methyl(naphthalen-1-ylmethyl)[(2E)-3-phenylprop-2-en-1-yl]amine hydrochloride

• ChemBase ID: 154747
• Molecular Formular: C21H22ClN
• Molecular Mass: 323.85908
• Monoisotopic Mass: 323.14407739
• SMILES: CN(C/C=C/c1ccccc1)Cc1cccc2c1cccc2.Cl
• Canonical SMILES: CN(Cc1cccc2c1cccc2)C/C=C/c1ccccc1.Cl
• InChI: InChI=1S/C21H21N.ClH/c1-22(16-8-11-18-9-3-2-4-10-18)17-20-14-7-13-19-12-5-6-15-21(19)20;/h2-15H,16-17H2,1H3;1H
• InChIKey: OLUNPKFOFGZHRT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl(naphthalen-1-ylmethyl)[(2E)-3-phenylprop-2-en-1-yl]amine hydrochloride; methyl(naphthalen-1-ylmethyl)(3-phenylprop-2-en-1-yl)amine hydrochloride
• IUPAC Traditional name: naftifine hydrochloride; naftin hydrochloride
• Synonyms: (E)-N-Methyl-N-(3-phenyl-2-propen-1-yl)-1-naphthalenemethanamine Hydrochloride; (E)-N-Cinnamyl-N-methyl-1-naphthalenemethanamine Hydrochloride; AW 105-843; Exoderil; Naftifungin; Naftin; SN 105-843; Naftifine Hydrochloride; Naftifine hydrochloride; Naftifine HCl

Database IDs

• CAS Number: 65473-14-5
• MDL Number: MFCD00059047
• PubChem SID: 162248885
• PubChem CID: 5281098

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.0022733
• LogD (pH = 7.4): 3.5597782
• Log P: 5.238508
• Molar Refractivity: 95.9821 cm^3
• Polarizability: 38.28094 Å^3
• Polar Surface Area: 3.24 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 172-175°C

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: nwg
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: Others

Product Information

• Purity: ≥99%
• Salt Data: HCl
• Empirical Formula (Hill Notation): C21H21N · HCl

DETAILS

Sigma Aldrich - N1790

Biochem/physiol Actions
Allylamine compound that has antifungal and antimycotic activities.3 Naftifine inhibits fungal squalene epoxidase and prevents ergosterol biosynthesis.4 Naftifine also has antibiotic activity against Gram-positive and Gram-negative bacteria2 and has demonstrated anti-inflammatory properties.5
Naftifine is an allylamine compound that has antifungal and antimycotic activities. Naftifine inhibits fungal squalene epoxidase and prevents ergosterol biosynthesis. Naftifine also has antibiotic activity against Gram-positive and Gram-negative bacteria. It has demonstrated anti-inflammatory properties such as a reduction in superoxide production and a reduction in polymorphonuclear leukocyte chemotaxis/endothelial adhesion2. Naftifine appears to interfere with sterol biosynthesis by inhibiting the squalene 2,3-epoxidase. This inhibition results in decreased amounts of ergosterol and an accumulation of squalene in the cells1.
Application
Naftifine is a synthetic, broad spectrum, antifungal agent and allylamine derivative. It is used topically to treat superficial dermatomycoses such as tinea pedis, tinea cruris, and tinea corporis1.

Toronto Research Chemicals - N213100

Antimycotic allylamine. An antifungal (topical) agent.

REFERENCES

• Georgopoulos, A., et al.: Antimicrob. Ag. Chemother., 19, 386 (1981)
• Meingassner, J.C., et al.: J. Invest. Dermatol., 77, 444 (1981)
• Paltauf, F., et al.: Biochim Biophys. Acta, 712, 268 (1981)
• Aggarwal, D., et al.: J. Pharm. Pharmacol., 56, 1509 (2004)