Methyl salicylate

Identification

Name
Methyl salicylate
Accession Number
DB09543
Type
Small Molecule
Groups
Approved, Vet Approved
Description

Methyl salicylate (oil of wintergreen or wintergreen oil) is an organic ester naturally produced by many species of plants, particularly wintergreens. The compound was first extracted and isolated from plant species Gaultheria procumbens in 1843. It is also synthetically produced, used as a fragrance, in foods and beverages, and in liniments. It forms a colorless to yellow or reddish liquid and exhibits a characteristic odor and taste of wintergreen. For acute joint and muscular pain, methyl salicylate is used as a rubefacient and analgesic in deep heating liniments. It is used as a flavoring agent in chewing gums and mints in small concentrations and added as antiseptic in mouthwash solutions.

Structure
Thumb
Synonyms
  • 2-(Methoxycarbonyl)phenol
  • 2-Carbomethoxyphenol
  • 2-Hydroxybenzoic acid methyl ester
  • Betula oil
  • Gaultheria oil
  • Methyl 2-hydroxybenzoate
  • Methyl o-hydroxybenzoate
  • Natural wintergreen oil
  • Oil of wintergreen
  • Spicewood Oil
  • Sweet birch oil
  • Teaberry oil
External IDs
Not Available
Product Ingredients
Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
SportgelEmulsion10 %TopicalMeyer Zall Laboratories Pty Ltd.Not applicableNot applicableCanada
Approved Generic Prescription Products
Not Available
Approved Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Aspi-Rub Pain RelieverSpray23 g/100gTopicalAspi Rub Enterprises Llc2014-08-29Not applicableUs
Balsamo de Ubre MascuraOintment10.5 g/90gTopicalMenper Distributors2011-05-10Not applicableUs
Bumooly-SSolution3 g/100mLTransdermalScott Holdings Co., Ltd.2014-09-25Not applicableUs
Bumooly-SSolution3 g/100mLTransdermalScott Holdings Co., Ltd.2014-05-16Not applicableUs
Coats Aloe AnalgesicLotion10 g/gTopicalTychasis Corporation2015-09-29Not applicableUs
Coats Aloe AnalgesicLotion10 g/100mLTopicalTychasis Corporation2015-11-02Not applicableUs
Foot Works Arthritis Achy Foot and MuscleCream250 mg/mLTopicalNew Avon Llc2012-05-30Not applicableUs
Humco Wintergreen OilLiquid980 mg/mLTopicalHumco Holding Grou, Inc.1998-03-25Not applicableUs
Hyundai Moolpas FSolution3 g/100mLTransdermalScott Holdings Co., Ltd.2014-09-25Not applicableUs
Hyundai Moolpas FSolution3 g/100mLTransdermalScott Holdings Co., Ltd.2014-05-16Not applicableUs
Imada Red Flower AnalgesicOil60 g/100mLTopicalLUEN WAH HK MEDICINE LTD2014-01-25Not applicableUs
Jason Cooling Minerals and Tea Tree Pain TherapyOintment13.5 g/100gTopicalThe Hain Celestial Group2011-09-23Not applicableUs
Kofal TOintment10.5 g/100gTopicalPharmadel LLC2012-02-21Not applicableUs
La Flecha JaponesaOil105 mg/mLTopicalMenper Distributors2012-02-21Not applicableUs
Neuro Max Pain and Muscle Relief GelLotion20 g/100gTopicalStarman Consulting Llc2015-04-09Not applicableUs
Oil Of WintergreenLiquidTopicalDawson Traders Ltd.1977-12-312006-03-22Canada
Oil Of Wintergreen 100%LiquidTopicalRegal Pharms, Division Of Bradcan Corporation1977-12-311998-07-29Canada
SmartRx Natural Pain Relief Sleeve ANKLELiquid10 g/100gTopicalNiche Brands, Inc.2013-12-27Not applicableUs
SmartRx Natural Pain Relief Sleeve BACKLiquid10 g/100gTopicalNiche Brands, Inc.2013-12-27Not applicableUs
SmartRx Natural Pain Relief Sleeve ELBOWLiquid10 g/100gTopicalNiche Brands, Inc.2013-12-27Not applicableUs
SmartRx Natural Pain Relief Sleeve KNEELiquid10 g/100gTopicalNiche Brands, Inc.2013-12-27Not applicableUs
SmartRx Natural Pain Relief Sleeve WRISTLiquid10 g/100gTopicalNiche Brands, Inc.2013-12-27Not applicableUs
SoCalm External AnalgesicPatch10 mg/100mgTopicalAb7 Industries2010-12-312017-01-28Us
soCALM Pain RelievingPatch10 g/100gTopicalAb7 Industries2011-08-232017-01-26Us
soCALM Pain RelievingPatch10 g/100gTopicalAb7 Industries2011-08-232017-01-26Us
soCALM Pain RelievingPatch10 g/100gTopicalAb7 Industries2011-08-242017-01-26Us
soCALM Pain RelievingPatch10 g/100gTopicalAb7 Industries2011-08-222017-01-26Us
soCALM Pain RelievingPatch10 g/100gTopicalAb7 Industries2011-08-232017-01-26Us
Ted s PainCream100 mg/gTopicalCersci Therepeutics, Inc.2015-12-14Not applicableUs
Veneno de Abeja Aceite De Vibora BrandOintment15.75 g/150gTopicalDannso corp./d.b.a. Essential Products2015-05-01Not applicableUs
Veneno de Abeja Aceite De Vibora BrandOintment10.5 g/90gTopicalMenper Distributors2011-05-10Not applicableUs
Wintergreen Oil OfLiquidTopicalStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1972-12-312000-07-27Canada
Zenol CoolPoultice160 mg/17gTransdermalGreen Cross Corporation2013-11-23Not applicableUs
Zenol Mild HotPoultice105 mg/17.5gTransdermalGreen Cross Corporation2013-12-03Not applicableUs
Zims Max HeatLiquid200 mg/gTopicalKobayashi Healthcare International, Inc.2017-08-15Not applicableUs
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Natralia Cramp ReliefGel105 mg/gTopicalLaderma Trading Pty Ltd.2009-03-01Not applicableUs
International/Other Brands
Not Available
Brand mixtures
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
701 Dieda Zhengtong Yaogao Medicated PlasterPlasterTopical; TransdermalGUANGZHOU BAIYUNSHAN PHARMACEUTICAL CO., LTD. BAIYUNSHAN HEJIGONG PHARMACEUTICAL FACTORY2001-10-15Not applicableUs
AdazinCreamTopicalSterling Knight Pharmaceuticals, Llc2014-12-03Not applicableUs
Advanced AntisepticMouthwashOralWakfern Food Corporation2010-11-24Not applicableUs
Advanced Antiseptic CitrusMouthwashOralH.E.B.2010-10-15Not applicableUs
Advanced CitrusMouthwashOralWalmart Stores2010-07-22Not applicableUs
Advanced Citrus AntisepticMouthwashOralPublix Supermarkets, Inc.2001-05-03Not applicableUs
Ageless Pain ReliefCreamTopicalIsagenix International, Llc2011-04-23Not applicableUs
Air Sinsin PasAerosol, sprayCutaneous; Topical; TransdermalSinsin Pharmaceutical Co., Ltd.2011-07-01Not applicableUs
Air Sinsinpas-EXSprayTopicalSinsin Pharmaceutical Co., Ltd.2017-08-22Not applicableUs
Alsirub OntOintmentTopicalAlsi Cie Ltee1977-12-312003-05-21Canada
Amber Mouth RinseLiquidOralFilo America2013-07-30Not applicableUs
AMPlify Relief MMCreamTopicalInternational Brand Management, Llc2017-01-17Not applicableUs
Amrutanjan Relief Pain BalmOintmentTopicalAmrutanjan Health Care Limited2015-04-23Not applicableUs
Amrutanjan Relief Strong Pain BalmOintmentTopicalAmrutanjan Health Care Limited2015-04-23Not applicableUs
Analgesic BalmOintmentTopicalGeritrex Llc2012-03-09Not applicableUs
Anitseptic Mouth RinseMouthwashOralPharmacy Vlaue Alliance Llc2003-08-19Not applicableUs
Antiphlogistine Rub A 535 Extra StrengthOintmentTopicalCarter Products, Division Of Carter Wallace Ns Inc.1983-12-311997-08-14Canada
Antiphlogistine Rub A535OintmentTopicalCarter Products, Division Of Carter Wallace Ns Inc.1957-12-311997-08-14Canada
AntisepticMouthwashOralTarget Corporation.1996-07-15Not applicableUs
Antiseptic Blue Mint MouthwashLiquidOralFore Supply, Inc2017-06-05Not applicableUs
Antiseptic Lil Drug Store ProductsLiquidOralLil' Drug Store Products, Inc.2014-12-01Not applicableUs
Antiseptic Mouth RinseMouthwashOralVi Jon1989-07-15Not applicableUs
Antiseptic MouthrinseMouthwashOralWalmart Stores1989-11-11Not applicableUs
Antiseptic RinseMouthwashOralMeijer2006-08-08Not applicableUs
AntispeticMouthwashOralWalgreen2013-09-10Not applicableUs
Antispetic Mouth RinseMouthwashOralOnpoint, Inc2010-07-16Not applicableUs
Apanol Arthritis Extra StrengthOintmentTopicalDelon Laboratories (1990) Ltd.2010-11-192016-10-13Us
Apanol Linimento ObreroOintmentTopicalDelon Laboratories (1990) Ltd.2010-11-072016-10-13Us
Apanol Muscle RubOintmentTopicalDelon Laboratories (1990) Ltd.2010-11-072016-10-13Us
Apeaz UltraCreamTopicalInnovus Pharmaceuticals, Inc.2013-08-06Not applicableUs
Arctic HeatCreamTopicalRenu Laboratories, Inc.2015-09-17Not applicableUs
Arex Sinsin PasPatchCutaneous; Topical; TransdermalSinsin Pharmaceutical Co., Ltd.2015-08-31Not applicableUs
Arthritis HotCreamTopicalChattem, Inc.1998-12-01Not applicableUs
Arthritis Pain Reliever HerbalifeLiquidTopicalHerbalife International Of America1983-12-311996-10-23Canada
Arthritis Pain Relieving CreamCreamTopicalInternational Nature Nutraceuticals1993-09-01Not applicableUs
Arthritis Plus GelCreamTopicalJi Well Health Company2013-07-01Not applicableUs
Arthrocare LotionLiquidTopicalAvacare, Division Of Jeunique International Inc.1984-12-311997-11-10Canada
AssuredPatchTopicalZhejiang Bangli Medical Products Co., Ltd2013-05-012016-10-13Us
Athletic LinimentLiquidTopicalMueller Sports Medicine, Inc.1970-12-312002-07-15Canada
Atomic BalmOintmentTopicalPerformance Health, Inc.2017-05-19Not applicableUs
ATOPALM Deep Penetrating Pain RelievingCreamTopicalNeopharm Co., Ltd2012-01-17Not applicableUs
Atopalm Moisturizing Muscle RubCreamTopicalNeopharm Co., Ltd2011-03-16Not applicableUs
Aurora Blue MintMouthwashBuccalAPOLLO HEALTH AND BEAUTY CARE2016-06-13Not applicableUs
Aurora Fresh BurstMouthwashBuccalAPOLLO HEALTH AND BEAUTY CARE2016-06-13Not applicableUs
Aveda Active CompositionLiquidTopicalAveda Corporation2011-03-08Not applicableUs
Axe Brand MedicatedOilTopicalLeung Kai Fook Medical Co Pte Ltd2001-04-13Not applicableUs
Back Pain Relieving OilOilTopicalInternational Nature Nutraceuticals1966-09-01Not applicableUs
Bakers Best Arthritis Pain ReliefCreamTopicalBaker's Best2011-02-10Not applicableUs
Balm StickStickTopicalIndo Abadi Sari Makmur, Pt2016-07-31Not applicableUs
Balsang Pain ReliefSolutionTopicalGenuine Drugs2015-04-20Not applicableUs
BanalgLotionTopicalRebel Distributors2007-01-01Not applicableUs
Barox SGelTopicalBarox Co., Ltd.2014-03-01Not applicableUs
bB Medicated Pain Relieving OilOilPercutaneous; Topical; TransdermalBb Biochem Laboratories, Inc.2014-07-01Not applicableUs
Being Well AntisepticMouthwashOralSave A Lot Food Stores, Ltd.2014-10-03Not applicableUs
Bengay Arthritis Pain RelievingCreamTopicalJohnson & Johnson Consumer Products Company, Division Of Johnson Consumer Companies, Inc.2012-05-232017-08-01Us
Bengay Greaseless Pain RelievingCreamTopicalJohnson & Johnson2013-12-152017-12-15Us
Bengay Pain Relieving GreaselessCreamTopicalJohnson & Johnson Consumer Products Company, Division Of Johnson Consumer Companies, Inc.2011-07-072016-01-01Us
Bengay Ultra Strength Non Greasy Pain RelievingCreamTopicalJohnson & Johnson2008-06-01Not applicableUs
Berri-Freez PlusGelTopicalGeritrex Llc2015-07-31Not applicableUs
BorasolPowderTopicalLaboratorios Dr. Collado, C x A.2013-01-01Not applicableUs
Bronchodex-rubCreamTopicalTheralab Inc.1981-12-312007-06-21Canada
Buenos Dias de Personna citrus flavourMouthwashOralInternational Cosmetic Limited2013-01-10Not applicableUs
Buenos Dias de Personna cool mintMouthwashOralInternational Cosmetic Limited2013-01-10Not applicableUs
Buenos Dias de Personna mintMouthwashOralInternational Cosmetic Limited2013-01-10Not applicableUs
Buenos Dias de Personna originalMouthwashOralInternational Cosmetic Limited2013-01-10Not applicableUs
Cal Mo Dol OntOintmentTopicalHerbes Universelles Inc.1980-12-312009-07-15Canada
CalmadolLinimentTopicalGrandall Distributing Co., Inc.2015-07-08Not applicableUs
Calypxo Pain ReliefCreamTopicalAsclemed Usa, Inc2014-01-15Not applicableUs
Cam Sun (huile Therapeutique)LiquidTopicalProdemdis Enr.Not applicableNot applicableCanada
CarboseptolOintmentTopicalHerbes Universelles Inc.1966-12-312009-07-15Canada
Care One Cool Heat Extra StrengthCreamTopicalAmerican Sales Company2008-06-20Not applicableUs
Care One Cool Heat Pain RelievingCreamTopicalAmerican Sales Company2012-03-01Not applicableUs
Care One Pain ReliefCreamTopicalAmerican Sales Company2008-08-01Not applicableUs
CAREALL Muscle Rub Ultra StrengthCreamTopicalNew World Imports2012-06-01Not applicableUs
Carmatis OntOintmentTopicalCarmaran LtÉe1981-12-311999-09-14Canada
Castiva CoolingCreamTopicalHumco Holding Group. Inc.2006-12-01Not applicableUs
Chan Yat Hing She Kun Wool Lok Medicated OilOilTopicalChan Yat Hing Medicine Factory2011-12-01Not applicableUs
Cold and Hot CVSSprayTopicalCvs Health2014-11-13Not applicableUs
Cold Spot Point ReliefGelTopicalFabrication Enterprises2010-08-24Not applicableUs
Comfort EZ Extra Strength Pain Relief PatchPatchTopicalSimple Diagnostics. Inc.2015-03-062015-12-29Us
Comfort EZ Extra StrengthTransdermal PatchPatchTopicalSimple Diagnostics. Inc.2015-03-232015-12-29Us
Comfort EZ Pain Relief PatchPatchTopicalSimple Diagnostics. Inc.2014-11-182015-12-29Us
Cool HeatCreamTopicalRite Aid2005-07-26Not applicableUs
Cool Mint Antiseptic MouthwashMouthwashDentalScott Chemical Canada1994-12-311998-09-09Canada
Coral AnalgesicOintmentTopicalHysan Pharmaceutical Co Ltd2016-05-09Not applicableUs
Coralite Muscle JointPatchTopicalUnited Exchange Corporation2013-12-11Not applicableUs
Coralite Pain ReliefPatchTopicalUnited Exchange Corporation2014-03-26Not applicableUs
Coralite Pain Relief StickStickTopicalUnited Exchange Corporation2016-02-10Not applicableUs
CramergesicOintmentTopicalCramer Products, Inc1992-07-15Not applicableUs
CVS Cold and Hot Pain Relieving StickStickTopicalVvf Kansas Services2009-03-27Not applicableUs
CVS Extra Strength Cold and Hot Pain RelievingCreamTopicalCvs Health2014-10-13Not applicableUs
CVS Extra Strength Pain ReliefGelTopicalCvs Health2010-07-10Not applicableUs
CVS Health Cold and Hot Pain Relieving Extra StrengthCreamTopicalCvs Health2016-10-03Not applicableUs
CVS Health Muscle Rub Ultra StrengthCreamTopicalCvs Health2016-10-03Not applicableUs
CVS Medicated PainPatchTopicalCvs Health2013-07-28Not applicableUs
CVS Medicated Pain RelievingPatchTopicalCvs Health2013-06-30Not applicableUs
Dendracin NeurodendraxcinLotionTopicalPhysicians Science & Nature Inc.2007-01-01Not applicableUs
DINGTAI PHARMATopical AnalgesicPatchTopicalZhejiang Dingtai Pharmaceutical Co.; Ltd2015-07-272017-02-11Us
Discount Drug Mart Blue Mint MouthwashLiquidOralDiscount Dollar Mart2014-05-06Not applicableUs
Discount Drug Mart Original Flavor MouthwashLiquidOralDiscount Drug Mart2014-05-06Not applicableUs
Discount Drug Mart Spring Mint MouthwashLiquidOralDiscount Drug Mart2014-05-06Not applicableUs
DoctorReliefGelTopicalBiotanico Inc.2009-12-04Not applicableUs
Dolor-parche With Lidocaine-RXPatchTopicalTwo Hip Consulting, Llc2013-07-312016-10-13Us
Doloracin RxCreamTopicalTwo Hip Consulting, Llc2013-08-112016-10-13Us
Doloracin/l Rx With LidocaineCreamTopicalTwo Hip Consulting, Llc2013-07-312016-10-13Us
DoloranOintmentTopicalHector Rivera Garzon Y Compania. S. En C.2016-10-242017-01-14Us
Double Prawn RumagonLinimentTopicalTai Tong Ah Co., Pte. Ltd.2001-08-05Not applicableUs
Dr Sheffield Muscle Rub CreamCreamTopicalFaria Llc Dba Sheffield Pharmaceutcials2002-04-24Not applicableUs
Dr. J.I.s Arthritis Plus GelCreamTopicalJi Well Health Company2013-07-01Not applicableUs
Dr. JIs Arthritis PlusGelTopicalJi Well Health Company2010-05-04Not applicableUs
Dr.'s CreamCreamTopicalArjohuntleigh1994-12-311997-11-12Canada
DragonOilTopicalAlbert Max, Inc.2009-07-01Not applicableUs
Duane Reade hot and cold balmSalveTopicalDuane Reade2011-02-28Not applicableUs
Dynarex Muscle Rub CreamCreamTopicalDynarex Corporation2016-05-16Not applicableUs
E Mei Shan MedicatedPlasterTransdermalSichuan Emeishan Pharmaceutical Co., Ltd.2013-02-19Not applicableUs
Eagle Brand Medicated OilLiquidTopicalBorden Company Pte LimitedNot applicableNot applicableCanada
Eagle Extra StrengthLiquidTopicalBorden Company (Private) Limited2015-06-15Not applicableUs
Eagle MedicatedOilTopicalBorden Company (Private) Limited2012-05-14Not applicableUs
Eagle Medicated AromaticOilTopicalBorden Company (Private) Limited2015-06-15Not applicableUs
Earths Care Pain RelievingOintmentTopicalDLC Laboratories, Inc.2011-11-29Not applicableUs
Electric Medicated BalmOintmentTopicalFei Fah Medical Manufacturing Pte Ltd2008-02-13Not applicableUs
Equaline cool heatCreamTopicalSupervalu2010-03-30Not applicableUs
Equaline Muscle RubCreamTopicalSupervalu2014-01-03Not applicableUs
Equaline muscle rub ultra strengthCreamTopicalSupervalu2008-12-04Not applicableUs
Equate Cool and HeatCreamTopicalWalmart Stores2013-08-20Not applicableUs
Equate Pain RelievingCreamTopicalWalmart Stores2005-06-28Not applicableUs
Equate Pain Relieving Ultra StrengthCreamTopicalWalmart Stores2011-06-13Not applicableUs
Equate Tartar Control PlusLiquidOralWalmart Stores2017-01-05Not applicableUs
Exchange Select Cool HeatCreamTopicalArmy + Air Force Exchange Service2016-05-23Not applicableUs
Exoten-CLotionTopicalMed Chem Manufacturing, Inc2012-05-08Not applicableUs
Family Care Menthol ReliefStickTopicalUnited Exchange Corporation2012-03-012016-02-17Us
Family Care Muscle Rub Pain RelieverCreamTopicalUnited Exchange Corporation2012-09-30Not applicableUs
Family Care Pain ReliefPatchTopicalUnited Exchange Corporation2013-11-26Not applicableUs
Family Care Thera Flex PainPatchTopicalUnited Exchange Corporation2012-09-30Not applicableUs
Family Dollar Antiseptic Mouth RinseMouthwashOralFamily Dollar2011-05-16Not applicableUs
Family Dollar Antiseptic Mouth Rinse Blue MintMouthwashOralFamily Dollar Services2011-05-16Not applicableUs
Family Dollar Antiseptic Mouth Rinse Spring MintMouthwashOralFamily Dollar2011-05-16Not applicableUs
Fast Relief ArtrosaminCreamTopicalChemco Corporation2013-11-11Not applicableUs
Fast Relief ReumacetinCreamTopicalChemco Corporation2013-08-26Not applicableUs
FlanaxLinimentTopicalBelmora LLC2012-12-06Not applicableUs
Flexall PlusGelTopicalChattem, Inc.1997-01-01Not applicableUs
Flower O Life Pain Relieving BalmOilTopicalSkin Deep2011-08-08Not applicableUs
Foot Rehab Pain relief and moisturizer MissionCreamTopicalMission Product Holdings2012-11-05Not applicableUs
Formula45 Arthritis BlendCreamTopicalShift Consulting Group, Inc.2015-10-16Not applicableUs
Freezin Cold ToastCreamTopicalQ.A. Laboratories2012-06-12Not applicableUs
FriccilicontCreamTopicalLabocont Industrial2012-08-15Not applicableUs
GADADERM Frozen Ice Advance Pain ReliefGelTopicalGadal Laboratories, Inc.2016-09-01Not applicableUs
Genorthix Pain Relieving Roll OnSolutionTopicalGenorthix2015-11-11Not applicableUs
Genuine EfficascentOilTopicalInternational Pharmaceuticals, Inc.2010-05-24Not applicableUs
GinsenggoPatchCutaneous; Topical; TransdermalSinsin Pharmaceutical Co., Ltd.2013-08-22Not applicableUs
Golden Sunshine Far Infrared COOL HerbalPatchTopicalNan Mei Pharmaceutical Co., Ltd.2004-08-02Not applicableUs
Golden Sunshine Far Infrared HerbalPasteTopicalNan Mei Pharmaceutical Co., Ltd.2009-02-23Not applicableUs
Golden Sunshine Far Infrared HOT HerbalPatchTopicalNan Mei Pharmaceutical Co., Ltd.2004-08-02Not applicableUs
Golden Sunshine HerbalSprayTopicalNan Mei Pharmaceutical Co., Ltd.2004-08-02Not applicableUs
Good Neighbor Pharmacy Cold and Hot Therapy Pain Relief Balm Extra StrengthOintmentTopicalAmerisource Bergen Drug Corportaion2000-05-24Not applicableUs
Good Neighbor pharmacy muscle rubCreamTopicalAmerisource Bergen2006-01-17Not applicableUs
Good Neighbor Pharmacy Muscle Rub Ultra StrengthCreamTopicalAmerisource Bergen2005-08-02Not applicableUs
Good Sense Cool HeatCreamTopicalL. Perrigo Company2014-04-15Not applicableUs
Good Sense MuscleCreamTopicalL. Perrigo Company2009-03-24Not applicableUs
Green MINT Mouth RinseLiquidOralFilo America2013-07-30Not applicableUs
Half and Half BalmOintmentTopicalMueller Sports Medicine, Inc.1970-12-312003-08-01Canada
Handy Solutions Cool Mint LISTERINE ANTISEPTIC MOUTHWASHMouthwashOralNavajo Manuracturing Company2013-08-21Not applicableUs
Handy Solutions LISTERINE ANTISEPTIC MOUTHWASHMouthwashOralNavajo Manuracturing Company2013-08-21Not applicableUs
Health Mart muscleCreamTopicalMc Kesson2011-12-23Not applicableUs
Health Mart Muscle RubCreamTopicalMc Kesson2013-10-14Not applicableUs
Health Mart Pain ReliefPatchTopicalMc Kesson2017-01-23Not applicableUs
Healthy Accents Muscle RubCreamTopicalDza Brands,2013-11-20Not applicableUs
Healthy Accents muscle ultra strengthCreamTopicalDza Brands,2010-08-25Not applicableUs
Heat RubCreamTopicalStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1998-12-082002-07-31Canada
Heet Liniment LiqLiquidTopicalWhitehall Robins Inc.1993-12-311997-08-07Canada
Herbal HeatPatchTopicalEu Yan Sang (Usa) Inc2013-01-31Not applicableUs
Herbal Pain RelievingOilTopicalAlbert Max, Inc.2009-07-01Not applicableUs
Herbal UTAPLAS External Analgesic PlasterPatchTopicalAlbert Max, Inc.2004-12-01Not applicableUs
Herbal UTAPLAS.TNPatchTopicalAlbert Max, Inc.2004-12-01Not applicableUs
HerbalgyOilTopicalWicsun Trading2012-03-15Not applicableUs
Hua Tuo Huo Lu OilOilTopicalHysan Pharmaceutical Co Ltd2013-11-27Not applicableUs
Human Science Muscle Pain ReliefCreamTopicalHuman Science, Llc2017-03-28Not applicableUs
Hysan Hua Tuo Huo LuOilTopicalHysan Pharmaceutical Co Ltd2017-03-01Not applicableUs
Hysan Hua Tuo Medicated PlasterPlasterTopicalHysan Pharmaceutical Co Ltd2013-12-04Not applicableUs
Hysan Huo Lu MedicatedOilTopicalHysan Pharmaceutical Co Ltd2013-12-04Not applicableUs
Hysan Pain RelieverOilTopicalHysan Pharmaceutical Co Ltd2012-09-20Not applicableUs
Hyvee Antiseptic Blue MintLiquidOralHyvee2015-04-08Not applicableUs
Hyvee Antiseptic MintLiquidOralHyvee2014-03-21Not applicableUs
Hyvee Antiseptic OriginalLiquidOralHyvee2013-09-12Not applicableUs
Hyvee Blue MintLiquidOralHyvee2014-03-19Not applicableUs
Hyvee Health Cool Blue Sugar FreeMouthwashOralHyvee2016-03-08Not applicableUs
Hyvee Health Green Mint Sugar FreeMouthwashOralHyvee2016-03-08Not applicableUs
ICE QUAKE Analgesic Cream WhiteCreamTopicalSouthern Sales & Service, Inc.2016-10-01Not applicableUs
Ice Quake PlusGelTopicalGadal Laboratories, Inc.2013-01-01Not applicableUs
Ice Quake WhiteCreamTopicalGadal Laboratories, Inc.2013-01-01Not applicableUs
Icy HotOintmentTopicalChattem, Inc.1991-06-01Not applicableUs
Imbue Pain ReliefPatchTopicalImbue Body Llc2011-06-01Not applicableUs
Inarub CrmCreamTopicalFrega Inc.1979-12-312008-02-13Canada
Infraline LiqLiquidTopicalRolmex International Inc.1963-12-311997-08-08Canada
Jimin Zhuifeng GaoPlasterTransdermalGuangdong Zhanjiang Jimin Pharmaceutical Company, Ltd.2007-07-01Not applicableUs
Jun Wai Lung Medicine Pain relievingOilTopicalUncle Bill Trading Usa Inc.2013-10-01Not applicableUs
Katinko Pain And Itch RelievingOintmentTopicalGreenstone Pharmaceutical H.K. Inc.2010-05-24Not applicableUs
Kaz InhalantLiquidRespiratory (inhalation)Kaz Incorporated1981-10-162009-08-17Canada
KeratekGelTopicalGeritrex Llc2013-10-21Not applicableUs
KeVUENO Pain RelievingOintmentTopicalPrilumar Laboratorios2013-09-25Not applicableUs
KGS Bao Zhen Gao Medicated Plaster Extra StrengthPatchTopicalKingsway Trading2016-05-09Not applicableUs
KGS Zhitong Gao Medicated Plaster Extra StrengthPatchTopicalKingsway Trading2016-03-14Not applicableUs
KINeSYS Analgesic SportStickTopicalKinesys Pharmaceutical Inc2012-05-31Not applicableUs
Kiro RubOintmentTopicalProduits Mameca1998-11-232005-09-12Canada
Kiro-rubOintmentTopicalCentre De Recherches En Medication Naturelle Inc.1999-07-052001-07-01Canada
Kobi - CrmCreamTopicalThe Emu Man Company L.C.1996-12-311999-07-08Canada
Kung Fu Pain ReliefPatchTopical6c23, Llc2017-03-09Not applicableUs
Kwan LoongOilTopicalHaw Par Healthcare Ltd.2005-09-01Not applicableUs
La VaquitaOintmentTopicalDelon Laboratories (1990) Ltd.2010-11-072016-10-13Us
La Vaquita Extra StrengthOintmentTopicalDelon Laboratories (1990) Ltd.2010-11-072016-10-13Us
La Vaquita New ExtraOintmentTopicalDelon Laboratories (1990) Ltd.2011-04-26Not applicableUs
La Vaquita New RegularOintmentTopicalDelon Laboratories (1990) Ltd.2011-03-01Not applicableUs
LaBella Linimento ObreroCreamTopicalGolden Sun Inc Dba Newhall Laboratories2013-01-02Not applicableUs
Lao Wei Wood Lock OilOilTopicalRfx Pharmaceutical Co Ltd2014-06-15Not applicableUs
LCDO. ORLANDO RIVERA ARTHRITIS Topical AnalgesicCreamTopicalPure Source, Llc2014-04-21Not applicableUs
Leader Medicated Relief PatchPatchTopicalCardinal Health2016-12-01Not applicableUs
Leader Pain Relieving Rub UltraCreamTopicalCardinal Health2012-07-312018-01-12Us
Leader Ultra Strength Muscle RubCreamTopicalCardinal Health2017-08-16Not applicableUs
Leader Ultra Strength Muscle Rub Topical AnalgesicCreamTopicalCardinal Health2017-05-24Not applicableUs
LidoProOintmentTopicalTerrain Pharmaceuticals2014-01-01Not applicableUs
LidoPro PatchPatchTopicalTerrain Pharmaceuticals2014-12-02Not applicableUs
Listerine Advanced with Tartar Protection Antiseptic CitrusMouthwashOralJohnson & Johnson Healthcare Products, Division Of Mc Neil Ppc, Inc.2013-10-112016-10-13Us
Listerine AntisepticMouthwashOralJohnson & Johnson Healthcare Products, Division Of Mc Neil Ppc, Inc.2012-02-21Not applicableUs
Listerine Cool Mint AntisepticMouthwashOralJohnson & Johnson2012-02-21Not applicableUs
Listerine FreshBurst AntisepticMouthwashOralJohnson & Johnson2012-02-21Not applicableUs
Listerine Naturals Antiseptic - Herbal MintMouthwashOralJohnson & Johnson Healthcare Products, Division Of Mc Neil Ppc, Inc.2013-12-15Not applicableUs
Listerine Ultraclean Antiseptic Arctic MintMouthwashOralJohnson & Johnson Healthcare Products, Division Of Mc Neil Ppc, Inc.2012-07-03Not applicableUs
Listerine Ultraclean Antiseptic Cool MintMouthwashOralJohnson & Johnson Healthcare Products, Division Of Mc Neil Ppc, Inc.2012-07-09Not applicableUs
Listerine Ultraclean Antiseptic Fresh CitrusMouthwashOralJohnson & Johnson Healthcare Products, Division Of Mc Neil Ppc, Inc.2012-07-10Not applicableUs
Lucky SuperSoft Muscle and JointCreamTopicalDelta Brands, Inc2015-01-31Not applicableUs
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Categories
UNII
LAV5U5022Y
CAS number
119-36-8
Weight
Average: 152.1473
Monoisotopic: 152.047344122
Chemical Formula
C8H8O3
InChI Key
OSWPMRLSEDHDFF-UHFFFAOYSA-N
InChI
InChI=1S/C8H8O3/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5,9H,1H3
IUPAC Name
methyl 2-hydroxybenzoate
SMILES
COC(=O)C1=CC=CC=C1O

Pharmacology

Indication

Ointments or liniments containing methyl salicylate are applied topically as counter irritant for relief of acute pain associated with lumbago,sciatica and rheumatic conditions. Local analgesics for human and veterinary medicine.

Structured Indications
Pharmacodynamics

Methyl salicylate relieve musculoskeletal pain in the muscles, joints, and tendons by causing irritation and reddening of the skin due to dilated capillaries and increased blood flow. It is pharmacologically similar to aspirin and other NSAIDs but as a topical agent it primarily acts as a rubefacient and skin irritant. Counter-irritation is believed to cause a soothing sensation of warmth.

Mechanism of action

Counter-irritation is thought to be effective at alleviating musculoskeletal pain as the irritation of the sensory nerve endings is thought to alter or offset pain in the underlying muscle or joints that are served by the same nerves [5]. This is thought to mask the underlying musculoskeletal pain and discomfort. When applied topically, methyl salicylate is thought to penetrate the skin and underlying tissues where it reversibly inhibits cyclooxygenase enzyme and locally and peripherally prevents the production of inflammatory mediators such as prostaglandin and thromboxane A2.

Absorption

Approximately 12-20% of topically applied methyl salicylate may be systemically absorbed through intact skin within 10 hours of application, and absorption varies with different conditions such as surface area and pH. Dermal bioavailability is in the range of 11.8 – 30.7%. For the assessment of potential oral exposure to salicylates, bioavailability is assumed to be 100% [9].

Volume of distribution

After absorption, methyl salicylate is distributed throughout most body tissues and most transcellular fluids, primarily by pH dependent passive processes. Salicylate is actively transported by a low-capacity, saturable system out of the CSF across the choroid plexus. The drug readily crosses the placental barrier.

Protein binding

Degree of albumin binding depends on the plasma concentration of the compound

Metabolism

Minor metabolism may occur in various tissues but hepatic metabolism constitutes the majority of metabolic processes of absorbed methyl salicylate. It is mainly hydrolyzed to salicylic acid via hepatic esterase enzymes. Conjugation with glycine forms salicyluric acid and conjugation with glucuronic forms ester or acyl and ether or phenolic glucuronide, which are the three main metabolites.

Route of elimination

Excreted by kidneys as free salicylic acid (10%), salicyluric acid (75%), salicylic phenolic (10%) and acyl glucuronide (5%), and gentisic acid (less than 1%).

Half life

The plasma half-life for salicylate is 2 to 3 hr in low doses and about 12 hr at usual anti-inflammatory doses. The half-life of salicylate may be as long as 15 to 30 hr at high therapeutic doses or when there is intoxication.

Clearance
Not Available
Toxicity

Oral LD50 values (mg/kg) for mouse, rat and rabbit are 1110, 887 and 1300, respectively. Oral LD50 values for child and adult human (mg/kg) are 228 and 506, respectively. Although systemic toxicity from topical administration is rare, methyl salicylate can be absorbed in intract skin to cause stimulation of the central nervous system respiratory center, disturbance of lipid and carbohydrate metabolism, and disturbance of intracellular respiration. Severe toxicity can result in acute lung injury, lethargy, coma, seizures, cerebral edema, and death. In case of salicylate poisoning, the treatment consists of general supportive care, gastrointestinal decontamination with activated charcoal in cases of salicylate ingestion, and monitoring of serum salicylate concentrations. Bicarbonate infusions or hemodialysis can be used to achieve enhanced salicylate elimination [7].

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference
Not Available
General References
  1. He YY, Yan Y, Zhang HF, Lin YH, Chen YC, Yan Y, Wu P, Fang JS, Yang SH, Du GH: Methyl salicylate 2-O-beta-d-lactoside alleviates the pathological progression of pristane-induced systemic lupus erythematosus-like disease in mice via suppression of inflammatory response and signal transduction. Drug Des Devel Ther. 2016 Sep 29;10:3183-3196. eCollection 2016. [PubMed:27729775 ]
  2. Xin W, Huang C, Zhang X, Xin S, Zhou Y, Ma X, Zhang D, Li Y, Zhou S, Zhang D, Zhang T, Du G: Methyl salicylate lactoside inhibits inflammatory response of fibroblast-like synoviocytes and joint destruction in collagen-induced arthritis in mice. Br J Pharmacol. 2014 Jul;171(14):3526-38. doi: 10.1111/bph.12715. [PubMed:24712652 ]
  3. Mason L, Moore RA, Edwards JE, McQuay HJ, Derry S, Wiffen PJ: Systematic review of efficacy of topical rubefacients containing salicylates for the treatment of acute and chronic pain. BMJ. 2004 Apr 24;328(7446):995. Epub 2004 Mar 19. [PubMed:15033879 ]
  4. Higashi Y, Kiuchi T, Furuta K: Efficacy and safety profile of a topical methyl salicylate and menthol patch in adult patients with mild to moderate muscle strain: a randomized, double-blind, parallel-group, placebo-controlled, multicenter study. Clin Ther. 2010 Jan;32(1):34-43. doi: 10.1016/j.clinthera.2010.01.016. [PubMed:20171409 ]
  5. Derry S, Matthews PR, Wiffen PJ, Moore RA: Salicylate-containing rubefacients for acute and chronic musculoskeletal pain in adults. Cochrane Database Syst Rev. 2014 Nov 26;(11):CD007403. doi: 10.1002/14651858.CD007403.pub3. [PubMed:25425092 ]
  6. Moore RA, Derry S, McQuay HJ: Topical analgesics for acute and chronic pain in adults. Cochrane Database Syst Rev. 2010;(7). pii: CD008609. [PubMed:25411557 ]
  7. Thompson TM, Toerne T, Erickson TB: Salicylate Toxicity from Genital Exposure to a Methylsalicylate-Containing Rubefacient. West J Emerg Med. 2016 Mar;17(2):181-3. doi: 10.5811/westjem.2016.1.29262. Epub 2016 Mar 2. [PubMed:26973745 ]
  8. FDA SALONPAS® Pain Relief Patch Clinical Review [Link]
  9. Norwegian Food Safety Authority: Methyl salicylate risk review [Link]
External Links
Human Metabolome Database
HMDB34172
KEGG Drug
D01087
KEGG Compound
C12305
ChemSpider
13848808
ChEBI
31832
ChEMBL
CHEMBL108545
Drugs.com
Drugs.com Drug Page
Wikipedia
Methyl_salicylate
ATC Codes
Not Available
AHFS Codes
Not Available
PDB Entries
Not Available
FDA label
Not Available
MSDS
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Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2WithdrawnTreatmentPain, Acute1
2, 3WithdrawnTreatmentHIV-infection/AIDS / Immune Reconstitution Inflammatory Syndrome / Immune Reconstitution Syndrome / Tuberculosis1
4CompletedPreventionNeonatal Infections1
4CompletedTreatmentAggressive Periodontitis1
4RecruitingTreatmentChronic Low Back Pain (CLBP)2
4RecruitingTreatmentSub-acute Back Pain1
Not AvailableRecruitingTreatmentPeriodontitis / Type 2 Diabetes Mellitus1
Not AvailableUnknown StatusTreatmentPain1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Aerosol, sprayCutaneous; Topical; Transdermal
RinseOral
MouthwashOral
SprayTopical23 g/100g
MouthwashBuccal
SolutionTopical
OilPercutaneous; Topical; Transdermal
PowderTopical
LotionTopical10 g/100mL
LotionTopical10 g/g
SprayTopical
OintmentTopical
LinimentTopical
SalveTopical
LiquidTopical
OilTopical
CreamTopical250 mg/mL
PatchCutaneous; Topical; Transdermal
PasteTopical
LiquidTopical980 mg/mL
SolutionTransdermal3 g/100mL
LiquidOral
StickTopical
OilTopical60 g/100mL
OintmentTopical13.5 g/100g
LiquidRespiratory (inhalation)
OintmentTopical10.5 g/100g
OilTopical105 mg/mL
LotionTopical
JellyNasal
GelTopical105 mg/g
LotionTopical20 g/100g
PatchTopical
EmulsionTopical
GelPercutaneous; Topical; Transdermal
PatchPercutaneous; Topical; Transdermal
Aerosol, sprayPercutaneous; Topical; Transdermal
Aerosol, foamPercutaneous; Topical; Transdermal
PlasterTransdermal
PlasterTopical
LiquidCutaneous; Topical; Transdermal
Kit
LiquidTopical10 g/100g
PatchTopical10 mg/100mg
PatchTopical10 g/100g
MouthwashDental
EmulsionTopical10 %
CreamTopical100 mg/g
GelTopical
PatchTransdermal
OintmentTopical10.5 g/90g
OintmentTopical15.75 g/150g
CreamTopical
OilTransdermal
LiquidTopical
PlasterTopical; Transdermal
PoulticeTransdermal160 mg/17g
PoulticeTransdermal105 mg/17.5g
LiquidTopical200 mg/g
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US8809615 No2010-01-032030-01-03Us
US9233184 No2007-08-012027-08-01Us

Properties

State
Liquid
Experimental Properties
PropertyValueSource
melting point (°C)-8.6MSDS
boiling point (°C)220-224MSDS
water solubilitySlightly solubleMSDS
logP2.5MSDS
Predicted Properties
PropertyValueSource
Water Solubility5.73 mg/mLALOGPS
logP2.07ALOGPS
logP2.32ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)9.72ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.06 m3·mol-1ChemAxon
Polarizability14.98 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-00dl-9800000000-4c121b87ee97a30f4150
GC-MS Spectrum - EI-BGC-MSsplash10-00dl-9800000000-aeff759175e190d33827
GC-MS Spectrum - EI-BGC-MSsplash10-00dl-9700000000-8449a003796d4c61d429
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0fk9-3900000000-e2029bf3c75775175ff3
Predicted LC-MS/MS Spectrum - 10V, PositivePredicted LC-MS/MSsplash10-0udi-0900000000-eba52e49290e16ea60c0
Predicted LC-MS/MS Spectrum - 20V, PositivePredicted LC-MS/MSsplash10-0uk9-0900000000-684f1c8a3cf324183257
Predicted LC-MS/MS Spectrum - 40V, PositivePredicted LC-MS/MSsplash10-0uk9-9300000000-a594ffaab84fc15a2edc
Predicted LC-MS/MS Spectrum - 10V, NegativePredicted LC-MS/MSsplash10-0udi-0900000000-76d5fc81bafad7c2222c
Predicted LC-MS/MS Spectrum - 20V, NegativePredicted LC-MS/MSsplash10-0udi-0900000000-dae7a80af6333acd66fc
Predicted LC-MS/MS Spectrum - 40V, NegativePredicted LC-MS/MSsplash10-0gb9-9600000000-09304803bc773495c704
Mass Spectrum (Electron Ionization)MSsplash10-00dl-9800000000-1d56d6cf07db519b50e2
1H NMR Spectrum1D NMRNot applicable
13C NMR Spectrum1D NMRNot applicable

Taxonomy

Description
This compound belongs to the class of chemical entities known as o-hydroxybenzoic acid esters. These are benzoic acid esters where the benzene ring is ortho-substituted with a hydroxy group.
Kingdom
Chemical entities
Super Class
Organic compounds
Class
Benzenoids
Sub Class
Benzene and substituted derivatives
Direct Parent
o-Hydroxybenzoic acid esters
Alternative Parents
Salicylic acid and derivatives / Benzoyl derivatives / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Vinylogous acids / Methyl esters / Monocarboxylic acids and derivatives / Organooxygen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
O-hydroxybenzoic acid ester / Salicylic acid or derivatives / Benzoyl / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Vinylogous acid / Methyl ester / Carboxylic acid ester / Carboxylic acid derivative
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
salicylates, benzoate ester (CHEBI:31832 ) / a small molecule (CPD-6442 )
Drug created on November 30, 2015 12:10 / Updated on September 01, 2017 12:06