LEVOMENTHOL

US Approved OTC

First marketed in 1921

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H20O
Molecular Weight	156.2652
Optical Activity	( - )
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O

InChI

InChIKey=NOOLISFMXDJSKH-KXUCPTDWSA-N

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

HIDE SMILES / InChI

Molecular Formula	C10H20O
Molecular Weight	156.2652
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18640220https://www.drugbank.ca/drugs/DB00825https://www.google.com/patents/WO1996014840A1
Curator's Comment: description was created based on several sources, including: http://www.tera.org/OARS/Menthol%20WEEL%20FINAL.pdf | http://www.inchem.org/documents/sids/sids/MENTHOLS.pdf

Menthyl lactate is derived from menthol, a compound that comes from peppermint oil, or is made synthetically. Menthol has a natural cooling effect, which makes it useful as a topical analgesic to treat skin irritation, pain, itching or sunburn. Despite its cooling benefits, menthol can be a skin irritant. Like menthol, menthyl lactate is cooling, but it causes less skin irritation than menthol. Menthyl lactate also has a refreshing, minty taste. For this reason, some manufacturers use it as a flavoring ingredient. The compound is recommended for use as a flavor in concentrations of 0.005% to 0.2% and in cosmetic and other external products in concentrations ranging from 0.2% to 2.0%. Menthyl lactate is a known compound available e.g. from Haarmann & Reimer GmbH (Germany) under the name FRESCOLAT, Type ML.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Cytochrome P450 2A6 16 Target ID: CHEMBL5282 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18640220	Inhibitor 8504	37.8 µM [IC50]
Cytochrome P450 3A4 127 Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18640220	Inhibitor 8504	300.0 µM [IC50]
Transient receptor potential cation channel subfamily M member 8 18 Target ID: Q7Z2W7 Gene ID: 79054.0 Gene Symbol: TRPM8 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16829128	Agonist 2752	30.0 µM [EC50]
Transient receptor potential cation channel subfamily A member 1 38 Target ID: O75762 Gene ID: 8989.0 Gene Symbol: TRPA1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16829128	Antagonist 2849	68.0 µM [IC50]
Kappa-type opioid receptor 61 Target ID: P41145 Gene ID: 4986.0 Gene Symbol: OPRK1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/11897159	Activator 1447

Conditions

Condition	Modality	Highest Phase	Product
Simple backache 18 Sources: https://www.drugs.com/otc/100498/bengay-vanishing-scent-pain-relieving.html	Palliative	Approved 8583	BENGAY Approved Use temporarily relieves the minor aches and pains of muscles and joints associated with a simple backache, arthritis, strains, bruises, sprains.
Arthritis 87 Sources: https://www.drugs.com/otc/100498/bengay-vanishing-scent-pain-relieving.html	Palliative	Approved 8583	BENGAY Approved Use temporarily relieves the minor aches and pains of muscles and joints associated with a simple backache, arthritis, strains, bruises, sprains.
Sore throat 18 Sources: http://www.tabletwise.com/medicine/racementhol	Palliative	Approved 8583	Unknown Approved Use Unknown
Common cold 58 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e69a7c9b-fd04-4109-a7c8-6edfd83855fc	Palliative	Approved 8583	VICKS VAPORUB Approved Use On chest and throat, temporarily relieves cough due to common cold
Mild pain 6 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e69a7c9b-fd04-4109-a7c8-6edfd83855fc	Primary	Approved 8583	VICKS VAPORUB Approved Use On muscles and joints, temporarily relieves minor aches and pains
Itching 52 Sources: https://www.drugs.com/otc/108969/cvs-anti-itch.html	Primary	Approved 8583	CVS ANTI ITCH Approved Use For the temporary relief of pain and itching associated with minor skin irritations such as poison ivy/oak/sumac, sunburn, insect bites and minor cuts and scrapes.
Rhinitis 19 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12662469	Palliative	Approved 8583	VICKS VAPORUB Approved Use Treatment for rhinitis that is associated with acute upper respiratory tract infection and allergy
Gastrointestinal endoscopy 6 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26632191	Palliative	Phase III 665	Unknown Approved Use Unknown
Pain 619 Sources: https://www.google.com/patents/WO1996014840A1	Primary	Not Provided 511	FRESCOLAT ML Approved Use The compund is uses as a flavoring ingredient and in cosmetics as a cooling agent

C_max

Value	Dose	Analyte	Population
32.89 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2010/P201000059/530277000_22200AMX00965_A100_1.pdf#page=20 \| https://www.pmda.go.jp/drugs/2010/P201000059/530277000_22200AMX00965_K101_1.pdf#page=20 \| https://pubmed.ncbi.nlm.nih.gov/21544078/	80 mg single, intragastric dose: 80 mg route of administration: Intragastric experiment type: SINGLE co-administered:	LEVOMENTHOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
31.6 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2010/P201000059/530277000_22200AMX00965_A100_1.pdf#page=20 \| https://www.pmda.go.jp/drugs/2010/P201000059/530277000_22200AMX00965_K101_1.pdf#page=20 \| https://pubmed.ncbi.nlm.nih.gov/21544078/	160 mg single, intragastric dose: 160 mg route of administration: Intragastric experiment type: SINGLE co-administered:	LEVOMENTHOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
48 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2010/P201000059/530277000_22200AMX00965_A100_1.pdf#page=20 \| https://www.pmda.go.jp/drugs/2010/P201000059/530277000_22200AMX00965_K101_1.pdf#page=20 \| https://pubmed.ncbi.nlm.nih.gov/21544078/	320 mg single, intragastric dose: 320 mg route of administration: Intragastric experiment type: SINGLE co-administered:	LEVOMENTHOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
5617.46 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2010/P201000059/530277000_22200AMX00965_A100_1.pdf#page=20 \| https://www.pmda.go.jp/drugs/2010/P201000059/530277000_22200AMX00965_K101_1.pdf#page=20 \| https://pubmed.ncbi.nlm.nih.gov/21544078/	80 mg single, intragastric dose: 80 mg route of administration: Intragastric experiment type: SINGLE co-administered:	MENTHOL GLUCURONIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
9882.69 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2010/P201000059/530277000_22200AMX00965_A100_1.pdf#page=20 \| https://www.pmda.go.jp/drugs/2010/P201000059/530277000_22200AMX00965_K101_1.pdf#page=20 \| https://pubmed.ncbi.nlm.nih.gov/21544078/	160 mg single, intragastric dose: 160 mg route of administration: Intragastric experiment type: SINGLE co-administered:	MENTHOL GLUCURONIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
17601.81 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2010/P201000059/530277000_22200AMX00965_A100_1.pdf#page=20 \| https://www.pmda.go.jp/drugs/2010/P201000059/530277000_22200AMX00965_K101_1.pdf#page=20 \| https://pubmed.ncbi.nlm.nih.gov/21544078/	320 mg single, intragastric dose: 320 mg route of administration: Intragastric experiment type: SINGLE co-administered:	MENTHOL GLUCURONIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
45.46 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2010/P201000059/530277000_22200AMX00965_A100_1.pdf#page=20 \| https://www.pmda.go.jp/drugs/2010/P201000059/530277000_22200AMX00965_K101_1.pdf#page=20 \| https://pubmed.ncbi.nlm.nih.gov/21544078/	80 mg single, intragastric dose: 80 mg route of administration: Intragastric experiment type: SINGLE co-administered:	LEVOMENTHOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
52.64 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2010/P201000059/530277000_22200AMX00965_A100_1.pdf#page=20 \| https://www.pmda.go.jp/drugs/2010/P201000059/530277000_22200AMX00965_K101_1.pdf#page=20 \| https://pubmed.ncbi.nlm.nih.gov/21544078/	160 mg single, intragastric dose: 160 mg route of administration: Intragastric experiment type: SINGLE co-administered:	LEVOMENTHOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
109.34 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2010/P201000059/530277000_22200AMX00965_A100_1.pdf#page=20 \| https://www.pmda.go.jp/drugs/2010/P201000059/530277000_22200AMX00965_K101_1.pdf#page=20 \| https://pubmed.ncbi.nlm.nih.gov/21544078/	320 mg single, intragastric dose: 320 mg route of administration: Intragastric experiment type: SINGLE co-administered:	LEVOMENTHOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
9676.67 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2010/P201000059/530277000_22200AMX00965_A100_1.pdf#page=20 \| https://www.pmda.go.jp/drugs/2010/P201000059/530277000_22200AMX00965_K101_1.pdf#page=20 \| https://pubmed.ncbi.nlm.nih.gov/21544078/	80 mg single, intragastric dose: 80 mg route of administration: Intragastric experiment type: SINGLE co-administered:	MENTHOL GLUCURONIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
15639.85 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2010/P201000059/530277000_22200AMX00965_A100_1.pdf#page=20 \| https://www.pmda.go.jp/drugs/2010/P201000059/530277000_22200AMX00965_K101_1.pdf#page=20 \| https://pubmed.ncbi.nlm.nih.gov/21544078/	160 mg single, intragastric dose: 160 mg route of administration: Intragastric experiment type: SINGLE co-administered:	MENTHOL GLUCURONIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
32115.5 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2010/P201000059/530277000_22200AMX00965_A100_1.pdf#page=20 \| https://www.pmda.go.jp/drugs/2010/P201000059/530277000_22200AMX00965_K101_1.pdf#page=20 \| https://pubmed.ncbi.nlm.nih.gov/21544078/	320 mg single, intragastric dose: 320 mg route of administration: Intragastric experiment type: SINGLE co-administered:	MENTHOL GLUCURONIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
1.0306 h OTHER GOV'T https://www.pmda.go.jp/drugs/2010/P201000059/530277000_22200AMX00965_A100_1.pdf#page=20 \| https://www.pmda.go.jp/drugs/2010/P201000059/530277000_22200AMX00965_K101_1.pdf#page=20 \| https://pubmed.ncbi.nlm.nih.gov/21544078/	80 mg single, intragastric dose: 80 mg route of administration: Intragastric experiment type: SINGLE co-administered:	LEVOMENTHOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1.7739 h OTHER GOV'T https://www.pmda.go.jp/drugs/2010/P201000059/530277000_22200AMX00965_A100_1.pdf#page=20 \| https://www.pmda.go.jp/drugs/2010/P201000059/530277000_22200AMX00965_K101_1.pdf#page=20 \| https://pubmed.ncbi.nlm.nih.gov/21544078/	160 mg single, intragastric dose: 160 mg route of administration: Intragastric experiment type: SINGLE co-administered:	LEVOMENTHOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1.222 h OTHER GOV'T https://www.pmda.go.jp/drugs/2010/P201000059/530277000_22200AMX00965_A100_1.pdf#page=20 \| https://www.pmda.go.jp/drugs/2010/P201000059/530277000_22200AMX00965_K101_1.pdf#page=20 \| https://pubmed.ncbi.nlm.nih.gov/21544078/	320 mg single, intragastric dose: 320 mg route of administration: Intragastric experiment type: SINGLE co-administered:	LEVOMENTHOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
7.8072 h OTHER GOV'T https://www.pmda.go.jp/drugs/2010/P201000059/530277000_22200AMX00965_A100_1.pdf#page=20 \| https://www.pmda.go.jp/drugs/2010/P201000059/530277000_22200AMX00965_K101_1.pdf#page=20 \| https://pubmed.ncbi.nlm.nih.gov/21544078/	80 mg single, intragastric dose: 80 mg route of administration: Intragastric experiment type: SINGLE co-administered:	MENTHOL GLUCURONIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
5.5689 h OTHER GOV'T https://www.pmda.go.jp/drugs/2010/P201000059/530277000_22200AMX00965_A100_1.pdf#page=20 \| https://www.pmda.go.jp/drugs/2010/P201000059/530277000_22200AMX00965_K101_1.pdf#page=20 \| https://pubmed.ncbi.nlm.nih.gov/21544078/	160 mg single, intragastric dose: 160 mg route of administration: Intragastric experiment type: SINGLE co-administered:	MENTHOL GLUCURONIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
5.8693 h OTHER GOV'T https://www.pmda.go.jp/drugs/2010/P201000059/530277000_22200AMX00965_A100_1.pdf#page=20 \| https://www.pmda.go.jp/drugs/2010/P201000059/530277000_22200AMX00965_K101_1.pdf#page=20 \| https://pubmed.ncbi.nlm.nih.gov/21544078/	320 mg single, intragastric dose: 320 mg route of administration: Intragastric experiment type: SINGLE co-administered:	MENTHOL GLUCURONIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
15.3% OTHER GOV'T https://www.pmda.go.jp/drugs/2010/P201000059/530277000_22200AMX00965_A100_1.pdf#page=13 \| https://www.pmda.go.jp/drugs/2010/P201000059/530277000_22200AMX00965_I100_1.pdf#page=20			LEVOMENTHOL plasma	Homo sapiens

Doses

Dose	Population	Adverse events
3 % single, topical Studied dose Dose: 3 % Route: topical Route: single Dose: 3 % Sources: https://pubmed.ncbi.nlm.nih.gov/31353997/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/31353997/	Other AEs: Swelling of limbs... Other AEs: Swelling of limbs (1 pt) Sources: https://pubmed.ncbi.nlm.nih.gov/31353997/

AEs

AE	Significance	Dose	Population
Swelling of limbs	1 pt	3 % single, topical Studied dose Dose: 3 % Route: topical Route: single Dose: 3 % Sources: https://pubmed.ncbi.nlm.nih.gov/31353997/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/31353997/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
UGT1A9 148 CYP2C19 2057 CYP1A2 2153 UGT2B17 31 UGT2B10 31 UGT2B7 197 CYP19A1 429 UGT1A10 37	UGT2B17 237 UGT2B7 456 UGT2A1 39 UGT1A10 331 UGT1A9 423

Drug as perpetrator

Target	Modality	Activity
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/165675#section=Biological-Test-Results Page: 1.0	no [IC50 5.1153 uM]
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/165675#section=Biological-Test-Results Page: 15.0	no
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/165675#section=Biological-Test-Results Page: 47.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/165675#section=Biological-Test-Results Page: 46.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/165675#section=Biological-Test-Results Page: 46.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/165675#section=Biological-Test-Results Page: 47.0	no
UGT1A9 155	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/31578206/	weak [IC50 1215 uM]
UGT1A10 46	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/31578206/	weak [IC50 1419 uM]
UGT2B10 33	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/31578206/	weak [IC50 202 uM]
UGT2B7 210	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/31578206/	weak [IC50 343 uM]
UGT2B17 33	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/31578206/	weak [IC50 995 uM]

Drug as victim

Target	Modality	Activity
UGT1A10 331	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/31578206/	yes [Km 1900 uM]
UGT2B7 456	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/31578206/	yes [Km 330 uM]
UGT2A1 39	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/31578206/	yes [Km 370 uM]
UGT2B17 237	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/31578206/	yes [Km 760 uM]
UGT1A9 423	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/31578206/	yes [Km 800 uM]

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/165675#section=Biological-Test-Results Page: 46.0

PubMed

Title	Date	PubMed
Effects of d-menthol stress on the growth of and microcystin release by the freshwater cyanobacterium Microcystis aeruginosa FACHB-905.	2014-10	25065786
Different effects of l- and d-menthol on the microstructure of ceramide 5/cholesterol/palmitic acid bilayers.	2010-12-15	20932885
Fragrance material review on d-menthol.	2008-11	18640220
Characterization of the mouse cold-menthol receptor TRPM8 and vanilloid receptor type-1 VR1 using a fluorometric imaging plate reader (FLIPR) assay.	2004-02	14757700
Characterization of essential oils from lamiaceae species by fourier transform Raman spectroscopy.	2002-09-25	12236670
Evaluation of peppermint oil and ascorbyl palmitate as inhibitors of cytochrome P4503A4 activity in vitro and in vivo.	2002-09	12235445
Cold- and menthol-sensitive C afferents of cat urinary bladder.	2002-08-15	12181293
Voltage-dependent block of neuronal and skeletal muscle sodium channels by thymol and menthol.	2002-08	12200946
Phytochemical induction by herbivores could affect quality of essential oils from aromatic plants.	2002-07-03	12083883
Antimicrobial screening of Mentha piperita essential oils.	2002-07-03	12083863
A novel treatment of postherpetic neuralgia using peppermint oil.	2002-06-06	12048423
Preparation and self-assembly of chiral porphyrin diads on the gold electrodes of quartz crystal microbalances: a novel potential approach to the development of enantioselective chemical sensors.	2002-06-03	12180326
Field evaluation of three plant-based insect repellents against malaria vectors in Vaca Diez Province, the Bolivian Amazon.	2002-06	12083351
Mentholated cigarettes and smoking cessation: findings from COMMIT. Community Intervention Trial for Smoking Cessation.	2002-06	12035007
Ion channels activated by cold and menthol in cultured rat dorsal root ganglion neurones.	2002-05-17	11988352
[TRP channels--sensitive for heat and cold, capsaicin and menthol].	2002-05-16	12082951
Anti-HIV activity of thiosemicarbazone and semicarbazone derivatives of (+/-)-3-menthone.	2002-05	12210774
Insecticidal properties of essential plant oils against the mosquito Culex pipiens molestus (Diptera: Culicidae).	2002-05	11997977
Analysis of menthol in three traditional Chinese medicinal herbs and their compound formulation by GC-MS.	2002-05	11920950
Extraction of thymol, eucalyptol, menthol, and camphor residues from honey and beeswax. Determination by gas chromatography with flame ionization detection.	2002-04-19	12058905
Menthol: a natural analgesic compound.	2002-04-12	11897159
An analysis of the mainstream smoke chemistry of samples of the U.S. cigarette market acquired between 1995 and 2000.	2002-04	12052000
A chlorinated monoterpene ketone, acylated beta-sitosterol glycosides and a flavanone glycoside from Mentha longifolia (Lamiaceae).	2002-04	11937172
Signal transduction. Hot and cold TRP ion channels.	2002-03-22	11910099
Preparation and in vitro characterization of a eutectic based semisolid self-nanoemulsified drug delivery system (SNEDDS) of ubiquinone: mechanism and progress of emulsion formation.	2002-03-20	11879759
Essential oil composition of sachalinmint from Norway detected by solid-phase microextraction and gas chromatography-mass spectrometry analysis.	2002-03-13	11879034
A TRP channel that senses cold stimuli and menthol.	2002-03-08	11893340
Identification of a cold receptor reveals a general role for TRP channels in thermosensation.	2002-03-07	11882888
Neurobiology: a cool ion channel.	2002-03-07	11882874
The dark side of marketing seemingly "Light" cigarettes: successful images and failed fact.	2002-03	11893811
Specificity of cold thermotransduction is determined by differential ionic channel expression.	2002-03	11836533
Neuroscience. How neurons know that it's c-c-c-c-cold outside.	2002-02-22	11859171
Transdermal drug delivery of imipramine hydrochloride. I. Effect of terpenes.	2002-02-19	11853921
Sensory and physiologic effects of menthol and non-menthol cigarettes with differing nicotine delivery.	2002-01-29	11812507
Factors affecting the resolution of dl-menthol by immobilized lipase-catalyzed esterification in organic solvent.	2002-01-16	11782192
Topical mononitrate treatment in patients with anal fissure.	2002-01	11856083
In vitro skin permeation of morphine hydrochloride during the finite application of penetration-enhancing system containing water, ethanol and l-menthol.	2002-01	11824544
Effect of the vesicular-arbuscular mycorrhizal (VAM) fungus Glomus fasciculatum on the essential oil yield related characters and nutrient acquisition in the crops of different cultivars of menthol mint (Mentha arvensis) under field conditions.	2002-01	11708758
Penetration enhancing effect of menthol on the percutaneous flux of nicardipine hydrochloride through excised rat epidermis from hydroxypropyl cellulose gels.	2002	12229262
Measurements by gas chromatography/pyrolysis/mass spectrometry: fundamental conditions in (2)H/(1)H isotope ratio analysis.	2002	11857733
Metabolism of (R)-(+)-pulegone in F344 rats.	2001-12	11717176
Fullerene modified supported lipid membrane as sensitive element of sensor for odorants.	2001-12	11679270
Smoking among Asian American and Hawaiian/Pacific Islander youth: data from the 2000 National Youth Tobacco Survey.	2001-11-27	11720409
Pulmonary peptide delivery: effect of taste-masking excipients on leuprolide suspension metered-dose inhalers.	2001-11	11775953
Systematic studies on structure and physiological activity of cyclic alpha-keto enamines, a novel class of "cooling" compounds.	2001-11	11714332
Smoking and pregnancy outcome among African-American and white women in central North Carolina.	2001-11	11679790
Effect of Mentha x piperita essential oil and monoterpenes on cucumber root membrane potential.	2001-11	11672734
Menthone and isomenthone biosynthesis in Pelargonium tomentosum Jacq.	2001	11958337
Final report on the safety assessment of Mentha Piperita (Peppermint) Oil, Mentha Piperita (Peppermint) Leaf Extract, Mentha Piperita (Peppermint) Leaf, and Mentha Piperita (Peppermint) Leaf Water.	2001	11766133
The effects of D and L isomers of menthol upon nasal sensation of airflow.	1988-06	3397650

Patents

Sample Use Guides

In Vivo Use Guide

2.5% of RACEMENTHOL apply to affected area not more than 3 to 4 times daily

Route of Administration: Topical

In Vitro Use Guide

After the d-menthol exposure (2.0 g in the 600 ml culture medium), the dry weight of the Microcystis aeruginosa FACHB-905 cells gradually decreased; the decrease in the dry weight after 5d exposure was 29, 12, and 2 mgL(-1) when the initial cell densities were 1.4×10(7), 1.2×10(6), and 2.9×10(5) cellmL(-1), respectively.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:34:50 GMT 2025` Edited by `admin` on `Mon Mar 31 17:34:50 GMT 2025`
Record UNII	BZ1R15MTK7
Record Status	`Validated (UNII)`
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Name

Type

Language

LEVOMENTHOL

Official Name

English

FEMA NO. 2665, (-)-

Preferred Name

English

levomenthol [INN]

Common Name

English

(1R,2S,5R)-5-METHYL-2-(1-METHYLETHYL)CYCLOHEXANOL

Systematic Name

English

CYCLOHEXANOL, 5-METHYL-2-(1-METHYLETHYL)-, (1R,2S,5R)-

Systematic Name

English

Levomenthol [WHO-DD]

Common Name

English

(-)-MENTHOL

Systematic Name

English

MENTHOL, (1R,3R,4S)-(-)-

Systematic Name

English

(-)-MENTHYL ALCOHOL

Systematic Name

English

(-)-TRANS-P-METHAN-CIS-3-OL

Common Name

English

(1R,2S,5R)-(-)-MENTHOL

Common Name

English

1R-MENTHOL

Common Name

English

L-(-)-MENTHOL

Common Name

English

(1R)-(-)-MENTHOL

Systematic Name

English

LEVOMENTHOL [EP MONOGRAPH]

Common Name

English

L-MENTHOLUM

Common Name

English

(R)-(-)-MENTHOL

Systematic Name

English

(1R,3R,4S)-(-)-MENTHOL

Systematic Name

English

MENTHOL, (-)-

Systematic Name

English

NPO-11

Code

English

MENTHOL [MI]

Common Name

English

(-)-(1R,3R,4S)-MENTHOL

Systematic Name

English

(1R,2S,5R)-2-ISOPROPYL-5-METHYLCYCLOHEXANOL

Systematic Name

English

CYCLOHEXANOL, 5-METHYL-2-(1-METHYLETHYL)-, (1R-(1.ALPHA.,2.BETA.,5.ALPHA.))-

Common Name

English

NSC-62788

Code

English

L-MENTHOL

Common Name

English

LEVOMENTHOL [HSDB]

Common Name

English

L-MENTHOL [JAN]

Common Name

English

LEVOMENTHOL [II]

Common Name

English

(1R,2S,5R)-2-ISOPROPYL-5-METHYLCYCLOHEXAN-1-OL

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C860