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(e)-n-(6,6-dimethyl-2-hepten-4-ynyl)-n-methyl-1-naphthalenemethanamine monohydrochloride
n,6,6-trimethyl-n-(naphthalen-1-ylmethyl)hept-2-en-4-yn-1-amine hydrochloride
Terbinafine hdyrochloride
Lamisil, N-[(2E)-6,6-Dimethyl-2-hepten-4-ynyl]-N-methyl-1-naphthalenemethanamine
1-Naphthalenemethanamine, N-(2E)-6,6-dimethyl-2-hepten-4-ynyl-N-methyl-, hydrochloride
({[(2E)-6,6-Dimethylhept-2-en-4-yn-1-yl](methyl)amino}methyl)naphthalene hydrochloride
Trebinafine hydrochloride
Molecular Formula
MDL Number
Molecular Weight
MOL File

Chemical Properties

Crystalline Powder
Melting point 
storage temp. 
methanol: soluble50mg/mL
An orally active, antimycotic allylamine related to naftifine. A specfic inhibitor of squalene epoxidase, a key enzyme in fungal ergosterol biosynthesis
CAS DataBase Reference
78628-80-5(CAS DataBase Reference)

Safety Data

Hazard Codes 
Risk Statements 
R36/37/38:Irritating to eyes, respiratory system and skin .
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
Safety Statements 
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S60:This material and/or its container must be disposed of as hazardous waste .
UN 3077 9/PG 3
WGK Germany 
HS Code 
LD50 in mice, rats (mg/kg): 4000, 4000 orally; 393, 213 i.v. (Ganzinger)

Raw materials And Preparation Products

Preparation Products
Terbinafine hydrochloride

Hazard Information

Terbinafine hydrochloride is the first orally active allylamine antifungal with 30-fold greater antifungal activity than naftifine. The compound is indicated for the treatment of ringworm and fungal nail infections. Terbinatine hydrochloride acts on a single fungal enzyme, squalene epoxidase, interfering with the biosynthesis of ergosterols in cell membranes. Unlike other antifungal agents, it does not inhibit cytochrome P450 enzymes.
Sandoz (Switzerland)
An orally active, antimycotic allylamine related to Naftifine. A specfic inhibitor of squalene epoxidase, a key enzyme in fungal ergosterol biosynthesis. Antifungal.
Terbinafine hydrochloride is a synthetic allylamine antifungal. It is used to treat dermatophyte infections of the toenail/fingernail, ringworm and jock itch. It is used in adsorption, partition and stability studies.
ChEBI: A hydrochloride obtained by reaction of terbinafine with one molar equivalent of hydrogen chloride.
Manufacturing Process
To an ice-cooled solution of N-methyl-1-naphthalenemethylamine hydrochloride (2.1 g) in methanol (40 ml) and water (10 ml) was added sodium hydroxide powder (2 g) followed by dropwise addition of epichlorohydrin (8 ml). The mixture was heated at 60°C for 3 h, then cooled to room temperature. Volatile materials were removed in vacuo and the residue was taken up in ethyl acetate and washed with water. The organic phase was collected, dried over sodium sulfate, filtered and evaporated to dryness. The crude mixture was purified by flash chromatrography on silica gel (grade 9385, Merck, 230-400 mesh, 60 A) using a solvent gradient of a mixture of hexane and ethyl acetate (95:5, 90:10 and 85:15) as eluent, affording the N-methyl-N-naphthylmethyl-2,3-epoxypropane (1.85 g, 81.5%) as an oil.
To a solution of 3,3-dimethylbutyne (2.95 ml) in dry THF (50 ml) at -78°C was added a 2.5 M solution of n-BuLi in hexane (10 ml) dropwise. The mixture was allowed to warm to room temperature over 15 min and stirred at that temparature for a further 15 min, then was cooled back to -78°C and BF3OEt2 (3 ml) was added dropwise. The mixture was stirred for 15 min and 1.8 g of N-methyl-N-naphthylmethyl-2,3-epoxypropane, dissolved in THF (10 ml), was added dropwise. After stirring at -78°C for 2 h, saturated sodium bicarbonate solution (15 ml) was added, and the reaction mixture was allowed to warm to room temperature. The mixture was extracted with ethyl acetate (2 times 25 ml), and the combined organic fractions was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatrography on silica gel (grade 9385, Merck, 230-400 mesh, 60 a) using a mixture of hexane and ethyl acetate (85:15) as eluent, thereby affording the N-methyl-N-(1-naphthylmethyl)-2-hydroxy-heptan-4-ynyl-1-amine as an oil (1.95 g, 79%).
To an ice-cooled solution of N-methyl-N-(1-naphthylmethyl)-2-hydroxyheptan- 4-ynyl-1-amine (155 mg) in THF (10 ml) was added Et3N (0.35 ml) followed by methanesulfonyl chloride (0.075 ml). The resulting mixture was stirred at 0°C for 3 h, then filtered. The filtrate was concentrated in vacuo, dissolved in toluene (10 ml) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (0.37 ml) was added. The resulting mixture was heated at 80°C for 4 h, cooled to room temperature then poured onto a silica gel column and eluted with hexane (100%) followed by a mixture of hexane and ethyl acetate (95:5). Thus, a mixture of E- and Z-isomers of N-methyl-N-(1- naphthylmethyl)-6,6-dimethylhept-2-en-4-ynyl)-1-amine were obtained in a ratio of 2:5 (95 mg, 66%).
Brand name
Therapeutic Function
General Description
Allylamine derivative.

Biochem/physiol Actions
Mode of Action: Inhibits squalene epoxidase, preventing biosynthesis of ergosterol.Antimicrobial spectrum: Antifungal and antimycotic. Fungicidal against dermatopytes and some yeasts; fungistatic against Candida albicans.
Clinical Use
Terbinafine hydrochloride (Lamisil) is available for topical and systemic use (oral tablet) in the treatment of dermatophyte skin and nail infections. Terbinafine also exhibits in vitro activity against filamentous and dimorphic fungi, but its clinical utility in treating infections with these organisms has not yet been established. It is used most commonly in the treatment of onychomycosis; in this setting, terbinafine is superior to griseofulvin and at least equivalent to itraconazole.When given systemically, terbinafine is 99% protein bound and accumulates in fat, skin, and nails, persisting for weeks. Cerebrospinal fluid penetration is less than 10%. Dosage reductions are required with renal or hepatic insufficiency. Although terbinafine has little effect on hepatic cytochrome P450 enzyme systems, it does minimally enhance cyclosporine clearance. Oral terbinafine is generally well tolerated but occasionally causes gastric distress and liver enzyme elevation.
Clinical Use
(E)-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalene-methanamine hydrochloride (Lamisil) is an off-whitecrystalline material that is soluble in polar organic solventssuch as methanol, ethanol, and methylene chloride but isonly slightly soluble in water. The highly lipophilic freebase is insoluble in water. Terbinafine hydrochloride isavailable in a 1% cream for topical administration for thetreatment of tinea pedis, tinea corporis, and tinea cruris.Terbinafine is more potent than naftifine and has alsodemonstrated oral activity against onychomycosis (ringwormof the nails). It has not been approved in the UnitedStates for oral administration.
Side effects
Adverse reactions include lens and retinal disturbances (red/green visual perception), metallic taste disturbance that may last up to 4 weeks after medication discontinuation, hepatoxicity, and pancytopenia. Five percent of patients will experience delayed gastric emptying with symptoms of nausea, fullness, and/or dyspepsia. Terbinafine does not appear to have any effect on the cytochrome P-450 systems (Check baseline CBC and LFTs; repeat if taken for >6 weeks).
Veterinary Drugs and Treatments
Terbinafine may be useful for treating dermatophytic and other fungal infections in dogs and cats.
Terbinafine may also be useful for treating birds for systemic mycotic (e.g., aspergillosis) infections.

Questions And Answer

Dermatologist Broad-spectrum Antifungal Drugs
Terbinafine hydrochloride is a kind of broad-spectrum dermatologist allyl amine antifungal drugs. It is developed by Swiss Novartis in the 1980 s, and appeared in the market of UK for the first time in 1991. Approved by FDA of the United States for OTC drugs in 1996, and appeared in the market of the United States in the same year. At present, the drug is been sold in more than 90 countries of the word. It can specificity trouble the late biological decomposition of fungus sterol, selectively inhibit the activity of fungal squalene ring oxidase, and inhibit the squalene epoxidation in the formation of ungal cell membrane, thus to kill or inhibit the active of the fungus. Suitable for treatment of candidiasis skin, such as tinea manuum, tinea, tinea, ringworm of the body, tinea versicolor, it is also the best medicine for the treatment of onychomycosis.
Terbinafine hydrochloride entered the the first batch of country announced OTC directory in 2000. This product belongs to antifungal drugs. It has strong effect on shallow fungal infection, and can cure most of the fungal skin diseases through external use.
According to reports in the literatures, after 250 mg of Terbinafine hydrochloride been taken orally, it reaches peak plasma concentration of 0.97 m ug/ml within 2 hours. The absorption half-life is 0.8 hours, spread half-life is 4.6 hours, the degree of biological application is slightly affected by eating, but not used for dose adjustments. The combination rate of drugs and plasma protein is 99%, and can quickly disperse and concentrate in the lipophilic corneous layer through the dermis. Terbinafine hydrochloride can be spread in the skin, therefore, a very high concentration can be reached in the hair follicle, hair and skin layers of fat, and it can enter in the deck in the last few weeks of healing. The metabolites after the bioconversion have no antifungal activity, then discharged through urine. The half-life is 17 hours, no accumulation in the body, and its steady blood drug concentration is not affected by age. But the alleviation rate can reduce for people with liver and kidney disorders, thus triggers blood drug concentration decreasing.
1.Skin, hair and nail infection caused by Btrichophyta (white hair versicolor bacterium, Trichophyton mentagrophytes, Trichophyton verrucosum, trichophyton tonsurans and Trichophyton violaceum, etc.), microsporum canis, epidermophyton floccosum, ect.
2.Skin yeast infections caused by all kinds of tinea disease (ringworm of the body, tinea, tinea manus and tinea capitis, etc.) and candida (candida albicans, etc.).
3.Onychomycosis (nail fungus infection) caused by molds.
Usage and Dosage
Local external use: apply adequate amount to the affected area and its surrounding, 1-2 times a day. Ringworm of the body, 2-4 weeks, tinea of feet and hands, tinea versicolor, 4 to 6 weeks.
Oral: 0.25 grams each time for adult, once per day, period of treatment is as follows:
Skin infection treatment: tinea of feet and hands [toe (means) and plantar]: 2~6 weeks; Ringworm of the body, tinea, 2~4 weeks.
Skin candidiasis: 2~4 weeks. normal skin appearance and loss of infection can only be visible in a few weeks for curing.
Hair and scalp infection treatment: tinea capitis: 4 weeks, tinea capitis most happen in children.
Onychomycosis: The most treatment course of patients is 6 weeks to three months. Young patients with normal growth can shorten the treatment course, and less than 3 months of treatment may be enough in addition to the thumb (foot) armour.
In other cases, the treatment is usually 3 months. Some patients, especially whose thumb (toe) infected, may take 6 months or longer. The treatment may take more than 3 months if the nail grew slowly in the first week. In healing of mycology and stopping for a few months after treatment, the continuous improvement of nail appearance then completely normal can be seen, this is because that the healthy tissue growth needs time.
Chemical Properties
White crystalline powder. Melting point is 204-208 oC.
Terbinafine hydrochloride is a kind of broad-spectrum dermatologist allyl amine antifungal drugs. It has a significant effect on all kinds of tinea diseases , including fungus, trichophyton, ringworm of the body, tinea, tinea versicolor and onychomycosis caused by dermophyte. It can also be used for bronchial asthma, asthmatic bronchitis and emphysema, etc.
This information is edited by ChemicalBook Xiao Nan.

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