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Phentolamine

Names

[ CAS No. ]:
50-60-2

[ Name ]:
Phentolamine

[Synonym ]:
Fentolamin
EINECS 200-053-1
MFCD00242985
Phenol, 3-(((4,5-dihydro-1H-imidazol-2-yl)methyl)(4-methylphenyl)amino)-
2-(N-[m-Hydroxyphenyl]-p-toluidinomethyl)imidazoline
Phenol, 3-[[(4,5-dihydro-1H-imidazol-2-yl)methyl](4-methylphenyl)amino]-
Phentalamine
Regitin
Phenotolamine
3-[(4,5-Dihydro-1H-imidazol-2-ylmethyl)(4-methylphenyl)amino]phenol
Dibasin
Fentolamina
Regitine
Phentolaminum
Phentolamine
3-[N-(4,5-dihydro-1H-imidazol-2-ylmethyl)-4-methylanilino]phenol
Rogitine

Biological Activity

[Description]:

Phentolamine is a potent, selective and orally active α1 adrenergic and α2 adrenergic receptor antagonist. Phentolamine can be used for the treatment of erectile dysfunction[1][2][3].

[Related Catalog]:

Research Areas >> Endocrinology
Signaling Pathways >> GPCR/G Protein >> Adrenergic Receptor

[In Vivo]

Phentolamine (5-20 mg/kg; i.p.) effectively inhibits the seizures elicited by strychnine (2 mg/kg, i.p.) and attenuates the seizure-potentiating effect of DOPS (4 mg/kg, i.p.) in mouse[2]. Phentolamine (1 mg/kg; i.p.) increases insulin secretion by inhibition of b-cell a2A-adrenoceptors in mouse[3]. Animal Model: WT mice[3] Dosage: 1 mg/kg Administration: IP Result: Reduced blood glucose and increased insulin levels.

[References]

[1]. Goldstein I I. Oral phentolamine: an alpha-1, alpha-2 adrenergic antagonist for the treatment of erectile dysfunction. Int J Impot Res. 2000 Mar;12(S1):S75-S80

[2]. Amabeoku G, et al. Strychnine-induced seizures in mice: the role of noradrenaline. Prog Neuropsychopharmacol Biol Psychiatry. 1994 Jul;18(4):753-63.

[3]. Fagerholm V, et al. alpha2A-adrenoceptor antagonism increases insulin secretion and synergistically augments the insulinotropic effect of glibenclamide in mice. Br J Pharmacol. 2008 Jul;154(6):1287-96.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
551.0±45.0 °C at 760 mmHg

[ Melting Point ]:
177 - 178ºC

[ Molecular Formula ]:
C17H19N3O

[ Molecular Weight ]:
281.352

[ Flash Point ]:
287.0±28.7 °C

[ Exact Mass ]:
281.152802

[ PSA ]:
47.86000

[ LogP ]:
3.60

[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C

[ Index of Refraction ]:
1.626

[ Storage condition ]:
-20°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
SL0700000
CHEMICAL NAME :
Phenol, 3-(((4,5-dihydro-1H-imidazol-2-yl)methyl)(4-methylphe nyl)amino)-
CAS REGISTRY NUMBER :
50-60-2
BEILSTEIN REFERENCE NO. :
0272944
LAST UPDATED :
199612
DATA ITEMS CITED :
7
MOLECULAR FORMULA :
C17-H19-N3-O
MOLECULAR WEIGHT :
281.39
WISWESSER LINE NOTATION :
T5M CN BUTJ B1NR CQ&R D1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 112,319,1957
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
200 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - ptosis Behavioral - tremor Behavioral - ataxia
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 21,1727,1971
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
35 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 105,317,1956
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
2 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
CLDND* Compilation of LD50 Values of New Drugs. (J.R. MacDougal, Dept. of National Health and Welfare, Food and Drug Divisions, 35 John St., Ottawa, Ont., Canada)
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
200 mg/kg
TOXIC EFFECTS :
Peripheral Nerve and Sensation - spastic paralysis with or without sensory change Behavioral - convulsions or effect on seizure threshold
REFERENCE :
SMWOAS Schweizerische Medizinische Wochenschrift. (Schwabe & Co., Steintorst 13, 4010 Basel, Switzerland) V.50- 1920- Volume(issue)/page/year: 81,352,1951
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
28 mg/kg
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - dyspnea Lungs, Thorax, or Respiration - cyanosis Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 174,243,1968 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
100 ug/kg
SEX/DURATION :
female 8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - uterus, cervix, vagina
REFERENCE :
DPTHDL Developmental Pharmacology and Therapeutics. (S. Karger Pub., Inc., 79 Fifth Ave., New York, NY 10003) V.1- 1980- Volume(issue)/page/year: 7(Suppl 1),72,1984

Safety Information

[ Safety Phrases ]:
S26-S36/37/39-S45-S8-S25

[ RIDADR ]:
UN 3264 8/PG 2

[ WGK Germany ]:
3

[ Packaging Group ]:
II

[ Hazard Class ]:
8

[ HS Code ]:
2933290090

Synthetic Route

Precursor & DownStream

Customs

[ HS Code ]: 2933290090

[ Summary ]:
2933290090. other compounds containing an unfused imidazole ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%


Related Compounds