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Phentolamine hydrochloride

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Phentolamine hydrochloride Basic information

Product Name:
Phentolamine hydrochloride
Synonyms:
  • PHENTOLAMINE HYDROCHLORIDE
  • 2-[N-(3-HYDROXYPHENYL)-4-TOLUIDINOMETHYL]-2-IMIDAZOLIDINE HYDROCHLORIDE
  • 2-[N-(M-HYDROXYPHENYL)-P-TOLUIDINOMETHYL]IMIDAZOLINE HYDROCHLORIDE
  • 3-(((4,5-dihydro-1h-imidazol-2-yl)methyl)(4-methylphenyl)amino)phenolhydroch
  • 3-(((4,5-dihydro-1h-imidazol-2-yl)methyl)(4-methylphenyl)amino)-phenomonoh
  • c-7337
  • m-(n-(2-imidazolin-2-ylmethyl)-p-toluidino)-phenomonohydrochloride
  • phentolaminechloride
CAS:
73-05-2
MF:
C17H20ClN3O
MW:
317.81
EINECS:
200-793-5
Product Categories:
  • Aromatics
  • Heterocycles
  • Diagnostic
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • BUTESIN
Mol File:
73-05-2.mol
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Phentolamine hydrochloride Chemical Properties

Melting point:
>230 (dec.)°C
storage temp. 
-20°C Freezer
solubility 
methanol: 10 mg/mL, clear, colorless
form 
powder
color 
white to off-white
Merck 
13,7348
BRN 
3764617
CAS DataBase Reference
73-05-2
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Safety Information

Hazard Codes 
Xn,C
Risk Statements 
22-34
Safety Statements 
22-24/25-45-36/37/39-27-26
RIDADR 
3249
WGK Germany 
3
RTECS 
SL0701000
3-10
HazardClass 
6.1(b)
PackingGroup 
III
Toxicity
LD50 in rats (mg/kg): 75 i.v.; 275 s.c.; 1250 orally (Meier)

MSDS

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Phentolamine hydrochloride Usage And Synthesis

Chemical Properties

Phentolamine hydrochloride is Tan Solid

Originator

Regitine, Ciba, US ,1952

Uses

Phentolamine Hydrochloride ia an adrenergic blocking agent. An antihypertensive. Used for the treatment of pheochromocytoma.

Uses

anesthetic (local); inhibitor of DRG IA/Kv4.2 current

Uses

Phentolamine hydrochloride is an adrenergic blocking agent. An antihypertensive. Used for the treatment of pheochromocytoma.

Manufacturing Process

199.24 parts of N-(p-methylphenyl)-m'-hydroxyphenylamine and 77.52 parts of 2-chloromethylimidazoline hydrochloride are heated for sixteen hours in an oil bath having a temperature of 150°C, while stirring and introducing a current of nitrogen. The viscous contents of the flask are then cooled to about 100°C, mixed with 400 parts by volume of hot water, and stirred for a short time.
After further cooling to about 60°C, 200 parts by volume of water and 500 parts by volume of ethyl acetate at 60°C are added, and the aqueous layer is separated. The excess of starting material may be recovered from the ethyl acetate.
The aqueous portion is chilled in a cooling chamber at -10°C, whereupon the hydrochloride of 2-[N-(p-methylphenyl)-N-(m'-hydroxyphenyl)-aminomethyl]imidazoline crystallizes. Upon being concentrated and cooled the mother liquor yields a further quantity of the hydrochloride. The combined quantities of hydrochloride are treated with a small quantity of cold water, dried with care, and washed with ethyl acetate. The product is then crystallized from a mixture of alcohol and ethyl acetate, and there is obtained a hydrochloride melting at 239°-240°C.

brand name

Regitine Hydrochloride (Ciba-Geigy).

Therapeutic Function

Adrenergic blocker

Biochem/physiol Actions

α-adrenoceptor antagonist; peripheral vasodilator.

Phentolamine hydrochlorideSupplier

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