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C7897

Sigma-Aldrich

Clonidine hydrochloride

solid

Synonym(s):

2-(2,6-Dichloroanilino)-2-imidazoline hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C9H9Cl2N3 · HCl
CAS Number:
Molecular Weight:
266.55
Beilstein:
4163525
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

form

solid

color

white

solubility

H2O: soluble
methanol: soluble

originator

Boehringer Ingelheim

storage temp.

2-8°C

SMILES string

Cl[H].Clc1cccc(Cl)c1NC2=NCCN2

InChI

1S/C9H9Cl2N3.ClH/c10-6-2-1-3-7(11)8(6)14-9-12-4-5-13-9;/h1-3H,4-5H2,(H2,12,13,14);1H

InChI key

ZNIFSRGNXRYGHF-UHFFFAOYSA-N

Gene Information

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General description

Clonidine hydrochloride has antihypertensive analgesic and antidiarrheal properties. It lowers short-circuit current, blocks anion secretion, improves mucosal absorption of fluids and electrolytes in vitro. Clonidine is used to treat attention deficit and hyperactivity disorders (ADHD), menopausal flushing, drug withdrawal and Tourette′s syndrome.

Application

Clonidine hydrochloride has been used as an adrenergic receptor (ADRA2A) agonist:
  • in ex vivo leptin release assay
  • to study its effects on pain hypersensitivity in 6-OHDA lesioned rats
  • to study its influence on the sleep of larval zebrafish
  • to manipulate noradrenaline and examine its influence on behavioral flexibility and motivation

Clonidine hydrochloride has been used:
  • to reduce central noradrenaline levels
  • to inhibit allyl isothiocyanate (AITC) sensitized thermal aversion
  • to attenuate thermal and mechanical pain hypersensitivity in rats
  • as a positive control for pertussis toxin (PTX)

Biochem/physiol Actions

α2-adrenoceptor agonist; I1 imidazoline binding site ligand.
Clonidine hydrochloride is used for management of hypertension in pregnant women. In addition, it also acts as a therapeutic for neonatal abstinence syndrome. Clonidine hydrochloride binds to central α-adrenergic receptors and reduces the efferent sympathetic neuronal vasoconstrictor tone to the heart, kidneys and peripheral vasculature leading to vasodilatation and reduction in the blood pressure.

Features and Benefits

This compound is featured on the Imidazoline Binding Sites page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Boehringer Ingelheim. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 3 Oral

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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R M Eglen et al.
Trends in pharmacological sciences, 19(9), 381-390 (1998-10-24)
Although imidazoline sites have been the subject of research for several years, there is still controversy about their structure, diversity and physiology. The I1 site is thought to exist principally as a binding site and is widely purported to play
Clonidine hydrochloride--a safe and effective antihypertensive agent in pregnancy.
Horvath JS, et al.
Obstetrics and Gynecology, 66(5), 634-638 (1985)
Safety and efficacy of clonidine and clonidine extended-release in the treatment of children and adolescents with attention deficit and hyperactivity disorders
Ming X, et al.
Adolescent health, medicine and therapeutics, 2(2), 105-105 (2011)
Clonidine for smoking cessation
Gourlay SG, et al.
Cochrane database of systematic reviews (Online), 3, 105-105 (2004)
Z P Khan et al.
Anaesthesia, 54(2), 146-165 (1999-04-24)
Clonidine has proved to be a clinically useful adjunct in clinical anaesthetic practice as well as in chronic pain therapy because it has both anaesthetic and analgesic-sparing activity. The more selective alpha-2 adrenoceptor agonists, dexmedetomidine and mivazerol, may also have

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