Desmetramadol free base | CAS#80456-81-1 | central analgesic

MedKoo Cat#: 561110 | Name: Desmetramadol free base

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Desmetramadol, also known as O-desmethyltramadol (O-DSMT), is the primary active metabolite of tramadol, generated via hepatic CYP2D6-mediated demethylation. In vitro studies reveal that (+)-desmetramadol functions as a G-protein biased full agonist at the μ-opioid receptor, exhibiting significantly lower affinity for δ- and κ-opioid receptors. Notably, while both enantiomers lack serotonin reuptake inhibition, (−)-desmetramadol maintains norepinephrine reuptake inhibitory activity, contributing to tramadol's multifaceted pharmacological effects. Additionally, desmetramadol acts as a competitive antagonist at the serotonin 5-HT₂C receptor, potentially underpinning some of tramadol's antidepressant properties.

Chemical Structure

Desmetramadol free base

CAS#80456-81-1 (free base)

Theoretical Analysis

MedKoo Cat#: 561110

Name: Desmetramadol free base

CAS#: 80456-81-1 (free base)

Chemical Formula: C15H23NO2

Exact Mass: 249.1729

Molecular Weight: 249.35

Elemental Analysis: C, 72.25; H, 9.30; N, 5.62; O, 12.83

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Related CAS #

80456-81-1 (free base) 185453-02-5 (HCl)

Synonym

Desmetramadol; O-desmethyl tramadol; O desmethyl tramadol; Mono-O-demethyltramadol; Mono O demethyltramadol; Tramadol M1 metabolite;

IUPAC/Chemical Name

3-((1R,2R)-2-((dimethylamino)methyl)-1-hydroxycyclohexyl)phenol

InChi Key

UWJUQVWARXYRCG-HIFRSBDPSA-N

InChi Code

InChI=1S/C15H23NO2/c1-16(2)11-13-6-3-4-9-15(13,18)12-7-5-8-14(17)10-12/h5,7-8,10,13,17-18H,3-4,6,9,11H2,1-2H3/t13-,15+/m1/s1

SMILES Code

OC1=CC=CC([C@]2(O)[C@@H](CN(C)C)CCCC2)=C1

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 249.35 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Allegaert K, Holford N, Anderson BJ, Holford S, Stuber F, Rochette A, Trocóniz IF, Beier H, de Hoon JN, Pedersen RS, Stamer U. Tramadol and o-desmethyl tramadol clearance maturation and disposition in humans: a pooled pharmacokinetic study. Clin Pharmacokinet. 2015 Feb;54(2):167-78. doi: 10.1007/s40262-014-0191-9. PubMed PMID: 25258277. 2: Horishita T, Minami K, Uezono Y, Shiraishi M, Ogata J, Okamoto T, Shigematsu A. The tramadol metabolite, O-desmethyl tramadol, inhibits 5-hydroxytryptamine type 2C receptors expressed in Xenopus Oocytes. Pharmacology. 2006;77(2):93-9. Epub 2006 May 5. PubMed PMID: 16679816. 3: Perez Jimenez TE, Mealey KL, Grubb TL, Greene SA, Court MH. Tramadol metabolism to O-desmethyl tramadol (M1) and N-desmethyl tramadol (M2) by dog liver microsomes: Species comparison and identification of responsible canine cytochrome P-450s (CYPs). Drug Metab Dispos. 2016 Oct 6. pii: dmd.116.071902. [Epub ahead of print] Erratum in: Drug Metab Dispos. 2017 Jul;45(7):706. PubMed PMID: 27758804; PubMed Central PMCID: PMC5118633. 4: Minami K, Yokoyama T, Ogata J, Uezono Y. The tramadol metabolite O-desmethyl tramadol inhibits substance P-receptor functions expressed in Xenopus oocytes. J Pharmacol Sci. 2011;115(3):421-4. Epub 2011 Mar 2. PubMed PMID: 21372504. 5: Pypendop BH, Ilkiw JE. Pharmacokinetics of tramadol, and its metabolite O-desmethyl-tramadol, in cats. J Vet Pharmacol Ther. 2008 Feb;31(1):52-9. doi: 10.1111/j.1365-2885.2007.00921.x. PubMed PMID: 18177319. 6: Arjunan V, Santhanam R, Marchewka MK, Mohan S. Comprehensive quantum chemical and spectroscopic (FTIR, FT-Raman, 1H, 13C NMR) investigations of O-desmethyltramadol hydrochloride an active metabolite in tramadol--an analgesic drug. Spectrochim Acta A Mol Biomol Spectrosc. 2014 Mar 25;122:315-30. doi: 10.1016/j.saa.2013.11.040. Epub 2013 Nov 20. PubMed PMID: 24316546. 7: Coller JK, Michalakas JR, James HM, Farquharson AL, Colvill J, White JM, Somogyi AA. Inhibition of CYP2D6-mediated tramadol O-demethylation in methadone but not buprenorphine maintenance patients. Br J Clin Pharmacol. 2012 Nov;74(5):835-41. doi: 10.1111/j.1365-2125.2012.04256.x. PubMed PMID: 22369095; PubMed Central PMCID: PMC3495148. 8: Salman S, Sy SK, Ilett KF, Page-Sharp M, Paech MJ. Population pharmacokinetic modeling of tramadol and its O-desmethyl metabolite in plasma and breast milk. Eur J Clin Pharmacol. 2011 Sep;67(9):899-908. doi: 10.1007/s00228-011-1023-6. Epub 2011 Mar 11. PubMed PMID: 21394525. 9: Nakamura M, Minami K, Uezono Y, Horishita T, Ogata J, Shiraishi M, Okamoto T, Terada T, Sata T. The effects of the tramadol metabolite O-desmethyl tramadol on muscarinic receptor-induced responses in Xenopus oocytes expressing cloned M1 or M3 receptors. Anesth Analg. 2005 Jul;101(1):180-6, table of contents. PubMed PMID: 15976229. 10: Curticapean A, Muntean D, Curticapean M, Dogaru M, Vari C. Optimized HPLC method for tramadol and O-desmethyl tramadol determination in human plasma. J Biochem Biophys Methods. 2008 Apr 24;70(6):1304-12. doi: 10.1016/j.jprot.2008.01.012. Epub 2008 Feb 9. PubMed PMID: 18396334. 11: Kanaan M, Daali Y, Dayer P, Desmeules J. Uptake/efflux transport of tramadol enantiomers and O-desmethyl-tramadol: focus on P-glycoprotein. Basic Clin Pharmacol Toxicol. 2009 Sep;105(3):199-206. doi: 10.1111/j.1742-7843.2009.00428.x. Epub 2009 May 26. PubMed PMID: 19496778; PubMed Central PMCID: PMC2774482. 12: Ilett KF, Paech MJ, Page-Sharp M, Sy SK, Kristensen JH, Goy R, Chua S, Christmas T, Scott KL. Use of a sparse sampling study design to assess transfer of tramadol and its O-desmethyl metabolite into transitional breast milk. Br J Clin Pharmacol. 2008 May;65(5):661-6. doi: 10.1111/j.1365-2125.2008.03117.x. Epub 2008 Feb 20. PubMed PMID: 18294329; PubMed Central PMCID: PMC2432475. 13: Tao Q, Stone DJ, Borenstein MR, Codd EE, Coogan TP, Desai-Krieger D, Liao S, Raffa RB. Differential tramadol and O-desmethyl metabolite levels in brain vs. plasma of mice and rats administered tramadol hydrochloride orally. J Clin Pharm Ther. 2002 Apr;27(2):99-106. PubMed PMID: 11975693. 14: Cagnardi P, Villa R, Zonca A, Gallo M, Beccaglia M, Luvoni GC, Vettorato E, Carli S, Fonda D, Ravasio G. Pharmacokinetics, intraoperative effect and postoperative analgesia of tramadol in cats. Res Vet Sci. 2011 Jun;90(3):503-9. doi: 10.1016/j.rvsc.2010.07.015. Epub 2010 Aug 13. PubMed PMID: 20708759. 15: Giorgi M, Del Carlo S, Łebkowska-Wieruszewska B, Kowalski CJ, Saccomanni G. Pharmacokinetics of tramadol and metabolites after injective administrations in dogs. Pol J Vet Sci. 2010;13(4):639-44. PubMed PMID: 21370741. 16: Vettorato E, Zonca A, Isola M, Villa R, Gallo M, Ravasio G, Beccaglia M, Montesissa C, Cagnardi P. Pharmacokinetics and efficacy of intravenous and extradural tramadol in dogs. Vet J. 2010 Mar;183(3):310-5. doi: 10.1016/j.tvjl.2008.11.002. Epub 2009 Jan 12. PubMed PMID: 19138866. 17: Tao Q, Stone DJ Jr, Borenstein MR, Jean-Bart V, Codd EE, Coogan TP, Desai-Krieger D, Liao S, Raffa RB. Gas chromatographic method using nitrogen-phosphorus detection for the measurement of tramadol and its O-desmethyl metabolite in plasma and brain tissue of mice and rats. J Chromatogr B Biomed Sci Appl. 2001 Nov 5;763(1-2):165-71. PubMed PMID: 11710575. 18: Correction to "Tramadol Metabolism to O-Desmethyl Tramadol (M1) and N-Desmethyl Tramadol (M2) by Dog Liver Microsomes: Species Comparison and Identification of Responsible Canine Cytochrome P450s". Drug Metab Dispos. 2017 Jul;45(7):706. doi: 10.1124/dmd.115.071902err. PubMed PMID: 28559373; PubMed Central PMCID: PMC5458504. 19: Sevcik J, Nieber K, Driessen B, Illes P. Effects of the central analgesic tramadol and its main metabolite, O-desmethyltramadol, on rat locus coeruleus neurones. Br J Pharmacol. 1993 Sep;110(1):169-76. PubMed PMID: 8220877; PubMed Central PMCID: PMC2175982. 20: Haage P, Kronstrand R, Carlsson B, Kugelberg FC, Josefsson M. Quantitation of the enantiomers of tramadol and its three main metabolites in human whole blood using LC-MS/MS. J Pharm Biomed Anal. 2016 Feb 5;119:1-9. doi: 10.1016/j.jpba.2015.11.012. Epub 2015 Nov 17. PubMed PMID: 26625281.