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Details

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

SHOW SMILES / InChI
Structure of RACEMENTHOL

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
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
Understanding childhood asthma in focus groups: perspectives from mothers of different ethnic backgrounds.
2001
Menthol-induced asthma: a case report.
2001
The influence of verbal labeling on the perception of odors: evidence for olfactory illusions?
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
Highly diastereoselective synthesis of vinylcyclopropane derivatives with (-)-8-phenylmenthol as chiral auxiliary.
2001 Aug 24
Metabolism of (R)-(+)-pulegone in F344 rats.
2001 Dec
Fullerene modified supported lipid membrane as sensitive element of sensor for odorants.
2001 Dec
Efficacy and safety of Ascoril in the management of cough--National Study Group report.
2001 Feb
Chiral auxiliaries for asymmetric radical cyclization reactions: application to the enantioselective synthesis of (+)-triptocallol.
2001 Jan 11
A new colorimetric assay for studying and rapid screening of membrane penetration enhancers.
2001 Jul
Perception of trigeminal chemosensory qualities in the elderly.
2001 Jul
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
A multicenter study of patch test reactions with dental screening series.
2001 Jun
Demonstration that menthofuran synthase of mint (Mentha) is a cytochrome P450 monooxygenase: cloning, functional expression, and characterization of the responsible gene.
2001 Jun 15
Oral irritant properties of menthol: sensitizing and desensitizing effects of repeated application and cross-desensitization to nicotine.
2001 May
Pulmonary peptide delivery: effect of taste-masking excipients on leuprolide suspension metered-dose inhalers.
2001 Nov
Systematic studies on structure and physiological activity of cyclic alpha-keto enamines, a novel class of "cooling" compounds.
2001 Nov
Smoking and pregnancy outcome among African-American and white women in central North Carolina.
2001 Nov
Effect of Mentha x piperita essential oil and monoterpenes on cucumber root membrane potential.
2001 Nov
The development of new methods for the recycling of chiral catalysts.
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
Smoking among Asian American and Hawaiian/Pacific Islander youth: data from the 2000 National Youth Tobacco Survey.
2001 Winter-Spring
Penetration enhancing effect of menthol on the percutaneous flux of nicardipine hydrochloride through excised rat epidermis from hydroxypropyl cellulose gels.
2002
Measurements by gas chromatography/pyrolysis/mass spectrometry: fundamental conditions in (2)H/(1)H isotope ratio analysis.
2002
A chlorinated monoterpene ketone, acylated beta-sitosterol glycosides and a flavanone glycoside from Mentha longifolia (Lamiaceae).
2002 Apr
Menthol: a natural analgesic compound.
2002 Apr 12
Extraction of thymol, eucalyptol, menthol, and camphor residues from honey and beeswax. Determination by gas chromatography with flame ionization detection.
2002 Apr 19
Voltage-dependent block of neuronal and skeletal muscle sodium channels by thymol and menthol.
2002 Aug
Cold- and menthol-sensitive C afferents of cat urinary bladder.
2002 Aug 15
Neuroscience. How neurons know that it's c-c-c-c-cold outside.
2002 Feb 22
Topical mononitrate treatment in patients with anal fissure.
2002 Jan
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 Jan
Factors affecting the resolution of dl-menthol by immobilized lipase-catalyzed esterification in organic solvent.
2002 Jan 16
Sensory and physiologic effects of menthol and non-menthol cigarettes with differing nicotine delivery.
2002 Jan-Feb
Phytochemical induction by herbivores could affect quality of essential oils from aromatic plants.
2002 Jul 3
Antimicrobial screening of Mentha piperita essential oils.
2002 Jul 3
Field evaluation of three plant-based insect repellents against malaria vectors in Vaca Diez Province, the Bolivian Amazon.
2002 Jun
Mentholated cigarettes and smoking cessation: findings from COMMIT. Community Intervention Trial for Smoking Cessation.
2002 Jun
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 Jun 3
Essential oil composition of sachalinmint from Norway detected by solid-phase microextraction and gas chromatography-mass spectrometry analysis.
2002 Mar 13
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
Anti-HIV activity of thiosemicarbazone and semicarbazone derivatives of (+/-)-3-menthone.
2002 May
Insecticidal properties of essential plant oils against the mosquito Culex pipiens molestus (Diptera: Culicidae).
2002 May
Ion channels activated by cold and menthol in cultured rat dorsal root ganglion neurones.
2002 May 17
Evaluation of peppermint oil and ascorbyl palmitate as inhibitors of cytochrome P4503A4 activity in vitro and in vivo.
2002 Sep
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
RACEMENTHOL
HSDB   INN   WHO-DD  
INN  
Official Name English
DL-MENTHOL
Common Name English
MENTHOL, (±)-
Systematic Name English
MENTHOL, DL-
Common Name English
FEMA NO. 2665, (±)-
Code English
RAC-MENTHOL
Common Name English
(1R,2S,5R)-REL-5-METHYL-2-(1-METHYLETHYL)CYCLOHEXANOL
Common Name English
racementhol [INN]
Common Name English
NSC-2603
Code English
MENTHOL, CIS-1,3,TRANS-1,4-
Common Name English
(±)-MENTHOL
Systematic Name English
(±)-(1R*,3R*,4S*)-MENTHOL
Systematic Name English
CYCLOHEXANOL, 5-METHYL-2-(1-METHYLETHYL)-, (1.ALPHA.,2.BETA.,5.ALPHA.)-
Common Name English
DL-MENTHOL [JAN]
Common Name English
MEGGEZONE
Common Name English
MENTHOL RACEMATE [MI]
Common Name English
CYCLOHEXANOL, 5-METHYL-2-(1-METHYLETHYL)-, (1R,2S,5R)-REL-
Common Name English
RACEMENTHOL [HSDB]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C245
Created by admin on Sat Dec 16 17:56:06 GMT 2023 , Edited by admin on Sat Dec 16 17:56:06 GMT 2023
NCI_THESAURUS C860
Created by admin on Sat Dec 16 17:56:06 GMT 2023 , Edited by admin on Sat Dec 16 17:56:06 GMT 2023
Code System Code Type Description
RXCUI
1430390
Created by admin on Sat Dec 16 17:56:06 GMT 2023 , Edited by admin on Sat Dec 16 17:56:06 GMT 2023
PRIMARY RxNorm
HSDB
89-78-1
Created by admin on Sat Dec 16 17:56:06 GMT 2023 , Edited by admin on Sat Dec 16 17:56:06 GMT 2023
PRIMARY
DRUG BANK
DB14123
Created by admin on Sat Dec 16 17:56:06 GMT 2023 , Edited by admin on Sat Dec 16 17:56:06 GMT 2023
PRIMARY
NSC
2603
Created by admin on Sat Dec 16 17:56:06 GMT 2023 , Edited by admin on Sat Dec 16 17:56:06 GMT 2023
PRIMARY
NCI_THESAURUS
C75073
Created by admin on Sat Dec 16 17:56:06 GMT 2023 , Edited by admin on Sat Dec 16 17:56:06 GMT 2023
PRIMARY
FDA UNII
YS08XHA860
Created by admin on Sat Dec 16 17:56:06 GMT 2023 , Edited by admin on Sat Dec 16 17:56:06 GMT 2023
PRIMARY
CHEBI
76310
Created by admin on Sat Dec 16 17:56:06 GMT 2023 , Edited by admin on Sat Dec 16 17:56:06 GMT 2023
PRIMARY
PUBCHEM
16666
Created by admin on Sat Dec 16 17:56:06 GMT 2023 , Edited by admin on Sat Dec 16 17:56:06 GMT 2023
PRIMARY
INN
6724
Created by admin on Sat Dec 16 17:56:06 GMT 2023 , Edited by admin on Sat Dec 16 17:56:06 GMT 2023
PRIMARY
ChEMBL
CHEMBL256087
Created by admin on Sat Dec 16 17:56:06 GMT 2023 , Edited by admin on Sat Dec 16 17:56:06 GMT 2023
PRIMARY
DAILYMED
YS08XHA860
Created by admin on Sat Dec 16 17:56:06 GMT 2023 , Edited by admin on Sat Dec 16 17:56:06 GMT 2023
PRIMARY
CAS
89-78-1
Created by admin on Sat Dec 16 17:56:06 GMT 2023 , Edited by admin on Sat Dec 16 17:56:06 GMT 2023
PRIMARY
ChEMBL
CHEMBL2106989
Created by admin on Sat Dec 16 17:56:06 GMT 2023 , Edited by admin on Sat Dec 16 17:56:06 GMT 2023
PRIMARY
ECHA (EC/EINECS)
201-939-0
Created by admin on Sat Dec 16 17:56:06 GMT 2023 , Edited by admin on Sat Dec 16 17:56:06 GMT 2023
PRIMARY
MERCK INDEX
m7175
Created by admin on Sat Dec 16 17:56:06 GMT 2023 , Edited by admin on Sat Dec 16 17:56:06 GMT 2023
PRIMARY
EVMPD
SUB10232MIG
Created by admin on Sat Dec 16 17:56:06 GMT 2023 , Edited by admin on Sat Dec 16 17:56:06 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of RACEMENTHOL
NIH
NCATS
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