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enzymes (4)transporters (2) Show 6 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-10-17 08:44:13 UTC

Update Date

2022-09-22 17:43:53 UTC

HMDB ID

HMDB0005016

Secondary Accession Numbers

HMDB05016

Metabolite Identification

Common Name

Venlafaxine

Description

Venlafaxine (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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0243747
     RDKit          3D
(S)-Venlafaxine
 47 48  0  0  0  0  0  0  0  0999 V2000
    5.6817   -0.4772   -0.6565 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5089   -0.4181   -1.4067 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2358   -0.1754   -0.9749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1572   -0.1490   -1.8489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8749    0.0923   -1.4338 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6378    0.3205   -0.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7597    0.5733    0.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3594    1.6681   -0.4499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5336    2.8371   -0.2572 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7070    3.2859    1.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7280    3.8605   -1.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5682   -0.6869    0.4102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8603   -0.3964    0.8479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6457   -1.4513   -0.8578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5953   -2.6314   -0.6047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0070   -3.5247    0.4840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9350   -2.6965    1.7494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9571   -1.5804    1.5016 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6811    0.3015    0.8076 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9744    0.0531    0.3509 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2168    0.5007   -0.7545 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5389   -0.6506    0.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3329   -1.2811   -1.1115 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4149   -0.3353   -2.8891 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0680    0.1057   -2.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6986    0.9225    1.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4672    1.3819   -1.5169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4098    1.8294   -0.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1756    2.9690    1.6871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6434    2.9472    1.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6820    4.4149    1.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7756    4.0431   -1.5156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0717    3.6483   -2.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3471    4.8149   -0.8146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8491    0.3060    1.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6863   -1.9284   -1.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1171   -0.8430   -1.6477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7499   -3.2115   -1.5194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5615   -2.2574   -0.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9746   -3.8508    0.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6931   -4.3554    0.6542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9651   -2.2643    1.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6145   -3.2928    2.6280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8508   -0.9538    2.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0179   -1.9876    1.1987 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5080    0.4753    1.8431 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7889    0.0476    1.0944 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  7 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  6 19  1  0
 19 20  2  0
 20  3  1  0
 18 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
 10 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 11 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 18 45  1  0
 19 46  1  0
 20 47  1  0
M  END

285
  Mrv1652305271900322D          

 20 21  0  0  1  0            999 V2000
    2.1615    0.1106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2866    0.1106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9866    1.5395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5741   -0.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9866    0.1106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8596   -1.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2885   -1.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8596   -1.8415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2885   -1.8415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5741   -2.2540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5741    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8116    0.1106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2241    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2241   -0.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5741    2.2540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8116    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0491    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0491   -0.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4616    0.1106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6991    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  2 19  1  0  0  0  0
  2 20  1  0  0  0  0
  3 11  1  0  0  0  0
  3 15  1  0  0  0  0
  3 16  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5 11  1  0  0  0  0
  5 12  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 10  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 13 17  1  0  0  0  0
 14 18  2  0  0  0  0
 17 19  2  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005016

> <DATABASE_NAME>
hmdb

> <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_KEY>
PNVNVHUZROJLTJ-UHFFFAOYSA-N

> <FORMULA>
C17H27NO2

> <MOLECULAR_WEIGHT>
277.4018

> <EXACT_MASS>
277.204179113

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
32.33187254376001

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexan-1-ol

> <ALOGPS_LOGP>
2.69

> <JCHEM_LOGP>
2.7385227043333327

> <ALOGPS_LOGS>
-3.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.420211448909786

> <JCHEM_PKA_STRONGEST_BASIC>
8.907956538395576

> <JCHEM_POLAR_SURFACE_AREA>
32.7

> <JCHEM_REFRACTIVITY>
83.02420000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.30e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
venlafaxine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0243747
     RDKit          3D
(S)-Venlafaxine
 47 48  0  0  0  0  0  0  0  0999 V2000
    5.6817   -0.4772   -0.6565 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5089   -0.4181   -1.4067 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2358   -0.1754   -0.9749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1572   -0.1490   -1.8489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8749    0.0923   -1.4338 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6378    0.3205   -0.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7597    0.5733    0.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3594    1.6681   -0.4499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5336    2.8371   -0.2572 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7070    3.2859    1.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7280    3.8605   -1.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5682   -0.6869    0.4102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8603   -0.3964    0.8479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6457   -1.4513   -0.8578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5953   -2.6314   -0.6047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0070   -3.5247    0.4840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9350   -2.6965    1.7494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9571   -1.5804    1.5016 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6811    0.3015    0.8076 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9744    0.0531    0.3509 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2168    0.5007   -0.7545 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5389   -0.6506    0.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3329   -1.2811   -1.1115 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4149   -0.3353   -2.8891 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0680    0.1057   -2.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6986    0.9225    1.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4672    1.3819   -1.5169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4098    1.8294   -0.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1756    2.9690    1.6871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6434    2.9472    1.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6820    4.4149    1.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7756    4.0431   -1.5156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0717    3.6483   -2.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3471    4.8149   -0.8146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8491    0.3060    1.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6863   -1.9284   -1.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1171   -0.8430   -1.6477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7499   -3.2115   -1.5194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5615   -2.2574   -0.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9746   -3.8508    0.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6931   -4.3554    0.6542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9651   -2.2643    1.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6145   -3.2928    2.6280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8508   -0.9538    2.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0179   -1.9876    1.1987 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5080    0.4753    1.8431 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7889    0.0476    1.0944 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  7 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  6 19  1  0
 19 20  2  0
 20  3  1  0
 18 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
 10 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 11 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 18 45  1  0
 19 46  1  0
 20 47  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 285                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0       4.035   0.206   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      11.735   0.206   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       5.575   2.874   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       4.805  -1.127   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.575   0.206   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.471  -1.897   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.139  -1.897   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.471  -3.437   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.139  -3.437   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.805  -4.207   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.805   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.115   0.206   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.885   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.885  -1.127   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.805   4.207   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.115   2.874   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.425   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.425  -1.127   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.195   0.206   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.505   1.540   0.000  0.00  0.00           C+0
CONECT    1    4                                                            
CONECT    2   19   20                                                       
CONECT    3   11   15   16                                                  
CONECT    4    1    5    6    7                                             
CONECT    5    4   11   12                                                  
CONECT    6    4    8                                                       
CONECT    7    4    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   10                                                       
CONECT   10    8    9                                                       
CONECT   11    3    5                                                       
CONECT   12    5   13   14                                                  
CONECT   13   12   17                                                       
CONECT   14   12   18                                                       
CONECT   15    3                                                            
CONECT   16    3                                                            
CONECT   17   13   19                                                       
CONECT   18   14   19                                                       
CONECT   19    2   17   18                                                  
CONECT   20    2                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0005016
HETATM    1  C1  UNL     1       5.676  -0.667   1.096  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.925  -0.417  -0.066  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.568  -0.256  -0.099  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.927  -0.016  -1.284  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.538   0.150  -1.332  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.784   0.073  -0.171  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.713   0.244  -0.253  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.026   1.539  -0.910  1.00  0.00           C  
HETATM    9  N1  UNL     1      -0.477   2.616  -0.148  1.00  0.00           N  
HETATM   10  C8  UNL     1      -1.085   2.869   1.120  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.361   3.860  -0.851  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.259  -0.980  -0.929  1.00  0.00           C  
HETATM   13  O2  UNL     1      -0.681  -1.066  -2.202  1.00  0.00           O  
HETATM   14  C11 UNL     1      -2.760  -0.998  -1.048  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.455  -1.879  -0.063  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.834  -1.855   1.296  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.412  -2.340   1.195  1.00  0.00           C  
HETATM   18  C15 UNL     1      -0.806  -2.195  -0.169  1.00  0.00           C  
HETATM   19  C16 UNL     1       1.436  -0.168   1.018  1.00  0.00           C  
HETATM   20  C17 UNL     1       2.826  -0.331   1.047  1.00  0.00           C  
HETATM   21  H1  UNL     1       5.179  -1.469   1.702  1.00  0.00           H  
HETATM   22  H2  UNL     1       5.804   0.271   1.658  1.00  0.00           H  
HETATM   23  H3  UNL     1       6.695  -1.036   0.805  1.00  0.00           H  
HETATM   24  H4  UNL     1       3.498   0.047  -2.208  1.00  0.00           H  
HETATM   25  H5  UNL     1       1.103   0.344  -2.302  1.00  0.00           H  
HETATM   26  H6  UNL     1      -1.037   0.296   0.823  1.00  0.00           H  
HETATM   27  H7  UNL     1      -0.516   1.558  -1.917  1.00  0.00           H  
HETATM   28  H8  UNL     1      -2.117   1.660  -1.071  1.00  0.00           H  
HETATM   29  H9  UNL     1      -1.785   3.757   1.038  1.00  0.00           H  
HETATM   30  H10 UNL     1      -1.663   2.039   1.548  1.00  0.00           H  
HETATM   31  H11 UNL     1      -0.301   3.250   1.839  1.00  0.00           H  
HETATM   32  H12 UNL     1       0.147   3.742  -1.819  1.00  0.00           H  
HETATM   33  H13 UNL     1       0.277   4.532  -0.219  1.00  0.00           H  
HETATM   34  H14 UNL     1      -1.395   4.277  -0.952  1.00  0.00           H  
HETATM   35  H15 UNL     1      -1.310  -0.842  -2.911  1.00  0.00           H  
HETATM   36  H16 UNL     1      -3.241  -0.019  -1.055  1.00  0.00           H  
HETATM   37  H17 UNL     1      -2.989  -1.444  -2.064  1.00  0.00           H  
HETATM   38  H18 UNL     1      -4.514  -1.515   0.051  1.00  0.00           H  
HETATM   39  H19 UNL     1      -3.488  -2.939  -0.397  1.00  0.00           H  
HETATM   40  H20 UNL     1      -3.430  -2.523   1.951  1.00  0.00           H  
HETATM   41  H21 UNL     1      -2.934  -0.842   1.729  1.00  0.00           H  
HETATM   42  H22 UNL     1      -1.461  -3.454   1.388  1.00  0.00           H  
HETATM   43  H23 UNL     1      -0.770  -1.962   2.009  1.00  0.00           H  
HETATM   44  H24 UNL     1       0.307  -2.090  -0.015  1.00  0.00           H  
HETATM   45  H25 UNL     1      -1.008  -3.075  -0.816  1.00  0.00           H  
HETATM   46  H26 UNL     1       0.864  -0.228   1.944  1.00  0.00           H  
HETATM   47  H27 UNL     1       3.270  -0.516   2.014  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3
CONECT    3    4    4   20
CONECT    4    5   24
CONECT    5    6    6   25
CONECT    6    7   19
CONECT    7    8   12   26
CONECT    8    9   27   28
CONECT    9   10   11
CONECT   10   29   30   31
CONECT   11   32   33   34
CONECT   12   13   14   18
CONECT   13   35
CONECT   14   15   36   37
CONECT   15   16   38   39
CONECT   16   17   40   41
CONECT   17   18   42   43
CONECT   18   44   45
CONECT   19   20   20   46
CONECT   20   47
END

HMDB0243747
     RDKit          3D
(S)-Venlafaxine
 47 48  0  0  0  0  0  0  0  0999 V2000
    5.6817   -0.4772   -0.6565 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5089   -0.4181   -1.4067 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2358   -0.1754   -0.9749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1572   -0.1490   -1.8489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8749    0.0923   -1.4338 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6378    0.3205   -0.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7597    0.5733    0.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3594    1.6681   -0.4499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5336    2.8371   -0.2572 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7070    3.2859    1.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7280    3.8605   -1.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5682   -0.6869    0.4102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8603   -0.3964    0.8479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6457   -1.4513   -0.8578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5953   -2.6314   -0.6047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0070   -3.5247    0.4840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9350   -2.6965    1.7494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9571   -1.5804    1.5016 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6811    0.3015    0.8076 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9744    0.0531    0.3509 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2168    0.5007   -0.7545 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5389   -0.6506    0.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3329   -1.2811   -1.1115 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4149   -0.3353   -2.8891 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0680    0.1057   -2.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6986    0.9225    1.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4672    1.3819   -1.5169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4098    1.8294   -0.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1756    2.9690    1.6871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6434    2.9472    1.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6820    4.4149    1.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7756    4.0431   -1.5156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0717    3.6483   -2.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3471    4.8149   -0.8146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8491    0.3060    1.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6863   -1.9284   -1.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1171   -0.8430   -1.6477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7499   -3.2115   -1.5194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5615   -2.2574   -0.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9746   -3.8508    0.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6931   -4.3554    0.6542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9651   -2.2643    1.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6145   -3.2928    2.6280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8508   -0.9538    2.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0179   -1.9876    1.1987 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5080    0.4753    1.8431 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7889    0.0476    1.0944 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  7 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  6 19  1  0
 19 20  2  0
 20  3  1  0
 18 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
 10 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 11 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 18 45  1  0
 19 46  1  0
 20 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Elafax	ChEBI
Venlafaxina	ChEBI
Venlafaxinum	ChEBI
Efectin	Kegg
Efexor	HMDB, MeSH
Effexor	HMDB, MeSH
Trevilor	HMDB, MeSH
Venlafaxin	HMDB
Venlafexine	HMDB
Cyclohexanol, 1-(2-(dimethylamino)-1-(4-methoxyphenyl)ethyl)-, hydrochloride	MeSH, HMDB
Hydrochloride, venlafaxine	MeSH, HMDB
1-(2-(dimethylamino)-1-(4-Methoxyphenyl)ethyl)cyclohexanol HCL	MeSH, HMDB
Dobupal	MeSH, HMDB
Sila venlafaxine	MeSH, HMDB
Vandral	MeSH, HMDB
Sila-venlafaxine	MeSH, HMDB
Venlafaxine hydrochloride	MeSH, HMDB

Chemical Formula

C₁₇H₂₇NO₂

Average Molecular Weight

277.4018

Monoisotopic Molecular Weight

277.204179113

IUPAC Name

1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexan-1-ol

Traditional Name

venlafaxine

CAS Registry Number

93413-69-5

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 Key

PNVNVHUZROJLTJ-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.

Kingdom

Super Class

Class

Sub Class

Direct Parent

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

tertiary alcohol (CHEBI:9943 )
tertiary amino compound (CHEBI:9943 )
monomethoxybenzene (CHEBI:9943 )
cyclohexanols (CHEBI:9943 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	74 - 76 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	171.6	30932474
[M+H]+	Not Available	169.891	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000862

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.23 g/L	ALOGPS
logP	2.69	ALOGPS
logP	2.74	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	14.42	ChemAxon
pKa (Strongest Basic)	8.91	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	32.7 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	83.02 m³·mol⁻¹	ChemAxon
Polarizability	32.33 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	167.422	31661259
DarkChem	[M-H]-	167.814	31661259
DeepCCS	[M+H]+	170.101	30932474
DeepCCS	[M-H]-	167.743	30932474
DeepCCS	[M-2H]-	200.629	30932474
DeepCCS	[M+Na]+	176.195	30932474
AllCCS	[M+H]+	167.9	32859911
AllCCS	[M+H-H2O]+	164.4	32859911
AllCCS	[M+NH4]+	171.1	32859911
AllCCS	[M+Na]+	172.1	32859911
AllCCS	[M-H]-	173.7	32859911
AllCCS	[M+Na-2H]-	174.2	32859911
AllCCS	[M+HCOO]-	174.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Venlafaxine	COC1=CC=C(C=C1)C(CN(C)C)C1(O)CCCCC1	2558.7	Standard polar	33892256
Venlafaxine	COC1=CC=C(C=C1)C(CN(C)C)C1(O)CCCCC1	2076.1	Standard non polar	33892256
Venlafaxine	COC1=CC=C(C=C1)C(CN(C)C)C1(O)CCCCC1	2092.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Venlafaxine,1TMS,isomer #1	COC1=CC=C(C(CN(C)C)C2(O[Si](C)(C)C)CCCCC2)C=C1	2064.8	Semi standard non polar	33892256
Venlafaxine,1TBDMS,isomer #1	COC1=CC=C(C(CN(C)C)C2(O[Si](C)(C)C(C)(C)C)CCCCC2)C=C1	2329.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Venlafaxine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9110000000-10fdc1f0eb77f9e8ed4e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Venlafaxine GC-MS (1 TMS) - 70eV, Positive	splash10-0ab9-9512000000-579bd169c5d6903163c2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Venlafaxine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Venlafaxine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Venlafaxine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Venlafaxine LC-ESI-QTOF , positive-QTOF	splash10-004i-0090000000-d413fb5f16658fcc5acb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Venlafaxine LC-ESI-QTOF , positive-QTOF	splash10-004i-0090000000-182f1032c3f72220679d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Venlafaxine LC-ESI-QTOF , positive-QTOF	splash10-00dj-0910000000-c7a4a25a9bc95faa6db1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Venlafaxine LC-ESI-QTOF , positive-QTOF	splash10-00di-0900000000-7be3d65db3af35be404e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Venlafaxine LC-ESI-QTOF , positive-QTOF	splash10-00di-0900000000-615322444dcf11a7fb8d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Venlafaxine LC-ESI-ITFT , positive-QTOF	splash10-03di-0090000000-d212108d9a8267ed7dad	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Venlafaxine LC-ESI-ITFT , positive-QTOF	splash10-004i-0090000000-0c4e12d13e69311b26bf	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Venlafaxine LC-ESI-ITFT , positive-QTOF	splash10-0bvi-4090000000-8bf2805a95084bfd952a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Venlafaxine LC-ESI-ITFT , positive-QTOF	splash10-0a4i-9520000000-de599153aa118f97ad81	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Venlafaxine LC-ESI-ITFT , positive-QTOF	splash10-0ab9-8900000000-6e9f54b654899b486e4d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Venlafaxine LC-ESI-ITFT , positive-QTOF	splash10-0ab9-9800000000-d762b2d7edeba1e12b28	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Venlafaxine LC-ESI-ITFT , positive-QTOF	splash10-0ab9-9700000000-2b8ebcefcf1274550d32	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Venlafaxine LC-ESI-ITFT , positive-QTOF	splash10-004i-0090000000-c592b4ae2ead9b2bb7ea	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Venlafaxine LC-ESI-ITFT , positive-QTOF	splash10-0bvi-4090000000-30b9b5dca017215ebaa4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Venlafaxine LC-ESI-ITFT , positive-QTOF	splash10-0a4i-9620000000-ab905f15470a13b750c5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Venlafaxine LC-ESI-ITFT , positive-QTOF	splash10-0ab9-8900000000-52ec7a86d35dbbd47681	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Venlafaxine LC-ESI-ITFT , positive-QTOF	splash10-0ab9-9800000000-7a7cc5b11e1a30499063	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Venlafaxine LC-ESI-ITFT , positive-QTOF	splash10-0ab9-9700000000-062f05f9fe2a1540985c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Venlafaxine LC-ESI-ITFT , positive-QTOF	splash10-03di-0090000000-8eb971c1dc9a14696c31	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Venlafaxine 10V, Positive-QTOF	splash10-03fr-0090000000-479240d2112a5b71fa58	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Venlafaxine 20V, Positive-QTOF	splash10-02w9-4190000000-4942ed295b70fa38aa2a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Venlafaxine 40V, Positive-QTOF	splash10-0ldl-9030000000-2af1eebea0622a8f7757	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Venlafaxine 10V, Negative-QTOF	splash10-004i-0090000000-99e5b56ecf6f61518e30	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Venlafaxine 20V, Negative-QTOF	splash10-004i-1390000000-58c1f11113a0c69c42d9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Venlafaxine 40V, Negative-QTOF	splash10-03dl-6930000000-bcbc7b00748a2c2bec30	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Brain
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Venlafaxine Metabolism Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	2.0 (0.02-4.5) uM	Adult (>18 years old)	Both	Normal	17465011	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5454

KEGG Compound ID

C07187

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Venlafaxine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

9943

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Husbands, 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)

Not Available

General References

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 ]
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 ]
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 ]
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 ]
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

Enzyme Details

1. Cytochrome P450 2D6

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

Enzyme Details

2. 5-hydroxytryptamine receptor 1B

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

Enzyme Details

3. 5-hydroxytryptamine receptor 1A

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

Enzyme Details

4. 5-hydroxytryptamine receptor 2A

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

Enzyme Details

1. Sodium-dependent noradrenaline transporter

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

Enzyme Details

2. Sodium-dependent serotonin transporter

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

Showing metabocard for Venlafaxine (HMDB0005016)

MOL for HMDB0005016 (Venlafaxine)

3D MOL for HMDB0005016 (Venlafaxine)

3D SDF for HMDB0005016 (Venlafaxine)

3D-SDF for HMDB0005016 (Venlafaxine)

PDB for HMDB0005016 (Venlafaxine)

3D PDB for HMDB0005016 (Venlafaxine)

SMILES for HMDB0005016 (Venlafaxine)

INCHI for HMDB0005016 (Venlafaxine)

Structure for HMDB0005016 (Venlafaxine)

3D Structure for HMDB0005016 (Venlafaxine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Transporters