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Identification
NameMenthol
Accession NumberDB00825  (APRD01604)
Typesmall molecule
Groupsapproved
Description

Menthol is a covalent organic compound made synthetically or obtained from peppermint or other mint oils. It is a waxy, crystalline substance, clear or white in color, which is solid at room temperature and melts slightly above. The main form of menthol occurring in nature is (-)-menthol, which is assigned the (1R,2S,5R) configuration. Menthol has local anesthetic and counterirritant qualities, and it is widely used to relieve minor throat irritation.

Structure
Thumb
Synonyms
SynonymLanguageCode
(-)-mentholNot AvailableNot Available
(r)-(-)-mentholNot AvailableNot Available
L-(-)-mentholNot AvailableNot Available
L-mentholNot AvailableNot Available
LevomentholNot AvailableINN
SaltsNot Available
Brand namesNot Available
Brand mixtures
Brand NameIngredients
A.P.R 15lidocaine hydrochloride + menthol
Absorbine analgesic cremecamphor + eucalyptus oil + menthol + methyl salicylate
Absorbine arthritis strength liquidcapsicum + menthol
Absorbine JR antifungal liqmenthol + tolnaftate
Absorbine JR extra strength linimentchloroxylenol + menthol
Absorbine junior patchcamphor + eucalyptus oil + menthol
Absorbine power gelchloroxylenol + menthol
Acti bleu lotioncamphor + menthol + methyl salicylate
Acti poulticeeucalyptus oil + magnesium sulfate + menthol + methyl salicylate + thymol
Acti vapocamphor + eucalyptus oil + menthol
Adult formulabelladonna + bryonia + drosera rotundifolia + ipecac + menthol + oil of turpentine + peppermint + spongia tosta + sticta pulmonaria + wild thyme
Amber mouthwash - liqeucalyptol + menthol + thymol
Amolcinnamon oil + clove oil + lavender oil + menthol + myristica oil + oil of citronella + oil of lemon + peppermint oil
Analgesic sport stickmenthol + methyl salicylate
Anbesol liquidbenzocaine + camphor + menthol + phenol
Anifen cough DPSfennel oil + menthol + oil of anise
Antiseptic mouth rinse - liqeucalyptol + menthol + thymol
Antiseptic mouthwash cool minteucalyptol + menthol + thymol
Antiseptic mouthwash minteucalyptol + menthol + thymol
Arthricare for women nighttimementhol + methyl nicotinate + methyl salicylate
Arthricare for women ultra strengthcapsaicin (capsicum oleoresin) + menthol
Arthriflexeucalyptol + menthol
Arthritis pain reliever herbalifecamphor + menthol + methyl salicylate
Arthro rheuma creamcamphor + menthol
Arthrocare lotioncamphor + eucalyptus oil + histamine dihydrochloride + menthol + methyl salicylate
Artrikor creme analgesiquecamphor + capsaicin + eucalyptus oil + menthol
Artritol creme rubefiantementhol + methyl salicylate
Avon healthy remedies menthol & camphor soothing relief gelcamphor + menthol
Balminil camphorubcamphor + eucalyptol + menthol
Balminil nasal ointmentcamphor + chlorobutanol + ephedrine hydrochloride + eucalyptol + l-menthol
Banana boat sooth-a-caine spray gellidocaine + menthol
Baumodyne gelmenthol + methyl salicylate
Beech nut black cough dropmenthol + oil of anise
Beech nut black cough dropsmenthol + oil of anise
Beech nut honey lemon cough dropeucalyptus oil + menthol
Beech nut honey lemon cough dropseucalyptus + menthol
Beech nut menthol cough dropanethole + eucalyptus oil + menthol
Beech nut wild cherry cough DPSeucalyptus oil + menthol
Beech nut wild cherry cough dropeucalyptus oil + menthol
Beech nut wild cherry cough dropseucalyptus oil + menthol
Beech-nut menthol cough dropsanethole + eucalyptus oil + menthol
Ben-gay arthritis pain rub ontmenthol + methyl salicylate
Ben-gay ultra strength pain relieving rubcamphor + menthol + methyl salicylate
Bengay arthritis extra strengthmenthol + methyl salicylate
Bengay muscle pain regular strengthmenthol + methyl salicylate
Bengay muscle pain ultra strengthcamphor + menthol + methyl salicylate
Bentasil cherryanethole + menthol
Bentasil extra strength eucalyptuseucalyptus oil + menthol
Bentasil extra strength mentholeucalyptus oil + menthol
Bentasil greenanethole + eucalyptol + menthol
Bentasil honey-lemonanethole + menthol
Bentasil redanethole + menthol
Bentasil yellowanethole + menthol
Benylin DM-d-e extra strength with menthactindextromethorphan hydrobromide + guaifenesin + menthol + pseudoephedrine hydrochloride
Benylin DM-e extra strength with menthactindextromethorphan hydrobromide + guaifenesin + menthol
Benylin e extra strength with menthactinguaifenesin + menthol
Benylin first defense cough lozengesechinacea (echinacea angustifolia, echinacea purpurea) + menthol (peppermint oil)
Benylin first defense herbal syrupechinacea (echinacea angustifolia) + menthol (peppermint oil)
Bigeloilalcohol anhydrous + menthol + methyl salicylate + salicylic acid + thymol
Bigeloil liquid gelalcohol anhydrous + menthol + methyl salicylate + thymol
Biofreezecamphor + menthol
Bite reliefbenzocaine + camphor + menthol + phenol
Braceoilalcohol anhydrous + camphor + menthol + methyl salicylate + salicylic acid + thymol
Bronchex cough syrupammonia + ammonium carbonate + ammonium chloride + glycerine + glycyrrhiza glabra + menthol + oil of fir + white pine
Bronchilon cough pastilleseucalyptus + menthol
Broncho rubcamphor + menthol + oil of cajeput + turpentine
Bronchodex vapo ontcamphor + eucalyptus oil + menthol
Bronchodex-rubcamphor + eucalyptus oil + menthol + methyl salicylate
Bronchyl SYRalcohol anhydrous + beechwood creosote + cocillana + eucalyptus + guaiacol oleate + ipecac + lobelia inflata + menthol + myroxylon balsamum + theophylline + white pine
Buckley's bedtimediphenhydramine hydrochloride + menthol
Buckley's completeacetaminophen + menthol
Buckley's mixtureammonium carbonate + camphor + menthol + potassium bicarbonate
Buckley's pain relief rubmenthol + methyl salicylate
Buckley's white rubcamphor + menthol + methyl salicylate + thymol
Cal mo dol ontcamphor + eucalyptol + menthol + methyl salicylate + oil of turpentine + peppermint oil
Calmitol itching relief ontcamphor + chloral hydrate + hyoscyamine + menthol + zinc oxide
Campho rexcamphor + menthol
Camphorated ointment compoundcamphor + eucalyptol + menthol
Camphro septhal ontcamphor + eucalyptus + menthol + methyl salicylate
Carboseptoleucalyptol + menthol + methyl salicylate + thymol + zinc oxide
Chapstick medicated lip balm - STKcamphor + menthol + petrolatum + phenol
Chapstick medicated lip balm - tubecamphor + menthol + petrolatum + phenol
Chase coldsorexbenzoin + camphor + menthol + MYRRH
Chest rub ontcamphor + eucalyptus oil + menthol
Chloraseptic sore throat lozenges - cherrybenzocaine + menthol
Chloraseptic sore throat lozenges - mentholbenzocaine + menthol
Chloraseptic sore throat relief stripsbenzocaine + menthol
Choates veterinary horse linimentcamphor + capsicum + menthol
Cold sore lotionbenzoin + camphor + menthol
Cool mint antiseptic mouthwasheucalyptol + menthol + thymol
Coolmint antiseptic mouthwasheucalyptol + menthol + thymol
Cou formulabelladonna + bryonia + drosera rotundifolia + ipecac + menthol + spongia tosta + sticta pulmonaria + wild thyme
Cuticura medicated body powdermenthol + zinc oxide
Deep heating ultra strength rub CRMmenthol + methyl salicylate
Denorex medicated shampoo - regularchloroxylenol + coal tar + menthol
Denorex medicated shampoo spring freshchloroxylenol + coal tar + menthol
Dentalgar liqbenzocaine + camphor + clove oil + guaiacol + menthol
Dermarest plus - geldiphenhydramine hydrochloride + menthol
Dermoplastbenzocaine + menthol
Dermoplast aerosol spraybenzethonium chloride + benzocaine + menthol + oxyquinoline benzoate
DR. C's itch not lotioncamphor + menthol
DR.'s creamcapsaicin + menthol + methyl salicylate
Eagle brand medicated oileucalyptus oil + menthol + methyl salicylate
Em eukal cough DPSeucalyptus oil + menthol
Eucamentheucalyptus oil + menthol + oil of camphor
Expectorineammonium chloride + eucalyptus oil + menthol
Extra strength gold bondmenthol + zinc oxide
Flex-o-flexcapsaicin + menthol
Flex-o-flex extra-fortcapsaicin + menthol
Flex-o-flex kamucamphor + menthol
Flexall stickmenthol + menthyl salicylate
Flexogan arthritis paincamphor + menthol + methyl salicylate
Flexogan muscle paincamphor + menthol
Flexogan sportcamphor + menthol
Flexogan sport ultracamphor + menthol + methyl salicylate
Formula t.t. cold sore creamcamphor + menthol + phenol
Formule 12eucalyptol + menthol
Forshner's blue lotioncamphor + eucalyptus oil + menthol + methyl salicylate
Freeze liqcamphor + ethyl ether + glycerine + isopropyl alcohol + menthol
Fresh taste antiseptic mouthwasheucalyptol + menthol + thymol
Gold bondmenthol + zinc oxide
Gold bond extra strength medicated body lotiondimethicone + menthol
Gold bond medicated body powdermenthol + zinc oxide
Gold bond medicated cream 28Gmenthol + pramoxine hydrochloride
Gold bond medicated lotionregular strength) (dimethicone + menthol
Gouttes dentairesbenzocaine + camphor + clove oil + guaiacol + menthol
Halls blueberryeucalyptus oil + menthol
Halls centres cherry lozengeseucalyptus oil + menthol
Halls centres honey lemoneucalyptus oil + menthol
Halls centres honey-lemon lozeucalyptus oil + menthol
Halls centres regulareucalyptus oil + menthol
Halls extra strongeucalyptus oil + menthol
Halls extra strong mentho-lyptus cough tabeucalyptus oil + menthol
Halls extra strong mentho-lyptus cough tabletseucalyptus oil + menthol
Halls lemon-limeeucalyptus oil + menthol
Halls mentho lyptus cough tabeucalyptus oil + menthol
Halls mentho lyptus cough tab black curranteucalyptus oil + menthol
Halls mentho lyptus cough tab cherryeucalyptus oil + menthol
Halls mentho lyptus cough tab honey lemoneucalyptus oil + menthol
Halls mentho lyptus tab coolminteucalyptus oil + menthol
Halls mentho-lyptus cough tablets black cherryeucalyptus oil + menthol
Halls mentho-lyptus cough tablets black curranteucalyptus oil + menthol
Halls mentho-lyptus cough tablets cherryeucalyptus oil + menthol
Halls mentho-lyptus cough tablets cool minteucalyptus oil + menthol
Halls mentho-lyptus cough tablets honey lemoneucalyptus oil + menthol
Halls mentho-lyptus cough tablets mountain mentholeucalyptus oil + menthol
Halls mentho-lyptus cough tablets orangeeucalyptus oil + menthol
Halls mentho-lyptus cough tablets regulareucalyptus oil + menthol
Halls mentho-lyptus cough tablets strawberryeucalyptus oil + menthol
Heat rubcamphor + eucalyptus oil + menthol + methyl salicylate
Herbal medicated lozengeechinacea angustifolia + echinacea purpurea + menthol
Herbal throat lozengescamphor + elm bark + horehound + menthol + parsley + thyme
Herbon cough drops adventurous tingle with a hint of orange flavourechinacea (echinacea angustifolia, echinacea purpurea) + glycyrrhiza glabra + menthol
Herbon cough drops glacial mintchamomile + echinacea (echinacea angustifolia, echinacea purpurea) + eucalyptus oil + fritillaria cirrhosa + horehound + menthol + salvia + thyme
Herbon lemon honey flavour herbal throat dropsechinacea (echinacea angustifolia, echinacea purpurea) + menthol
Herbon wild cherry flavour throat dropsechinacea (echinacea angustifolia, echinacea purpurea) + glycyrrhiza glabra + lime tree flower + menthol + sambucus nigra + wild cherry
Honey lemon menthol eucalyptus cough DPSeucalyptus oil + menthol
Infraline liqeucalyptol + menthol + methyl salicylate
Inno rheuma massage oillavender oil + menthol + rosemary oil
Instant rub ointmentmenthol + methyl salicylate
Itch nixcamphor + menthol
Kama sutra pleasure balmbenzocaine + camphor + menthol
Kiro rubmenthol + methyl salicylate
Kiro rub ontcamphor + eucalyptus oil + menthol + methyl salicylate
Kiro-rubeucalyptol + menthol + methyl salicylate
Kiroflexcamphor + eucalyptus oil + menthol + thymol
Kobi - CRMmenthol + methyl salicylate
Koffex DM-d-e - liqdextromethorphan hydrobromide + guaifenesin + pseudoephedrine hydrochloride
Kwan loong oileucalyptus oil + menthol + methyl salicylate
Kwan tak hing plaster - pad-PLSborneol + menthol
Lakota topical pain relievercapsaicin + menthol
Lakota topical pain reliever - extra strengthcapsaicin + menthol
Lamberts SYRmenthol + pine tar
Leg paint & sweatglycerine + iodine + isopropyl alcohol + menthol + phenol + potassium iodide
Leg solutioniodine + menthol + methyl salicylate + potassium iodide + thymol
Lin o gelcamphor + clove oil + iodine + isopropyl alcohol + menthol + thymol + turpentine
Lip conditioner lip balmcamphor + menthol + meradimate + padimate o + phenol
Lip medexcamphor + menthol + phenol
Lipsorexbenzethonium chloride + menthol + thymol
Lipsorex - gelbenzethonium chloride + menthol + thymol
Lipsorex plusbenzethonium chloride + lidocaine + menthol + thymol
Lipsorex-gelbenzethonium chloride + menthol + thymol
Listerine antiseptic mouthwasheucalyptol + menthol + thymol
Listerine antiseptic mouthwash with fluorideeucalyptol + menthol + sodium fluoride + thymol
Listerine antiseptic tartar control mouthwasheucalyptol + menthol + thymol + zinc chloride
Lofthouse origin ext-strong fisherman friendeucalyptus oil + menthol
Lotion bleucamphor + menthol + methyl salicylate
Lotion pour feux sauvagesbenzoin + camphor + menthol + MYRRH
MÉdi-rubeucalyptus oil + menthol + methyl salicylate
Marathon deep heat rubmenthol + methyl salicylate
Marco rub camphorated ontcamphor + eucalyptol + menthol
Medi-kool pakaluminum sulfate + arnica + boric acid + calcium acetate + camphor + menthol + methyl salicylate + tannic acid
Medi-kool titenerarnica + camphor + menthol + methyl salicylate + tannic acid
Medicated body powdermenthol + zinc oxide
Medicated chest rubcamphor + eucalyptus oil + menthol
Medicated chest rub - ontcamphor + eucalyptus oil + menthol
Medicated chest rub - ont topcamphor + eucalyptus oil + menthol
Medicated ointmentcamphor + eucalyptus oil + menthol
Medicated vapourizer fluidcamphor + eucalyptus oil + menthol
Medimentol ontcamphor + eucalyptus oil + menthol + oil of camphor + oil of fir + turpentine
Menthacin - creamcapsaicin + menthol
Menthacin creamcapsaicin + menthol
Menthacin lotioncapsaicin + menthol
Mentholatum cough dropseucalyptus oil + menthol
Mentholatum deep heating lotmenthol + methyl salicylate
Mentholatum deep heating rubmenthol + methyl salicylate
Mentholatum extra strength ontcamphor + eucalyptus oil + menthol
Mentholatum ontcamphor + menthol
Minard's joint reliefmenthol + methyl salicylate
Multi rubeucalyptol + menthol + methyl salicylate
Multi-freeze ontcamphor + isopropyl alcohol + menthol
Muscle linimentcamphor + isopropyl alcohol + menthol + oil of dwarf pine needles
Muscle mistclove oil + menthol
Myoflex extra strength icementhol + trolamine salicylate
Myoflex ice cold plus - gelmenthol + trolamine salicylate
Myoflex ice plus - CRMmenthol + trolamine salicylate
Natur 911camphor + eucalyptus oil + menthol + phenol + thymol
Naturland sports creamcamphor + menthol
Nose head clearcamphor + eucalyptus oil + menthol
Obus form therapeutic heat rubmenthol + methyl salicylate
Onguent camphre menthol alsicamphor + eucalyptol + menthol
Onguent vaporisantcamphor + eucalyptus oil + menthol
Orajel denture plusbenzocaine + menthol
Orajel multi-action cold sore medicineallantoin + benzocaine + camphor + dimethicone + menthol + white petrolatum
Orajel ultra canker sore medicinebenzocaine + menthol
Original antiseptic mouthwasheucalyptol + menthol + thymol
Orthorubeucalyptol + menthol + methyl salicylate
Pain buster 2000camphor + eucalyptus oil + menthol + methyl salicylate
Pain relieving ointmentcamphor + cinnamon oil + clove oil + mentha arvensis + menthol + oil of cajeput
Pain relieving salonpas patchcamphor + l-menthol + methyl salicylate
Pain-a-trate creamcamphor + menthol + methyl salicylate
Pastilles valdaeucalyptol + guaiacol + menthol + terpin hydrate + thymol
Penetrating rub onteucalyptus oil + menthol + methyl salicylate + oil of cajeput + oil of mustard expressed
Physio-rubeucalyptol + menthol + methyl salicylate
Physiorub pluseucalyptol + menthol + methyl salicylate
Phytorub onteucalyptol + menthol + methyl salicylate
Polar ice pastecamphor + isopropyl alcohol + menthol
Pommade au the des boiscamphor + eucalyptol + menthol + methyl salicylate
Poudrementhol + zinc oxide
Pramegel 1%menthol + pramoxine hydrochloride
Prosync muscle rubmenthol + methyl salicylate
Pulmoll menthol - eucalyptol pastilleseucalyptus oil + menthol + peppermint oil
Pulmoll pastillesglycyrrhizin + menthol
Pulmosirum decongestionnant siropbeechwood creosote + cocillana + eucalyptus + guaiacol + ipecac + lobelia inflata + menthol + myroxylon balsamum + pseudoephedrine hydrochloride + white pine
Pulmosirum plus expectorantammonium chloride + beechwood creosote + cocillana + eucalyptus oil + guaiacol + guaifenesin + ipecac + lobelia inflata + menthol + myroxylon balsamum + white pine
R76aconite + ammi visnaga + convallaria majalis + drosera rotundifolia + lobelia inflata + menthol + potassium iodide + stramonium
Rheila medicated cough DPSglycyrrhiza glabra + menthol
Rheumalan ontbelladonna + camphor + capsicum oleoresin + croton oil + eucalyptus oil + menthol + methyl salicylate + oil of mustard expressed + salicylic acid
Rhino-vaccincamphor + chlorobutanol + eucalyptol + l-ephedrine hydrochloride + menthol
Rub a 535 ancient secret - natural sourcecamphor (cinnamomum camphora) + eucalyptus oil (eucalyptus globulus, eucalyptus fructicetorum, eucalyptus smithII) + menthol (peppermint) + methyl salicylate (wintergreen leaf)
Rub a 535 dual actioncamphor + eucalyptus oil + menthol + methyl salicylate
Salonpas - PLS topcamphor + glycol salicylate + l-menthol + methyl salicylate + thymol
Salonpas gel-patchcamphor + glycol salicylate + l-menthol
Savex with sunscreen ontcamphor + menthol + salicylic acid
Scalpicinmenthol + salicylic acid
Scarlet oil pump sprayeucalyptus oil + menthol + oil of camphor + oil of thyme + peruvian balsam + phenol + pine oil
Solucodan syruphydrocodone bitartrate + menthol + potassium guaiacol sulphonate + sodium citrate
Solucodan-hdiphenylpyraline hydrochloride + hydrocodone bitartrate + menthol + potassium guaiacol sulphonate + sodium citrate
Sore throat lozenges menthol flavourbenzocaine + menthol
Sore throat lozenges with benzocaine and mentholbenzocaine + menthol
Star-vi-dolammonium chloride + eucalyptol + menthol + myroxylon balsamum + white pine + wild cherry
Strepsils cherryamylmetacresol + dichlorobenzyl alcohol + menthol
Sucrets cherry vapour action lozhexylresorcinol + menthol
Tensoliodine + menthol + potassium iodide
Thera patchcamphor + menthol + methyl salicylate
Therapatch vapor - chestcamphor + eucalyptus oil + menthol
Therapatch vapour - nose & chincamphor + eucalyptus oil + menthol
Thermo-gelbenzocaine + camphor + menthol + thymol
Thuna balsam salve onteucalyptus oil + menthol + methyl salicylate
Thunas salve for rheumatic painscamphor + menthol + methyl salicylate
Tiger balm arthritis rubcamphor + clove oil + dementholised mint oil + menthol + oil of cajeput
Tiger balm linimenteucalyptus oil + menthol + methyl salicylate
Tiger balm patch warmcamphor + capsaicin + dementholised mint oil + eucalyptus oil + menthol
Tiger balm red extra strengthcamphor + cinnamon oil + clove oil + menthol + oil of cajeput + peppermint oil
Tiger balm red strongcamphor + cinnamon oil + clove oil + menthol + oil of cajeput + peppermint oil
Tiger balm ultracamphor + cinnamon oil + clove oil + menthol + oil of cajeput + peppermint oil
Tiger balm white extra strengthcamphor + clove oil + menthol + oil of cajeput + peppermint oil
Tiger balm white regularcamphor + clove oil + menthol + oil of cajeput + peppermint oil
Tobtoxbenzene + cactus grandiflorus + coffea tosta + daphne indica + delphinium staphisagria + eucalyptus + lobelia inflata + lycopodium clavatum + menthol + naphthalene + nitric acid + oats + phosphorus + potassium phosphate dibasic + tobacco
Trialinementhol + methyl salicylate
Triaminic vapour patchcamphor + eucalyptus oil + menthol
Valda pastilleseucalyptol + guaiacol + menthol + terpin hydrate + thymol
Valda pastilles lemon flavouredeucalyptol + guaiacol + menthol + terpin hydrate + thymol
Vaporisateur medicamentecamphor + eucalyptol + menthol + thymol
Vaporisateur medicamente aerocamphor + eucalyptus oil + menthol + thymol
Vaporizing colds rub - ontcamphor + eucalyptus oil + menthol
Vapourizing colds rubcamphor + eucalyptus oil + menthol
Vicks inhalercamphor + menthol
Vicks vapo steam medicationcamphor + eucalyptus oil + lavender oil + menthol + methyl salicylate + peppermint oil
Vicks vaporub lemon ointmentcamphor + eucalyptus oil + menthol
Vicks vaporub lotioncamphor + eucalyptus oil + menthol
Vitarub onteucalyptol + menthol + methyl salicylate
Watkins analgesic balmcapsicum oleoresin + menthol + methyl salicylate + oil of turpentine
Watkins medicated ointmentcamphor + menthol
Watkins medicated ontcamphor + eucalyptus oil + menthol + oil of camphor + phenol
White flower analgesic balmcamphor + eucalyptus oil + menthol + methyl salicylate + peppermint oil
Wrigley's alpineeucalyptus oil + menthol
Wrigley's alpine cherryeucalyptus oil + menthol
Youngflex massage ointment 168eucalyptus oil + menthol + oil of cajeput
Zevammonium carbonate + buckthorn + camphor + menthol + potassium bicarbonate + squill
Zilactin-lipregular and cherry flavour) (dimethicone + homosalate + menthol + octinoxate + oxybenzone
Categories
CAS number2216-51-5
WeightAverage: 156.2652
Monoisotopic: 156.151415262
Chemical FormulaC10H20O
InChI KeyInChIKey=NOOLISFMXDJSKH-KXUCPTDWSA-N
InChI
InChI=1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3/t8-,9+,10-/m1/s1
IUPAC Name
(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol
SMILES
CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O
Mass Specshow(2.96 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassPrenol Lipids
SubclassMonoterpenes
Direct parentMonocyclic Monoterpenes
Alternative parentsCyclohexanols; Cyclic Alcohols and Derivatives; Polyamines
Substituentscyclohexanol; cyclic alcohol; secondary alcohol; polyamine; alcohol
Classification descriptionThis compound belongs to the monocyclic monoterpenes. These are monoterpenes containing 1 ring in the isoprene chain.
Pharmacology
IndicationUsed to treat occasional minor irritation, pain, sore mouth, and sore throat as well as cough associated with a cold or inhaled irritants.
PharmacodynamicsMenthol is a covalent organic compound made synthetically or obtained from peppermint or other mint oils. Menthol's ability to chemically trigger cold-sensitive receptors in the skin is responsible for the well known cooling sensation that it provokes when inhalated, eaten, or applied to the skin. It should be noted that menthol does not cause an actual drop in temperature.
Mechanism of actionMenthol primarily activates the cold-sensitive TRPM8 receptors in the skin. Menthol, after topical application, causes a feeling of coolness due to stimulation of 'cold' receptors by inhibiting Ca++ currents of neuronal membranes. It may also yield analgesic properties via kappa-opioid receptor agonism.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityMenthol, DL: ORAL (LD50): Acute: 2900 mg/kg [Rat], 3100 mg/kg [Mouse]. DERMAL (LD50): Acute: 5001 mg/kg [Rabbit].
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9944
Blood Brain Barrier + 0.9408
Caco-2 permeable + 0.8127
P-glycoprotein substrate Non-substrate 0.569
P-glycoprotein inhibitor I Non-inhibitor 0.8765
P-glycoprotein inhibitor II Non-inhibitor 0.9397
Renal organic cation transporter Non-inhibitor 0.8591
CYP450 2C9 substrate Non-substrate 0.7798
CYP450 2D6 substrate Non-substrate 0.746
CYP450 3A4 substrate Substrate 0.5912
CYP450 1A2 substrate Non-inhibitor 0.7188
CYP450 2C9 substrate Non-inhibitor 0.8484
CYP450 2D6 substrate Non-inhibitor 0.9451
CYP450 2C19 substrate Non-inhibitor 0.9185
CYP450 3A4 substrate Non-inhibitor 0.9458
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9546
Ames test Non AMES toxic 0.9132
Carcinogenicity Non-carcinogens 0.8439
Biodegradation Not ready biodegradable 0.7808
Rat acute toxicity 1.7142 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.8439
hERG inhibition (predictor II) Non-inhibitor 0.7727
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
CreamTopical
GelTopical
LiquidNasal
LiquidOral
LiquidTopical
LozengeOral
OintmentTopical
PatchTopical
PowderTopical
Solution / dropsOral
SprayTopical
Prices
Unit descriptionCostUnit
Cool & heat patch1.2USDpatch
Icy hot medicated 5% patch1.2USDpatch
Bengay pain relieving patch1.13USDpatch
CVS Pharmacy pain relieving patch1.11USDpatch
Cold & hot pain rel patch1.05USDpatch
Nuprin muscle & joint patch1.03USDpatch
Mentholatum pain patch0.93USDpatch
CVS Pharmacy cold & hot medicated patch0.89USDpatch
Salonsip aqua-patch0.69USDpatch
Menthol crystal0.49USDg
Menthol cough drops0.06USDeach
CVS Pharmacy menthol drops0.03USDeach
Pv menthol cough drops0.02USDeach
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point43 °CPhysProp
boiling point212 °CPhysProp
water solubility490 mg/L (at 25 °C)CHEM INSPECT TEST INST (1992)
logP3.40GRIFFIN,S ET AL. (1999)
Predicted Properties
PropertyValueSource
water solubility5.58e-01 g/lALOGPS
logP2.68ALOGPS
logP2.66ChemAxon
logS-2.5ALOGPS
pKa (strongest acidic)19.55ChemAxon
pKa (strongest basic)-0.81ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count1ChemAxon
hydrogen donor count1ChemAxon
polar surface area20.23ChemAxon
rotatable bond count1ChemAxon
refractivity47.45ChemAxon
polarizability19.69ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
Spectra
References
Synthesis Reference

Tatsuo Higashiyama, Isao Sakata, “Menthol glycoside, process for preparing the same and method for releasing menthol therefrom.” U.S. Patent US4038270, issued December, 1972.

US4038270
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD00064
KEGG CompoundC00400
PubChem Compound16666
PubChem Substance46506513
ChemSpider15803
ChEBI15409
ChEMBLCHEMBL256087
Therapeutic Targets DatabaseDAP000876
PharmGKBPA164776605
IUPHAR2430
Guide to Pharmacology2430
Drug Product Database2241935
Drugs.comhttp://www.drugs.com/cdi/menthol-cream.html
WikipediaMenthol
ATC CodesM02AX10R02AA20
AHFS Codes
  • 48:01.00*
  • 52:92.00
  • 84:08.01*
  • 84:24.04
  • 92:02.00*
  • 84:08.00
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(73.2 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

1. Transient receptor potential cation channel subfamily M member 8

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inducer

Components

Name UniProt ID Details
Transient receptor potential cation channel subfamily M member 8 Q7Z2W7 Details

References:

  1. Story GM, Peier AM, Reeve AJ, Eid SR, Mosbacher J, Hricik TR, Earley TJ, Hergarden AC, Andersson DA, Hwang SW, McIntyre P, Jegla T, Bevan S, Patapoutian A: ANKTM1, a TRP-like channel expressed in nociceptive neurons, is activated by cold temperatures. Cell. 2003 Mar 21;112(6):819-29. Pubmed
  2. Behrendt HJ, Germann T, Gillen C, Hatt H, Jostock R: Characterization of the mouse cold-menthol receptor TRPM8 and vanilloid receptor type-1 VR1 using a fluorometric imaging plate reader (FLIPR) assay. Br J Pharmacol. 2004 Feb;141(4):737-45. Epub 2004 Feb 2. Pubmed
  3. Bandell M, Story GM, Hwang SW, Viswanath V, Eid SR, Petrus MJ, Earley TJ, Patapoutian A: Noxious cold ion channel TRPA1 is activated by pungent compounds and bradykinin. Neuron. 2004 Mar 25;41(6):849-57. Pubmed
  4. Andersson DA, Chase HW, Bevan S: TRPM8 activation by menthol, icilin, and cold is differentially modulated by intracellular pH. J Neurosci. 2004 Jun 9;24(23):5364-9. Pubmed
  5. Stein RJ, Santos S, Nagatomi J, Hayashi Y, Minnery BS, Xavier M, Patel AS, Nelson JB, Futrell WJ, Yoshimura N, Chancellor MB, De Miguel F: Cool (TRPM8) and hot (TRPV1) receptors in the bladder and male genital tract. J Urol. 2004 Sep;172(3):1175-8. Pubmed
  6. Eccles R: Menthol and related cooling compounds. J Pharm Pharmacol. 1994 Aug;46(8):618-30. Pubmed
  7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Transient receptor potential cation channel subfamily A member 1

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inducer

Components

Name UniProt ID Details
Transient receptor potential cation channel subfamily A member 1 O75762 Details

References:

  1. Story GM, Peier AM, Reeve AJ, Eid SR, Mosbacher J, Hricik TR, Earley TJ, Hergarden AC, Andersson DA, Hwang SW, McIntyre P, Jegla T, Bevan S, Patapoutian A: ANKTM1, a TRP-like channel expressed in nociceptive neurons, is activated by cold temperatures. Cell. 2003 Mar 21;112(6):819-29. Pubmed
  2. Namer B, Seifert F, Handwerker HO, Maihofner C: TRPA1 and TRPM8 activation in humans: effects of cinnamaldehyde and menthol. Neuroreport. 2005 Jun 21;16(9):955-9. Pubmed
  3. Macpherson LJ, Hwang SW, Miyamoto T, Dubin AE, Patapoutian A, Story GM: More than cool: promiscuous relationships of menthol and other sensory compounds. Mol Cell Neurosci. 2006 Aug;32(4):335-43. Epub 2006 Jul 7. Pubmed
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

3. Transient receptor potential cation channel subfamily V member 3

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inducer

Components

Name UniProt ID Details
Transient receptor potential cation channel subfamily V member 3 Q8NET8 Details

References:

  1. Macpherson LJ, Hwang SW, Miyamoto T, Dubin AE, Patapoutian A, Story GM: More than cool: promiscuous relationships of menthol and other sensory compounds. Mol Cell Neurosci. 2006 Aug;32(4):335-43. Epub 2006 Jul 7. Pubmed

4. Kappa-type opioid receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Kappa-type opioid receptor P41145 Details

References:

  1. Galeotti N, Di Cesare Mannelli L, Mazzanti G, Bartolini A, Ghelardini C: Menthol: a natural analgesic compound. Neurosci Lett. 2002 Apr 12;322(3):145-8. Pubmed
  2. Taniguchi Y, Deguchi Y, Saita M, Noda K: [Antinociceptive effects of counterirritants] Nippon Yakurigaku Zasshi. 1994 Dec;104(6):433-46. Pubmed

Comments
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:12