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Details

Stereochemistry RACEMIC
Molecular Formula C15H23NO2
Molecular Weight 249.3486
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DESMETRAMADOL

SMILES

CN(C)C[C@H]1CCCC[C@]1(O)C2=CC(O)=CC=C2

InChI

InChIKey=UWJUQVWARXYRCG-HIFRSBDPSA-N
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

HIDE SMILES / InChI
Molecular Formula C15H23NO2
Molecular Weight 249.3486
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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.

CNS Activity

Approval Year

Unknown
139594
PubMed

PubMed

TitleDatePubMed
Modeling of the in vivo antinociceptive interaction between an opioid agonist, (+)-O-desmethyltramadol, and a monoamine reuptake inhibitor, (-)-O-desmethyltramadol, in rats.
2000 Oct
Effects of tramadol and o-desmethyltramadol on canine innate immune system function.
2015 May
Patents

Patents

20090005456
3
20090197905
5

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
In Vitro Use Guide
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 02:55:52 GMT 2023
Edited
by admin
on Sat Dec 16 02:55:52 GMT 2023
Record UNII
2WA8F50C3F
Record Status Validated (UNII)
Record Version
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Name Type Language
DESMETRAMADOL
INN  
Official Name English
(RR,SS)-3-(2-((DIMETHYLAMINO)METHYL)-1-HYDROXYCYCLOHEXYL)PHENOL
Systematic Name English
O-DESMETHYLTRAMADOL
Common Name English
TRAMADOL HYDROCHLORIDE IMPURITY D [EP IMPURITY]
Common Name English
RAC-3-((1R,2R)-2-((DIMETHYLAMINO)METHYL)-1-HYDROXYCYCLOHEXYL)PHENOLC
Systematic Name English
O-DESMETHYL TRAMADOL
Common Name English
PHENOL, 3-(2-((DIMETHYLAMINO)METHYL)-1-HYDROXYCYCLOHEXYL)-, CIS-(±)-
Common Name English
O-DEMETHYLTRAMADOL
Common Name English
MONO-O-DEMETHYLTRAMADOL
Common Name English
PHENOL, 3-((1R,2R)-2-((DIMETHYLAMINO)METHYL)-1-HYDROXYCYCLOHEXYL)-, REL-
Common Name English
desmetramadol [INN]
Common Name English
Desmetramadol [WHO-DD]
Common Name English
O-DSMT
Common Name English
Classification Tree Code System Code
WIKIPEDIA Designer-drugs-O-Desmethyltramadol
Created by admin on Sat Dec 16 02:55:53 GMT 2023 , Edited by admin on Sat Dec 16 02:55:53 GMT 2023
Code System Code Type Description
FDA UNII
2WA8F50C3F
Created by admin on Sat Dec 16 02:55:53 GMT 2023 , Edited by admin on Sat Dec 16 02:55:53 GMT 2023
PRIMARY
SMS_ID
100000124493
Created by admin on Sat Dec 16 02:55:53 GMT 2023 , Edited by admin on Sat Dec 16 02:55:53 GMT 2023
PRIMARY
PUBCHEM
9838803
Created by admin on Sat Dec 16 02:55:53 GMT 2023 , Edited by admin on Sat Dec 16 02:55:53 GMT 2023
PRIMARY
MESH
C080580
Created by admin on Sat Dec 16 02:55:53 GMT 2023 , Edited by admin on Sat Dec 16 02:55:53 GMT 2023
PRIMARY
INN
10450
Created by admin on Sat Dec 16 02:55:53 GMT 2023 , Edited by admin on Sat Dec 16 02:55:53 GMT 2023
PRIMARY
CAS
73986-53-5
Created by admin on Sat Dec 16 02:55:53 GMT 2023 , Edited by admin on Sat Dec 16 02:55:53 GMT 2023
NON-SPECIFIC STEREOCHEMISTRY
WIKIPEDIA
DesmetramadolOL
Created by admin on Sat Dec 16 02:55:53 GMT 2023 , Edited by admin on Sat Dec 16 02:55:53 GMT 2023
PRIMARY O-DSMT is considerably more potent as a .MU. opioid agonist compared to tramadol. Additionally, unlike tramadol, it is a high-affinity ligand of the .DELTA.- and .KAPPA.-opioid receptors.The two enantiomers of O-DSMT show quite distinct pharmacological profilesboth (+) and (-)-O-DSMT are inactive as serotonin reuptake inhibitors, but (-)-O-DSMT retains activity as a norepinephrine reuptake inhibitor, and so the mix of both the parent compound and metabolites contributes significantly to the complex pharmacological profile of tramadol. While the multiple receptor targets can be beneficial in the treatment of pain (especially complex pain syndromes such as neuropathic pain), it increases the potential for drug interactions compared to other opioids, and may also contribute to side effects.
CAS
80456-81-1
Created by admin on Sat Dec 16 02:55:53 GMT 2023 , Edited by admin on Sat Dec 16 02:55:53 GMT 2023
PRIMARY
NCI_THESAURUS
C166599
Created by admin on Sat Dec 16 02:55:53 GMT 2023 , Edited by admin on Sat Dec 16 02:55:53 GMT 2023
PRIMARY
EPA CompTox
DTXSID40894102
Created by admin on Sat Dec 16 02:55:53 GMT 2023 , Edited by admin on Sat Dec 16 02:55:53 GMT 2023
PRIMARY
MANUFACTURER PRODUCT INFORMATION
O-DESMETHYL TRAMADOL
Created by admin on Sat Dec 16 02:55:53 GMT 2023 , Edited by admin on Sat Dec 16 02:55:53 GMT 2023
PRIMARY Originally Posted by Wikipedia: O-Desmethyltramadol (M1) is an opioid analgesic which is made in the body from 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 .MU. opioid agonist than the parent compound, and indeed is so much more potent that tramadol can to some extent be regarded as a prodrug for O-desmethyltramadol in the same way that codeine is a prodrug for morphine. Tramadol is demethylated by the liver enzyme CYP2D6 in the same way as codeine, and so similarly to the variation in effects seen with codeine, individuals who have a less active form of CYP2D6 ("poor metabolisers") will tend to get reduced analgesic effects from tramadol. The two enantiomers of O-desmethyltramadol show quite distinct pharmacological profiles: both (+) and (-)-O-desmethyltramadol are inactive as serotonin reuptake inhibitors, but (-)-O-desmethyltramadol retains activity as a noradrenaline reuptake inhibitor and so the mix of both the parent compound and metabolites produced contributes significantly to the complex pharmacological profile of tramadol.
EVMPD
SUB32457
Created by admin on Sat Dec 16 02:55:53 GMT 2023 , Edited by admin on Sat Dec 16 02:55:53 GMT 2023
PRIMARY
Related Record Type Details
Structure of DESMETRAMADOL, CIS-(+)-
ENANTIOMER -> RACEMATE
Structure of O-DESMETHYL TRAMADOL HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Structure of DESMETRAMADOL, CIS-(-)-
ENANTIOMER -> RACEMATE
MU-TYPE OPIOID RECEPTOR
TARGET -> AGONIST
Opioid activity is due to both low affinity binding of the parent compound and higher affinity binding of the O-demethylated metabolite M1 to μ-opioid receptors. In animal models, M1 is up to 6 times more potent than tramadol in producing analgesia and 200 times more potent in μ-opioid binding.
Related Record Type Details
Structure of TRAMADOL
PRODRUG -> METABOLITE ACTIVE
MAJOR
Related Record Type Details
Structure of TRAMADOL HYDROCHLORIDE
PARENT -> IMPURITY
UNSPECIFIED
EP
Related Record Type Details
Structure of DESMETRAMADOL
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