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Substance Name: Phentolamine [INN:BAN]
RN: 50-60-2
UNII: Z468598HBV
InChIKey: MRBDMNSDAVCSSF-UHFFFAOYSA-N

Note

  • A nonselective alpha-adrenergic antagonist. It is used in the treatment of hypertension and hypertensive emergencies, pheochromocytoma, vasospasm of RAYNAUD DISEASE and frostbite, clonidine withdrawal syndrome, impotence, and peripheral vascular disease.

Molecular Formula

  • C17-H19-N3-O

Molecular Weight

  • 281.3571
 

Classification Codes

  • Adrenergic Agents
  • Adrenergic alpha-Antagonists
  • Adrenergic Antagonists
  • Antihypertensive Agents
  • Cardiovascular Agents
  • Drug / Therapeutic Agent
  • Neurotransmitter Agents
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Phentolamine
  • Phentolamine [INN:BAN]

MeSH Heading

  • Phentolamine

Synonyms

  • 2-((N-(m-Hydroxyphenyl)-p-toluidino)methyl)-2-imidazoline
  • 2-(m-Hydroxy-N-p-tolylanilinomethyl)-2-imidazoline
  • 2-(N'-p-Tolyl-N'-m-hydroxyphenylaminomethyl)-2-imidazoline
  • 2-(N-(m-Hydroxyphenyl)-p-toluidinomethyl)imidazoline
  • 2-Imidazoline, 2-((N-(m-hydroxyphenyl)-p-toluidino)methyl)-
  • 5-25-09-00365 (Beilstein Handbook Reference)
  • BRN 0272944
  • C 7337
  • C 7337 Ciba
  • Dibasin
  • EINECS 200-053-1
  • Fentolamin
  • Fentolamina
  • Fentolamina [INN-Spanish]
  • HSDB 3382
  • Phenol, 3-(((4,5-dihydro-1H-imidazol-2-yl)methyl)(4-methylphenyl)amino)-
  • Phenol, m-(N-(2-imidazolin-2-ylmethyl)-p-toluidino)-
  • Phentolamine
  • Phentolamine mesilate
  • Phentolamine mesylate
  • Phentolaminum
  • Phentolaminum [INN-Latin]
  • Regitin
  • Regitine
  • UNII-Z468598HBV

Systematic Names

  • Phenol, 3-(((4,5-dihydro-1H-imidazol-2-yl)methyl)(4-methylphenyl)amino)-
  • Phentolamine

Registry Numbers

CAS Registry Number

  • 50-60-2

FDA UNII

  • Z468598HBV

Related Registry Numbers

  • 65-28-1 (mesylate (salt))
  • 73-05-2 (mono-hydrochloride)

System Generated Number

  • 0000050602

Structure Descriptors

InChI

1S/C17H19N3O/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)

InChIKey

MRBDMNSDAVCSSF-UHFFFAOYSA-N

Smiles

Cc1ccc(cc1)N(CC2=NCCN2)c3cccc(c3)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 200mg/kg (200mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: TREMOR

BEHAVIORAL: ATAXIA
Arzneimittel-Forschung. Drug Research. Vol. 21, Pg. 1727, 1971.
mouse LD50 intravenous 35mg/kg (35mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 105, Pg. 317, 1956.
mouse LD50 oral 1gm/kg (1000mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 112, Pg. 319, 1957.
rabbit LD50 intravenous 28mg/kg (28mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

LUNGS, THORAX, OR RESPIRATION: CYANOSIS

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 174, Pg. 243, 1968.
rabbit LD50 oral 2gm/kg (2000mg/kg)   Compilation of LD50 Values of New Drugs.
rabbit LDLo subcutaneous 200mg/kg (200mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Schweizerische Medizinische Wochenschrift. Vol. 81, Pg. 352, 1951.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 174.5 deg C   EXP
log P (octanol-water) 3.360 (none)   EST
Atmospheric OH Rate Constant 2.82E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.