3-{[(4,5-dihydro-1H-imidazol-2-yl)methyl](4-methylphenyl)amino}phenol hydrochloride

• ChemBase ID: 121446
• Molecular Formular: C17H20ClN3O
• Molecular Mass: 317.8132
• Monoisotopic Mass: 317.12948996
• SMILES: N(c1cc(O)ccc1)(CC1=NCCN1)c1ccc(cc1)C.Cl
• Canonical SMILES: Cc1ccc(cc1)N(c1cccc(c1)O)CC1=NCCN1.Cl
• InChI: InChI=1S/C17H19N3O.ClH/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);1H
• InChIKey: TUEJFGFQYKDAPM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{[(4,5-dihydro-1H-imidazol-2-yl)methyl](4-methylphenyl)amino}phenol hydrochloride; 3-[(4,5-dihydro-1H-imidazol-2-ylmethyl)(4-methylphenyl)amino]phenol hydrochloride
• IUPAC Traditional name: phentolamine hydrochloride
• Synonyms: 2-[N-(m-Hydroxyphenyl)-p-toluidinomethyl]imidazoline Hydrochloride; 3-[[(4,5-Dihydro-1H-imidazol-2-yl)methyl](4-methylphenyl)amino]-phenol Hydrochloride; DNP; Regitine Hydrochloride; Phentolamine Hydrochloride; 2-[N-(3-Hydroxyphenyl)-p-toluidinomethyl]-2-imidazolidine hydrochloride; Phentolamine hydrochloride; 3-(4,5-dihydro-1h-imidazol-2-ylmethyl-(4-methylphenyl)amino)phenol hydrochloride; 3-(((4,5-dihydro-1H-imidazol-2-yl)methyl)(p-tolyl)amino)phenol hydrochloride; 酚妥拉明 盐酸盐

Database IDs

• CAS Number: 26786; 73-05-2
• EC Number: 200-793-5
• MDL Number: MFCD00079268
• Beilstein Number: 3764617
• PubChem SID: 162215799; 24898856
• PubChem CID: 5702144

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; ethanol: soluble14 mg/mL; H2O: soluble20 mg/mL; H2O: unstable (prepare immediately prior to use); Methanol; methanol: soluble10 mg/mL, clear, colorless; Water
• Apperance: Tan to Light Brown Solid; white to off-white powder
• Melting Point: >230 (dec.)°C

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: SL0701000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 22-24/25
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98% (TLC); ≥99.0% (TLC); 98%
• Salt Data: HCl
• Empirical Formula (Hill Notation): C17H19N3O · HCl

DETAILS

Sigma Aldrich - P7547

Biochem/physiol Actions
α-adrenoceptor antagonist; peripheral vasodilator.

Sigma Aldrich - 77790

Application
α-Adrenergic blocker
Biochem/physiol Actions
α-adrenoceptor antagonist; peripheral vasodilator.

Toronto Research Chemicals - P302550

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)