CAS No 122898-67-3 , N-[[4-[2-(dimethylamino)ethoxy]phenyl]methyl]-3,4-dimethoxybenzamide

Title: Itopride
CAS Registry Number: 122898-67-3
CAS Name: N-[[4-[2-(Dimethylamino)ethoxy]phenyl]methyl]-3,4-dimethoxy benzamide
Synonyms: N-[p-[2-(dimethylamino)ethoxy]benzyl]veratramide
Molecular Formula: C20H26N2O4
Molecular Weight: 358.43
Percent Composition: C 67.02%, H 7.31%, N 7.82%, O 17.85%
Literature References: Dopamine D2-receptor antagonist with anticholinesterase activity. Prepn: Y. Itoh et al., EP 306827; eidem, US 4983633 (1989, 1991 both to Hokuriku Pharm.); J. Sakaguchi et al., Chem. Pharm. Bull. 40, 202 (1992). Pharmacology: Y. Iwanaga et al., Jpn. J. Pharmacol. 56, 261 (1991). Toxicity studies: M. H. Barker et al., Yakuri to Chiryo 21, 1685, 1669 (1993). Metabolism study: T. Mushiroda et al., Drug Metab. Dispos. 28, 1231 (2000). HPLC determn in serum and clinical pharmacokinetics: S. S. Singh et al., J. Chromatogr. B 818, 213 (2005). Clinical study in postoperative ileus: R. Gürlich et al., Chir. Gastroenterol. Interdiszip. 20, 61 (2004); in dyspepsia: D. N. Amarapurkar, P. Rane, J. Indian Med. Assoc. 102, 735 (2004).
Properties: Crystals from ethanol + isopropyl ether, mp 111-112°.
Melting point: mp 111-112°
 
Derivative Type: Hydrochloride
CAS Registry Number: 122892-31-3
Manufacturers' Codes: HSR-803; HC-803
Trademarks: Itax (Axcan); Ganaton (Abbott)
Molecular Formula: C20H26N2O4.HCl
Molecular Weight: 394.89
Percent Composition: C 60.83%, H 6.89%, N 7.09%, O 16.21%, Cl 8.98%
Properties: Crystals from ethanol, mp 194-195°. Also reported as prisms from ethanol, mp 190.5-191.5° (Sakaguchi). Readily sol in water.
Melting point: mp 194-195°; mp 190.5-191.5° (Sakaguchi)
 
Therap-Cat: Gastroprokinetic.
Keywords: Gastroprokinetic.