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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-09-11 20:43:42 UTC
Update Date2019-07-23 07:16:14 UTC
HMDB IDHMDB0061345
Secondary Accession Numbers
  • HMDB0061166
  • HMDB61166
  • HMDB61345
Metabolite Identification
Common NameN,N,O-Tridesmethylvenlafaxine
DescriptionN,N,O-Tridesmethylvenlafaxine is a metabolite of venlafaxine (brand name: Effexor or Efexor). Venlafaxine is a bicyclic antidepressant and is usually categorized as a serotonin-norepinephrine reuptake inhibitor (SNRI), but it has been referred to as a serotonin-norepinephrine-dopamine reuptake inhibitor. It works by blocking the transporter reuptake proteins for key neurotransmitters affecting mood, thereby leaving more active neurotransmitters in the synapse.
Structure
Data?1563866174
Synonyms
ValueSource
1-[2-Amino-1-(4-hydroxyphenyl)ethyl]cyclohexanolHMDB
4-[2-Amino-1-(1-hydroxycyclohexyl)ethyl]phenolHMDB
O-Desmethyl-N,N-didesmethylvenlafaxineHMDB
TridesmethylvenlafaxineHMDB
Chemical FormulaC14H21NO2
Average Molecular Weight235.322
Monoisotopic Molecular Weight235.157228921
IUPAC Name4-[2-amino-1-(1-hydroxycyclohexyl)ethyl]phenol
Traditional Name4-[2-amino-1-(1-hydroxycyclohexyl)ethyl]phenol
CAS Registry Number149289-29-2
SMILES
NCC(C1=CC=C(O)C=C1)C1(O)CCCCC1
InChI Identifier
InChI=1S/C14H21NO2/c15-10-13(11-4-6-12(16)7-5-11)14(17)8-2-1-3-9-14/h4-7,13,16-17H,1-3,8-10,15H2
InChI KeyBHCUWXACHAFFSK-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentCyclohexanols
Alternative Parents
Substituents
  • Cyclohexanol
  • Phenol
  • Aralkylamine
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Tertiary alcohol
  • 1,3-aminoalcohol
  • Cyclic alcohol
  • Primary amine
  • Amine
  • Organonitrogen compound
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.83 g/LALOGPS
logP1.75ALOGPS
logP1.41ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)10.18ChemAxon
pKa (Strongest Basic)9.33ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area66.48 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity68.47 m³·mol⁻¹ChemAxon
Polarizability26.42 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9410000000-2a946521b39fd2a93a3aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0090000000-a0bc5a6c99ec3135d880Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gb9-2190000000-8b1f9d70e7c8a356da89Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1003-9210000000-5e3f08548da33fbadfedSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-da85f4b511ecb3f4b2d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0540-0590000000-f0d2e698e63813c65658Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05n4-6910000000-b1db238b53f83db3c8d1Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
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 ID8035200
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9859500
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Silverstone PH, Entsuah R, Hackett D: Two items on the Hamilton Depression rating scale are effective predictors of remission: comparison of selective serotonin reuptake inhibitors with the combined serotonin/norepinephrine reuptake inhibitor, venlafaxine. Int Clin Psychopharmacol. 2002 Nov;17(6):273-80. [PubMed:12409680 ]
  2. Rahman Z, Ring RH, Young K, Platt B, Lin Q, Schechter LE, Rosenzweig-Lipson S, Beyer CE: Inhibition of uptake 2 (or extraneuronal monoamine transporter) by normetanephrine potentiates the neurochemical effects of venlafaxine. Brain Res. 2008 Apr 8;1203:68-78. doi: 10.1016/j.brainres.2008.01.062. Epub 2008 Feb 5. [PubMed:18321472 ]