9946. Venlafaxine

Nomenclature

CAS number: 93413-69-5
1-[2-(Dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexanol; (±)-1-[α-[(dimethylamino)methyl]-p-methoxybenzyl]cyclohexanol; N,N-dimethyl-2-(1-hydroxycyclohexyl)-2-(4-methoxyphenyl)ethylamine; venlafexine.
C17H27NO2; mol wt 277.40.
C 73.61%, H 9.81%, N 5.05%, O 11.54%.

Description and references

Serotonin noradrenaline reuptake inhibitor (SNRI). Prepn: G. E. M. Husbands et al., EP 112669; US 4535186 (1984, 1985 both to Am. Home Prods.); and resolution of isomers: J. P. Yardley et al., J. Med. Chem. 33, 2899 (1990). Receptor binding studies: E. A. Muth et al., Biochem. Pharmacol. 35, 4493 (1986). HPLC-MS/ESI determn in plasma: W. Liu et al., J. Chromatogr. B 850, 405 (2007). Clinical pharmacokinetics: K. J. Klamerus et al., J. Clin. Pharmacol. 32, 716 (1992). Evaluation of suicide risk: A. Rubino et al., Br. Med. J. 334, 242 (2007). Review of pharmacology and clinical efficacy in depression: S. A. Montgomery, J. Clin. Psychiatry 54, 119-126 (1993); in anxiety disorders: M. E. Thase, Expert Rev. Neurother. 6, 269-282 (2006).

Chemical structure

Derivative

Hydrochloride.

Nomenclature

CAS number: 99300-78-4
Wy-45030; Effexor (Wyeth).
C17H27NO2.HCl; mol wt 313.86.
C 65.06%, H 8.99%, N 4.46%, O 10.20%, Cl 11.30%.

Properties

White to off-white crystalline solid from methanol/ethyl acetate, mp 215-217°. Soly (mg/ml): 572 water. Partition coefficient (octanol/water): 0.43.

Derivative

(+)-Form.

Properties

Crystals from ethyl acetate, mp 102-104°. [α]D25 +27.6° (c = 1.07 in 95% ethanol).

Derivative

(+)-Form hydrochloride.

Nomenclature

Wy-45655.

Properties

Crystals from methanol/ether, mp 240-240.5°. [α]D25 4.7° (c = 0.945 in ethanol).

Derivative

()-Form.

Properties

Crystals from ethyl acetate, mp 102-104°. [α]D25 27.1° (c = 1.04 in 95% ethanol).

Derivative

()-Form hydrochloride.

Nomenclature

Wy-45651.

Properties

Crystals from methanol/ether, mp 240-240.5°. [α]D25 +4.6° (c = 1.0 in ethanol).

Therapeutic Category

Antidepressant; anxiolytic.

Keywords

Antidepressant; Serotonin Noradrenaline Reuptake Inhibitor (SNRI); Anxiolytic