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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-04 19:03:19 UTC
Update Date2021-09-14 15:48:17 UTC
HMDB IDHMDB0060849
Secondary Accession Numbers
  • HMDB60849
Metabolite Identification
Common NameN,N-Didesmethyltramadol
DescriptionN,N-Didesmethyltramadol, also known as M3, belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. N,N-Didesmethyltramadol is a metabolite of tramadol. Tramadol hydrochloride (trademarked as Conzip, Ryzolt, Ultracet, Ultram in the USA; Ralivia and Zytram XL in Canada) is a centrally-acting synthetic analgesic used to treat moderate to moderately-severe pain. N,N-Didesmethyltramadol is a very strong basic compound (based on its pKa). N,N-didesmethyltramadol and formaldehyde can be biosynthesized from N-desmethyltramadol; which is mediated by the enzymes cytochrome P450 2B6 and cytochrome P450 3A4. In humans, N,N-didesmethyltramadol is involved in tramadol metabolism pathway. It was launched and marketed as Tramal by the German pharmaceutical company Grnenthal GmbH in 1977 (Wikipedia). The drug has a wide range of applications, including treatment of rheumatoid arthritis, restless legs syndrome, and fibromyalgia.
Structure
Data?1563866113
Synonyms
ValueSource
M3HMDB
Chemical FormulaC14H21NO2
Average Molecular Weight235.327
Monoisotopic Molecular Weight235.15722892
IUPAC Name(1R,2R)-2-(aminomethyl)-1-(3-methoxyphenyl)cyclohexan-1-ol
Traditional Name(1R,2R)-2-(aminomethyl)-1-(3-methoxyphenyl)cyclohexan-1-ol
CAS Registry Number931115-27-4
SMILES
COC1=CC=CC(=C1)[C@@]1(O)CCCC[C@@H]1CN
InChI Identifier
InChI=1S/C14H21NO2/c1-17-13-7-4-6-11(9-13)14(16)8-3-2-5-12(14)10-15/h4,6-7,9,12,16H,2-3,5,8,10,15H2,1H3/t12-,14+/m1/s1
InChI KeyQNPPIKMBCJUUTG-OCCSQVGLSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassAnisoles
Direct ParentAnisoles
Alternative Parents
Substituents
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Alkyl aryl ether
  • Cyclohexanol
  • Aralkylamine
  • Monocyclic benzene moiety
  • Tertiary alcohol
  • Cyclic alcohol
  • Ether
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organopnictogen compound
  • Alcohol
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0024 g/LALOGPS
logP1.99ALOGPS
logP1.63ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)13.8ChemAxon
pKa (Strongest Basic)9.67ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area55.48 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity68.2 m³·mol⁻¹ChemAxon
Polarizability26.58 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+158.92730932474
DeepCCS[M-H]-156.56930932474
DeepCCS[M-2H]-189.48830932474
DeepCCS[M+Na]+165.0230932474
AllCCS[M+H]+155.632859911
AllCCS[M+H-H2O]+151.732859911
AllCCS[M+NH4]+159.232859911
AllCCS[M+Na]+160.332859911
AllCCS[M-H]-159.932859911
AllCCS[M+Na-2H]-160.332859911
AllCCS[M+HCOO]-160.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N,N-DidesmethyltramadolCOC1=CC=CC(=C1)[C@@]1(O)CCCC[C@@H]1CN2591.5Standard polar33892256
N,N-DidesmethyltramadolCOC1=CC=CC(=C1)[C@@]1(O)CCCC[C@@H]1CN2159.4Standard non polar33892256
N,N-DidesmethyltramadolCOC1=CC=CC(=C1)[C@@]1(O)CCCC[C@@H]1CN2018.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N,N-Didesmethyltramadol,1TMS,isomer #1COC1=CC=CC([C@@]2(O[Si](C)(C)C)CCCC[C@@H]2CN)=C12026.5Semi standard non polar33892256
N,N-Didesmethyltramadol,1TMS,isomer #2COC1=CC=CC([C@@]2(O)CCCC[C@@H]2CN[Si](C)(C)C)=C12130.5Semi standard non polar33892256
N,N-Didesmethyltramadol,2TMS,isomer #1COC1=CC=CC([C@@]2(O[Si](C)(C)C)CCCC[C@@H]2CN[Si](C)(C)C)=C12095.7Semi standard non polar33892256
N,N-Didesmethyltramadol,2TMS,isomer #1COC1=CC=CC([C@@]2(O[Si](C)(C)C)CCCC[C@@H]2CN[Si](C)(C)C)=C12191.7Standard non polar33892256
N,N-Didesmethyltramadol,2TMS,isomer #1COC1=CC=CC([C@@]2(O[Si](C)(C)C)CCCC[C@@H]2CN[Si](C)(C)C)=C12580.4Standard polar33892256
N,N-Didesmethyltramadol,2TMS,isomer #2COC1=CC=CC([C@@]2(O)CCCC[C@@H]2CN([Si](C)(C)C)[Si](C)(C)C)=C12257.0Semi standard non polar33892256
N,N-Didesmethyltramadol,2TMS,isomer #2COC1=CC=CC([C@@]2(O)CCCC[C@@H]2CN([Si](C)(C)C)[Si](C)(C)C)=C12415.0Standard non polar33892256
N,N-Didesmethyltramadol,2TMS,isomer #2COC1=CC=CC([C@@]2(O)CCCC[C@@H]2CN([Si](C)(C)C)[Si](C)(C)C)=C12703.9Standard polar33892256
N,N-Didesmethyltramadol,3TMS,isomer #1COC1=CC=CC([C@@]2(O[Si](C)(C)C)CCCC[C@@H]2CN([Si](C)(C)C)[Si](C)(C)C)=C12226.2Semi standard non polar33892256
N,N-Didesmethyltramadol,3TMS,isomer #1COC1=CC=CC([C@@]2(O[Si](C)(C)C)CCCC[C@@H]2CN([Si](C)(C)C)[Si](C)(C)C)=C12351.5Standard non polar33892256
N,N-Didesmethyltramadol,3TMS,isomer #1COC1=CC=CC([C@@]2(O[Si](C)(C)C)CCCC[C@@H]2CN([Si](C)(C)C)[Si](C)(C)C)=C12485.0Standard polar33892256
N,N-Didesmethyltramadol,1TBDMS,isomer #1COC1=CC=CC([C@@]2(O[Si](C)(C)C(C)(C)C)CCCC[C@@H]2CN)=C12251.0Semi standard non polar33892256
N,N-Didesmethyltramadol,1TBDMS,isomer #2COC1=CC=CC([C@@]2(O)CCCC[C@@H]2CN[Si](C)(C)C(C)(C)C)=C12377.7Semi standard non polar33892256
N,N-Didesmethyltramadol,2TBDMS,isomer #1COC1=CC=CC([C@@]2(O[Si](C)(C)C(C)(C)C)CCCC[C@@H]2CN[Si](C)(C)C(C)(C)C)=C12552.2Semi standard non polar33892256
N,N-Didesmethyltramadol,2TBDMS,isomer #1COC1=CC=CC([C@@]2(O[Si](C)(C)C(C)(C)C)CCCC[C@@H]2CN[Si](C)(C)C(C)(C)C)=C12658.4Standard non polar33892256
N,N-Didesmethyltramadol,2TBDMS,isomer #1COC1=CC=CC([C@@]2(O[Si](C)(C)C(C)(C)C)CCCC[C@@H]2CN[Si](C)(C)C(C)(C)C)=C12777.8Standard polar33892256
N,N-Didesmethyltramadol,2TBDMS,isomer #2COC1=CC=CC([C@@]2(O)CCCC[C@@H]2CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C12713.9Semi standard non polar33892256
N,N-Didesmethyltramadol,2TBDMS,isomer #2COC1=CC=CC([C@@]2(O)CCCC[C@@H]2CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C12810.8Standard non polar33892256
N,N-Didesmethyltramadol,2TBDMS,isomer #2COC1=CC=CC([C@@]2(O)CCCC[C@@H]2CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C12888.8Standard polar33892256
N,N-Didesmethyltramadol,3TBDMS,isomer #1COC1=CC=CC([C@@]2(O[Si](C)(C)C(C)(C)C)CCCC[C@@H]2CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C12911.0Semi standard non polar33892256
N,N-Didesmethyltramadol,3TBDMS,isomer #1COC1=CC=CC([C@@]2(O[Si](C)(C)C(C)(C)C)CCCC[C@@H]2CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C12958.8Standard non polar33892256
N,N-Didesmethyltramadol,3TBDMS,isomer #1COC1=CC=CC([C@@]2(O[Si](C)(C)C(C)(C)C)CCCC[C@@H]2CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C12747.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N,N-Didesmethyltramadol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,N-Didesmethyltramadol 10V, Positive-QTOFsplash10-00lr-0090000000-a162894c2e533fc813162018-11-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,N-Didesmethyltramadol 20V, Positive-QTOFsplash10-014i-0690000000-35bdc24f97c303ada7be2018-11-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,N-Didesmethyltramadol 40V, Positive-QTOFsplash10-0553-4910000000-7ee3403dea071bc3efb42018-11-27Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8281015
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10105488
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available