3-[(4,5-dihydro-1H-imidazol-2-ylmethyl)(4-methylphenyl)amino]phenol

• ChemBase ID: 574
• Molecular Formular: C17H19N3O
• Molecular Mass: 281.35226
• Monoisotopic Mass: 281.15281224
• SMILES: Oc1cc(N(CC2=NCCN2)c2ccc(cc2)C)ccc1
• Canonical SMILES: Cc1ccc(cc1)N(c1cccc(c1)O)CC1=NCCN1
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(4,5-dihydro-1H-imidazol-2-ylmethyl)(4-methylphenyl)amino]phenol; 3-{[(4,5-dihydro-1H-imidazol-2-yl)methyl](4-methylphenyl)amino}phenol
• IUPAC Traditional name: phentolamine
• Brand Name: Phentolamine Mesilate; Phentolamine Mesylate; Phentolamine Mesylate [USAN]; Phentolamine Methanesulfonate; Phentolamine Methanesulphonate; Phentolamine, Methyl Sulfonate; Regitin; Regitin Methanesulphonate; Regitine; Regitine Mesylate; Regitine Methanesulfonate; Regitipe; Rogitine; Phenotolamine; Phentalamine
• Synonyms: Phentolamine; 3-[(4,5-dihydro-1H-imidazol-2-ylmethyl)(4-methylphenyl)amino]phenol; 3-((4,5-dihydro-1h-imidazol-2-yl)methyl-(4-methylphenyl)-amino)phenol

Database IDs

• CAS Number: 50-60-2
• MDL Number: MFCD00242985
• PubChem SID: 46506535; 160964037
• PubChem CID: 5775

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.779238
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.5305635
• LogD (pH = 7.4): 1.3010917
• Log P: 2.515108
• Molar Refractivity: 84.2513 cm^3
• Polarizability: 31.93207 Å^3
• Polar Surface Area: 47.86 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.91
• LOG S: -3.02
• Solubility (Water): 2.72e-01 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 3.3; 3.809

Product Information

• Purity: 95%; 96%

DETAILS

DrugBank - DB00692

• Drug Groups: approved
• Description: 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. [PubChem]
• Indication: Used as an aid for the diagnosis of pheochromocytoma, and may be administered immediately prior to or during pheochromocytomectomy to prevent or control paroxysmal hypertension resulting from anesthesia, stress, or operative manipulation of the tumor. Phentolamine has also been used to treat hypertensive crisis caused by sympathomimetic amines or catecholamine excess by certain foods or drugs in patients taking MAO inhibitors, or by clonidine withdrawal syndrome. Other indications include the prevention of dermal necrosis and sloughing following IV administration or extravasation of norepinephrine, decrease in impedance to left ventricular ejection and the infarct size in patients with MI associated with left ventricular failure, treatment of erectile dysfunction through self-injection of small doses combined with papaverine hydrochloride into the corpus cavernosum, and as an adjunct to the management of cocaine overdose to reverse coronary vasoconstriction following use of oxygen, benzodiazepines,and nitroglycerin.
• Pharmacology: Phentolamine is indicated for the control of episodes of hypertension and sweating that occur with a disease called pheochromocytoma. If tachycardia is excessive, it may be necessary to use a beta-blocking agent concomitantly. Phentolamine is a long-acting, adrenergic, alpha-receptor blocking agent which can produce and maintain "chemical sympathectomy" by oral administration. It increases blood flow to the skin, mucosa and abdominal viscera, and lowers both supine and erect blood pressures. It has no effect on the parasympathetic system. Phentolamine works by blocking alpha receptors in certain parts of the body. Alpha receptors are present in the muscle that lines the walls of blood vessels. When the receptors are blocked by Phentolamine, the muscle relaxes and the blood vessels widen. This widening of the blood vessels results in a lowering of blood pressure.
• Affected Organisms: Humans and other mammals
• Half Life: 19 minutes
• Elimination: 10-13% of the drug is excreted unchanged in urine, and the fate of the remainder of the drug is unknown.
• External Links: Wikipedia; RxList; Drugs.com