ChemicalBook--->CAS DataBase List--->73-05-2

73-05-2

73-05-2 Structure

73-05-2 Structure
IdentificationBack Directory
[Name]

Phentolamine hydrochloride
[CAS]

73-05-2
[Synonyms]

c-7337
phentolaminechloride
Regitine hydrochloride
PHENTOLAMINE HYDROCHLORIDE
Phentolamine Hydrochloride (300 mg)
2-[N-(M-HYDROXYPHENYL)-P-TOLUIDINOMETHYL]IMIDAZOLINE HYDROCHLORIDE
m-(n-(2-imidazolin-2-ylmethyl)-p-toluidino)-phenomonohydrochloride
2-[n-(3-hydroxyphenyl)-p-toluidinomethyl]-2-imidazolidine hydrochloride
2-[N-(3-HYDROXYPHENYL)-4-TOLUIDINOMETHYL]-2-IMIDAZOLIDINE HYDROCHLORIDE
3-(((4,5-dihydro-1h-imidazol-2-yl)methyl)(4-methylphenyl)amino)-phenomonoh
3-(((4,5-dihydro-1h-imidazol-2-yl)methyl)(4-methylphenyl)amino)phenolhydroch
3-[4,5-Dihydro-1H-imidazol-2-ylmethyl-(4-methylphenyl)amino]phenol hydrochloride
3-[[(4,5-Dihydro-1H-imidazol-2-yl)-methyl](4-methylphenyl)-amino]-phenol monohydrochloride
[EINECS(EC#)]

200-793-5
[Molecular Formula]

C17H20ClN3O
[MDL Number]

MFCD00079268
[MOL File]

73-05-2.mol
[Molecular Weight]

317.81
Chemical PropertiesBack Directory
[Appearance]

Tan Solid
[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
[InChI]

1S/C17H19N3O.ClH/c1-13-5-7-14(8-6-13)20(12-17-18-9-10-19-17)15-3-2-4-16(21)11-15;/h2-8,11,21H,9-10,12H2,1H3,(H,18,19);1H
[InChIKey]

TUEJFGFQYKDAPM-UHFFFAOYSA-N
[SMILES]

Cl[H].Cc1ccc(cc1)N(CC2=NCCN2)c3cccc(O)c3
[CAS DataBase Reference]

73-05-2
Hazard InformationBack Directory
[Chemical Properties]

Tan Solid
[Uses]

An adrenergic blocking agent. An antihypertensive. Used for the treatment of pheochromocytoma.
[Uses]

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

Regitine, Ciba, US ,1952
[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.
Safety DataBack Directory
[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
[F ]

3-10
[HazardClass ]

6.1(b)
[PackingGroup ]

III
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Acute Tox. 4 Oral
[Toxicity]

LD50 in rats (mg/kg): 75 i.v.; 275 s.c.; 1250 orally (Meier)
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