10226. Desvenlafaxine

Nomenclature

CAS number: 93413-62-8
4-[2-(Dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenol; O-desmethylvenlafaxine; 1-[2-(dimethylamino)-1-(4-hydroxyphenyl)ethyl]cyclohexanol.
C16H25NO2; mol wt 263.38.
C 72.96%, H 9.57%, N 5.32%, O 12.15%.

Description and references

Serotonin noradrenaline reuptake inhibitor (SNRI); major active metabolite of venlafaxine, q.v. Prepn: G. E. M. Husbands et al., EP 112669; eidem, US 4535186 (1984, 1985 both to Am. Home Prod.); J. P. Yardley et al., J. Med. Chem. 33, 2899 (1990) DOI PubMed. CE determn of enantiomers: S. Rudaz et al., J. Pharm. Biomed. Anal. 23, 107 (2000) DOI PubMed. LC/MS/MS determn in plasma: J. Bhatt et al., J. Chromatogr. B 829, 75 (2005) DOI PubMed. Pharmacological profile in animals: E. A. Muth et al., Drug Dev. Res. 23, 191 (1991) DOI. Mechanism of action study: D. C. Deecher et al., J. Pharmacol. Exp. Ther. 318, 657 (2006) DOI PubMed. Preclinical model in treatment of vasomotor symptoms associated with menopause: idem et al., Endocrinology 148, 1376 (2007) DOI PubMed. Clinical trial in major depressive disorder: N. A. DeMartinis et al., J. Clin. Psychiatry 68, 677 (2007) PubMed.

Chemical structure

Derivative

Fumarate monohydrate.

Nomenclature

CAS number: 313471-75-9; 135308-72-4 (anhydrous)
Wy-45233.
C16H25NO2.C4H4O4.H2O; mol wt 397.46.
C 60.44%, H 7.86%, N 3.52%, O 28.18%.

Properties

mp 140-142°.

Derivative

Succinate monohydrate.

Nomenclature

CAS number: 386750-22-7; 448904-47-0 (anhydrous)
DVS-233; Pristiq (Wyeth).
C16H25NO2.C4H6O4.H2O; mol wt 399.48.
C 60.13%, H 8.33%, N 3.51%, O 28.04%.

Properties

White to off-white powder. Sol in water. Partition coefficient (octanol/water, pH7): 0.21.

Therapeutic Category

Antidepressant.

Keywords

Antidepressant; Serotonin Noradrenaline Reuptake Inhibitor (SNRI)