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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 of LEVOMENTHOL

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

Description
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

Menthol, (+)- is a fragrance ingredient used in decorative cosmetics, fine fragrances, shampoos, toilet soaps and other toiletries as well as in non-cosmetic products such as household cleaners and detergents. Recent investigations have provided evidence for menthol to increase cough thresholds. Racementhol is used as a topical analgesic.

CNS Activity

CNS Penetrant
2554
Curator's Comment: 17 hours after oral administration of 470 mg/kg bw of [3-3 H]-menthol (unspecified isomer) to rats traces (< 0.1 %) of the dose was found in the brain. http://www.inchem.org/documents/sids/sids/MENTHOLS.pdf

Originator

Approval Year

1921
1467
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 37.8 µM [IC50]
Inhibitor
8297
 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)
Agonist
2678
 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)
Antagonist
2778
 68.0 µM [IC50]
Kappa-type opioid receptor
60
Target ID: P41145
Gene ID: 4986.0
Gene Symbol: OPRK1
Target Organism: Homo sapiens (Human)
Activator
1430
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Approved
8429
BENGAY

Approved Use

temporarily relieves the minor aches and pains of muscles and joints associated with a simple backache, arthritis, strains, bruises, sprains.
Palliative
Approved
8429
BENGAY

Approved Use

temporarily relieves the minor aches and pains of muscles and joints associated with a simple backache, arthritis, strains, bruises, sprains.
Palliative
Approved
8429
Unknown

Approved Use

Unknown
Palliative
Approved
8429
VICKS VAPORUB

Approved Use

On chest and throat, temporarily relieves cough due to common cold
Primary
Approved
8429
VICKS VAPORUB

Approved Use

On muscles and joints, temporarily relieves minor aches and pains
Primary
Approved
8429
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.
Palliative
Approved
8429
VICKS VAPORUB

Approved Use

Treatment for rhinitis that is associated with acute upper respiratory tract infection and allergy
Palliative
Phase III
656
Unknown

Approved Use

Unknown
Primary
Not Provided
504
FRESCOLAT ML

Approved Use

The compund is uses as a flavoring ingredient and in cosmetics as a cooling agent
PubMed

PubMed

TitleDatePubMed
Effects of (-)-menthol on arylamine N-acetyltransferase activity in human liver tumor cells.
2001
Pharmacokinetics of menthol and carvone after administration of an enteric coated formulation containing peppermint oil and caraway oil.
2001
Menthol-induced asthma: a case report.
2001
The water-soluble components of the essential oil of Melaleuca alternifolia (tea tree oil) suppress the production of superoxide by human monocytes, but not neutrophils, activated in vitro.
2001 Apr
[Determination of the antibacterial and antiviral activity of the essential oil from Minthostachys verticillata (Griseb.) Epling].
2001 Apr-Jun
Metabolites of dietary 1,8-cineole in the male koala (Phascolarctos cinereus).
2001 Aug
Efficacy and safety of Ascoril in the management of cough--National Study Group report.
2001 Feb
1,8-cineol, a food flavoring agent, prevents ethanol-induced gastric injury in rats.
2001 Feb
Oxidation of 1,8-cineole, the monoterpene cyclic ether originated from eucalyptus polybractea, by cytochrome P450 3A enzymes in rat and human liver microsomes.
2001 Feb
Perception of trigeminal chemosensory qualities in the elderly.
2001 Jul
Sensory experiences in humans and single-unit activity in cats evoked by polymodal stimulation of the cornea.
2001 Jul 15
Evaluation of percutaneous absorption and skin irritation of ketoprofen through rat skin: in vitro and in vivo study.
2001 Jul 17
Ambulation-promoting effect of peppermint oil and identification of its active constituents.
2001 Jul-Aug
Fumigant toxicity of volatile natural products from Korean spices and medicinal plants towards the rice weevil, Sitophilus oryzae (L).
2001 Jun
[Does the inhalation of a 1% L-menthol solution in the premedication of fiberoptic bronchoscopy affect coughing and the sensation of dyspnea?].
2001 Mar
Local anaesthetic activity of (+)- and (-)-menthol.
2001 Mar
The influence of essential oils on human attention. I: alertness.
2001 Mar
Synthetic studies of the HIV-1 protease inhibitive didemnaketals: stereocontrolled synthetic approach to the key mother spiroketals.
2001 Mar 22
Chiral auxiliary based approach toward the synthesis of C-glycosylated amino acids.
2001 May 3
Systematic studies on structure and physiological activity of cyclic alpha-keto enamines, a novel class of "cooling" compounds.
2001 Nov
A model of the pressure dependence of the enantioselectivity of Candida rugosalipase towards (+/-)-menthol.
2001 Oct
Physiology. Cold current in thermoreceptive neurons.
2001 Oct 4
Effect of melting point of chiral terpenes on human stratum corneum uptake.
2001 Oct 9
Promoting mechanism of menthol derivative, 1-O-ethyl-3-buthylcyclohexanol, on the percutaneous absorption of ketoprofen.
2001 Sep
Molecular-imprinted, polymer-coated quartz crystal microbalances for the detection of terpenes.
2001 Sep 1
Efficacy of essential oils of Caesulia axillaris and Mentha arvensis against some storage pests causing biodeterioration of food commodities.
2001 Sep 1
Effect of pH on skin permeation enhancement of acidic drugs by l-menthol-ethanol system.
2001 Sep 11
A chlorinated monoterpene ketone, acylated beta-sitosterol glycosides and a flavanone glycoside from Mentha longifolia (Lamiaceae).
2002 Apr
In vitro skin permeation of morphine hydrochloride during the finite application of penetration-enhancing system containing water, ethanol and l-menthol.
2002 Jan
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 Mar 20
Neurobiology: a cool ion channel.
2002 Mar 7
Characterization of essential oils from lamiaceae species by fourier transform Raman spectroscopy.
2002 Sep 25
Patents

Patents

20100324275
6
JP1031712A
7
JP2000001432A
6
JP2000026260A
15
JP2000038324A
6
JP2000063251A
6
JP2000118510A
6
JP2000159708A
7
JP2000229823A
11
JP2000229852A
6
JP2000281550A
6
JP2001278741A
6
JP2001503768A
14
JP2002020275A
6
JP2002030000A
6
JP2002241278A
6
JP2002241310A
6
JP2002338479A
6
JP2002536069A
6
JP2003055146A
6
JP2003095981A
6
JP2003125706A
6
JP2003277307A
6
JP2003504121A
9
JP2004035616A
6
JP2004091487A
6
JP2004115493A
6
JP2004143058A
6
JP2004143158A
6
JP2004149508A
12
JP2004315542A
6
JP2004339213A
11
JP2004500942A
7
JP2004537038A
6
JP2005002040A
6
JP2005047865A
6
JP2005082592A
6
JP2005097221A
8
JP2005120258A
6
JP2005143349A
6
JP2005179601A
6
JP2005218498A
6
JP2005255222A
6
JP2006036687A
6
JP2006104071A
7
JP2006160608A
6
JP2006248832A
6
JP2006257017A
6
JP2007015995A
6
JP2007077124A
6
JP2007091706A
9
JP2007161679A
7
US5602178
6
US5756864
6
US7173146
6
US7381834
6
US8496950
6
US8603550
6
WO1996014840
6

Sample Use Guides

In Vivo Use Guide
Curator's Comment: maximum daily exposure on the skin of 0.0573 mg/kg/day https://www.ncbi.nlm.nih.gov/pubmed/18640220
Levomenthol-containing ointments are applied topically on affected area of the body. Methnol is employed as a food flavoring.
Route of Administration: Other
In Vitro Use Guide
Menthol evoked stimulus-dependent [Ca2+]i responses in standard physiological solutions of pH 7.3 in CHO cells, expressing TRPM8 receptor.
Name Type Language
LEVOMENTHOL
EP   HSDB   II   INN   WHO-DD  
INN  
Official 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
FEMA NO. 2665, (-)-
Code 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
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
NCI_THESAURUS C245
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
Code System Code Type Description
RXCUI
236388
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
PRIMARY RxNorm
IUPHAR
2430
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
PRIMARY
SMS_ID
100000092317
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
PRIMARY
DRUG BANK
DB00825
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
PRIMARY
FDA UNII
BZ1R15MTK7
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
PRIMARY
CHEBI
15409
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
PRIMARY
ChEMBL
CHEMBL470670
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
PRIMARY
EPA CompTox
DTXSID1022180
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
PRIMARY
NSC
62788
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
PRIMARY
NCI_THESAURUS
C61809
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
PRIMARY
EVMPD
SUB08475MIG
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
PRIMARY
CAS
2216-51-5
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
PRIMARY
DAILYMED
BZ1R15MTK7
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
PRIMARY
PUBCHEM
16666
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
PRIMARY
ECHA (EC/EINECS)
218-690-9
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
PRIMARY
INN
6725
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
PRIMARY
MERCK INDEX
m7175
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
PRIMARY Merck Index
HSDB
5662
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
PRIMARY
DRUG CENTRAL
934
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
PRIMARY
RS_ITEM_NUM
1381709
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of LEVOMENTHOL
NIH
NCATS
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DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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