6194. Milnacipran

Nomenclature

CAS number: 92623-85-3
(1R,2S)-rel-2-(Aminomethyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide; 1-phenyl-1-(diethylaminocarbonyl)-2-(aminomethyl)cyclopropane; midalcipran.
C15H22N2O; mol wt 246.35.
C 73.13%, H 9.00%, N 11.37%, O 6.49%.

Description and references

Serotonin and norepinephrine reuptake inhibitor (SNRI). Prepn: G. Mouzin et al., EP 68999; eidem, US 4478836 (1983, 1984 both to Pierre Fabre); B. Bonnaud et al., J. Med. Chem. 30, 318 (1987) DOI PubMed. LC determn with spectrofluorimetric detection in plasma: C. Puozzo et al., J. Chromatogr. B 806, 221 (2004) DOI PubMed. Mechanism of action study: C. Moret et al., Neuropharmacology 24, 1211 (1985) DOI PubMed. Clinical inhibition of monoamine uptake: C. Palmier et al., Eur. J. Clin. Pharmacol. 37, 235 (1989) DOI PubMed. Clinical trial in fibromyalgia: D. J. Clauw et al., Clin. Ther. 30, 1988 (2008) DOI PubMed. Review of pharmacology and clinical efficacy in depression: C. M. Spencer, M. I. Wilde, Drugs 56, 405-427 (1998) DOI PubMed.

Chemical structure

Derivative

Hydrochloride.

Nomenclature

CAS number: 101152-94-7
F-2207; Ixel (Fabre); Savella (Forest); Toledomin (Asahi).
C15H22N2O.HCl; mol wt 282.81.
C 63.70%, H 8.20%, N 9.91%, O 5.66%, Cl 12.54%.

Properties

Crystals from ethanol-ethyl ether, mp 179-181°. LD50 orally in mice: 237 mg/kg (Bonnaud).

Therapeutic Category

Antidepressant.

Keywords

Antidepressant; Serotonin Noradrenaline Reuptake Inhibitor (SNRI); Serotonin Uptake Inhibitor