82-92-8

Basic information

• Product Name: CYCLIZINE HCL
• Synonyms: (n-benzhydryl)(n’-methyl)diethylenediamine;(N-Benzhydryl)(N'-methyl)diethylenediamine;1-(diphenylmethyl)-4-methyl-piperazin;1-Benzhydryl-4-methylpiperazine;1-Diphenylmethyl-4-methylpiperazine;Bw 47-83;bw47-83;Ciclizina
• CAS NO: 82-92-8
• Molecular Formula: C₁₈H₂₂N₂
• Molecular Weight: 302.84
• EINECS: 201-445-5
• Product Categories: Miscellaneous
• Mol File: 82-92-8.mol
• Article Data: 6

Chemical Properties

• Melting Point: 105.5-107.5°
• Boiling Point: 399.58°C (rough estimate)
• Appearance: /
• 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).
• CAS DataBase Reference: CYCLIZINE HCL(CAS DataBase Reference)
• NIST Chemistry Reference: CYCLIZINE HCL(82-92-8)
• EPA Substance Registry System: CYCLIZINE HCL(82-92-8)

Safety Data

• Hazardous Substances Data: 82-92-8(Hazardous Substances Data)

Usage

Description

Cyclizine hydrochloride, also known as marezine or migril, is an N-alkylpiperazine with antihistamine and anticholinergic properties. It is a light-sensitive, white crystalline powder with a bitter taste and is slightly soluble in water, alcohol, and chloroform.

Uses

Used in Pharmaceutical Industry:
Cyclizine HCL is used as an antihistamine with sedative effects for the treatment of nausea and vomiting associated with motion sickness.
Used in Motion Sickness Management:
Cyclizine HCL is used as a prophylactic and treatment agent for motion sickness, helping to alleviate symptoms such as vomiting and diarrhea.
Used in Intramuscular Injections:
The lactate salt of Cyclizine HCL (Cyclizine Lactate Injection, United States Pharmacopoeia [USP]) is used for intramuscular injections due to the limited water solubility of the hydrochloride form. It should be stored in a cold place to prevent the development of a slight yellow tint, which does not indicate a loss in biologic potency.

Synthesis

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

InChI:InChI=1S/C18H22N2/c1-19-12-14-20(15-13-19)18(16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,18H,12-15H2,1H3

Upstream product

• 109-01-3 1-methyl-piperazine 
• 90-99-3 diphenylchloromethane 
• 102552-76-1 1-benzhydryl-4-(ethoxycarbonyl)piperazine 
• 105-59-9 N-Methyldiethanolamine 
• 91-00-9 Benzhydrylamine 
• 110-85-0 piperazine 
• 776-74-9 Bromodiphenylmethane 
• 74-88-4 methyl iodide 
• 91-01-0 1,1-Diphenylmethanol 
• 50-00-0 formaldehyd 
• 841-77-0 diphenylmethylpiperazine 
• 1078-58-6 diphenylzinc 
• 100-52-7 benzaldehyde 

Downstream Products

• 115051-87-1 4-benzhydryl-1-isopropyl-1-methyl-piperazinium; iodide 
• 145823-14-9 4-Benzhydryl-1-((2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxy-tetrahydro-pyran-2-yl)-1-methyl-piperazin-1-ium; chloride 
• 841-77-0 diphenylmethylpiperazine 
• 157665-24-2 2-[4-(diphenylmethyl)-1-piperazinyl]-acetic acid 
• 139359-42-5 4-(4-Benzhydryl-piperazin-1-yl)-butyric acid ethyl ester 
• 113561-11-8 3-(4-Benzhydryl-piperazin-1-yl)-propionic acid ethyl ester 
• 788126-77-2 6-(4-Benzhydryl-piperazin-1-yl)-hexanoic acid methyl ester 
• 139329-22-9 5-(4-benzhydryl-piperazin-1-yl)-pentanoic acid ethyl ester 
• 58103-08-5 ethyl 2-(4-benzylhydrylpiperazin-1-yl)acetate 
• 303-25-3 cyclizine hydrochloride 

Relevant articles and documents

Atom-efficient transition-metal-free arylation ofN,O-acetals using diarylzinc reagents through Zn/Zn cooperativity

Exploiting the cooperative action of Lewis acid Zn(C6F5)2with diarylzinc reagents, the efficient arylation ofN,O-acetals to access diarylmethylamines is reported. Reactions take place under mild reaction conditions without the need for transtion-metal catalysis. Mechanistic investigations have revealed that Zn(C6F5)2not only acts as a Lewis acid activator, but also enables the regeneration of nucleophilic ZnAr2species, allowing a limiting 50 mol% to be employed.

Continuous-Flow Multistep Synthesis of Cinnarizine, Cyclizine, and a Buclizine Derivative from Bulk Alcohols

Cinnarizine, cyclizine, buclizine, and meclizine belong to a family of antihistamines that resemble each other in terms of a 1-diphenylmethylpiperazine moiety. We present the development of a four-step continuous process to generate the final antihistamines from bulk alcohols as the starting compounds. HCl is used to synthesize the intermediate chlorides in a short reaction time and excellent yields. This methodology offers an excellent way to synthesize intermediates to be used in drug synthesis. Inline separation allows the collection of pure products and their immediate consumption in the following steps. Overall isolated yields for cinnarizine, cyclizine, and a buclizine derivative are 82, 94, and 87 %, respectively. The total residence time for the four steps is 90 min with a productivity of 2 mmol h-1. The incredible bulk: Bulk alcohols are converted continuously into chlorides using HCl in a microflow. A reaction network that consists of four steps and two inline separations leads to the continuous preparation of cinnarizine, cyclizine, and a buclizine derivative with yields of 82, 94, and 87 %, respectively. The total residence time for the four steps is 90 min with a productivity of 2 mmol h-1.

Synthesis of tertiary amines using a polystyrene (REM) resin

A range of tertiary amines was constructed using a 'traceless' linker on a polystyrene resin (REM resin), starting from seconday amines, primary amines, and resin-bound 'ammonia'. The methodology is characterized by three essential steps conducted under ambient conditions: (1) coupling of the starting amine (Michael addition) to the resin, (2) activation (quaternization), and (3) cleavage of the product amine (Hofmann elimination). The linker is compatible with both acid and base sensitive protecting group strategies. The nature of the chemistry ensures that the tertiary amine products are obtained in consistently high purity (95% or greater). After cleavage of the product, REM resin is regenerated and can be reused for repeat syntheses. The yield and purity of repeat batches is maintained over 5 cycles, allowing the automated synthesis of >0.5 g quantities of pure tertiary amine.