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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-10-17 08:44:13 UTC
Update Date2021-09-14 15:48:20 UTC
HMDB IDHMDB0005016
Secondary Accession Numbers
  • HMDB05016
Metabolite Identification
Common NameVenlafaxine
DescriptionVenlafaxine (brand name: Effexor or Efexor) 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 neurotransmitter in the synapse. The neurotransmitters affected are serotonin (5-hydroxytryptamine) and norepinephrine (noradrenaline). Additionally, in high doses, it weakly inhibits the reuptake of dopamine. A comparison of adverse event rates in a fixed-dose study comparing venlafaxine 75, 225, and 375 mg/day with placebo revealed a dose dependency for some of the more common adverse events associated with venlafaxine use. The rule for including events was to enumerate those that occurred at an incidence of 5% or more for at least one of the venlafaxine groups and for which the incidence was at least twice the placebo incidence for at least one venlafaxine group. Tests for potential dose relationships for these events (Cochran-Armitage Test, with a criterion of exact 2-sided p-value <= 0.05) suggested a dose-dependency for several adverse events in this list, including chills, hypertension, anorexia, nausea, agitation, dizziness, somnolence, tremor, yawning, sweating, and abnormal ejaculation (Wyeth Monograph). Venlafaxine is an effective anti-depressant for many persons; however, it seems to be especially effective for those with treatment-resistant depression. Patients suffering from severe long-term depression typically respond better to venlafaxine than other drugs. However, venlafaxine has been reported to be more difficult to discontinue than other antidepressants. In addition, a September 2004 Consumer Reports study ranked venlafaxine as the most effective among six commonly prescribed antidepressants. However, this should not be considered a definitive finding, since responses to psychiatric medications can vary significantly from individual to individual. A black box warning has been issued with venlafaxine and with other SSRI and SNRI anti-depressants advising of risk of suicide. There is an additional risk if a physician misinterprets patient expression of adverse effects such as panic or akathisia. Careful assessment of patient history and comorbid risk factors such as drug abuse are essential in evaluating the safety of venlafaxine for individual patients. Another risk is serotonin syndrome. This is a serious effect that can be caused by interactions with other drugs and is potentially fatal. This risk necessitates clear information to patients and proper medical history. Venlafaxine is used primarily for the treatment of depression, generalized anxiety disorder, obsessive-compulsive disorder, social anxiety disorder, and panic disorder in adults. It is also used for other general depressive disorders. Although it is not approved for use in children or adolescents, there is considerable information by Wyeth on cautions if prescribed to this age group. Venlafaxine hydrochloride is a prescription antidepressant first introduced by Wyeth in 1993. As of August 2006, generic venlafaxine is available in the United States.
Structure
Data?1582752340
Synonyms
ValueSource
ElafaxChEBI
VenlafaxinaChEBI
VenlafaxinumChEBI
EfectinKegg
EfexorHMDB, MeSH
EffexorHMDB, MeSH
TrevilorHMDB, MeSH
VenlafaxinHMDB
VenlafexineHMDB
Cyclohexanol, 1-(2-(dimethylamino)-1-(4-methoxyphenyl)ethyl)-, hydrochlorideMeSH, HMDB
Hydrochloride, venlafaxineMeSH, HMDB
1-(2-(dimethylamino)-1-(4-Methoxyphenyl)ethyl)cyclohexanol HCLMeSH, HMDB
DobupalMeSH, HMDB
Sila venlafaxineMeSH, HMDB
VandralMeSH, HMDB
Sila-venlafaxineMeSH, HMDB
Venlafaxine hydrochlorideMeSH, HMDB
Chemical FormulaC17H27NO2
Average Molecular Weight277.4018
Monoisotopic Molecular Weight277.204179113
IUPAC Name1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexan-1-ol
Traditional Namevenlafaxine
CAS Registry Number93413-69-5
SMILES
COC1=CC=C(C=C1)C(CN(C)C)C1(O)CCCCC1
InChI Identifier
InChI=1S/C17H27NO2/c1-18(2)13-16(17(19)11-5-4-6-12-17)14-7-9-15(20-3)10-8-14/h7-10,16,19H,4-6,11-13H2,1-3H3
InChI KeyPNVNVHUZROJLTJ-UHFFFAOYSA-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
  • Aralkylamine
  • Cyclohexanol
  • Monocyclic benzene moiety
  • 1,3-aminoalcohol
  • Tertiary alcohol
  • Cyclic alcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ether
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point74 - 76 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM171.630932474
[M+H]+Not Available169.891http://allccs.zhulab.cn/database/detail?ID=AllCCS00000862
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.23 g/LALOGPS
logP10(2.69) g/LALOGPS
logP10(2.74) g/LChemAxon
logS10(-3.1) g/LALOGPS
pKa (Strongest Acidic)14.42ChemAxon
pKa (Strongest Basic)8.91ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area32.7 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity83.02 m³·mol⁻¹ChemAxon
Polarizability32.33 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+167.42231661259
DarkChem[M-H]-167.81431661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
VenlafaxineCOC1=CC=C(C=C1)C(CN(C)C)C1(O)CCCCC12558.7Standard polar33892256
VenlafaxineCOC1=CC=C(C=C1)C(CN(C)C)C1(O)CCCCC12076.1Standard non polar33892256
VenlafaxineCOC1=CC=C(C=C1)C(CN(C)C)C1(O)CCCCC12092.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Venlafaxine,1TMS,isomer #1COC1=CC=C(C(CN(C)C)C2(O[Si](C)(C)C)CCCCC2)C=C12064.8Semi standard non polar33892256
Venlafaxine,1TBDMS,isomer #1COC1=CC=C(C(CN(C)C)C2(O[Si](C)(C)C(C)(C)C)CCCCC2)C=C12329.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Venlafaxine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9110000000-10fdc1f0eb77f9e8ed4e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Venlafaxine GC-MS (1 TMS) - 70eV, Positivesplash10-0ab9-9512000000-579bd169c5d6903163c22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Venlafaxine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Venlafaxine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Venlafaxine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Venlafaxine LC-ESI-QTOF , positive-QTOFsplash10-004i-0090000000-d413fb5f16658fcc5acb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Venlafaxine LC-ESI-QTOF , positive-QTOFsplash10-004i-0090000000-182f1032c3f72220679d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Venlafaxine LC-ESI-QTOF , positive-QTOFsplash10-00dj-0910000000-c7a4a25a9bc95faa6db12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Venlafaxine LC-ESI-QTOF , positive-QTOFsplash10-00di-0900000000-7be3d65db3af35be404e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Venlafaxine LC-ESI-QTOF , positive-QTOFsplash10-00di-0900000000-615322444dcf11a7fb8d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Venlafaxine LC-ESI-ITFT , positive-QTOFsplash10-03di-0090000000-d212108d9a8267ed7dad2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Venlafaxine LC-ESI-ITFT , positive-QTOFsplash10-004i-0090000000-0c4e12d13e69311b26bf2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Venlafaxine LC-ESI-ITFT , positive-QTOFsplash10-0bvi-4090000000-8bf2805a95084bfd952a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Venlafaxine LC-ESI-ITFT , positive-QTOFsplash10-0a4i-9520000000-de599153aa118f97ad812017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Venlafaxine LC-ESI-ITFT , positive-QTOFsplash10-0ab9-8900000000-6e9f54b654899b486e4d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Venlafaxine LC-ESI-ITFT , positive-QTOFsplash10-0ab9-9800000000-d762b2d7edeba1e12b282017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Venlafaxine LC-ESI-ITFT , positive-QTOFsplash10-0ab9-9700000000-2b8ebcefcf1274550d322017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Venlafaxine LC-ESI-ITFT , positive-QTOFsplash10-004i-0090000000-c592b4ae2ead9b2bb7ea2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Venlafaxine LC-ESI-ITFT , positive-QTOFsplash10-0bvi-4090000000-30b9b5dca017215ebaa42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Venlafaxine LC-ESI-ITFT , positive-QTOFsplash10-0a4i-9620000000-ab905f15470a13b750c52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Venlafaxine LC-ESI-ITFT , positive-QTOFsplash10-0ab9-8900000000-52ec7a86d35dbbd476812017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Venlafaxine LC-ESI-ITFT , positive-QTOFsplash10-0ab9-9800000000-7a7cc5b11e1a304990632017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Venlafaxine LC-ESI-ITFT , positive-QTOFsplash10-0ab9-9700000000-062f05f9fe2a1540985c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Venlafaxine LC-ESI-ITFT , positive-QTOFsplash10-03di-0090000000-8eb971c1dc9a14696c312017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Venlafaxine 10V, Positive-QTOFsplash10-03fr-0090000000-479240d2112a5b71fa582016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Venlafaxine 20V, Positive-QTOFsplash10-02w9-4190000000-4942ed295b70fa38aa2a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Venlafaxine 40V, Positive-QTOFsplash10-0ldl-9030000000-2af1eebea0622a8f77572016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Venlafaxine 10V, Negative-QTOFsplash10-004i-0090000000-99e5b56ecf6f61518e302016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Venlafaxine 20V, Negative-QTOFsplash10-004i-1390000000-58c1f11113a0c69c42d92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Venlafaxine 40V, Negative-QTOFsplash10-03dl-6930000000-bcbc7b00748a2c2bec302016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue Locations
  • Brain
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.0 (0.02-4.5) uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5454
KEGG Compound IDC07187
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkVenlafaxine
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID9943
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceHusbands, George Edward Morris; Yardley, John Patrick; Muth, Eric Anthony. Phenethylamine derivatives and intermediates. Eur. Pat. Appl. (1984), 58 pp. CODEN: EPXXDW EP 112669 A2 19840704 CAN 102:5895 AN 1985:5895
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Fogelman SM, Schmider J, Venkatakrishnan K, von Moltke LL, Harmatz JS, Shader RI, Greenblatt DJ: O- and N-demethylation of venlafaxine in vitro by human liver microsomes and by microsomes from cDNA-transfected cells: effect of metabolic inhibitors and SSRI antidepressants. Neuropsychopharmacology. 1999 May;20(5):480-90. [PubMed:10192828 ]
  2. Saletu B, Grunberger J, Anderer P, Linzmayer L, Semlitsch HV, Magni G: Pharmacodynamics of venlafaxine evaluated by EEG brain mapping, psychometry and psychophysiology. Br J Clin Pharmacol. 1992 Jun;33(6):589-601. [PubMed:1389931 ]
  3. Degner D, Grohmann R, Kropp S, Ruther E, Bender S, Engel RR, Schmidt LG: Severe adverse drug reactions of antidepressants: results of the German multicenter drug surveillance program AMSP. Pharmacopsychiatry. 2004 Mar;37 Suppl 1:S39-45. [PubMed:15052513 ]
  4. Invernizzi RW, Garattini S: Role of presynaptic alpha2-adrenoceptors in antidepressant action: recent findings from microdialysis studies. Prog Neuropsychopharmacol Biol Psychiatry. 2004 Aug;28(5):819-27. [PubMed:15363606 ]
  5. Wikell C, Eap CB, Josefsson M, Apelqvist G, Ahlner J, Baumann P, Bengtsson F: Disposition of venlafaxine enantiomers in rats with hepatic encephalopathy after chronic drug treatment. Chirality. 2002 May 5;14(4):347-50. [PubMed:11968077 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:
HTR1B
Uniprot ID:
P28222
Molecular weight:
43567.5
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:
HTR1A
Uniprot ID:
P08908
Molecular weight:
46106.3
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
Gene Name:
HTR2A
Uniprot ID:
P28223
Molecular weight:
52602.6

Transporters

General function:
Involved in neurotransmitter:sodium symporter activity
Specific function:
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:
SLC6A2
Uniprot ID:
P23975
Molecular weight:
69331.42
General function:
Involved in neurotransmitter:sodium symporter activity
Specific function:
Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into the pre-synaptic terminal for re-utilization. Plays a key role in mediating regulation of the availability of serotonin to other receptors of serotonergic systems. Terminates the action of serotonin and recycles it in a sodium-dependent manner.
Gene Name:
SLC6A4
Uniprot ID:
P31645
Molecular weight:
70324.165