Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C15H23NO2.ClH |
| Molecular Weight | 285.81 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CN(C)C[C@H]1CCCC[C@]1(O)C2=CC(O)=CC=C2
InChI
InChIKey=IRGWVAWLHXDKIX-PBCQUBLHSA-N
InChI=1S/C15H23NO2.ClH/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;1H/t13-,15+;/m1./s1
O-Desmethyl tramadol (O-Desmethyltramadol, O-DSMT) is a metabolite of tramadol. O-Desmethyltramadol is an opioid analgesic and the main active metabolite of tramadol. (+)-O-Desmethyltramadol is the most important metabolite of tramadol produced in the liver after tramadol is consumed. This metabolite is considerably more potent as a μ-opioid agonist than the parent compound. O-desmethyl tramadol, inhibits 5-hydroxytryptamine type 2C receptors expressed in xenopus oocytes. O-desmethyl tramadol inhibits functions of M(1) receptors but has little effect on those of M(3) receptors. O-desmethyl tramadol has been widely used clinically and has analgesic activity.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Pharmacokinetic-pharmacodynamic modeling of the antinociceptive effects of main active metabolites of tramadol, (+)-O-desmethyltramadol and (-)-O-desmethyltramadol, in rats. | 2000 May |
|
| Modeling of the in vivo antinociceptive interaction between an opioid agonist, (+)-O-desmethyltramadol, and a monoamine reuptake inhibitor, (-)-O-desmethyltramadol, in rats. | 2000 Oct |
|
| Inhibition of CYP2D6-mediated tramadol O-demethylation in methadone but not buprenorphine maintenance patients. | 2012 Nov |
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| Effects of tramadol and o-desmethyltramadol on canine innate immune system function. | 2015 May |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment: The administration of 10 mg/kg (+)-O-desmethyl tramadol in a 10-min i.v. infusion significantly altered pCO(2), pO(2), and pH values in comparison with baseline and lower-dose groups. However, 2 mg/kg administered in a 10-min i.v. infusion was enough to achieve 100% antinociception without respiratory depression in rats. https://www.ncbi.nlm.nih.gov/pubmed/10773040
Oral
Light: 15 – 30 mg
Common: 30 – 50 mg
Strong: 50 – 70+ mg
Route of Administration:
Oral
O-desmethyl tramadol (0.1-100 uM) inhibited acetylcholine (ACh)-induced currents in oocytes expressing the M(1) receptors (half-maximal inhibitory concentration [IC(50)] = 2 +/- 0.6 uM), whereas it did not suppress ACh-induced currents in oocytes expressing the M(3) receptor. O-desmethyl tramadol inhibited the specific binding of [(3)H]quinuclidinyl benzilate ([(3)H]QNB) to the oocytes expressed M(1) receptors (IC(50) = 10.1 +/- 0.1 uM), whereas it did not suppress the specific binding of [(3)H]QNB to the oocytes expressed M(3) receptors.
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DTXSID10617163
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9838802
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XL5VDC061E
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16412-54-7
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185453-02-5
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ACTIVE MOIETY
SUBSTANCE RECORD
