Identification

Summary

Menthol is an organic compound used to treat mild to moderate muscle and joint pain.

Brand Names
Absorbine Jr Antifungal, Mentholatum, Salonpas Gel-patch
Generic Name
Levomenthol
Commonly known or available as Menthol
DrugBank Accession Number
DB00825
Background

Menthol is a covalent organic compound made synthetically or obtained from peppermint or other mint oils. Forming clear or white waxy, crystalline substance, menthol is typically solid at room temperature. (-)-Menthol is the naturally-occurring and main form of menthol, and is assigned the (1R,2S,5R) configuration. Menthol mediates anesthetic properties and anti-irritating properties locally, thus it is widely used to relieve minor throat irritations.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 156.2652
Monoisotopic: 156.151415262
Chemical Formula
C10H20O
Synonyms
  • (-)-Menthol
  • (−)-(1R,3R,4S)-menthol
  • (−)-menthol
  • (1alpha,2beta,5alpha)-5-methyl-2(1-methylethyl)cyclohexanol
  • (1R-(1-α,2-β,5-α))-5-methyl-2-(1-methylethyl)cyclohexanol
  • (1R,3R,4S)-(−)-menthol
  • L-menthol
  • Levomenthol
  • Lévomenthol
  • Levomentholum
  • Levomentol
  • Mentol
External IDs
  • FEMA NO. 2665, (-)-
  • NPO-11
  • NSC-62788

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.

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Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Menthol is a covalent organic compound made synthetically or obtained from peppermint or other mint oils. Menthol induces a cooling sensation on the skin upon inhalation, oral ingestion, or topical application by stimulating the cold-sensitive receptors expressed on the skin, without actually causing a drop in the skin 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
Humans
ATransient receptor potential cation channel subfamily A member 1
inducer
Humans
ATransient receptor potential cation channel subfamily V member 3
inducer
Humans
AVoltage-dependent L-type calcium channel
antagonist
Humans
UKappa-type opioid receptor
agonist
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Hover over products below to view reaction partners

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Menthol, DL: ORAL (LD50): Acute: 2900 mg/kg [Rat], 3100 mg/kg [Mouse]. DERMAL (LD50): Acute: 5001 mg/kg Rabbit.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbametapirThe serum concentration of Levomenthol can be increased when it is combined with Abametapir.
AcebutololLevomenthol may increase the arrhythmogenic activities of Acebutolol.
AceclofenacThe risk or severity of hyperkalemia can be increased when Levomenthol is combined with Aceclofenac.
AcemetacinThe risk or severity of hyperkalemia can be increased when Levomenthol is combined with Acemetacin.
AcetyldigitoxinAcetyldigitoxin may increase the arrhythmogenic activities of Levomenthol.
AcrivastineThe risk or severity of QTc prolongation can be increased when Levomenthol is combined with Acrivastine.
AdenosineAdenosine may increase the arrhythmogenic activities of Levomenthol.
AjmalineLevomenthol may increase the arrhythmogenic activities of Ajmaline.
AlclofenacThe risk or severity of hyperkalemia can be increased when Levomenthol is combined with Alclofenac.
AlfentanilAlfentanil may increase the bradycardic activities of Levomenthol.
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Food Interactions
No interactions found.

Products

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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
21ST CENTURY CHILDREN'S VAPOR BALMOintmentTopical21ST CENTURY PRODUCTS SDN. BHD.2020-09-08Not applicableMalaysia flag
Absorbine BackPatch5000 mg/8hTransdermalDSE Healthcare Solutions, LLC2013-10-152013-10-01US flag
AK47 Cooling Roll-OnLiquid4.2 g/84gTopicalRenu Laboratories, Inc.2020-06-01Not applicableUS flag
AK47 Cooling Roll-OnLiquid1.05 g/84gTopicalRenu Laboratories, Inc.2020-06-01Not applicableUS flag
Antiphlogistine Rub A-535 Ice Gel 4%Gel4 %TopicalCarter Products, Division Of Carter Wallace Ns Inc.1993-12-311997-08-14Canada flag
Aromalief Pain Relief CreamLotion1 g/100gTopicalMarketites Llc2020-04-01Not applicableUS flag
Arthritis WonderCream8.5 mg/85gTopicalG2 Products Llc2018-01-312018-01-31US flag
Artic Ice Analgesic Gel 2.5%Gel2.5 %TopicalScott Chemical Canada1998-10-282009-08-26Canada flag
Avon Healthy Remedies Menthol Celadrin Pain Relief CreamCream1.25 %TopicalAvon Products, Inc.2004-04-272009-03-05Canada flag
Ben-gay IceGel2.5 %TopicalPfizer Canada Inc., Consumer Healthcare Division1997-06-162001-08-02Canada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Absorbine Jr Antifungal LiqLevomenthol (200 mg / 100 mL) + Tolnaftate (1 g / 100 mL)LiquidTopicalClarion Brands, Llc1994-12-31Not applicableCanada flag
Absorbine Jr Extra Strength LinimentLevomenthol (4.0 %) + Chloroxylenol (0.5 %)LiquidTopicalBridges Consumer Healthcare Llc1992-12-31Not applicableCanada flag
Absorbine Jr LinimentLevomenthol (1.25 %) + Chloroxylenol (0.5 %)SolutionTopicalBridges Consumer Healthcare Llc1993-12-31Not applicableCanada flag
Absorbine Power GelLevomenthol (4 %) + Chloroxylenol (.5 %)GelTopicalW.F. Young, Inc.1993-12-31Not applicableCanada flag
Aflexeryl-LCLevomenthol (1 g/100g) + Lidocaine hydrochloride (4 g/100g)PatchTopicalEasy Distributors, Llc2015-01-142016-01-05US flag
Aflexeryl-MCLevomenthol (5 g/100g) + Capsaicin (0.0375 g/100g)PatchTopicalEasy Distributors, Llc2015-01-142016-01-05US flag
Air Sinsinpas-EXLevomenthol (6.4 g/200mL) + Methyl salicylate (3.5 g/200mL) + Synthetic camphor (6 g/200mL)SprayTopicalSinsin Pharmaceutical Co., Ltd.2017-08-22Not applicableUS flag
Alsirub OntLevomenthol (4 %) + Eucalyptol (2.5 %) + Methyl salicylate (7.5 %)OintmentTopicalAlsi Cie Ltee1977-12-312003-05-21Canada flag
Amber Mouth Wash - LiqLevomenthol (0.042 %) + Eucalyptol (0.092 %) + Thymol (0.064 %)LiquidDentalPerrigo International1996-10-091999-08-06Canada flag
Amber Mouthwash - LiqLevomenthol (0.042 %) + Eucalyptol (0.092 %) + Thymol (0.064 %)LiquidDentalPerrigo International1996-06-301999-08-06Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Antiphlamine Coin PlasterLevomenthol (2.769 mg/0.2832g) + Diphenhydramine (0.246 mg/0.2832g) + Synthetic camphor (1.108 mg/0.2832g)PatchTopicalHanul Trading Co., Ltd.2016-10-102017-04-14US flag
Antiphlamine Coin PlasterLevomenthol (2.769 mg/0.2832g) + DL-alpha-Tocopherol (0.308 mg/0.2832g) + Diphenhydramine (0.246 mg/0.2832g) + Methyl salicylate (5.541 mg/0.2832g) + Nonivamide (0.046 mg/0.2832g) + Peppermint oil (0.693 mg/0.2832g) + Synthetic camphor (1.108 mg/0.2832g)PatchTopicalHanul Trading Co., Ltd.2016-10-10Not applicableUS flag
Atomy Herbal Hair TonicLevomenthol (0.6 mL/200mL) + Dexpanthenol (0.4 mL/200mL) + Salicylic acid (0.5 mL/200mL)LiquidTopicalAtomy Co., Ltd.2010-04-29Not applicableUS flag
BenzocaineLevomenthol (1 mg/1g) + Benzocaine (20 mg/1g)SwabTopicalMcKesson2020-01-162024-06-01US flag
Crazyskin BeersLevomenthol (0.3 g/100g) + Dexpanthenol (0.2 g/100g) + Salicylic acid (0.25 g/100g)ShampooTopicalCrazy Skin Co., Ltd.2020-02-22Not applicableUS flag
Crazyskin Beers PremiumLevomenthol (0.3 g/100g) + Dexpanthenol (0.2 g/100g) + Salicylic acid (0.25 g/100g)ShampooTopicalCrazy Skin Co., Ltd.2020-12-05Not applicableUS flag
DbkLevomenthol (470 mg/1) + Lidocaine (2.35 mg/1)PatchTopicalKaylana Pharm, Inc.2015-01-012015-01-01US flag
EVERYTOKTOK Hair TonicLevomenthol (0.36 g/120mL) + Dexpanthenol (0.24 g/120mL) + Salicylic acid (0.30 g/120mL)LiquidTopicalDreamin2021-03-01Not applicableUS flag
Ion-TO Scalp Cleanser SLevomenthol (0.0025 g/500g)ShampooTopicalHUSAZOMO USA2019-06-10Not applicableUS flag
Jikimi PatchLevomenthol (0.03 1/1) + Ethanol (0.07 1/1) + Eucalyptus oil (0.2 1/1)PatchTopicalBM Pharmaceutical Co., Ltd.2020-05-01Not applicableUS flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Alcohol / Aliphatic homomonocyclic compound / Cyclic alcohol / Cyclohexanol / Hydrocarbon derivative / Monocyclic monoterpenoid / Organic oxygen compound / Organooxygen compound / P-menthane monoterpenoid / Secondary alcohol
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
p-menthan-3-ol (CHEBI:15409) / Menthane monoterpenoids, Cyclic monoterpenes (C00400) / Menthane monoterpenoids (LMPR0102090001)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
BZ1R15MTK7
CAS number
2216-51-5
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
CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O

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
Human Metabolome Database
HMDB0003352
KEGG Drug
D00064
KEGG Compound
C00400
PubChem Compound
16666
PubChem Substance
46506513
ChemSpider
15803
BindingDB
50318482
RxNav
236388
ChEBI
15409
ChEMBL
CHEMBL470670
ZINC
ZINC000001482164
Therapeutic Targets Database
DAP000876
PharmGKB
PA164776605
Guide to Pharmacology
GtP Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Menthol
MSDS
Download (73.2 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentActinic Keratosis (AK)1
4CompletedTreatmentDiaper Dermatitis1
4CompletedTreatmentSmoking / Smoking, Cessation1
4Not Yet RecruitingBasic ScienceAcute Exercise / Heat Exposure1
4Unknown StatusBasic ScienceGingivitis / Oral Biofilm / Periodontitis1
4Unknown StatusPreventionBiofilms / Oils, Essential / Periodontitis1
4Unknown StatusPreventionBiofilms / Oils, Essential / Substantivity1
4Unknown StatusPreventionOral Biofilm / Periodontitis / Plaque, Dental1
3CompletedDiagnosticPatients Undergoing Gastrointestinal Endoscopy1
3CompletedTreatmentColon Nos Polypectomy Tubular Adenoma / Gastric Adenoma / Malignant Neoplasm of Stomach1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Active and Innovative Inc.
  • Bergen Brunswig
  • Chain Drug
  • Chattem Chemicals Inc.
  • CVS Pharmacy
  • Dofs Laboratories
  • Gold Mints Products Co. Ltd.
  • Herbion Pakistan Pvt Ltd.
  • Hisamitsu Pharmaceuticals
  • Humco
  • Major Pharmaceuticals
  • Medicine Shop
  • Mentholatum Co.
  • Nutri Dyn Products Limited
  • Pfizer Inc.
  • Walgreen Co.
Dosage Forms
FormRouteStrength
OintmentTopical
OintmentNasal
PatchTransdermal5000 mg/8h
SprayTopical
LiquidTopical1.05 g/84g
LiquidTopical4.2 g/84g
LiquidBuccal
KitOral; Topical
GelTopical4 %
LotionTopical1 g/100g
CreamTopical8.5 mg/85g
AerosolTopical
LiquidRespiratory (inhalation)6 %
OilTopical
OilPercutaneous; Topical; Transdermal
CreamTopical8 g
GelTopical2.5 g
GelTopical2.5 %
TabletTransmucosal
OintmentCutaneous
CreamTopical100 mg / g
LozengeOral2.7 mg / loz
Tablet, chewableOral
SwabTopical
GelTopical3.5 %W/W
SprayTopical10 %W/W
SolutionTopical10 %
GelTopical3.5 g
CreamTopical10 g/100g
OintmentRespiratory (inhalation); Topical
LiquidOral
SolutionRespiratory (inhalation)
LozengeOral1 mg / loz
LozengeOral1.5 mg / loz
StickTopical
Oil
MouthwashBuccal; Oral
GelTransdermal
PatchTransdermal
LotionTopical160 mg/1mL
LozengeOral5 mg / loz
LozengeOral7 mg/1
GelTopical
ShampooTopical
PlasterTransdermal
SuppositoryRectal
LotionTopical
LozengeOral8.4 mg / loz
LozengeOral6.1 mg / loz
OintmentTopical
Solution / dropsBuccal
PatchTopical750 mg/1
LozengeOral8.5 mg/1
LiquidRespiratory (inhalation)1 %w/v
SprayTopical
SolutionBuccal; Oral
SyrupOral
Capsule
LiquidRespiratory (inhalation)
Plaster
LozengeOral
LozengeOral5.75 MG
Tablet
LozengeOral4.6 MG
JellyTopical10 %
GelTopical16 %
GelTopical7 %
GelTopical6 %
LozengeOral3 mg
LozengeOral6.0 mg
LinimentTopical
PatchCutaneous; Topical; Transdermal
Solution, concentrateOral
PowderTopical
LozengeOral10 mg/1
TabletOral
LozengeOral5.6 mg/1
LotionTopical4 g/100g
OintmentRectal
LozengeOral
PastilleOral0.281 mg/1
PlasterTopical
JellyTopical2 %
Drug delivery systemTopical5 g
GelTopical1.25 mL/100mL
ShampooTopical0.0025 g/500g
PastilleOral
LotionTopical3.5 g/100g
Plaster; swabTopical
PlasterTransdermal
GelTopical0.23 mg/1mL
LozengeOral2.5 mg/1
CreamTopical5.6 g/112g
LotionTopical11.2 g/224g
JellyTopical
PatchTopical20 mg/11.7g
LozengeOral17.3 mg
LozengeOral1.7 mg / loz
PowderTopical
PowderTopical1 %
PowderCutaneous
RinseOral
CreamTopical
GelTopical25 mg/1g
GelTopical5 %
CreamTopical1.25 %
GelDental
KitOral
GelTopical3 %
GelTopical
GelOral; Topical
PatchTopical
SolutionOral
LotionTopical0.5 g/100g
GelTopical2 g/100g
SolutionTopical
PasteTopical
LiquidTopical
CapsuleOral
SolutionCutaneous
CreamRectal
SprayCutaneous
Aerosol, sprayTopical
LiquidCutaneous; Topical; Transdermal
StickTopical0.5 %
GelTopical2 %
PlasterCutaneous
Ointment
CreamCutaneous
OintmentTopical4 g
OilTopical
SolutionIntrasinal; Respiratory (inhalation)
LozengeOral.3 %
LozengeOral.307 %
StickNasal
InhalantNasal
LozengeOral5 mg
OintmentTopical5 %
LiquidOral.125 %
SolutionNasal
Gum, chewingOral
Paste, dentifriceTopical
LozengeOral2.68 mg
EmulsionOral
SuspensionOral
Pill
LiquidDental
GelTopical4 %w/w
GelTopical7 %w/w
EmulsionTopical
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)Region
US8809615No2014-08-192030-01-03US flag
US9233184No2016-01-122027-08-01US flag

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

Targets

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Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  6. Eccles R: Menthol and related cooling compounds. J Pharm Pharmacol. 1994 Aug;46(8):618-30. [Article]
  7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Kind
Protein
Organism
Humans
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. [Article]
Kind
Protein group
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Voltage-gated calcium channel activity
Specific Function
Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hor...

Components:
References
  1. Grigoleit HG, Grigoleit P: Pharmacology and preclinical pharmacokinetics of peppermint oil. Phytomedicine. 2005 Aug;12(8):612-6. doi: 10.1016/j.phymed.2004.10.007. [Article]
  2. Hawthorn M, Ferrante J, Luchowski E, Rutledge A, Wei XY, Triggle DJ: The actions of peppermint oil and menthol on calcium channel dependent processes in intestinal, neuronal and cardiac preparations. Aliment Pharmacol Ther. 1988 Apr;2(2):101-18. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  2. Taniguchi Y, Deguchi Y, Saita M, Noda K: [Antinociceptive effects of counterirritants]. Nihon Yakurigaku Zasshi. 1994 Dec;104(6):433-46. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Uesawa Y, Takeuchi T, Mohri K: Integrated analysis on the physicochemical properties of dihydropyridine calcium channel blockers in grapefruit juice interactions. Curr Pharm Biotechnol. 2012 Jul;13(9):1705-17. [Article]

Drug created at June 13, 2005 13:24 / Updated at August 16, 2022 01:02