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

• ChemBase ID: 73251
• Molecular Formular: C18H23N3O4S
• Molecular Mass: 377.45792
• Monoisotopic Mass: 377.14092723
• SMILES: c1(N(c2ccc(cc2)C)CC2=NCCN2)cc(ccc1)O.CS(=O)(=O)O
• Canonical SMILES: CS(=O)(=O)O.Cc1ccc(cc1)N(c1cccc(c1)O)CC1=NCCN1
• InChI: InChI=1S/C17H19N3O.CH4O3S/c1-13-5-7-14(8-6-13)20(12-17-18-9-10-19-17)15-3-2-4-16(21)11-15;1-5(2,3)4/h2-8,11,21H,9-10,12H2,1H3,(H,18,19);1H3,(H,2,3,4)
• InChIKey: OGIYDFVHFQEFKQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(4,5-dihydro-1H-imidazol-2-ylmethyl)(4-methylphenyl)amino]phenol; methanesulfonic acid
• IUPAC Traditional name: phentolamine mesylate; methanesulfonic acid; phentolamine
• Synonyms: 2-[N-(m-Hydroxyphenyl)-p-toluidinomethyl]imidazoline, Methanesulfonate; Phentolamine Methanesulfonate Salt; Regitine; Phentolamine mesilate; Phentolamine methanesulfonate salt; REGITIN; 3-[[(4,5-Dihydro-1H-imidazol-2-yl)methyl](4-methylphenyl)-amino]phenol mesylate; 2-(N-[m-Hydroxyphenyl]-p-toluidinomethyl)imidazoline; PHENTOLAMINE MESYLATE; 2-(N-[m-羟基苯基]-p-甲苯氨基甲基)咪唑啉; 酚妥拉明 甲磺酸盐

Database IDs

• CAS Number: 65-28-1
• EC Number: 200-604-6
• MDL Number: MFCD00134201
• PubChem SID: 24898184; 24277798; 162038171
• PubChem CID: 91430

CALCULATED PROPERTIES

• 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

PROPERTIES

Physical Property

• Solubility: DMSO; ethanol: soluble26 mg/mL; H2O: soluble50 mg/mL; Methanol
• Apperance: White Solid; white to off-white powder
• Melting Point: 176-182°C; 177-181°C; 180-182 °C(lit.)

Safety Information

• Storage Condition: -20°C; Refrigerator; Room Temperature (15-30°C)
• Storage Warning: Aq. Solutions Cannot be Stored
• RTECS: SL5430000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H315-H319-H332-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Target: adrenergic receptor
• Gene Information: human ... ADRA1A(148), ADRA1B(147), ADRA1D(146), ADRA2A(150), ADRA2B(151), ADRA2C(152)

Product Information

• Purity: ≥98% (TLC); 99%
• Salt Data: mesilate
• Linear Formula: C17H19N3O · CH3SO3H

DETAILS

Selleck Chemicals - S2038

Biological Activity:

Sigma Aldrich - P131

Biochem/physiol Actions
α-肾上腺素受体拮抗剂；外周血管舒张剂。

Sigma Aldrich - P7561

Biochem/physiol Actions
α-肾上腺素受体拮抗剂；外周血管舒张剂。
包装
100, 500 mg in poly bottle

Sigma Aldrich - 361658

Biochem/physiol Actions
α-Adrenergic receptor antagonist; peripheral vasodilator.
Application
Useful α-adrenoceptor antagonist.1

Toronto Research Chemicals - P302560

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

REFERENCES

• Meier, R., et al.: Proc. Soc. Exp. Biol. Med., 71, 70 (1949)
• Spergel, G., et al.: J. Am. Med. Assoc., 211, 266 (1949)
• Gould, L. and Reddy, C.V.R.: Am. Heart J., 92, 397 (1976)