147762-57-0

Basic information

• Product Name: (+)-N-Desmethyl Tramadol
• Synonyms: (1R,2R)-(+)-1-(3-Methoxyphenyl)-2-[(methylamino)methyl]-cyclohexanol;(+)-N-Desmethyl Tramadol
• CAS NO: 147762-57-0
• Molecular Formula: C15H23NO2
• Molecular Weight: 249.35
• Product Categories: Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 147762-57-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 389.494 °C at 760 mmHg
• Flash Point: 189.359 °C
• Appearance: /
• Density: 1.055 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.531
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• PKA: 14.46±0.40(Predicted)
• CAS DataBase Reference: (+)-N-Desmethyl Tramadol(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-N-Desmethyl Tramadol(147762-57-0)
• EPA Substance Registry System: (+)-N-Desmethyl Tramadol(147762-57-0)

Safety Data

• Hazardous Substances Data: 147762-57-0(Hazardous Substances Data)

Usage

Chemical Properties

Colourless Oil

InChI:InChI=1/C15H23NO2/c1-16-11-13-6-3-4-9-15(13,17)12-7-5-8-14(10-12)18-2/h5,7-8,10,13,16-17H,3-4,6,9,11H2,1-2H3/t13-,15+/m0/s1

Upstream product

• 147762-57-0 (±)-cis-2-[(methylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol 
• 36282-47-0 tramadol hydrochloride 
• 1426536-05-1 C₁₈H₂₇NO₄ 
• 1426536-04-0 C₁₁H₁₉NO₃ 

Downstream Products

• 147762-57-0 (+)-N-desmethyltramadol 
• 147762-57-0 (-)-N-desmethyltramadol 

Relevant articles and documents

Simultaneous analysis of tramadol, O-desmethyltramadol, and N-desmethyltramadol enantiomers in rat plasma by high-performance liquid chromatography-tandem mass spectrometry: Application to pharmacokinetics

Tramadol (T) is available as a racemic mixture of (+)-trans-T and (-)-trans-T. The main metabolic pathways are O-demethylation and N-demethylation, producing trans-O-desmethyltramadol (M1) and trans-N-desmethyltramadol (M2) enantiomers, respectively. The analgesic effect of T is related to the opioid activity of (+)-trans-T and (+)-M1 and to the monoaminergic action of (+/-)-trans-T. This is the first study using tandem mass spectrometry as a detection system for the simultaneous analysis of trans-T, M1, and M2 enantiomers. The analytes were resolved on a ChiralpakA AD column using hexane:ethanol (95.5:4.5, v/v) plus 0.1% diethylamine as the mobile phase. The quantitation limits were 0.5 ng/ml for trans-T and M1 and 0.1 ng/ml for M2. The method developed and validated here was applied to a pharmacokinetic study in rats. Male Wistar rats (n = 6 at each time point) received a single oral dose of 20 mg/kg racemic trans-T. Blood samples were collected up to 12 h after drug administration. The kinetic disposition of trans-T and M2 was enantioselective (AUC(+)/(-) ratio = 4.16 and 6.36, respectively). The direction and extent of enantioselectivity in the pharmacokinetics of trans-T and M2 in rats were comparable to data previously reported for healthy volunteers, suggesting that rats are a suitable model for enantioselective studies of trans-T pharmacokinetics. Chirality, 2011.

COMPOSITIONS AND METHODS FOR THE TREATMENT OF RESTLESS LEG SYNDROME AND FIBROMYALGIA

The invention relates to the compounds of formula I or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula I, and methods for the treatment of fibromyalgia, restless leg syndrome may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be used to treatment of motor neurone disease, diabetic neuropathy, postherpetic neuralgia, acute opioid withdrawal management, obsessive-compulsive disorder, premature ejaculation, PTSD, injury, post-operative pain, osteoarthritis, rheumatoid arthritis, multiple sclerosis, spinal cord injury, migraine, HIV related neuropathic pain, bipolar depression, depression, stress, cancer pain and lower back pain.