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82-92-8

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82-92-8 Usage

Chemical Properties

White or almost white, crystalline powder.

Uses

Different sources of media describe the Uses of 82-92-8 differently. You can refer to the following data:
1. 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.
2. Cyclizine is an antihistamine with a sedative effect used in the treatment of nausea and vomiting associated with motion sickness.

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.

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.

Synthesis

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

Check Digit Verification of cas no

The CAS Registry Mumber 82-92-8 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 2 respectively; the second part has 2 digits, 9 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 82-92:
(4*8)+(3*2)+(2*9)+(1*2)=58
58 % 10 = 8
So 82-92-8 is a valid CAS Registry Number.
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

82-92-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name cyclizine

1.2 Other means of identification

Product number -
Other names Marzine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:82-92-8 SDS

82-92-8Relevant articles and documents

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

Borys, Andryj M.,Gil-Negrete, Jose M.,Hevia, Eva

, p. 8905 - 8908 (2021/09/10)

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

Borukhova, Svetlana,Nol, Timothy,Hessel, Volker

, p. 67 - 74 (2016/01/16)

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

Brown, Angus R.,Rees, David C.,Rankovic, Zoran,Morphy, J. Richard

, p. 3288 - 3295 (2007/10/03)

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.

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