O-Demethyltramadol

Base Information

• Chemical Name: O-Demethyltramadol
• CAS No.: 73986-53-5
• Molecular Formula: C15H23NO2
• Molecular Weight: 249.353
• DSSTox Substance ID: DTXSID40894102
• Nikkaji Number: J79.316G
• Wikipedia: Desmetramadol
• Wikidata: Q1949486
• ChEMBL ID: CHEMBL4650315
• Mol file: 73986-53-5.mol

Synonyms:O-demethyl tramadol;O-demethyltramadol;O-demethyltramadol hydrochloride;O-desmethyltramadol;tramadol M1 metabolite

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Chemical Property of O-Demethyltramadol

Chemical Property:

• Vapor Pressure: 3.14E-07mmHg at 25°C
• Refractive Index: 1.561
• Boiling Point: 403.3 °C at 760 mmHg
• Flash Point: 201.2 °C
• PSA: 43.70000
• Density: 1.104 g/cm³
• LogP: 2.33160
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 249.172878976
• Heavy Atom Count: 18
• Complexity: 269

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)CC1CCCCC1(C2=CC(=CC=C2)O)O
• Uses: O-Desmethyl Tramadol, is a metabolite of Tramadol, an analgesic.

Technology Process of O-Demethyltramadol

There total 5 articles about O-Demethyltramadol 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: 80.0%

cis-tramadol (27203-92-5,2914-77-4,73806-46-9,123134-25-8,123154-38-1,36282-47-0,152538-36-8,181289-58-7,181289-59-8) → (±)-cis-2-[(dimethylamino)methyl]-1-(3-hydroxyphenyl)cyclohexanol (73986-53-5,80456-81-1,144830-14-8,144830-15-9)

Guidance literature:

With diisobutylaluminium hydride; In toluene; for 23h; Cooling with ice; Inert atmosphere; Reflux;

Reference yield:

tramadol (2914-77-4,152538-36-8,181289-58-7,181289-59-8) → (±)-cis-2-[(dimethylamino)methyl]-1-(3-hydroxyphenyl)cyclohexanol (73986-53-5,80456-81-1,144830-14-8,144830-15-9)

Guidance literature:

With potassium hydroxide; In ethylene glycol; at 195 - 200 ℃; for 28h; Inert atmosphere;

Reference yield:

tramadol hydrochloride (36282-47-0,22204-88-2) → (±)-cis-2-[(dimethylamino)methyl]-1-(3-hydroxyphenyl)cyclohexanol (73986-53-5,80456-81-1,144830-14-8,144830-15-9) + (±)-cis-2-[(methylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol (147762-57-0,75377-45-6)

Guidance literature:

With titanium dioxide P-25; water; at 25 ℃; for 0.25h; Kinetics; Photolysis;

DOI:10.1016/j.apcata.2016.02.005

upstream raw materials:

tramadol hydrochloride

cis-tramadol

tramadol

Downstream raw materials:

(+/-)-mono-O-demethyltramadol hydrochloride

(1R₂R,1S₂S)-3-(2-((dimethylamino)methyl)-1-hydroxycyclohexyl)phenyl 2-(1-((tert-butoxycarbonylamino)methyl)cyclohexyl)acetate

Refernces

• 1、 Antonopoulou, Maria,Konstantinou, Ioannis. "Photocatalytic degradation and mineralization of tramadol pharmaceutical in aqueous TiO2 suspensions: Evaluation of kinetics, mechanisms and ecotoxicity". . p. 136 - 143. Retrieved 2016/02/26.