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| Name | Menthol | ||||||||||||||||||||||||||||||||||||||||||
| Accession Number | DB00825 (APRD01604) | ||||||||||||||||||||||||||||||||||||||||||
| Type | small molecule | ||||||||||||||||||||||||||||||||||||||||||
| Groups | approved | ||||||||||||||||||||||||||||||||||||||||||
| Description | Menthol is a covalent organic compound made synthetically or obtained from peppermint or other mint oils. It is a waxy, crystalline substance, clear or white in color, which is solid at room temperature and melts slightly above. The main form of menthol occurring in nature is (-)-menthol, which is assigned the (1R,2S,5R) configuration. Menthol has local anesthetic and counterirritant qualities, and it is widely used to relieve minor throat irritation. |
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| Structure |
Download: MOL | SDF | SMILES | InChI Display: 2D Structure | 3D Structure |
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| Brand names | Not Available | ||||||||||||||||||||||||||||||||||||||||||
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| CAS number | 2216-51-5 | ||||||||||||||||||||||||||||||||||||||||||
| Weight |
Average: 156.2652 Monoisotopic: 156.151415262 |
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| Chemical Formula | C10H20O | ||||||||||||||||||||||||||||||||||||||||||
| InChI Key | InChIKey=NOOLISFMXDJSKH-KXUCPTDWSA-N | ||||||||||||||||||||||||||||||||||||||||||
| InChI |
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
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| IUPAC Name |
(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol
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| SMILES |
CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O
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| Mass Spec | show (3 KB) | ||||||||||||||||||||||||||||||||||||||||||
| Taxonomy | |||||||||||||||||||||||||||||||||||||||||||
| Kingdom | Organic | ||||||||||||||||||||||||||||||||||||||||||
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| Substructures |
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| Pharmacology | |||||||||||||||||||||||||||||||||||||||||||
| Indication | Used to treat occasional minor irritation, pain, sore mouth, and sore throat as well as cough associated with a cold or inhaled irritants. | ||||||||||||||||||||||||||||||||||||||||||
| Pharmacodynamics | Menthol is a covalent organic compound made synthetically or obtained from peppermint or other mint oils. Menthol's ability to chemically trigger cold-sensitive receptors in the skin is responsible for the well known cooling sensation that it provokes when inhalated, eaten, or applied to the skin. It should be noted that menthol does not cause an actual drop in temperature. | ||||||||||||||||||||||||||||||||||||||||||
| Mechanism of action | Menthol primarily activates the cold-sensitive TRPM8 receptors in the skin. Menthol, after topical application, causes a feeling of coolness due to stimulation of 'cold' receptors by inhibiting Ca++ currents of neuronal membranes. It may also yield analgesic properties via kappa-opioid receptor agonism. | ||||||||||||||||||||||||||||||||||||||||||
| Absorption | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Volume of distribution | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Protein binding | Not Available | ||||||||||||||||||||||||||||||||||||||||||
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| Route of elimination | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Half life | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Clearance | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Toxicity | Menthol, DL: ORAL (LD50): Acute: 2900 mg/kg [Rat], 3100 mg/kg [Mouse]. DERMAL (LD50): Acute: 5001 mg/kg [Rabbit]. | ||||||||||||||||||||||||||||||||||||||||||
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| Pathways | Not Available | ||||||||||||||||||||||||||||||||||||||||||
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| Manufacturers | Not Available | ||||||||||||||||||||||||||||||||||||||||||
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| Patents | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Properties | |||||||||||||||||||||||||||||||||||||||||||
| State | solid | ||||||||||||||||||||||||||||||||||||||||||
| Melting point | 43 oC | ||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties |
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| Synthesis Reference | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| General Reference | Not Available | ||||||||||||||||||||||||||||||||||||||||||
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| PDB Entries | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| FDA label | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| MSDS | show (73.2 KB) | ||||||||||||||||||||||||||||||||||||||||||
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| Food Interactions | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Targets |
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1. Transient receptor potential cation channel subfamily M member 8 Pharmacological action: yesActions: inducer Receptor-activated non-selective cation channel involved in detection of sensations such as coolness, by being activated by cold temperature below 25 degrees Celsius. Activated by icilin, eucalyptol, menthol, cold and modulation of intracellular pH. Involved in menthol sensation. Permeable for monovalent cations sodium, potassium, and cesium and divalent cation calcium. Temperature sensing is tightly linked to voltage-dependent gating. Activated upon depolarization, changes in temperature resulting in graded shifts of its voltage-dependent activation curves. The chemical agonists menthol functions as a gating modifier, shifting activation curves towards physiological membrane potentials. Temperature sensitivity arises from a tenfold difference in the activation energies associated with voltage-dependent opening and closing Organism class: humanUniProt ID: Q7Z2W7  Gene: TRPM8 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References:
2. Transient receptor potential cation channel subfamily A member 1 Pharmacological action: yesActions: inducer Receptor-activated non-selective cation channel involved in detection of sensations such as cold, pain or sounds perception. Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes. Also involved in pain sensation triggered by capsaicin, the pungent ingredient in chilli peppers. Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana. Not involved in menthol sensation. May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system Organism class: humanUniProt ID: O75762 Gene: TRPA1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References:
3. Transient receptor potential cation channel subfamily V member 3 Pharmacological action: yesActions: inducer Putative receptor-activated non-selective calcium permeant cation channel. It is activated by innocuous (warm) temperatures and shows an increased response at noxious temperatures greater than 39 degrees Celsius. Activation exhibits an outward rectification. May associate with TRPV1 and may modulate its activity Organism class: humanUniProt ID: Q8NET8 Gene: TRPV3 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References:
Pharmacological action: unknown
Actions: agonist Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for dynorphins. May play a role in arousal and regulation of autonomic and neuroendocrine functions Organism class: humanUniProt ID: P41145 Gene: OPRK1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References:
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Drug created on June 13, 2005 07:24 / Updated on November 10, 2010 13:43
This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.