(3,3-diphenylpropyl)(1-phenylpropan-2-yl)amine

• ChemBase ID: 4369
• Molecular Formular: C24H27N
• Molecular Mass: 329.47788
• Monoisotopic Mass: 329.21434987
• SMILES: N(CCC(c1ccccc1)c1ccccc1)C(Cc1ccccc1)C
• Canonical SMILES: CC(Cc1ccccc1)NCCC(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C24H27N/c1-20(19-21-11-5-2-6-12-21)25-18-17-24(22-13-7-3-8-14-22)23-15-9-4-10-16-23/h2-16,20,24-25H,17-19H2,1H3
• InChIKey: IFFPICMESYHZPQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3,3-diphenylpropyl)(1-phenylpropan-2-yl)amine
• IUPAC Traditional name: difril; prenylamine
• Brand Name: Bismethin; Carditin; Corontin; Corpax; Elecor; Falliocor; Hostaginan; Segontin; Synadrin; Valecor
• Synonyms: 1-Phenyl-2-(1',1'-diphenylpropyl-3'-amino)propane; DL-prenylamine; N-(1-Methyl-2-phenylethyl)-3,3-diphenyl-1-propanamine; N-(3,3-Diphenylpropyl)-alpha-methylphenaethylamin [German]; N-(3,3-Diphenylpropyl)-alpha-methylphenethylamine; N-(3'-Phenyl-2-propyl)-1,1-diphenyl-3-propyloamine; N-(1-Methyl-2-phenylethyl)-gamma-phenylbenzenepropanamine; Prenilamina [inn-spanish]; Prenylaminum [inn-latin]; Prenylamine; N-(1-Methyl-2-phenylethyl)-γ-phenylbenzenepropanamine; N-(3,3-Diphenylpropyl)-α-methylphenethylamine; Elecor; SAN 13-194; Sandoz 13-194; Segontin

Database IDs

• CAS Number: 390-64-7
• PubChem SID: 160967801; 46508663
• PubChem CID: 9801

CALCULATED PROPERTIES

JChem

• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 2.8811786
• LogD (pH = 7.4): 3.261855
• Log P: 6.115357
• Molar Refractivity: 107.092 cm^3
• Polarizability: 42.115356 Å^3
• Polar Surface Area: 12.03 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 5.89
• LOG S: -6.97
• Solubility (Water): 3.54e-05 g/l

PROPERTIES

Physical Property

• Solubility: 0.05 mg/mL at 37 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; Chloroform; Ethyl Acetate; Methanol
• Apperance: Pale Yellow Oil

Safety Information

• Storage Condition: Refrigerator

DETAILS

DrugBank - DB04825

• Drug Groups: withdrawn
• Description: Prenylamine was withdrawn from the Canadian, US, and UK markets in 1988 due to concerns regarding cardiac arrhythmias.
• Affected Organisms: Humans and other mammals

Toronto Research Chemicals - P712800

Vasodilator (coronary).

REFERENCES

• Hay, D., et al.: Br. J. Pharmacol., 76, 103 (1982)
• Tanaka, T., et al.: Biochemistry, 24, 5281 (1982)
• Rampe, D., et al.: Pharmacol. Exp. Ther., 265, 1125 (1982)