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Tolnaftate
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Name

Tolnaftate

 EINECS 219-266-6
CAS No. 2398-96-1 Density 1.223 g/cm3
PSA 44.56000 LogP 4.94830
Solubility <0.1 g/100 mL at 22 °C in water Melting Point 110.5-111.5°C
Formula C19H17NOS Boiling Point 453.4 °C at 760 mmHg
Molecular Weight 307.416 Flash Point 228 °C
Transport Information N/A Appearance white powder
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 2398-96-1 (Tolnaftate) Hazard Symbols N/A
Synonyms

Dungistop;Focusan;Hi-Alarzin;NaphthiomateT;O-2-Naphthyl m,N-dimethylthiocarbanilate;Phytoderm;Pitrex;Sch 10144;Sporiline;Timoped;Tinactin;Tinaderm;Tineacure;Tniaderm;Tolnaphthate;Tolsanil;Tonoftal;Tritin;TolnaftateUSP;Carbamothioicacid, methyl(3-methylphenyl)-, O-2-naphthalenyl ester (9CI);Carbanilic acid, m,N-dimethylthio-,O-2-naphthyl ester (7CI,8CI);2-Naphthyl N-methyl-N-(3-tolyl)thiocarbamate;2-Naphthyl N-methyl-N-(3-tolyl)thionocarbamate;2-NaphthylN-methyl-N-m-tolylthiocarbamate;Aftate;Chinofungin;Dermoxin;Dr. Scholl'sAthlete's Foot Spray;

Article Data 6

Tolnaftate Synthetic route

39970-42-8

N-methyl-N-(3-methylphenyl)carboxamide

2398-96-1

tolnaftate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: tetraphosphorus decasulfide / toluene / Reflux
2: thionyl chloride / toluene / 2 h / Reflux
3: tetrabutylammomium bromide; sodium carbonate / toluene / 5 h / Reflux
View Scheme
696-44-6

N-methyl-m-toluidine

2398-96-1

tolnaftate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: zinc / 40 °C / Reflux
2: tetraphosphorus decasulfide / toluene / Reflux
3: thionyl chloride / toluene / 2 h / Reflux
4: tetrabutylammomium bromide; sodium carbonate / toluene / 5 h / Reflux
View Scheme
36592-58-2

N-methyl-N-(3-methylphenyl)thioformyl chloride

135-19-3

β-naphthol

2398-96-1

tolnaftate

Conditions
ConditionsYield
With tetrabutylammomium bromide; sodium carbonate In toluene for 5h; Reflux;100 g
2398-96-1

tolnaftate

110210-11-2

1-(2,4-dinitrophenoxy)piperidine

O-(1-(piperidin-1-yl)naphthalen-2-yl) methyl(m-tolyl)carbamothioate

Conditions
ConditionsYield
With perchloric acid; tris(2,2'-bipyridyl)ruthenium dichloride In water; acetonitrile at 20℃; Sealed tube; Inert atmosphere; Irradiation;62%
2398-96-1

tolnaftate

15300-27-3

Methyl-m-tolyl-carbamic acid naphthalen-2-yl ester

Conditions
ConditionsYield
In methanol for 4h; Rate constant; Irradiation; also in var. formulations;
2398-96-1

tolnaftate

A

methyl(m-tolyl)carbamic acid

B

7783-06-4

hydrogen sulfide

C

135-19-3

β-naphthol

Conditions
ConditionsYield
With water; sodium hydroxide at 80℃; for 24h;

Tolnaftate Chemical Properties

Structure of Tolnaftate (CAS NO.2398-96-1):

IUPAC Name: O-naphthalen-2-yl N-methyl-N-(3-methylphenyl)carbamothioate
Molecular Formula: C19H17NOS
Molar mass: 307.4094 g/mol
H bond acceptors: 2
H bond donors: 0
Freely Rotating Bonds: 3
Polar Surface Area: 44.56Å2
Density: 1.223 g/cm3
Flash Point: 228 °C
Storage temp: 2-8°C
Index of Refraction: 1.697
Melting point: 110.5-111.5°C
Appearance:Crystals or white powder
Boiling Point: 453.4 °C at 760 mmHg
Water solubility: <0.1 g/100 mL at 22 °C
Vapour Pressure: 2.08E-08 mmHg at 25°C 
Molar Refractivity: 96.77 cm3
Molar Volume: 251.1 cm3
Classification Code: Anti-Infective Agents; Antifungal; Antifungal agents; Drug / Therapeutic Agent; Mutation data; Reproductive Effect
InChI
InChI=1/C19H17NOS/c1-14-6-5-9-17(12-14)20(2)19(22)21-18-11-10-15-7-3-4-8-16(15)13-18/h3-13H,1-2H3
Smiles
c12c(cc(OC(N(c3cc(ccc3)C)C)=S)cc1)cccc2

Tolnaftate Toxicity Data With Reference

dog LD50 oral > 14gm/kg (14000mg/kg)   Antimicrobial Agents and Chemotherapy Vol. -, Pg. 615, 1964.
guinea pig LD50 oral > 4gm/kg (4000mg/kg)   Toxicology and Applied Pharmacology. Vol. 8, Pg. 380, 1966.
mouse LD50 intraperitoneal 120mg/kg (120mg/kg)   Drug and Chemical Toxicology. Vol. 13, Pg. 195, 1990.
mouse LD50 intravenous 4800mg/kg (4800mg/kg)   Drugs in Japan Vol. 6, Pg. 530, 1982.
mouse LD50 oral 10gm/kg (10000mg/kg)   Drugs in Japan Vol. 6, Pg. 530, 1982.
mouse LD50 subcutaneous > 6gm/kg (6000mg/kg)   Toxicology and Applied Pharmacology. Vol. 8, Pg. 380, 1966.
rabbit LD intravenous > 50mg/kg (50mg/kg)   Toxicology and Applied Pharmacology. Vol. 8, Pg. 380, 1966.
rat LD50 oral > 6gm/kg (6000mg/kg)   Toxicology and Applied Pharmacology. Vol. 8, Pg. 380, 1966.
rat LD50 subcutaneous > 4gm/kg (4000mg/kg)   Toxicology and Applied Pharmacology. Vol. 8, Pg. 380, 1966.

Tolnaftate Consensus Reports

EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.

Tolnaftate Safety Profile

Mildly toxic by ingestion. An experimental teratogen. When heated to decomposition it emits toxic fumes of SOx and NOx. A fungicide used to control athlete’s foot. See also Esters and Carbamates.
WGK Germany: 2
RTECS: FD8891300

Tolnaftate Specification

 Tolnaftate , with CAS number of 2398-96-1, can be called Chinofungin ; Tinaderm ; Sporiline ; Aftate ; 2-Naphthyl N-methyl-N-(3-tolyl)thionocarbamate ; Methyl-(3-methylphenyl)carbamothioic acid O-2-naphthyl ester ; Tinactin ; Tonoftal .  When used to treat tinea pedis, tolnaftate (CAS NO.2398-96-1) has been found to be generally slightly less effective than azoles. However, It is useful when dealing with ringworm, especially when passed from pets to humans.

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