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50-60-2 molecular structure
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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 and InChIs

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

Cite this record

CBID:574 http://www.chembase.cn/molecule-574.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
50-60-2
MDL Number
MFCD00242985
PubChem SID
46506535
160964037
PubChem CID
5775

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 9.779238  H Acceptors
H Donor LogD (pH = 5.5) 0.5305635 
LogD (pH = 7.4) 1.3010917  Log P 2.515108 
Molar Refractivity 84.2513 cm3 Polarizability 31.93207 Å3
Polar Surface Area 47.86 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.91  LOG S -3.02 
Solubility (Water) 2.72e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Product Information Bioassay(PubChem)
Hydrophobicity(logP)
3.3 expand Show data source
3.809 expand Show data source
Purity
95% expand Show data source
96% expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00692 external link
Item Information
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

REFERENCES

REFERENCES

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PATENTS

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