5777. Meclizine

Nomenclature

CAS number: 569-65-3
1-[(4-Chlorophenyl)phenylmethyl]-4-[(3-methylphenyl)methyl]piperazine; 1-(p-chloro-α-phenylbenzyl)-4-(m-methylbenzyl)piperazine; 1-(p-chlorobenzhydryl)-4-(m-methylbenzyl)piperazine; meclozine; parachloramine.
C25H27ClN2; mol wt 390.95.
C 76.80%, H 6.96%, Cl 9.07%, N 7.17%.

Description and references

Antihistaminic antinauseant. Synthesis: H. Morren, BE 502889 (1951); idem, US 2709169 (1955 to U.C.B.). Outline of reactions: Grivsky, Ind. Chim. Belge 17, 735 (1952). HPLC determn in tablet formulations: N. H. Foda et al., Anal. Lett. 21, 1177 (1988). Clinical evaluation in vertigo: B. Cohen, J. M. B. Vianney de Jong, Arch. Neurol. 27, 129 (1972) PubMed; in treatment of postoperative nausea and vomiting: C. M. Forrester et al., AANA J. 75, 27 (2007) PubMed.

Chemical structure

Properties

bp2 230°.

Derivative

Dihydrochloride monohydrate.

Nomenclature

CAS number: 31884-77-2
UCB-5062; Agyrax (Vedim); Ancolan (Boots); Antivert (Pfizer); Bonamine (Pfizer); Bonine (Insight); Postafen (UCB).
C25H27ClN2.2HCl.H2O; mol wt 481.89.
C 62.31%, H 6.48%, Cl 22.07%, N 5.81%, O 3.32%.

Properties

mp 215°. Freely sol in chloroform, pyridine; slightly sol in dil acids, alc. Practically insol in water (0.1 gm/100 ml), ether.

Therapeutic Category

Antiemetic; antivertigo; in treatment of motion sickness.

Therapeutic Category (Veterinary)

Antiemetic.

Keywords

Antiemetic; Antivertigo