Talk:Menthol

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Summary sheet: Menthol

Menthol
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Chemical Nomenclature
Common names	Menthol, levomenthol
Substitutive name	Menthol
Systematic name	5-Methyl-2-(propan-2-yl)cyclohexan-1-ol
Routes of Administration
WARNING: Always start with lower doses due to differences between individual body weight, tolerance, metabolism, and personal sensitivity. See responsible use section. DISCLAIMER: PW's dosage information is gathered from users and resources for educational purposes only. It is not a recommendation and should be verified with other sources for accuracy.

Menthol is an organic compound, more specifically a monoterpenoid, made synthetically or obtained from the oils of corn mint, peppermint, or other mints. It is a waxy, clear or white crystalline substance, 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. Menthol also acts as a weak κ-opioid receptor agonist.

History and culture

This History and culture section is a stub. As a result, it may contain incomplete or wrong information. You can help by expanding it.

In the West, menthol was first isolated in 1771, by the German, Hieronymus David Gaubius. Early characterizations were done by Oppenheim, Beckett, Moriya, and Atkinson. It was named by F. L. Alphons Oppenheim (1833–1877) in 1861.

Chemistry

This chemistry section is incomplete. You can help by adding to it.

The biosynthesis of menthol has been investigated in Mentha × piperita and the enzymes involved in have been identified and characterized. It begins with the synthesis of the terpene limonene, followed by hydroxylation, and then several reduction and isomerization steps.

Pharmacology

This pharmacology section is incomplete. You can help by adding to it.

Menthol's ability to chemically trigger the cold-sensitive TRPM8 receptors in the skin is responsible for the well-known cooling sensation it provokes when inhaled, eaten, or applied to the skin. In this sense, it is similar to capsaicin, the chemical responsible for the spiciness of hot chilis (which stimulates heat sensors, also without causing an actual change in temperature).

Menthol's analgesic properties are mediated through a selective activation of κ-opioid receptors. Menthol blocks calcium channels and voltage-sensitive sodium channels, reducing neural activity that may stimulate muscles.

Some studies show that menthol acts as a GABAA receptor positive allosteric modulator and increases GABAergic transmission in PAG neurons. Menthol has anesthetic properties similar to, though less potent than, propofol because it interacts with the same sites on the GABAA receptor. Menthol may also enhance the activity of glycine receptors and negatively modulate 5-HT3 receptors and nAChRs.

Menthol is widely used in dental care as a topical antibacterial agent, effective against several types of streptococci and lactobacilli. Menthol also lowers blood pressure and antagonizes vasoconstriction through TRPM8 activation.

Subjective effects

This subjective effects section is a stub. As such, it is still in progress and may contain incomplete or wrong information. You can help by expanding or correcting it.

Experience reports

There are currently 0 experience reports which describe the effects of this substance in our experience index.

Additional experience reports can be found here:

• Erowid Experience Vaults: Menthol

Toxicity and harm potential

This toxicity and harm potential section is a stub. As a result, it may contain incomplete or even dangerously wrong information! You can help by expanding upon or correcting it. Note: Always conduct independent research and use harm reduction practices if using this substance.

It is strongly recommended that one use harm reduction practices when using this substance.

Lethal dosage

The estimated lethal dose for menthol (and peppermint oil) in humans may be as low as 50–500 mg/kg, (LD50 Acute: 3300 mg/kg [Rat]. 3400 mg/kg [Mouse]. 800 mg/kg [Cat]). Survival after doses of 8 to 9 g has been reported.

See also

• Responsible use

External links

(List along order below)

• Menthol (Wikipedia)
• Menthol (Erowid Vault)

Literature

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