| Identification | Back Directory | [Name]
O-Desmethylvenlafaxine | [CAS]
93413-62-8 | [Synonyms]
DVS 233
Wy-45233
desvenlafaxine
Desvenlafaxine Base
Desmethylvenlafaxine
O-desMethylvenlafaxin
O-Desmethylvenlafaxine
DL-O-Desmethylvenlafaxin
Desvenlafaxine impurity C
O-Desmethylvenlafaxine(DL)
O-DESMETHYL VENLAFAXINE-D10
O-Desmethylvenlafaxine solution
Venlafaxine O-DesMethyl IMpurity
Desvenlafaxine(O-Desnethylvenfaxine)
O-DesMethyl Venlafaxine Hydrochloride
Desvenlafaxine (O-DesMethyl venlafaxine)
Venlafaxine-d10 HCl
O-Desmethyl Venlafaxine-d10
4-[2-(Dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenol
1-[1-(4-Hydroxyphenyl)-2-dimethylaminoethyl]cyclohexanol
4-[1-(1-Hydroxycyclohexyl)-2-(dimethylamino)ethyl]phenol
Phenol,4-[2-(diMethylaMino)-1-(1-hydroxycyclohexyl)ethyl]- | [EINECS(EC#)]
200-659-6 | [Molecular Formula]
C16H25NO2 | [MDL Number]
MFCD00871934 | [MOL File]
93413-62-8.mol | [Molecular Weight]
263.38 |
| Chemical Properties | Back Directory | [Appearance]
White Solid | [Melting point ]
208-213°C | [Boiling point ]
403.8±25.0 °C(Predicted) | [density ]
1.115±0.06 g/cm3(Predicted) | [Fp ]
9℃ | [storage temp. ]
-20°C Freezer | [solubility ]
insoluble in EtOH; ≥13.2 mg/mL in DMSO; ≥2.45 mg/mL in EtOH | [form ]
neat | [pka]
10.04±0.26(Predicted) | [color ]
White to off-white | [Major Application]
clinical testing | [InChI]
1S/C16H25NO2/c1-17(2)12-15(13-6-8-14(18)9-7-13)16(19)10-4-3-5-11-16/h6-9,15,18-19H,3-5,10-12H2,1-2H3 | [InChIKey]
KYYIDSXMWOZKMP-UHFFFAOYSA-N | [SMILES]
N(CC(C2(CCCCC2)O)c1ccc(cc1)O)(C)C | [LogP]
0.33 at 25℃ and pH6 |
| Hazard Information | Back Directory | [Chemical Properties]
White Solid | [Uses]
A metabolite of Venlafaxine (V120000), a selective serotonin noradrenaline reuptake inhibitor (SNRI). Used as an antidepressant. | [Uses]
a metabolite of Venlafaxine .;Labeled Venlafaxine, intended for use as an internal standard for the quantification of Venlafaxine by GC- or LC-mass spectrometry. | [Uses]
A metabolite of Venlafaxine, a selective serotonin noradrenaline reuptake inhibitor. Used as an antidepressant | [Definition]
ChEBI: A tertiary amino compound that is N,N-dimethylethanamine substituted at position 1 by a 1-hydroxycyclohexyl and 4-hydroxyphenyl group. It is a metabolite of the drug venlafaxine. | [Description]
Desvenlafaxine is a new member of the SNRI class of antidepressants.
It is marketed as an extended release tablet for once-daily oral treatment
of MDD in adult patients. Desvenlafaxine (O-desmethylvenlafaxine) is
the major active metabolite of the previously marketed antidepressant
venlafaxine (Effexor). Similar to venlafaxine, desvenlafaxine is a more
potent inhibitor of serotonin and norepinephrine reuptake (IC50＝47 and
531 nM, respectively) than that of dopamine (62% inhibition at 100 mM)
in in vitro studies. It does not have significant in vitro affinity for other
neurotransmitter reporters such as a1-adrenergic, H1-histaminergic,
or muscarine-cholinergic receptors. Desvenlafaxine is marketed as a
racemic mixture. Specific pharmacological properties of the enantiomers
of desvenlafaxine have not been reported. | [Originator]
Wyeth (United States) | [Brand name]
Pristiq | [General Description]
An analytical reference standard applicable for use as starting material in calibrators or controls for a variety of LC/MS or GC/MS applications such as urine drug testing, forensic analysis, or clinical toxicology. Also known as desvenlafaxine, O-desmethylvenlafaxine is an SNRI antidepressant marketed under the trade name Pristiq? for the treatment of depression. O-desmethylvenlafaxine is also a major urinary metabolite of venlafaxine, an SNRI antidepressant sold as Effexor? or Efexor and used to treat major depressive disorder, generalized anxiety disorder, and other anxiety disorders associated with depression. | [Synthesis]
Desvenlafaxine is chemically derived from 4-benzyloxyphenylacetic acid, by first converting to the acid chloride with oxalyl chloride and then condensing with dimethylamine to produce the corresponding N,N-dimethyl amide. Deprotonation of the amide with butyllithium, followed by condensation with cyclohexanone gives a b-hydroxyamide intermediate, which is reduced with alane, and debenzylated by using palladium on carbon and 1,4-cyclohexadiene to produce desvenlafaxine. |
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