Identification

Name
Menthol
Accession Number
DB00825  (APRD01604)
Type
Small Molecule
Groups
Approved
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
  • (-)-(1R,3R,4S)-Menthol
  • (-)-menthol
  • (1alpha,2beta,5alpha)-5-Methyl-2(1-methylethyl)cyclohexanol
  • (1R-(1-alpha,2-beta,5-alpha))-5-Methyl-2-(1-methylethyl)cyclohexanol
  • (1R,3R,4S)-(-)-Menthol
  • (r)-(-)-menthol
  • L-(-)-menthol
  • L-menthol
  • Levomenthol
  • Levomentholum
  • Levomentol
External IDs
FEMA NO. 2665, (-)- / NPO-11 / NSC-62788
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
0 Degrees Pain RelievingGel5 g/100mLTopicalRlabs, Llc2016-04-012016-10-13Us
Absorbine BACK Therapeutic Pain ReliefPatch5 g/100gTopicalTeh Seng Pharmaceutical Mfg. Co., Ltd.2013-10-10Not applicableUs
Absorbine JrPatch5000 mg/hTopicalClarion Brands, Llc2015-07-15Not applicableUs
Absorbine JrCream2.5 g/100gTopicalClarion Brands, Llc2015-08-15Not applicableUs
Absorbine Jr Plus Ultra Strength PainPatch6500 mg/hTopicalClarion Brands, Llc2015-08-15Not applicableUs
Absorbine Jr Ultra Strength Pain RelievingPatch6500 mg/8hTopicalW.F. Young, Inc.2000-01-012015-11-30Us
Absorbine Jr.Liquid.0127 g/mLTopicalW.F. Young, Inc.1901-01-012018-02-28Us
Absorbine Jr. BackPatch5000 mg/8hTopicalW.F. Young, Inc.2005-01-012016-01-31Us
Absorbine Jr. PlusLiquid4 g/100mLTopicalClarion Brands, Llc2010-06-24Not applicableUs
AchyCream28 g/90mLTopicalKelada Creative Group Llc Dba Salve2016-12-19Not applicableUs
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
A.C.C Fresh and Cooling Scalp MistLiquid.3 g/100mLTopicalNature4 Co., Ltd.2017-07-26Not applicableUs
Assured Medicated Body PowderPowder.15 g/100gTopicalDavion, Inc.2017-11-29Not applicableUs
Assured Medicated Foot PowderPowder1 g/100gTopicalDavion, Inc.2017-11-29Not applicableUs
Avedana Cool Hot IceGel2 g/100gTopicalUnipack2017-11-04Not applicableUs
Cellbn Mega PlusShampoo.3 g/100mLTopicalWorldcostec.co.,ltd2017-05-26Not applicableUs
Cherry cough dropsLozenge5.8 mg/1OralBig Lots2017-11-17Not applicableUs
Cherry Cough DropsLozenge5.8 mg/1OralValu Merchandisers2017-11-09Not applicableUs
CHRIOLOGY Relax UpGel.1 mg/mLTopicalChrio Korea Co., Ltd2013-07-302017-07-27Us
Honey Ginger Cough DropsLozenge3.18 mg/1OralInva Tech Pharma Solutions Llc2017-10-31Not applicableUs
Honey Lemon Cough DropsLozenge7.5 mg/1OralBig Lots2017-11-17Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
1st RELIEF TOPICALMenthol (10 mg/mL) + Lidocaine (40 mg/mL)SprayTopical1st Class Pharmaceuticals2014-12-02Not applicableUs
701 Dieda Zhengtong Yaogao Medicated PlasterMenthol (8 g/1) + Camphor (3.1 g/1) + Methyl salicylate (10 g/1)PlasterTopical; TransdermalGUANGZHOU BAIYUNSHAN PHARMACEUTICAL CO., LTD. BAIYUNSHAN HEJIGONG PHARMACEUTICAL FACTORY2001-10-15Not applicableUs
999 Itch ReliefMenthol (200 mg/20000mg) + Camphor (200 mg/20000mg) + Dexamethasone (15 mg/20000mg)OintmentTopicalChina Resources Sanjiu Medical & Pharmaceutical Co., Ltd.2003-07-03Not applicableUs
Abee MedMenthol (15 mg/g) + Histamine dihydrochloride (.5 mg/g)CreamTopicalCrossover Telecom Llc2016-05-25Not applicableUs
Absorbine Jr Antifungal LiqMenthol (200 mg) + Tolnaftate (1 g)LiquidTopicalClarion Brands, Llc1994-12-31Not applicableCanada
Absorbine Jr Extra Strength LinimentMenthol (4.0 %) + Chloroxylenol (0.5 %)LiquidTopicalClarion Brands, Llc1992-12-31Not applicableCanada
Absorbine Jr LinimentMenthol (1.25 %) + Chloroxylenol (0.5 %)LiquidTopicalClarion Brands, Llc1993-12-31Not applicableCanada
Absorbine Power GelMenthol (4 %) + Chloroxylenol (.5 %)GelTopicalW.F. Young, Inc.1993-12-31Not applicableCanada
Aching Head RubMenthol (2.55 g/100g) + Camphor (3.09 g/100g)OintmentTopicalLittle Moon Essentials2016-09-26Not applicableUs
ActisepMenthol (.5 g/100mL) + Benzocaine (2 g/100mL) + Cetylpyridinium (.1 g/100mL)SolutionTopicalActipharma, Inc2015-12-28Not applicableUs
Categories
UNII
BZ1R15MTK7
CAS number
2216-51-5
Weight
Average: 156.2652
Monoisotopic: 156.151415262
Chemical Formula
C10H20O
InChI Key
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

Pharmacology

Indication

Used to treat occasional minor irritation, pain, sore mouth, and sore throat as well as cough associated with a cold or inhaled irritants.

Structured Indications
Pharmacodynamics

Menthol 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 action

Menthol 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.

TargetActionsOrganism
ATransient receptor potential cation channel subfamily M member 8
inducer
Human
ATransient receptor potential cation channel subfamily A member 1
inducer
Human
ATransient receptor potential cation channel subfamily V member 3
inducer
Human
UKappa-type opioid receptor
agonist
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

Menthol, 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
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

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 References
Not Available
External Links
Human Metabolome Database
HMDB03352
KEGG Drug
D00064
KEGG Compound
C00400
PubChem Compound
16666
PubChem Substance
46506513
ChemSpider
15803
BindingDB
50318482
ChEBI
15409
ChEMBL
CHEMBL470670
Therapeutic Targets Database
DAP000876
PharmGKB
PA164776605
IUPHAR
2430
Guide to Pharmacology
GtP Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Menthol
AHFS Codes
  • 84:08.00 — Antipruritics and Local Anesthetics
  • 84:24.04 — Basic Lotions and Liniments
  • 52:92.00 — EENT Drugs, Miscellaneous
  • 92:01.00* — Herbs and Natural Products
  • 84:08.01* — Other Analgesics
  • 48:01.00* — Other Cold and Cough Preparations
MSDS
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Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Not Yet RecruitingHealth Services ResearchNicotine Dependence1
0RecruitingOtherBioavailability1
0RecruitingTreatmentNicotine Addiction / Panic Attacks1
1CompletedOtherPain3
1CompletedTreatmentPain1
1RecruitingOtherArterial Stiffness1
1RecruitingTreatmentCutaneous T Cell Lymphomas (CTCL)1
1RecruitingTreatmentMinor burns1
1, 2RecruitingTreatmentDiabetic Peripheral Neuropathy (DPN)1
1, 2WithdrawnTreatmentInjuries and Wounds1
2CompletedTreatmentAllergic Rhinoconjunctivitis1
2CompletedTreatmentImmunosuppresion / Neutropenias / Pancytopenia / Thrombocytopenias1
2CompletedTreatmentLymphoma, Large B-Cell, Diffuse (DLBCL)1
2CompletedTreatmentLymphoma, Large-Cell, Diffuse1
2CompletedTreatmentPain / Postherpetic Neuralgia1
2Not Yet RecruitingTreatmentToothache1
2Unknown StatusNot AvailableSmoking, Cigarette1
2WithdrawnTreatmentPain, Acute1
2, 3RecruitingTreatmentMalaria caused by Plasmodium falciparum1
2, 3Unknown StatusPreventionHigh Blood Pressure (Hypertension) / Prehypertension1
2, 3WithdrawnTreatmentHIV-infection/Aids / Immune Reconstitution Inflammatory Syndrome / Immune Reconstitution Syndrome / Tuberculosis1
3CompletedPreventionRadiation Dermatitis1
3CompletedTreatmentColon Nos Polypectomy Tubular Adenoma / Gastric Adenoma / Malignant Neoplasm of Stomach1
3CompletedTreatmentHealthy Volunteers1
3CompletedTreatmentMalignant Neoplasm of Stomach1
3CompletedTreatmentNon-Hodgkin's Lymphoma (NHL)1
3CompletedTreatmentPain1
3CompletedTreatmentPain, Neuropathic1
3CompletedTreatmentPatients Undergoing Gastric Endoscopy1
3CompletedTreatmentStomach Diseases1
3Not Yet RecruitingTreatmentMalaria caused by Plasmodium falciparum1
3RecruitingDiagnosticColorectal Polyps / Malignant Neoplasm of Colon1
3RecruitingTreatmentThroat Pain2
3Unknown StatusTreatmentCoughing1
3WithdrawnTreatmentKnee Osteoarthritis (Knee OA)1
4CompletedPreventionCoronary Heart Disease (CHD)1
4CompletedPreventionNeonatal Infections1
4CompletedTreatmentAdherence / Cessation, Smoking / Motivation / Nicotine Dependence / Smoking1
4CompletedTreatmentAggressive Periodontitis1
4CompletedTreatmentCaudal epidural block therapy / Forearm Injuries / Orthopedic Procedures / Traumas / Upper Extremity1
4CompletedTreatmentCaudal epidural block therapy / Orthopedic Procedures / Shoulder1
4CompletedTreatmentSub-acute Back Pain1
4CompletedTreatmentTobacco Dependence1
4Not Yet RecruitingTreatmentActinic Keratosis (AK)1
4RecruitingTreatmentChronic Low Back Pain (CLBP)2
4TerminatedTreatmentPregnancy / Smoking1
4Unknown StatusTreatmentPruritis1
Not AvailableCompletedOtherNicotine Dependence1
Not AvailableCompletedTreatmentCerebral Palsy (CP)1
Not AvailableCompletedTreatmentCervical Pain1
Not AvailableCompletedTreatmentHeadaches / Migraines1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedTreatmentLow Back Pain (LBP) / Pain1
Not AvailableCompletedTreatmentRecession, Gingival1
Not AvailableCompletedTreatmentShoulder Pain1
Not AvailableCompletedTreatmentStings1
Not AvailableEnrolling by InvitationNot AvailableArthritis / Gout Acute / Headaches / Migraines / Muscle Spasms / Radicular syndrome / Synovitis / Tendonitis1
Not AvailableRecruitingBasic ScienceDermatology/Skin - Other / Pain / Pain, Neuropathic / Pruritus1
Not AvailableRecruitingBasic ScienceHeart Failure, Unspecified1
Not AvailableRecruitingTreatmentArthritis / Back Pain1
Not AvailableRecruitingTreatmentPeriodontitis / Type 2 Diabetes Mellitus1
Not AvailableUnknown StatusTreatmentCessation, Smoking1
Not AvailableUnknown StatusTreatmentPain1
Not AvailableUnknown StatusTreatmentPain Relief1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
LiquidTopical.3 g/100mL
PatchTopical5000 mg/h
PatchTopical6500 mg/h
PatchTopical6500 mg/8h
LiquidTopical.0127 g/mL
PatchTopical5000 mg/8h
LiquidTopical4 g/100mL
CreamTopical28 g/90mL
StickTopical.05138 g/g
Aerosol, sprayCutaneous; Topical; Transdermal
DiscTopical
CreamTopical20 mg/mL
PatchTopical30 mg/1
OintmentTopical.31 g/100g
LiquidDental
SprayTopical.07 g/mL
SprayTopical700 mL/L
LiquidBuccal
SprayTopical5 mL/100mL
LotionTopical.15 g/100g
GelTopical4 %
RinseOral
SprayTopical5 g/100mL
SprayTopical10 g/100mL
GelTopical3.2 g/100mL
GelTopical3 g/100mL
LiquidTopical3 g/100mL
GelTopical1 g/100g
GelTopical3.969 g/113.4g
GelTopical3.969 g/90g
CreamTopical3.7 g/100g
CreamTopical5 g/100g
CreamTopical12.5 mg/g
GelTopical10 g/100mL
LozengeOral2.8 mg/1
PatchTopical5 mg/100mg
PatchTopical750 mg/1
GelTopical1.25 g/100g
PowderTopical.15 g/100g
StickTopical1.34 g/57g
Gel, dentifriceTopical10 mg/g
CreamTopical10 g/100g
MouthwashBuccal
SolutionTopical100 mg/mL
SprayTopical9 g/100g
StickTopical2.6 mg/g
OintmentNasal
LinimentTopical3.7 g/100mL
GelTopical3 g/120mL
GelTopical2.4 mg/120mL
GelTopical3 mg/120mL
OilPercutaneous; Topical; Transdermal
GelTopical2.5 %
GelTopical50 mg/g
CreamTopical100 mg
LozengeOral2.7 mg
Tablet, chewableOral
GelTopical4.5 g/100g
GelTopical5.085 g/113g
SprayTopical11.8 g/118mL
LiquidTopical4.2 mL/60mL
LotionTopical5.11 g/113g
GelTopical30 mg/g
GelTopical4 g/100mL
GelTopical.03 g/g
SprayTopical105 mg/mL
SprayTopical59 mL/100mL
SalveTopical1 g/100g
SalveTopical1.1 g/100g
SoapTopical1 g/100mL
GelTopical.02 g/g
PowderTopical1.5 mg/g
PowderTopical10 mg/g
CreamTopical170 g/90mL
OintmentRespiratory (inhalation); Topical
SyrupOral
GelTopical2.5 g/100g
GelTopical.025 g/g
OintmentRespiratory (inhalation)
LiquidTopical5 mg/mL
CreamTopical.5 g/100g
GelTopical25 mg/g
PatchTopical.05 mg/1
OilTopical.08 kg/kg
CreamTopical1.5 g/100g
LozengeOral1 mg
LozengeOral1.5 mg
LiquidTransdermal
ShampooTopical.3 g/100mL
OilTopical1.5 g/50g
LozengeOral4.5 mg/1
LozengeOral5.8 1/1
SalveTopical27.6 mg/g
JellyTopical
OintmentTopical1 g/100g
GelTopical.1 mg/mL
SprayTopical16 g/100mL
PatchTopical240 mg/1
PatchTopical50 mg/1
PatchTopical500 mg/1
PatchTopical875 mg/1
PatchTopical400 mg/1
LipstickTopical
Aerosol, sprayTopical12 mL/120mL
OintmentTopical13 mL/90mL
SwabTopical.96 mL/8mL
PatchTopical1.14 g/100g
Granule, for solutionOral490 mg/5g
MouthwashBuccal; Oral
PatchTopical.05 mg/g
SprayTopical160 mg/mL
Granule, for solutionTopical11.7 mg/mL
GelTopical2.5 g/100mL
LotionTopical16 mL/100mL
PatchTopical5 mg/g
TabletOral5.8 mg/5.8mg
TabletOral7.5 mg/7.5mg
LozengeOral5 mg
LozengeOral7 mg/1
LotionRespiratory (inhalation)
PatchTopical.05 g/g
LiquidTopical160 mg/mL
Gel, dentifriceDental
LozengeOral4 mg/1
LotionTopical1 mg/mL
CreamTopical.025 g/g
SprayTopical60 mg/mL
SolutionTopical60 mg/mL
CreamTopical100 mg/mL
ShampooTopical
Patch, extended releaseTransmucosal2.5 mg/194.85mg
CreamTopical1.8 g/100g
LozengeOral8.4 mg
LozengeOral6.1 mg
LiquidTopical20 mg/mL
OilTopical3.5 g/100mL
SprayTopical
PatchTopical.5 g/g
GelTopical3.89 g/100g
GelTopical4.58 g/100g
CreamTopical40 mg/mL
SolutionTopical
CreamTopical2.625 g/75g
CreamTopical100 mg/g
PatchCutaneous
LozengeOral8.3 mg/1
LozengeOral8.5 mg/1
CreamTopical50 mg/mL
LiquidTopical35 mg/mL
LiquidTopical
OilTopical
PatchTopical4 g/1
SprayTopical1000 mg/100mL
SprayTopical1700 mg/100mL
SprayTopical865.4 mg/50mL
CreamTopical60 mg/mL
SprayTopical1.25 g/100mL
SprayTopical4 g/100mL
CreamTopical12.13 mg/mL
OintmentTopical9.6 mL/60mL
LotionTopical.1 mL/100mL
LotionTopical.1 g/100mL
GelTopical100 mg/mL
PatchTopical5 g/100g
SprayTopical8 mL/100mL
LiquidTopical8 mL/100mL
GelTopical2 g/100mL
GelTopical35 mg/g
SprayTopical100 mg/g
SolutionOral
JellyTopical10 %
GelTopical16 %
GelTopical7 %
GelTopical6 %
Granule, for solutionOral270 mg/6g
LotionTopical13.5 mg/mL
CreamTopical.1 g/100mL
LozengeOral3 mg
LozengeOral6.0 mg
OilTopical24 mg/mL
SprayOropharyngeal
PatchCutaneous; Topical; Transdermal
PowderTopical.008 g/g
SprayTopical1 g/100g
PowderTopical.0015 g/g
CreamTopical16 g/100g
LotionCutaneous
GelTopical2 g/100g
OilTopical20 mg/500mg
LozengeOral5.7 mg/1
LozengeOral6.8 mg/1
LozengeOral7.5 mg/1
LozengeOral8.8 mg/1
LozengeOral8.2 mg/1
TabletOral
LozengeOral5.4 mg/1
LozengeOral6.4 mg/1
LozengeOral4.3 mg/1
LozengeOral5 mg/1
LozengeOral4.6 mg/1
LozengeOral5.6 mg/1
LozengeOral2.7 mg/1
LozengeOral3.2 mg/1
LozengeOral9.4 mg/1
LozengeOral3.7 mg/1
LozengeOral5.8 mg/1
LozengeOral6.6 mg/1
LozengeOral6.7 mg/1
LozengeOral15 mg/1
LozengeOral2.5 mg/1
LozengeOral7.6 mg/1
LozengeOral3.1 mg/1
LozengeOral18 mg/1
SyrupOral.1 g/100mL
PoulticeTransdermal280 mg/12g
OintmentRectal
LozengeOral5.5 mg/2.51
LozengeOral1.6 mg/1
LozengeOral5.5 mg/1
LozengeOral6 mg/1
GelTopical4840 mg/g
LozengeOral3.18 mg/1
LozengeOral7.5 1/1
LozengeOral3.9 mg/1
LozengeOral8.6 mg/2.5g
CreamTopical12.5 mg/mL
GelTopical.3 g/100mL
LiquidTopical12.5 mg/mL
GelTopical34.79 mg/mL
CreamTopical2 mg/g
GelTopical2.27 g/227g
GelTopical2.84 mg/227mg
GelTopical.02 g/100g
GelTopical16.95 g/113g
JellyTopical2 %
GelTopical55 mg/mL
PatchTopical336 mg/1
StickTopical
PatchTopical210 mg/1
PatchTopical205.5 mg/1
PatchTopical428.5 mg/1
PatchTopical50.25 mg/1
LiquidTopical.16 g/mL
PatchTopical866.25 mg/1
PatchTopical787.5 mg/1
CreamTopical.075 g/g
GelTopical.16 g/g
OilTopical16 g/100mL
GelTopical5 mg/5mL
LiquidTopical.1 g/100mL
SoapTopical4 mg/mL
LozengeOral5 mg/100mg
CreamTopical50 mg/g
LotionTopical8.5 g/100mL
LiquidTopical10 g/100mL
ShampooTopical1 mg/mL
CreamTopical30 mg/mL
GelTopical10 g/100g
LotionTopical8.5 mg/88mL
LotionTopical3.5 g/100g
CreamDental
Plaster; swabTopical
PlasterTransdermal3 g/100g
OilTopical.8 mg/50mL
SprayTopical.005 g/g
PatchTopical50 mg/g
PatchTransdermal
KitOral
OintmentTopical1 mg/g
LozengeOral5.75 mg/1
PowderTopical
LozengeOral1 mg/1
LotionTopical3 g/100g
MouthwashDental; Oral
GelTopical50 mg/mL
PowderTopical.1 g/g
LipstickTopical5 mg/g
Aerosol, sprayTopical
GelTopical.07 g/g
SwabTopical
CreamTopical
StickTopical.9 g/100g
CreamTopical5 1/85g
ClothTopical.05 g/mL
PatchTopical
LozengeOral17.3 mg
LozengeOral1.7 mg
CreamTopical8 g/100g
OilTopical.5 mg/50mL
PowderTopical2.8 g/283g
PowderTopical2.83 g/283g
LozengeOral5.4 1/1
LozengeOral8 mg/1
OintmentTopical
GelTopical30 mg/mL
GelTopical20 mg/g
LotionTopical
SalveTopical.5 g/100g
LinimentPercutaneous; Transdermal1 g/3500mL
SalveTopical1 g/1500g
CreamTopical.028 g/28g
CreamTopical.224 g/224g
LiquidTopical1.8 mL/90mL
CreamTopical3 g/100g
CreamTopical1.5 g/100mL
SprayTopical5 mg/mL
LozengeOral8.6 mg/1
MouthwashOral
CreamTopical2.5 g/100g
GelTopical3.5 g/100mL
CreamTopical1.05 g/42g
GelTopical40 mg/mL
SprayTopical100 mg/mL
GelTopical5 %
CreamTopical5 uL/mL
CreamTopical20 uL/mL
LinimentTopical
LotionTopical60 mg/mL
MouthwashOral.3 mg/mL
LozengeOral1.8 mg/1
LozengeOral3 1/1
LozengeOral2 mg/1
LozengeOral3.5 mg/1
LozengeOral1.5 mg/1
LozengeOral1.2 mg/1
LozengeOral2 mg/3g
CreamTopical1.25 %
CreamTopical1.25 g/100g
Aerosol, foamTopical5 mg/100mg
Aerosol, sprayTopical1 mg/100mg
Aerosol, sprayTopical5 mg/100mg
CreamTopical10 mg/100mg
LiquidTopical10 mg/100mg
SprayTopical.1 mg/100mg
LiquidTopical.2 g/10mL
Tablet, solubleOral
PowderOral
SprayTopical.5 g/100mL
OintmentTopical1.25 g/100g
GelTopical3 %
GelTopical.33 mg/660mL
GelTopical.63 g/632.19g
LozengeOral10 mg/1
PastilleOral10 mg/1
LiquidOral
GelOral; Topical
PasteTopical
CreamTopical1.3 g/100g
CreamTopical14 g/280g
GranuleTopical1.6 mg/g
Kit
LiquidTopical2.23 mg/mL
OilTopical12.18 mg/mL
OilTopical17.62 mg/mL
PatchTopical160 mg/mL
TinctureTopical
GelTopical2.4 g/120g
GelTopical35 mg/mL
GelTopical4.54 g/g
PatchTopical.2 1/1
CreamTopical4.25 g/85g
LotionTopical160 mg/mL
PatchTopical5 g/1001
PatchTopical.75 g/1
PatchTopical1.22 g/1
PatchTopical350 mg/1
PatchTopical775 mg/1
PowderTopical1 g/100g
GelTopical31 mg/mL
SolutionTopical104 mg/mL
SprayTopical104 mg/mL
PowderTopical20 mg/2g
ShampooTopical.1 g/100mL
OintmentTopical13 g/100g
OilTopical15 g/100mL
EmulsionTopical
GelTopical2 mL/100mL
CreamCutaneous; Topical
OintmentCutaneous; Topical
GelCutaneous; Topical
SprayTopical8 g/100mL
GelTopical8 g/100mL
LotionTopical3 g/100mL
LiquidTopical80 mg/mL
PatchTopical.875 g/100g
LiquidTopical34.86 g/L
GelTopical3.5 mg/L
LiquidTopical34.79 g/L
CreamTopical118.29 mL/100mL
OintmentTopical12.7 mg/g
OintmentTopical937.5 mg/g
GelTopical27.5 mg/g
OilTopical7 mg/50mL
PatchTopical50 g/1
GelTopical6 g/100g
GelTopical20 mg/mL
GelPercutaneous; Topical; Transdermal
PatchPercutaneous; Topical; Transdermal
Aerosol, sprayPercutaneous; Topical; Transdermal
Aerosol, foamPercutaneous; Topical; Transdermal
CreamTopical4 g/100g
GelTopical140 mg/mL
Paste, dentifriceTopical.2 g/100g
PlasterTopical
GelTopical12.5 mg/g
GelTopical12.6 mg/g
GelTopical2.6 mg/100g
LiquidCutaneous; Topical; Transdermal
CreamOral6 g/100mL
KitOral; Topical
LozengeOral9.1 mg/1
LozengeOral6.5 mg/1
GelTopical2.25 g/100g
MouthwashDental
GelTopical.06 g/g
Solution / dropsTopical
StickTopical0.5 %
LozengeOral
GelTopical2 %
GelTopical.1 g/g
GelTopical100 g/mL
SprayTopical6 mL/100mL
GelTopical80 mg/g
GelTopical.08 g/g
OilTopical1 g/93mL
GelTopical3.9 g/100mL
LozengeOral6.9 mg/1
LozengeOral2.6 mg/1
LozengeOral4.1 mg/1
LozengeOral1.1 mg/1
LozengeOral3 mg/1
LozengeOral2.2 mg/1
LinimentTransdermal3.5 mg/100mL
OilTopical24.56 mg/mL
OilTopical1.3 mg/50mg
StickTopical.6 g/100g
GelTopical3.5 mL/100mL
LozengeOral4.8 mg/1
LozengeOral5.3 mg/1
GelTopical60 mg/mL
GelTopical.04 g/g
SprayTopical6 g/100mL
PastilleOral2.5 mg/1
PatchTransdermal3 g/1
CreamTopical.1 g/100g
PlasterTransdermal
PoulticeTransdermal
LotionTopical.5 g/100g
KitTopical
GelTopical5 g/100mL
LiquidRespiratory (inhalation)
SalveTopical
LozengeOral.3 %
LozengeOral.307 %
LozengeOral1.7 mg/1
LozengeOral3.3 mg/1
LiquidOral.125 %
GelTopical3 g/100g
GelTopical.1 g/100g
GelTopical
SprayOral2 g/100mL
GelTopical6 g/120g
PatchTopical5 1/1
OilTransdermal
LotionTopical1 g/100mL
Gum, chewingOral
PlasterTopical; Transdermal
GelTopical3 g/227g
LinimentPercutaneous; Transdermal3 g/100mL
LinimentPercutaneous; Transdermal
PatchTopical10 mg/1000mg
GelTopical20 g/L
GelTopical37 mg/mL
GelTopical37 mg/g
SprayTopical37 mg/g
Kit
Prices
Unit descriptionCostUnit
Cool & heat patch1.2USD patch
Icy hot medicated 5% patch1.2USD patch
Bengay pain relieving patch1.13USD patch
CVS Pharmacy pain relieving patch1.11USD patch
Cold & hot pain rel patch1.05USD patch
Nuprin muscle & joint patch1.03USD patch
Mentholatum pain patch0.93USD patch
CVS Pharmacy cold & hot medicated patch0.89USD patch
Salonsip aqua-patch0.69USD patch
Menthol crystal0.49USD g
Menthol cough drops0.06USD each
CVS Pharmacy menthol drops0.03USD each
Pv menthol cough drops0.02USD each
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US8809615No2010-01-032030-01-03Us
US9233184No2007-08-012027-08-01Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)43 °CPhysProp
boiling point (°C)212 °CPhysProp
water solubility490 mg/L (at 25 °C)CHEM INSPECT TEST INST (1992)
logP3.40GRIFFIN,S ET AL. (1999)
Predicted Properties
PropertyValueSource
Water Solubility0.558 mg/mLALOGPS
logP2.68ALOGPS
logP2.66ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)19.55ChemAxon
pKa (Strongest Basic)-0.81ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.45 m3·mol-1ChemAxon
Polarizability19.69 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9944
Blood Brain Barrier+0.9408
Caco-2 permeable+0.8127
P-glycoprotein substrateNon-substrate0.569
P-glycoprotein inhibitor INon-inhibitor0.8765
P-glycoprotein inhibitor IINon-inhibitor0.9397
Renal organic cation transporterNon-inhibitor0.8591
CYP450 2C9 substrateNon-substrate0.7798
CYP450 2D6 substrateNon-substrate0.746
CYP450 3A4 substrateSubstrate0.5912
CYP450 1A2 substrateNon-inhibitor0.7188
CYP450 2C9 inhibitorNon-inhibitor0.8484
CYP450 2D6 inhibitorNon-inhibitor0.9451
CYP450 2C19 inhibitorNon-inhibitor0.9185
CYP450 3A4 inhibitorNon-inhibitor0.9458
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9546
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.8439
BiodegradationNot ready biodegradable0.7808
Rat acute toxicity1.7142 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8439
hERG inhibition (predictor II)Non-inhibitor0.7727
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (2.96 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-0006-1900000000-cc06fe70d7649d059f92
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-00ea-9100000000-0be605183591bf5f33a0
GC-MS Spectrum - EI-BGC-MSsplash10-00ea-9100000000-977cf0c036d597693beb
GC-MS Spectrum - GC-MSGC-MSsplash10-0006-1900000000-cc06fe70d7649d059f92
Mass Spectrum (Electron Ionization)MSsplash10-00ea-9100000000-602436010653202a4da9
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-053r-9300000000-d9c35833e73c8655fb23
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-0ldl-9000000000-abf2f837df49fbedc53c
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-0007-9000000000-adee6385265c6606326d
MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , PositiveLC-MS/MSsplash10-00ea-9100000000-e3f1b7b69a021063fabb
MS/MS Spectrum - EI-B (JEOL JMS-DX-300) , PositiveLC-MS/MSsplash10-00ea-9100000000-d69777874c9615b7e751
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Monoterpenoids
Direct Parent
Menthane monoterpenoids
Alternative Parents
Monocyclic monoterpenoids / Cyclohexanols / Cyclic alcohols and derivatives / Hydrocarbon derivatives
Substituents
P-menthane monoterpenoid / Monocyclic monoterpenoid / Cyclohexanol / Cyclic alcohol / Secondary alcohol / Organic oxygen compound / Hydrocarbon derivative / Organooxygen compound / Alcohol / Aliphatic homomonocyclic compound
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
p-menthan-3-ol (CHEBI:15409) / Menthane monoterpenoids, Cyclic monoterpenes (C00400) / Menthane monoterpenoids (LMPR0102090001)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inducer
General Function
Calcium channel activity
Specific Function
Receptor-activated non-selective cation channel involved in detection of sensations such as coolness, by being activated by cold temperature below 25 degrees Celsius. Activated by icilin, eucalypto...
Gene Name
TRPM8
Uniprot ID
Q7Z2W7
Uniprot Name
Transient receptor potential cation channel subfamily M member 8
Molecular Weight
127684.035 Da
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:12654248]
  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:14757700]
  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:15046718]
  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:15190109]
  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:15311065]
  6. Eccles R: Menthol and related cooling compounds. J Pharm Pharmacol. 1994 Aug;46(8):618-30. [PubMed:7529306]
  7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inducer
General Function
Temperature-gated cation channel activity
Specific Function
Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in t...
Gene Name
TRPA1
Uniprot ID
O75762
Uniprot Name
Transient receptor potential cation channel subfamily A member 1
Molecular Weight
127499.88 Da
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:12654248]
  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:15931068]
  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:16829128]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inducer
General Function
Calcium channel activity
Specific Function
Putative receptor-activated non-selective calcium permeant cation channel. It is activated by innocuous (warm) temperatures and shows an increased response at noxious temperatures greater than 39 d...
Gene Name
TRPV3
Uniprot ID
Q8NET8
Uniprot Name
Transient receptor potential cation channel subfamily V member 3
Molecular Weight
90635.115 Da
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:16829128]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Opioid receptor activity
Specific Function
G-protein coupled opioid receptor that functions as receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as receptor for various synt...
Gene Name
OPRK1
Uniprot ID
P41145
Uniprot Name
Kappa-type opioid receptor
Molecular Weight
42644.665 Da
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:11897159]
  2. Taniguchi Y, Deguchi Y, Saita M, Noda K: [Antinociceptive effects of counterirritants]. Nihon Yakurigaku Zasshi. 1994 Dec;104(6):433-46. [PubMed:7851817]

Drug created on June 13, 2005 07:24 / Updated on December 10, 2017 17:18