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CAS No 91161-71-6 , (E)-N,6,6-trimethyl-N-(naphthalen-1-ylmethyl)hept-2-en-4-yn-1-amine

  • Name: (E)-N,6,6-trimethyl-N-(naphthalen-1-ylmethyl)hept-2-en-4-yn-1-amine
  • Synonyms: Terbina; SF-86-327; Bramazil; Lamasil;(E)-N,6,6-trimethyl-N-(naphthalen-1-ylmethyl)hept-2-en-4-yn-1-amine; Lamisil AT;Lamisil; Ternbinafine HCl; Lamisil Tablet; 91161-71-6;
  • CAS Registry Number:
  • Density: 1.007g/cm3
  • Safety Statements: 26-36
  • Hazard Symbols: Xi
  • Molecular Weight: 291.4299
  • InchiKey: DOMXUEMWDBAQBQ-WEVVVXLNSA-N
  • InChI: InChI=1S/C21H25N/c1-21(2,
    3)15-8-5-9-16-22(4)17-19-13-10-12-18-11-6-7-14-20(18)19/h5-7,9-14H,
    16-17H2,1-4H3/b9-5+
  • Risk Statements: 36/37/38
  • Molecular Formula: C21H25N
  • Molecular Structure:CAS No:91161-71-6 (E)-N,6,6-trimethyl-N-(naphthalen-1-ylmethyl)hept-2-en-4-yn-1-amine

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References of (E)-N,6,6-trimethyl-N-(naphthalen-1-ylmethyl)hept-2-en-4-yn-1-amine
Title: Terbinafine
CAS Registry Number: 91161-71-6
CAS Name: N-[(2E)-6,6-Dimethyl-2-hepten-4-ynyl]-N-methyl-1-naphthalenemethanamine
Synonyms: trans-N-methyl-N-(1-naphthylmethyl)-6,6-dimethylhept-2-en-4-ynyl-1-amine
Molecular Formula: C21H25N
Molecular Weight: 291.43
Percent Composition: C 86.55%, H 8.65%, N 4.81%
Literature References: Orally active, antimycotic allylamine related to naftifine, q.v. Specific inhibitor of squalene epoxidase, a key enzyme in fungal ergosterol biosynthesis. Prepn: A. Stütz, EP 24587; idem, US 4755534 (1981, 1988 both to Sandoz); A. Stütz, G. Petranyi, J. Med. Chem. 27, 1539 (1984). Mode of action: G. Petranyi et al., Science 224, 1239 (1984); N. S. Ryder, Antimicrob. Agents Chemother. 27, 252 (1985). In vitro antifungal activity: S. Shadomy et al., Sabouraudia 23, 125 (1985). Toxicity data: U. Ganzinger et al., Proc. 13th Int. Congr. Chemother. 6, 116/52 (1983). Symposium on pharmacology and clinical trials: J. Am. Acad. Dermatol. 23, Suppl., 775-812 (1990). Clinical trial as systemic treatment of toenail onychomycosis: E. G. V. Evans et al., Br. Med. J. 318, 1031 (1999).
 
Derivative Type: Hydrochloride
CAS Registry Number: 78628-80-5
Manufacturers' Codes: SF-86-327
Trademarks: Lamisil (Novartis)
Molecular Formula: C21H25N.HCl
Molecular Weight: 327.89
Percent Composition: C 76.92%, H 7.99%, N 4.27%, Cl 10.81%
Properties: Crystals from 2-propanol + diethyl ether, mp 195-198° (change in crystal structure begins ~150°). Freely sol in methanol, methylene chloride; sol in ethanol; slightly sol in water. LD50 in mice, rats (mg/kg): 4000, 4000 orally; 393, 213 i.v. (Ganzinger).
Melting point: mp 195-198° (change in crystal structure begins ~150°)
Toxicity data: LD50 in mice, rats (mg/kg): 4000, 4000 orally; 393, 213 i.v. (Ganzinger)
 
Therap-Cat: Antifungal.
Keywords: Antifungal (Synthetic); Allylamines.