Record Information
Version1.0
Creation date2011-09-21 00:32:02 UTC
Update date2015-10-09 22:33:06 UTC
Primary IDFDB023588
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameVenlafaxine
DescriptionVenlafaxine is an effective antidepressant for many persons; 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 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. Some of these persons have taken two or more antidepressants prior to venlafaxine with no relief. Patients suffering with 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; however, it seems to be especially effective for those with treatment-resistant depression. Some of these persons have taken two or more antidepressants prior to venlafaxine with no relief. Patients suffering with 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; Venlafaxine hydrochloride is a prescription antidepressant that belongs to the class of antidepressants called serotonin-norepinephrine reuptake inhibitors (SNRI). The chemical structure of venlafaxine is designated (R/S)-1-[2-(dimethylamino)-1-(4 methoxyphenyl)ethyl] cyclohexanol hydrochloride or (+/-)-1-[alpha [alpha- (dimethylamino)methyl] p-methoxybenzyl] cyclohexanol hydrochloride and it has the empirical formula of C17H27NO2. It is a white to off-white crystalline solid. Venlafaxine is structurally and pharmacologically related to the analgesic tramadol, but not to any of the conventional antidepressant drugs, including tricyclic antidepressants, SSRIs, MAOIs, or reversible inhibitors of monoamine oxidase (RIMAs); A Black Box Warning has been issued with Effexor and with other SSRI and SNRI anti-depressants advising of risk of suicide. Thoughts of suicide (suicide ideation) as potential risk of suicide as shown in studies by Wyeth and reported on their datasheet for effexor were twice that of placebo (4% compared to 2%, however, no suicides occurred in these trials). The black box warnings advise physicians to carefully monitor patients for suicide risk at start of usage and whenever the dosage is changed. There is an additional risk if a physician misinterprets patient expression of adverse effects such as panic or akithesia. Careful assessment of patient history and comorbid risk factors such as drug abuse are essential in evaluating the safety of Effexor for individual patients. These cautions are emphasized in Wyeth's detailed information sheet with special precautions if prescribed to children. The extent of this effect and the actual risk are not known as studies may exclude individuals with higher risk. This is another reason why careful patient monitoring at start of use of this medication, as well as at any change of dosage is emphasized. 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. For example, the drug abuse by at risk patients of certain non-prescription drugs can cause this serious effect and emphasizes the importance of good medical history sharing between General Practitioners and Psychiatrists as both may prescribe Venlafaxine. Involvement of family in awareness of risk factors is highlighted in Wyeth information sheets on Effexor; The chemical structure of venlafaxine is designated (R/S)-1-[2-(dimethylamino)-1-(4 methoxyphenyl)ethyl] cyclohexanol hydrochloride or (+/-)-1-[alpha [alpha- (dimethylamino)methyl] p-methoxybenzyl] cyclohexanol hydrochloride and it has the empirical formula of C17H27NO2. It is a white to off-white crystalline solid. Venlafaxine is structurally and pharmacologically related to the analgesic tramadol, but not to any of the conventional antidepressant drugs, including tricyclic antidepressants, SSRIs, MAOIs, or reversible inhibitors of monoamine oxidase (RIMAs); 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 a considerable information by Wyeth on cautions if presecribed to this age group. Venlafaxine hydrochloride is a prescription antidepressant first introduced by Wyeth in 1993. It belongs to class of antidepressants called serotonin-norepinephrine reuptake inhibitors (SNRI). As of August 2006, generic venlafaxine is available in the United States. It was previously available only under the brand names Effexor and Effexor XR. [HMDB]
CAS Number93413-69-5
Structure
Thumb
Synonyms
SynonymSource
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
Predicted Properties
PropertyValueSource
Water Solubility0.23 g/LALOGPS
logP2.69ALOGPS
logP2.74ChemAxon
logS-3.1ALOGPS
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
Chemical FormulaC17H27NO2
IUPAC name1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexan-1-ol
InChI IdentifierInChI=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
Isomeric SMILESCOC1=CC=C(C=C1)C(CN(C)C)C1(O)CCCCC1
Average Molecular Weight277.4018
Monoisotopic Molecular Weight277.204179113
Classification
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Environmental role:

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSVenlafaxine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-9110000000-10fdc1f0eb77f9e8ed4eSpectrum
Predicted GC-MSVenlafaxine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ab9-9512000000-579bd169c5d6903163c2Spectrum
Predicted GC-MSVenlafaxine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVenlafaxine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVenlafaxine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0090000000-d413fb5f16658fcc5acbSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0090000000-182f1032c3f72220679dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00dj-0910000000-c7a4a25a9bc95faa6db1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0900000000-7be3d65db3af35be404eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0900000000-615322444dcf11a7fb8dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0090000000-d212108d9a8267ed7dadSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0090000000-0c4e12d13e69311b26bfSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0bvi-4090000000-8bf2805a95084bfd952aSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-9520000000-de599153aa118f97ad81Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0ab9-8900000000-6e9f54b654899b486e4dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0ab9-9800000000-d762b2d7edeba1e12b28Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0ab9-9700000000-2b8ebcefcf1274550d32Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0090000000-c592b4ae2ead9b2bb7eaSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0bvi-4090000000-30b9b5dca017215ebaa4Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-9620000000-ab905f15470a13b750c5Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0ab9-8900000000-52ec7a86d35dbbd47681Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0ab9-9800000000-7a7cc5b11e1a30499063Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0ab9-9700000000-062f05f9fe2a1540985cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0090000000-8eb971c1dc9a14696c31Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03fr-0090000000-479240d2112a5b71fa58Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02w9-4190000000-4942ed295b70fa38aa2aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ldl-9030000000-2af1eebea0622a8f7757Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-99e5b56ecf6f61518e30Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1390000000-58c1f11113a0c69c42d9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dl-6930000000-bcbc7b00748a2c2bec30Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID5454
ChEMBL IDCHEMBL637
KEGG Compound IDC07187
Pubchem Compound ID5656
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB00285
HMDB IDHMDB05016
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDVenlafaxine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
5-hydroxytryptamine receptor 1BHTR1BP28222
5-hydroxytryptamine receptor 1AHTR1AP08908
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference