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Clonidine hydrochloride

CAS No.
4205-91-8
Chemical Name:
Clonidine hydrochloride
Synonyms
CLONIDINE HCL;dcai;2-(2,6-DICHLOROANILINO)-2-IMIDAZOLINE HYDROCHLORIDE;DIXARIT;hemiton;Neuclon;atensina;capresin;clofelin;haemiton
CBNumber:
CB3763159
Molecular Formula:
C9H10Cl3N3
Molecular Weight:
266.55
MDL Number:
MFCD00036705
MOL File:
4205-91-8.mol
Last updated:2024-03-14 15:25:22

Clonidine hydrochloride Properties

Melting point 312 °C
storage temp. 2-8°C
solubility H2O: 50 mg/mL, clear, colorless
form solid
color white
PH pH(50g/l, 25℃) : 3.5~6.0
Water Solubility Soluble in water (50 mg/ml), DMSO (75 mM), methanol, chloroform (slightly), and dehydrated alcohol.
Merck 14,2390
BRN 4163525
BCS Class 1 (LogP), 3 (CLogP)
Stability Hygroscopic
InChIKey GLEWMLFXCSBZLK-UHFFFAOYSA-N
CAS DataBase Reference 4205-91-8(CAS DataBase Reference)
NCI Dictionary of Cancer Terms clonidine hydrochloride
FDA UNII W76I6XXF06
NCI Drug Dictionary clonidine hydrochloride
EPA Substance Registry System 1H-Imidazol-2-amine, N-(2,6-dichlorophenyl)-4,5-dihydro-, hydrochloride (1:1) (4205-91-8)

Pharmacokinetic data

Protein binding 30-40%
Excreted unchanged in urine 40-60%
Volume of distribution 3-6(L/kg)
Biological half-life 10-20 / 41

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS06
Signal word  Danger
Hazard statements  H301-H330
Precautionary statements  P260-P301+P330+P331+P310-P304+P340+P310-P403+P233
Hazard Codes  T+
Risk Statements  25-26
Safety Statements  22-26-28-36/37/39-45
RIDADR  UN 2811 6.1/PG 1
WGK Germany  3
RTECS  NJ2490000
10
HazardClass  6.1(b)
PackingGroup  III
HS Code  2933290000
Toxicity LD50 in mice, rats (mg/kg): 328, 270 orally; 18, 29 i.v. (Walland)
NFPA 704
0
4 0

Clonidine hydrochloride price More Price(52)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich C7897 Clonidine hydrochloride solid 4205-91-8 1g $454 2024-03-01 Buy
Sigma-Aldrich BP085 Clonidine hydrochloride British Pharmacopoeia (BP) Reference Standard 4205-91-8 100MG $234 2024-03-01 Buy
Sigma-Aldrich 1140407 Clonidine hydrochloride United States Pharmacopeia (USP) Reference Standard 4205-91-8 200mg $436 2024-03-01 Buy
TCI Chemical D1353 2-(2,6-Dichloroanilino)-2-imidazoline Hydrochloride >98.0%(HPLC)(T) 4205-91-8 1g $73 2024-03-01 Buy
TCI Chemical D1353 2-(2,6-Dichloroanilino)-2-imidazoline Hydrochloride >98.0%(HPLC)(T) 4205-91-8 5g $216 2024-03-01 Buy
Product number Packaging Price Buy
C7897 1g $454 Buy
BP085 100MG $234 Buy
1140407 200mg $436 Buy
D1353 1g $73 Buy
D1353 5g $216 Buy

Clonidine hydrochloride Chemical Properties,Uses,Production

Chemical Properties

White Solid

Originator

Catapresan,Boehringer,Ingelheim,1966

Uses

In shaving soaps.

Uses

`a2-adrenoceptor agonist, imidazoline receptor ligand, anti-hypertensive

Uses

Clonidine hydrochloride tablets are indicated in the treatment of hypertension. It has found new uses, including treatment of some types of neuropathic pain, opioid detoxification, sleep hyperhidrosis, anaesthetic use, and off-label, to counter the side effects of stimulant medications such as methylphenidate or amphetamine. It is becoming a more accepted treatment for insomnia, as well as for relief of menopausal symptoms. Clonidine(4205-91-8) is increasingly used in conjunction with stimulants to treat attention-deficit hyperactivity disorder (ADHD).

Uses

Labelled Clonidine. α2-Adrenergic agonist. Antihypertensive; analgesic for neuropathic pain.

Definition

ChEBI: Clonidine hydrochloride is a dichlorobenzene.

Manufacturing Process

N-(2,6-dichlorophenyl)thiourea (MP 149°C) was prepared in customary manner from 2,6-dichloroaniline (Organic Synthesis III, 262-263) and ammonium thiocyanate. 16.0 g of this thiourea derivative were refluxed for
2.5 hours together with 16 g of methyl iodide in 150 cc of methanol. Thereafter, the methanol was evaporated out of the reaction mixture in vacuo, leaving as a residue 22 g of N-(2,6-dichlorophenyl)-S-methyl-isothiouronium hydroiodide of the formula having a melting point of 170°C. The entire residue was then admixed with an excess (120%) above the molar equivalent of ethylenediamine, and the mixture was heated for about one hour at 130° to 150°C. Methyl mercaptan was given off. Thereafter, the reaction mixture comprising 2-(2',6'-dichloroanilino)-1,3-diazacyclopentene-(2) hydroiodide was taken up in hot dilute acetic acid, and the resulting solution was made alkaline with 2 N NaOH. A precipitate formed which was separated by vacuum filtration, washed with water and dried. 4.0 g of 2-(2',6'-dichloroanilino)-1,3- diazacyclopentene-(2) were obtained. The product had a melting point of 130°C.
The free base was then dissolved in absolute methanol, and the resulting solution was then adjusted to an acid pH value with an ethereal hydrochloric acid solution. The acidified solution was purified with charcoal and then dry ether was added thereto until crystallization took place. The hydrochloride, prepared in this customary manner, had a melting point of 305°C according to US Patent 3,202,660

brand name

Catapres (Boehrin- ger Ingelheim); Duraclon (Xanodyne).

Therapeutic Function

Antihypertensive

Synthesis Reference(s)

Synthesis, p. 64, 1987 DOI: 10.1055/s-1987-27847

General Description

Clonidine hydrochloride, 2-[(2,6-dichlorophenyl)imino]imidazolidine monohydrochloride(Catapres), was the first antihypertensive known to acton the CNS. It was synthesized in 1962 as a derivativeof the known -sympathomimetic drugs naphazoline andtolazoline, potential nasal vasoconstrictors, but instead itproved to be effective in the treatment of mild-to-severe hypertension.Clonidine hydrochloride acts by both peripheral andcentral mechanisms in the body to affect blood pressure. Itstimulates the peripheral -adrenergic receptors to producevasoconstriction, resulting in a brief period of hypertension.

Biological Activity

Prototypical I 1 imidazoline receptor ligand. α 2 -adrenergic receptor agonist. Antihypertensive.

Biochem/physiol Actions

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.

Clinical Use

Clonidine hydrochloride acts by both peripheral andcentral mechanisms in the body to affect blood pressure. Itstimulates the peripheral α-adrenergic receptors to producevasoconstriction, resulting in a brief period of hypertension.Clonidine hydrochloride acts centrally to inhibitthe sympathetic tone and cause hypotension that is ofmuch longer duration than the initial hypertensive effect.Administration of clonidine hydrochloride thus produces abiphasic change in blood pressure, beginning with a briefhypertensive effect and followed by a hypotensive effectthat persists for about 4 hours. This biphasic response isaltered by dose only. Larger doses produce a greater hypertensiveeffect and delay the onset of the hypotensiveproperties of the drug. Clonidine hydrochloride acts on 2-adrenoreceptors located in the hindbrain to produce itshypotensive action. Clonidine hydrochloride also acts centrallyto cause bradycardia and to reduce plasma levels ofrenin. Sensitization of baroreceptor pathways in the CNSappears to be responsible for the bradycardia transmittedby way of the vagus nerve. The central mechanism that resultsin decreased plasma renin is not known, however.The hypotensive properties of clonidine in animals can beblocked by applying -adrenergic blocking agents directlyto the brain.

Drug interactions

Potentially hazardous interactions with other drugs
Antidepressants: tricyclics antagonise hypotensive effect and also increase risk of hypertension on clonidine withdrawal; increased hypotensive effect with MAOIs; hypotensive effect possibly antagonised by mirtazapine.
Beta-adrenoreceptor antagonists: increased risk of hypertension on withdrawal.
Ciclosporin: may increase ciclosporin levels.
Sympathomimetics: possibly increased risk of hypertension with adrenaline and noradrenaline; serious adverse effects reported with methylphenidate.

Metabolism

About 50% of a of clonidine dose is metabolised in the liver.
It is excreted in the urine as unchanged drug and metabolites, 40-60% of an oral dose being excreted in 24 hours as unchanged drug; about 20% of a dose is excreted in the faeces, probably via enterohepatic circulation.

storage

Store at RT

Purification Methods

This antihypertensive is recrystallised from EtOH/Et2O and dried in a vacuum (solubility in H2O is 5%). The free base has m 124-125o and is recrystallised from hexane. [Jen et al. J Med Chem 18 90 1975, NMR: Jackman & Jen J Am Chem Soc 97 2811 1975.]

Clonidine hydrochloride Preparation Products And Raw materials

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View Lastest Price from Clonidine hydrochloride manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Clonidine hydrochloride pictures 2024-03-22 Clonidine hydrochloride
4205-91-8
US $100.00 / kg 1kg 99.9% 20tons Hong Kong Excellence Biotechnology Co., Ltd.
Clonidine hydrochloride pictures 2024-03-16 Clonidine hydrochloride
4205-91-8
US $0.00 / KG 100g 98%+ 100kg WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
Clonidine hydrochloride pictures 2024-03-15 Clonidine hydrochloride
4205-91-8
US $3.00-1.00 / kg 1kg 99.9% 10 tons Shanghai Aosiris new Material Technology Co., LTD
CLONIDINE HYDROCHLORIDE DIXARIT 2-[2,6-DICHLOROANILINE]-2-IMIDAZOLINE HYDROCHLORIDE 2-(2,6-DICHLOROANILINO)-2-IMIDAZOLINE, HCL 2-(2,6-DICHLOROPHENYLAMINO)-2-IMIDAZOLINE HYDROCHLORIDE katapresan klophelin n-(2,6-dichlorophenyl)-4,5-dihydro-1h-imidazol-2-aminmonohydrochloride normopresan TIMTEC-BB SBB003065 2-((2,6-dichlorophenyl)imino)imidazolidinemonohydrochloride 2-(2,6-dichloroanilino)-2-imidazolinmonohydrochloride 2-(2,6-dichlorophenylamino)-2-imidazolinhydrochlorid 2,6-dichloro-n-2-imidazolidinylidene-benzenaminhydrochloride atensina capresin chlophazolin clofelin clonidinemonohydrochloride haemiton hemiton isoglaucon Clonidine Hydrochloride BP2000/USP25 ClonidineHclC9H9C12N3.HCL 1H-Imidazol-2-amine, N-(2,6-dichlorophenyl)-4,5-dihydro-, monohydrochloride CLONIDINEHYDROCHLORIDE,USP 2-IMIDAZOLONE,2-(2,6-DICHLOROANILINO)-,MONOHYDROCHLORIDE Clomiding Hydrochloride ClonidineHydrochlorideUsp27 NormopresanClonidine monohydrochloride Clonidine hydrochlor Clonidine Hydrochloride (200 mg) Neuclon Clonidine Hydrochloride 2-(2,6-Dichlorophenylamino)-2-imidazoline Hydrochloride N-(2,6-dichlorophenyl)-4,5-dihydro-1H-imidazol-2-amine,hydrochloride (1:1) catapresan Clonidine hydrochloride CRS 2-(2,6-Dichloroanilino)-2-imidazoline Hydrochloride > 2,6-dichloro-N-(imidazolidin-2-ylidene)aniline hydrochloride N-(2,6-Dichlorophenyl)-4,5-dihydro-1H-imidazol-2-amine HCl Clonidine hydrochloride USP/EP/BP Clonidine HydrochlorideQ: What is Clonidine Hydrochloride Q: What is the CAS Number of Clonidine Hydrochloride Q: What is the storage condition of Clonidine Hydrochloride Q: What are the applications of Clonidine Hydrochloride Clonidine Hydrochloride (1140407) CLONIDINE HCL 2-(2,6-DICHLOROANILINO)-2-IMIDAZOLINE HYDROCHLORIDE dcai 4205-91-8 C9H10Cl3N3 C9H9Cl2N3ClH C9H9Cl12N3HCl C9H9Cl2N3HCl C9H9CI2N3HCl alpha2-adrenoceptor agonist; I1 imidazoline binding site ligand. CATAPRES Other APIs Adrenoceptor Amines Aromatics