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Clonidine hydrochloride

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Clonidine hydrochloride Basic information
Product Name:Clonidine hydrochloride
Product Categories:CATAPRES;Other APIs;Adrenoceptor;Amines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:4205-91-8.mol
Clonidine hydrochloride Structure
Clonidine hydrochloride Chemical Properties
Melting point 312 °C
storage temp. 2-8°C
solubility H2O: 50 mg/mL, clear, colorless
form solid
color white
PHpH(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
CAS DataBase Reference4205-91-8(CAS DataBase Reference)
EPA Substance Registry System1H-Imidazol-2-amine, N-(2,6-dichlorophenyl)-4,5-dihydro-, hydrochloride (1:1) (4205-91-8)
Safety Information
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
HazardClass 6.1(b)
PackingGroup III
HS Code 2933290000
ToxicityLD50 in mice, rats (mg/kg): 328, 270 orally; 18, 29 i.v. (Walland)
MSDS Information
SigmaAldrich English
Clonidine hydrochloride Usage And Synthesis
Chemical PropertiesWhite Solid
UsesLabelled Clonidine. α2-Adrenergic agonist. Antihypertensive; analgesic for neuropathic pain.
Uses`a2-adrenoceptor agonist, imidazoline receptor ligand, anti-hypertensive
UsesIn shaving soaps.
Manufacturing ProcessN-(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 nameCatapres (Boehrin- ger Ingelheim); Duraclon (Xanodyne).
Therapeutic FunctionAntihypertensive
Synthesis Reference(s)Synthesis, p. 64, 1987 DOI: 10.1055/s-1987-27847
General DescriptionClonidine 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 ActivityPrototypical I 1 imidazoline receptor ligand. α 2 -adrenergic receptor agonist. Antihypertensive.
Clinical UseClonidine 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.
Purification MethodsThis 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
Raw materials2,6-Dichloroaniline-->Iodomethane-->Hydrogen-->thiocyanate-->Ethylenediamine
Tag:Clonidine hydrochloride(4205-91-8) Related Product Information
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