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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
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
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
The generalizability of capsaicin sensitization and desensitization.
1999 Jul
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
Pharmacokinetics of menthol and carvone after administration of an enteric coated formulation containing peppermint oil and caraway oil.
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
1,8-cineole protects against liver failure in an in-vivo murine model of endotoxemic shock.
2001 Apr
Abuse of topical analgesic.
2001 Apr
[Determination of the antibacterial and antiviral activity of the essential oil from Minthostachys verticillata (Griseb.) Epling].
2001 Apr-Jun
Fullerene modified supported lipid membrane as sensitive element of sensor for odorants.
2001 Dec
Response properties of isolated mouse olfactory receptor cells.
2001 Jan 1
Fumigant toxicity of volatile natural products from Korean spices and medicinal plants towards the rice weevil, Sitophilus oryzae (L).
2001 Jun
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
[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
Effect of (+)-pulegone and other oil components of Mentha x Piperita on cucumber respiration.
2001 May
Systematic studies on structure and physiological activity of cyclic alpha-keto enamines, a novel class of "cooling" compounds.
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
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
Feasibility study of repeated harvesting of menthol from biologically viable Mentha x piperata using ultrasonic extraction.
2001 Sep-Oct
An analysis of the mainstream smoke chemistry of samples of the U.S. cigarette market acquired between 1995 and 2000.
2002 Apr
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
Antimicrobial screening of Mentha piperita essential oils.
2002 Jul 3
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
A TRP channel that senses cold stimuli and menthol.
2002 Mar 8
Insecticidal properties of essential plant oils against the mosquito Culex pipiens molestus (Diptera: Culicidae).
2002 May
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:56:05 GMT 2023
Edited
by admin
on Sat Dec 16 17:56:05 GMT 2023
Record UNII
YS08XHA860
Record Status Validated (UNII)
Record Version
  • Download
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
Related Record Type Details
Structure of LEVOMENTHOL
ENANTIOMER -> RACEMATE
Related Record Type Details
Structure of RACEMENTHOL
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