General
Preferred name
LEVOMENTHOL
Synonyms
Hexahydrothymol ()
(±)-Menthol ()
L-Menthol|Levomenthol|Menthomenthol|Menthacamphor ()
MENTHOL ()
DL-Menthol ()
RACEMENTHOL ()
L-Menthol, Levomenthol, Menthomenthol, Menthacamphor ()
(-)-menthol ()
Levomentol ()
L-Menthol ()
(–)-Menthol ()
P&D ID
PD001064
CAS
2216-51-5
114376-98-6
89-78-1
Tags
available
drug
natural product
Approved by
FDA
Drug Status
approved
investigational
Max Phase
3.0
Drug indication
Chronic obstructive pulmonary disease
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
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.
DESCRIPTION Natural menthol principally occurs as the (-)-enantiomer, also known as levomenthol. This (-)-enantiomer is also one of the components of the INN-assigned racementhol. (GtoPdb)
PRICE 29
DESCRIPTION (-)-Menthol (Levomenthol) is a levo isomer of menthol, an organic compound made synthetically or obtained from peppermint or mint oils with flavoring and local anesthetic properties. When added to pharmaceuticals and foods, menthol functions as a fortifier for peppermint flavors. It also has a counterirritant effect on skin and mucous membranes, thereby producing a local analgesic or anesthetic effect.
DESCRIPTION DL-Menthol ((??)-Menthol) is a racemic mixture of the monoterpene alcohols (?C)-menthol and (+)-menthod, which have been found in Cannabis. (?C)-Menthol is more common than (+)-menthol in nature and exhibits analgesic, antibacterial, and anticancer properties, as well as inhibits cholinesterase.2 (+)-Menthol inhibits the growth of F. verticillioides (MIC: 1.5 mM) but, unlike (?C)-menthol, does not exhibit analgesic, antibacterial, anticancer, or cholinesterase inhibitory activities.
DESCRIPTION DL-Menthol (Racementhol) is an orally active, GABAaR positive allosteric modulator and UDP-glucuronosyltransferase (UGT) inhibitor that can cross the blood-brain barrier. DL-Menthol binds to GABAAR and exhibits an allosteric activation effect, enhancing GABA-mediated chloride influx and inhibiting neuronal excitability. DL-Menthol can induce surgical anesthesia in fish and inhibit the metabolic detoxification of tobacco carcinogens by human liver and intestinal UGT enzymes, resulting in reduced NNAL-N-Gluc production[1][2].
DESCRIPTION (-)-Menthol is a covalent organic compound made synthetically or obtained from peppermint or other mint oils. It is used to treat occasional minor irritation, pain, sore mouth, and sore throat as well as cough associated with a cold or inhaled irritants. (Enamine Bioactive Compounds)
DESCRIPTION DL-Menthol ((±)-Menthol) is a racemic mixture of the monoterpene alcohols (–)-menthol and (+)-menthod, which have been found in Cannabis. (–)-Menthol is more common than (+)-menthol in nature and exhibits analgesic, antibacterial, and anticancer properties, as well as inhibits cholinesterase.2 (+)-Menthol inhibits the growth of F. verticillioides (MIC: 1.5 mM) but, unlike (–)-menthol, does not exhibit analgesic, antibacterial, anticancer, or cholinesterase inhibitory activities. (TargetMol Bioactive Compound Library)
Compound Sets
21
Cayman Chemical Bioactives
30384
ChEMBL Drugs
CHEMBL470670
Concise Guide to Pharmacology 2017/18
2430
Concise Guide to Pharmacology 2019/20
2430
Concise Guide to Pharmacology 2021/22
2430
Concise Guide to Pharmacology 2023/24
2430
Drug Repurposing Hub
DrugBank
DB00825
DrugBank Approved Drugs
DB00825
DrugCentral
934
DrugCentral Approved Drugs
934
Enamine Bioactive Compounds
EBC-07707
Enamine BioReference Compounds
Guide to Pharmacology
2430
MedChem Express Bioactive Compound Library
HY-Y1683
NCATS Inxight Approved Drugs
BZ1R15MTK7
Novartis Chemogenetic Library (NIBR MoA Box)
ReFrame library
Selleckchem Bioactive Compound Library
dl-menthol
-menthol
TargetMol Bioactive Compound Library
T2979
The Spectrum Collection
External IDs
53
Properties
(calculated by RDKit )
Molecular Weight
156.15
Hydrogen Bond Acceptors
1
Hydrogen Bond Donors
1
Rotatable Bonds
1
Ring Count
1
Aromatic Ring Count
0
cLogP
2.44
TPSA
20.23
Fraction CSP3
1.0
Chiral centers
3.0
Largest ring
6.0
QED
0.62
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Pathway
Neuronal Signaling
Membrane Transporter/Ion Channel
Neuroscience
Target
cholinesterase
GABA Receptor
OPRK1, TRPA1, TRPM8, TRPV3
TRP Channel
Member status
member
MOA
TRPM8 (TRP-p8
CMR1) Agonists
Indication
pain relief
Source data