

3-methoxy-benzaldehyde

(±)-3-(1-(dimethylamino)-2-methylpentan-3-yl)phenol

(βR,γR)-γ-ethyl-N,N,β-trimethyl-3-methoxybenzenepropanamine

Downstream raw materials:

tapentadol hydrochloride

(R,R)-tapentadol-(PABA tert-butyl ester) carbamate

3-[(1R,2R)-3-(dimethylamino)-1-ethyl-2-methylpropyl]phenol hydrochloride

tapentadol/γ-cyclodextrin inclusion complex

Refernces

• 1、 -. "TWO-STEP PROCESS FOR PREPARING 3-SUBSTITUTED PHENYLALKYLAMINES". Paragraph 0158; 0159. . Retrieved 2017/01/31.
• 2、 -. "PROCESS FOR PREPARING SUBSTITUTED PHENYLALKANES". Paragraph 0170. . Retrieved 2016/01/25.