3-((4,5-Dihydro-1H-imidazol-2-yl)-methyl)(4-methyl-phenyl)amino)phenol

Bezeichnung:3-((4,5-Dihydro-1H-imidazol-2-yl)-methyl)(4-methyl-phenyl)amino)phenol

CAS-Nr50-60-2

Englisch Name:Phentolamine

CBNumberCB6665216

SummenformelC17H19N3O

Molgewicht281.35

MOL-Datei50-60-2.mol

Synonyma

Phentolamin

3-((4,5-Dihydro-1H-imidazol-2-yl)-methyl)(4-methyl-phenyl)amino)phenol

3-((4,5-Dihydro-1H-imidazol-2-yl)-methyl)(4-methyl-phenyl)amino)phenol physikalisch-chemischer Eigenschaften

Schmelzpunkt	174-175°
Siedepunkt	424.02°C (rough estimate)
Dichte	1.0510 (rough estimate)
Brechungsindex	1.6500 (estimate)
storage temp.	Hygroscopic, -20°C Freezer, Under inert atmosphere
Löslichkeit	DMSO (Slightly), Methanol (Slightly)
Aggregatzustand	Solid
pka	pKa 7.7 (Uncertain)
Farbe	Crystals
Stabilität	Hygroscopic
CAS Datenbank	50-60-2(CAS DataBase Reference)

Sicherheit

Giftige Stoffe Daten	50-60-2(Hazardous Substances Data)
Toxizität	LD50 orl-rat: 1250 mg/kg PSEBAA 71,70,49

Gefahreninformationscode (GHS)

Phentolamine Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
Phentolamine is also a derivative of imidazoline that exhibits a direct α-adrenoblocking, muscle-relaxant effect on smooth muscle as well as cholinomimetic, histamine, and sympathomimetic effects. The chemical variation of its structure permits a few of its properties to be more expressed. For example, the aforementioned tolazoline, 2-benzyl-2-imidazoline, a structural analog of phentolamine, has more of an expressed muscle-relaxant effect on smooth muscle than an α-adrenoblocking effect.
Originator
Regitine, Ciba, US ,1952
Verwenden
Phentolamine is used for peripheral blood circulation disorders, in particular in the beginning stages of gangrene, for treatment of trophic ulcers of the extremities, bedsores, and frostbite.
Verwenden
Anti-adrenergic.
Phentolamine is used to prevent or control hypertensive episodes that occurin patients with pheochromocytoma. It also has been used incombination with papaverine to treat impotence.
Definition
ChEBI: A substituted aniline that is 3-aminophenol in which the hydrogens of the amino group are replaced by 4-methylphenyl and 4,5-dihydro-1H-imidazol-2-ylmethyl groups respectively. An alpha-adrenergic antagonist, it is used fo the treatment of hypertension.
Indications
Human erectile tissue has a population of membrane receptors that are predominantly of the -adrenoceptor subtype. Phentolamine (Vasomax) is a nonselective - adrenoceptor blocking agent (see Chapter 11), and like other such agents, it has been used to treat ED. Nonselective adrenoceptor antagonists may provoke a reflex that increases both sympathetic outflow and the release of norepinephrine.
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.
Trademarks
Regitine (Novartis) [Name previously used: Phentolamine Methanesulfonate.].
Therapeutic Function
Adrenergic blocker
Allgemeine Beschreibung
Phentolamine isthe more effectiveα -blocker.
Mechanism of action
Its mechanism of action is as an α-adrenergic antagonist of both α1- and α2-receptors, causing vasodilation and reduction in peripheral resistance. When administered by intracavernosal injection, it is thought to cause relaxation of the cavernous smooth muscles and vasodilation of the penile arteries. This results in increased arterial blood flow into the corpus cavernosa as well as swelling and elongation of the penis. Venous outflow also is reduced, possibly as a result of increased venous resistance. Phentolamine is slowly released into venous circulation with minimal, if any, systemic effects. Time to peak effect is within 10 minutes, and duration of action when used with papaverine is 1 to 6 hours.
Clinical Use
Phentolamine has been used orally and intracavernosally in the treatment of ED. Following oral administration, phentolamine has a plasma half-life of about 30 minutes and a duration of action of 2 to 4 hours. An intracavernosal injection of phentolamine results in the drug reaching maximum serum levels in about 20 to 30 minutes. It is rapidly metabolized. Phentolamine has been used in combination with papaverine, chlorpromazine, and vasoactive peptides in the treatment of ED.
Nebenwirkungen
Side effects of phentolamine are dose related. It may cause orthostatic hypotension, reflex tachycardia, cardiac arrhythmias, and rarely, myocardial infarction. Phentolamine also may reduce sperm motility in vitro.
Sicherheitsprofil
Poison by subcutaneous, intravenous, and intraperitoneal routes. Moderately toxic by ingestion. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx.
Synthese
Phentolamine, 2-[[N-(3??-hydroxyphenyl)-para-toluidion]methyl]-2- imidazoline (12.2.8), is synthesized by alkylation of 3-(4-methylanilino)phenol using 2-chloromethylimidazoline [36, 37].

Phentolamine Upstream-Materialien And Downstream Produkte

3-((4,5-Dihydro-1H-imidazol-2-yl)-methyl)(4-methyl-phenyl)amino)phenol Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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