Cyclizine Chemical Properties

Melting point:

105.5-107.5°

Boiling point:

399.58°C (rough estimate)

Density 

0.9934 (rough estimate)

refractive index 

1.5840 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Slightly soluble in water and in ethanol (96 per cent).

form 

Solid

color 

White to off-white

Safety Information

Hazardous Substances Data

82-92-8(Hazardous Substances Data)

Cyclizine Usage And Synthesis

Chemical Properties

White or almost white, crystalline powder.

Originator

Marezine,BurroughsWellcome,US,1953

Uses

Cyclizine exhibits antihistamine and anticholinergic action and is used for vomiting and diarrhea. The exact mechanism of action is not known. Synonyms of this drug are marezine and migril.

Uses

Cyclizine is an antihistamine with a sedative effect used in the treatment of nausea and vomiting associated with motion sickness.

Uses

H1 antihistamine

Definition

ChEBI: An N-alkylpiperazine in which one nitrogen of the piperazine ring is substituted by a methyl group, while the other is substituted by a diphenylmethyl group.

Preparation

Cyclizine is prepared through the alkylation of N-methylpiperazine with benzhydryl chloride.

Manufacturing Process

One-tenth mol (20 g) of benzhydryl chloride was mixed with 0.19 mol (19 g) of N-methylpiperazine and about 10 cc of benzene and the whole was heated on the steam bath four hours. The contents of the flask was partitioned between ether and water, and the ethereal layer was washed with water until the washings were neutral. The base was then extracted from the ethereal layer by N hydrochloric acid and the extract, made acid to Congo red paper, was evaporated under vacuum. 29.5 g of the pure dihydrochloride of Nmethyl-N'-benzhydryl piperazine was recovered from the residue by recrystallization from 95% alcohol melting above 250°C with decomposition. The addition of alkali to an aqueous solution of the dihydrochloride liberated the base which was recovered by recrystallization from petroleum ether melting at 105.5° to 107.5°C.

brand name

Marezine (GlaxoSmithKline).

Therapeutic Function

Antinauseant

General Description

Cyclizine hydrochloride,1-(diphenylmethyl)-4-methylpiperazine monohydrochloride(Marezine), occurs as a light-sensitive, white crystallinepowder with a bitter taste. It is slightly soluble in water(1:115), in alcohol (1:115), and in chloroform (1:75). It isused primarily in the prophylaxis and treatment of motionsickness. The lactate salt (Cyclizine Lactate Injection,United States Pharmacopoeia [USP]) is used for intramuscular(IM) injection because of the limited water solubilityof the hydrochloride. The injection should be stored in acold place, because if it is stored at room temperature forseveral months, a slight yellow tint may develop. This doesnot indicate a loss in biologic potency.

Clinical Use

It can be used not only in the treatment of allergic diseases, but also in the management of postoperative, irradiation or druginduced vomiting. Cyclizine dependence has been suggested to occur when it is used in combination with analgesics in long-term therapy. For this reason, several countries have removed cyclicine from analgesic combination preparations.

Synthesis

Cyclizine, 1-(diphenylmethyl)-4-methylpiperazine (16.1.15), is synthesized by alkylating 1-methylpiperazine with benzhydrylbromide.

Cyclizine(82-92-8)Related Product Information

• Cyclizine
• BUCLIZINE, DIHYDROCHLORIDE
• Cetirizine
• BUCLIZINE
• CHLORCYCLIZINE
• CHLORCYCLIZINE HYDROCHLORIDE
• Flunarizine dihydrochloride
• Stugeron
• Hydroxyzine
• Meclozine
• Clocinizine
• Meclizine dihydrochloride
• Hydroxyzine dihydrochloride
• Cyclizine Hydrochloride
• 1-BENZHYDRYLPIPERAZINE
• 2-[2-[4-[(4-chlorophenyl)phenylmethyl]piperazin-1-yl]ethoxy]ethanol hydrochloride
• 2-(4-BENZHYDRYLPIPERAZINO)-6-PHENYL[1,2,4]TRIAZOLO[1,5-A]PYRIMIDIN-7-AMINE
• HYDROXYZINE PAMOATE