Chlorcyclizine hydrochloride

Product Name: Chlorcyclizine hydrochloride
CAS No.: 14362-31-3
Chemical Name: Chlorcyclizine hydrochloride
Synonyms: eramide;Perazil;NSC 169496;di-paralene;CHLORCYCLIZINE HCL;Ah-289 hydrochloride;Component of fedrazil;chlorcycliziniumchloride;CHLORCYCLIZINE HYDROCHLORIDE;CHLORCYCLIZINE HYDROCHLORIDE
CBNumber: CB3747267
Molecular Formula: C18H22Cl2N2
Formula Weight: 337.29
MOL File: 14362-31-3.mol

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Chlorcyclizine hydrochloride Property

Melting point:: 226-227 °C
storage temp.: Store at -20°C
solubility: ≥11 mg/mL in DMSO with gentle warming; ≥14.7 mg/mL in EtOH; ≥9.44 mg/mL in H2O with ultrasonic
form: Solid
color: White to off-white
InChI: InChI=1S/C18H21ClN2.ClH/c1-20-11-13-21(14-12-20)18(15-5-3-2-4-6-15)16-7-9-17(19)10-8-16;/h2-10,18H,11-14H2,1H3;1H
InChIKey: MSIJLVMSKDXAQN-UHFFFAOYSA-N
SMILES: C(C1C=CC=CC=1)(N1CCN(C)CC1)C1C=CC(Cl)=CC=1.Cl

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Safety

Hazard Codes: T
Risk Statements: 61-22
Safety Statements: 53-22-36/37/39-45
RIDADR: UN 2811 6.1 / PGIII
Toxicity: cat,LD50,intraperitoneal,75mg/kg (75mg/kg),"Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 213, 1972.

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: S511498
Product name: 1-(4-CHLORODIPHENYLMETHYL)-4-METHYLPIPERAZINE HYDROCHLORIDE
Purity: Aldrich
Packaging: 250mg
Price: $179
Updated: 2024/03/01

Sigma-Aldrich

Product number: C1435000
Product name: Chlorcyclizine hydrochloride
Purity: European Pharmacopoeia (EP) Reference Standard
Packaging: c1435000
Price: $153
Updated: 2024/03/01

Cayman Chemical

Product number: 19239
Product name: Chlorcyclizine (hydrochloride)
Purity: ≥98%
Packaging: 100mg
Price: $62
Updated: 2024/03/01

Cayman Chemical

Product number: 19239
Product name: Chlorcyclizine (hydrochloride)
Purity: ≥98%
Packaging: 1g
Price: $477
Updated: 2024/03/01

Cayman Chemical

Product number: 19239
Product name: Chlorcyclizine (hydrochloride)
Purity: ≥98%
Packaging: 250mg
Price: $142
Updated: 2024/03/01

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Chlorcyclizine hydrochloride Chemical Properties,Usage,Production

Description

Chlorcyclizine Hydrochloride, often marketed under trade names such as Ahist and Histade, is a first-generation antihistamine primarily used for its anticholinergic and sedative properties. This medication is widely recognized in treating various allergic conditions, including allergic rhinitis and urticaria. It acts on H1 histamine receptors, which play a crucial role in allergic responses. Several research institutions have conducted extensive studies to understand its efficacy and safety profile. The drug was first synthesized in the 1940s and has since been a staple in allergy relief therapy. Although first-generation antihistamines are often overshadowed by second-generation counterparts due to their sedative effects, Chlorcyclizine Hydrochloride remains a valuable option for individuals seeking rapid and effective symptom relief.

Uses

An antihistaminic drug

Health Hazard

Chlorcyclizine Hydrochloride can cause developmental toxicity according to state or federal government labelling requirements.

Biological Activity

chlorcyclizine is a phenylpiperazine antagonist for histamine h1 receptor [1].the histamine has been involved in modulating many physiological functions of the hypothalamus, such as arousal state, feeding, locomotor activity, and drinking. histamine has been involved in circadian rhythm of locomotor activity and exploratory behavior through h1r [1].

Mechanism of action

The primary mechanism of action of Chlorcyclizine Hydrochloride revolves around its ability to block H1 histamine receptors. Histamine is a compound involved in local immune responses and functions as a neurotransmitter. When an allergic reaction occurs, histamine is released from mast cells and binds to H1 receptors, leading to symptoms such as itching, swelling, and vasodilation. By blocking these receptors, Chlorcyclizine Hydrochloride effectively reduces the intensity of allergic symptoms. In addition to its antihistaminic activity, Chlorcyclizine Hydrochloride exhibits anticholinergic properties by blocking muscarinic acetylcholine receptors. This dual action can help in reducing secretions and providing sedation, which is beneficial in treating symptoms like runny nose and watery eyes. The sedative effect is due to its ability to cross the blood-brain barrier and act on central histamine and acetylcholine receptors, making it particularly useful for conditions requiring sedation, such as insomnia caused by allergic reactions.

Safety Profile

Poison by ingestion, subcutaneous, intravenous, and intraperitoneal routes. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits very toxic fumes of HCl and NOx.

in vitro

the ki value of chlorcyclizine for histamine h1 receptor was 9 nm [1]. chlorcyclizin was effective against hepatitis c virus (hcv) with an ec50 of 44 nm, preventing viral entry into host cells [2].

in vivo

in chimeric mice xenografted with primary human hepatocytes, chlorcyclizine (10-50 mg/kg) significantly inhibited infection of hcv genotypes 1b and 2a [2]. chlorcyclizine induced a resistance to sodium pentobarbital anesthesia. intraperitoneal injection of chlorcyclizine showed a sedative effect in small doses, but a convulsive effect in large doses. intraperitoneal injections of the drug did not affect the recovery time from pentobarbital anesthesia [3]. in rats, pretreatment with chlorcyclizine for several days shortened the duration of action of a subsequent dose of hexobarbital, pentobarbital or zoxazolamine, and accelerated in vivo metabolism of hexobarbital [4]. the administration of chlorcyclizine (50 g/kg) to rats by stomach tube daily for 1 week resulted in significant increases in liver weight, microsomal protein concentration and the activity of the nadph-dependent hepatic microsomal ethanol-oxidizing system (meos) [5].

References

[1] tran v t, chang r s, snyder s h. histamine h1 receptors identified in mammalian brain membranes with [3h] mepyramine[j]. proceedings of the national academy of sciences, 1978, 75(12): 6290-6294.
[2] he, s. ,xiao, j.,dulcey, a.e., et al. discovery, optimization, and characterization of novel chlorcyclizine derivatives for the treatment of hepatitis c virus infection. journal of medicinal chemistry 59(3), 841-853 (2016).
[3] thompson i d, dolowy w c, cole w h. development of a resistance to sodium pentobarbital in rats fed on a diet containing chlorcyclizine hydrochloride[j]. journal of pharmacology and experimental therapeutics, 1959, 127(2): 164-166.
[4] conney a h, burns j j, michaelson i a. stimulatory effect of chlorcyclizine on barbiturate metabolism[j]. journal of pharmacology and experimental therapeutics, 1961, 132(2): 202-206.
[5] khanna j m, kalant h, lin g. significance in vivo of the increase in micro-somal ethanol-oxidizing system after chronic administration of ethanol, pheno-barbital and chlorcyclizine[j]. biochemical pharmacology, 1972, 21(16): 2215-2226.

Chlorcyclizine hydrochloride Preparation Products And Raw materials

Raw materials

P-XYLENE Ethanol Sodium sulfate 1-Methylpiperazine 4-Chlorobenzhydrol Diethyl ether Hydrochloric acid Sodium bicarbonate Sulfuric acid Sodium carbonate

Preparation Products

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14362-31-3, Chlorcyclizine hydrochlorideRelated Search:

CHLORCYCLIZINE HYDROCHLORIDE Meclizine dihydrochloride Levocetirizine Cetirizine dihydrochloride Cetirizine BUCLIZINE, DIHYDROCHLORIDE Hydroxyzine dihydrochloride CHLORCYCLIZINE HYDROCHLORIDE CHLORCYCLIZINE 4-[(4-CHLOROPHENYL)PHENYLMETHYL]-1-PIPERAZINEETHANOL DIHYDROCHLORIDE migraleve Meclizine Dihydrochloride Monohydrate Chlorcyclizine dihydrochloride 1,4-BIS[(4-CHLOROPHENYL)PHENYLMETHYL]PIPERAZINE DIHYDROCHLORIDE 2-[2-[4-[(4-chlorophenyl)phenylmethyl]piperazin-1-yl]ethoxy]ethanol hydrochloride 4-[(4-Chlorophenyl)Phenylmethyl]-1-Piperazineethanol Hydrochloride CLOCINIZINE DIHYDROCHLORIDE Acetamide, 2-(2-(4-((2-chlorophenyl)phenylmethyl)-1-piperazinyl)ethoxy )-, dihydrochloride

chlorcycliziniumchloride

di-paralene

eramide

1-[(4-CHLOROPHENYL)PHENYL-METHYL]-4-METHYLPIPERAZINE HYDROCHLORIDE

CHLORCYCLIZINE HCL

CHLORCYCLIZINE HYDROCHLORIDE

Ah-289 hydrochloride

Chlorocyclizine hydrochloride

Component of fedrazil

1-(p-Chloro-α-phenylbenzyl)-4-Methylpiperazine Monohydrochloride

NSC 169496

Perazil

1-(4-CHLORODIPHENYLMETHYL)-4-METHYLPIPERAZINE HYDROCHLORIDE

1-[(4-Chlorophenyl)phenylmethyl]-4-methylpiperazine monohydrochloride

1-(p-chloro-alpha-phenylbenzyl)-4-methylpiperazinehydrochloride

1-(p-chloro-alpha-phenylbenzyl)-4-methyl-piperazinhydrochloride

1-(p-chlorobenzhydryl)-4-methylpiperazinehydrochloride

Chlorcyclizine hydrochloride CRS

CHLORCYCLIZINE HYDROCHLORIDE

14362-31-3

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Heterocycles

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