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Chemical Compound Review

MENTHOL     5-methyl-2-propan-2-yl- cyclohexan-1-ol

Synonyms: menthols, Racementhol, Neoisomenthol, dl-Menthol, d-Neomenthol, ...
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Disease relevance of MENTHOL


Psychiatry related information on MENTHOL


High impact information on MENTHOL

  • Here, we describe the characterization of ANKTM1, a cold-activated channel with a lower activation temperature compared to the cold and menthol receptor, TRPM8 [11].
  • Cells overexpressing the TRPM8 channel can be activated by cold temperatures and by a cooling agent, menthol [12].
  • A TRP channel that senses cold stimuli and menthol [12].
  • This cold- and menthol-sensitive receptor, CMR1, is a member of the TRP family of excitatory ion channels, and we propose that it functions as a transducer of cold stimuli in the somatosensory system [13].
  • Here we have characterized and cloned a menthol receptor from trigeminal sensory neurons that is also activated by thermal stimuli in the cool to cold range [13].

Chemical compound and disease context of MENTHOL


Biological context of MENTHOL

  • High-throughput random mutagenesis screen reveals TRPM8 residues specifically required for activation by menthol [19].
  • Menthol, a structurally unrelated compound to RA, also suppressed IL-6R expression and, correspondingly, inhibited cell growth [20].
  • We identified two potential N-linked glycosylation sites in TRPM8 (Asn-821 and Asn-934) and mutated them to show that only the site in the putative pore region at position 934 is modified and that glycosylation of this site is not absolutely necessary for cell surface expression or responsiveness to icilin, menthol, and cool temperatures [21].
  • After menthol capsule dosing, the decrease in heart rate was less than the decrease after placebo administration (P < .05) [22].
  • CONCLUSIONS: We conclude that pure menthol and menthol in food or beverages have a similar systemic bioavailability and that menthol has a small cardioaccelerating effect [22].

Anatomical context of MENTHOL


Associations of MENTHOL with other chemical compounds

  • The natural compounds capsaicin and menthol activate noxious heat-sensitive TRPV1 and cold-sensitive TRPM8, respectively [26].
  • Finally, aequorin-based measurements demonstrate that the TRPM8-independent menthol-induced Ca(2+) release originates from both endoplasmic reticulum and Golgi compartments [24].
  • Of the 35 characterized A delta mechanoreceptors, 8 responded to NaCl, 9 to KCl, 9 to NH4Cl, 0 to CaCl2, menthol, or hexanol, and 2 to nicotine [27].
  • An application study on the release of menthone and menthol from chewing gum by a group of six test persons was performed [28].
  • This shift in apoA-I mass to alpha electrophoretic mobility was blocked by the addition of either 1.4 mM DTNB or 10 mM menthol to the plasma prior to incubation, suggesting that lecithin:cholesterol acyltransferase (LCAT) activity was involved [29].

Gene context of MENTHOL

  • When exposed to menthol or cold, TRPM8 behaves like many ligand-gated channels, exhibiting rapid activation followed by moderate Ca(2+)-dependent adaptation [30].
  • We tested whether substances which are structurally related to menthol, or which produce a cooling sensation, could activate TRPM8, and compared the responses of TRPM8 and VR1 to these ligands [31].
  • Genetic elimination of ionotropic purinergic receptors (P2X2 and P2X3) eliminates taste responses in the taste nerves, although the nerves remain responsive to touch, temperature, and menthol [32].
  • When either the capsaicin receptor, TRPV1, the menthol receptor, TRPM8, or the ionotropic purinergic receptor P2X(2) was introduced into hippocampal neurons, the cells responded to pulsed applications of agonist with characteristic sequences of depolarization, spiking, and repolarization [33].
  • Since menthol inhibition of reductase was still observed in rats deprived of foods, we conclude that the effect is not mediated by those hormones whose concentration is changed during fasting (insulin, glucagon, and adrenaline) [25].

Analytical, diagnostic and therapeutic context of MENTHOL

  • We investigated the mechanisms of cold pain by studying the effect of menthol on pain, temperature perception, touch sensation and skin perfusion [3].
  • The authors analyzed data from a multihospital case-control study in the eastern United States to evaluate the hypothesis that smoking menthol cigarettes increases lung cancer risk compared with smoking nonmenthol cigarettes [34].
  • Menthol has a selective potentiating action on cutaneous cold receptors and shifts the temperature response curve of the bladder cooling reflex towards higher temperatures in animal experiments [35].
  • In this study, the few cases of headache were rapidly relieved with oral analgesia and menthol lozenges [36].
  • Little evidence that "denicotinized" menthol cigarettes have pharmacological effects: an EEG/heart-rate/sujective-response study [37].


  1. Biotransformation of monoterpenes, bile acids, and other isoprenoids in anaerobic ecosystems. Hylemon, P.B., Harder, J. FEMS Microbiol. Rev. (1998) [Pubmed]
  2. Use of mentholated cigarettes and lung cancer risk. Kabat, G.C., Hebert, J.R. Cancer Res. (1991) [Pubmed]
  3. Topical menthol--a human model for cold pain by activation and sensitization of C nociceptors. Wasner, G., Schattschneider, J., Binder, A., Baron, R. Brain (2004) [Pubmed]
  4. Novel role of cold/menthol-sensitive transient receptor potential melastatine family member 8 (TRPM8) in the activation of store-operated channels in LNCaP human prostate cancer epithelial cells. Thebault, S., Lemonnier, L., Bidaux, G., Flourakis, M., Bavencoffe, A., Gordienko, D., Roudbaraki, M., Delcourt, P., Panchin, Y., Shuba, Y., Skryma, R., Prevarskaya, N. J. Biol. Chem. (2005) [Pubmed]
  5. A cold- and menthol-activated current in rat dorsal root ganglion neurones: properties and role in cold transduction. Reid, G., Babes, A., Pluteanu, F. J. Physiol. (Lond.) (2002) [Pubmed]
  6. Clinical testing of olfaction reassessed. Pinching, A.J. Brain (1977) [Pubmed]
  7. Menthol cigarettes, smoking cessation, atherosclerosis, and pulmonary function: the Coronary Artery Risk Development in Young Adults (CARDIA) Study. Pletcher, M.J., Hulley, B.J., Houston, T., Kiefe, C.I., Benowitz, N., Sidney, S. Arch. Intern. Med. (2006) [Pubmed]
  8. Neural responses of thermal-sensitive lingual fibers to brief menthol stimulation. Lundy, R.F., Contreras, R.J. Brain Res. (1994) [Pubmed]
  9. Effect of topically applied menthol on thermal, pain and itch sensations and biophysical properties of the skin. Yosipovitch, G., Szolar, C., Hui, X.Y., Maibach, H. Arch. Dermatol. Res. (1996) [Pubmed]
  10. Sensitization and desensitization to capsaicin and menthol in the oral cavity: interactions and individual differences. Cliff, M.A., Green, B.G. Physiol. Behav. (1996) [Pubmed]
  11. ANKTM1, a TRP-like channel expressed in nociceptive neurons, is activated by cold temperatures. Story, G.M., Peier, A.M., Reeve, A.J., Eid, S.R., Mosbacher, J., Hricik, T.R., Earley, T.J., Hergarden, A.C., Andersson, D.A., Hwang, S.W., McIntyre, P., Jegla, T., Bevan, S., Patapoutian, A. Cell (2003) [Pubmed]
  12. A TRP channel that senses cold stimuli and menthol. Peier, A.M., Moqrich, A., Hergarden, A.C., Reeve, A.J., Andersson, D.A., Story, G.M., Earley, T.J., Dragoni, I., McIntyre, P., Bevan, S., Patapoutian, A. Cell (2002) [Pubmed]
  13. Identification of a cold receptor reveals a general role for TRP channels in thermosensation. McKemy, D.D., Neuhausser, W.M., Julius, D. Nature (2002) [Pubmed]
  14. Effects of essential oils on erythrocytes and hepatocytes from rats and dipalmitoyl phosphatidylcholine-liposomes. Manabe, A., Nakayama, S., Sakamoto, K. Jpn. J. Pharmacol. (1987) [Pubmed]
  15. Concomitant development of photoallergic contact dermatitis from ketoprofen and allergic contact dermatitis from menthol and rosin (colophony) in a compress. Ota, T., Oiso, N., Iba, Y., Narita, T., Kawara, S., Kawada, A. Contact Derm. (2007) [Pubmed]
  16. Development of a stable oral liquid dosage form of spironolactone. Pramar, Y., Das Gupta, V., Bethea, C. Journal of clinical pharmacy and therapeutics. (1992) [Pubmed]
  17. The risk of jaundice in glucose-6-phosphate dehydrogenase deficient babies exposed to menthol. Olowe, S.A., Ransome-Kuti, O. Acta paediatrica Scandinavica. (1980) [Pubmed]
  18. Extinguishing the rewarding value of smoke cues: pharmacological and behavioral treatments. Rose, J.E., Behm, F.M. Nicotine Tob. Res. (2004) [Pubmed]
  19. High-throughput random mutagenesis screen reveals TRPM8 residues specifically required for activation by menthol. Bandell, M., Dubin, A.E., Petrus, M.J., Orth, A., Mathur, J., Hwang, S.W., Patapoutian, A. Nat. Neurosci. (2006) [Pubmed]
  20. Retinoic acid-induced growth inhibition of a human myeloma cell line via down-regulation of IL-6 receptors. Sidell, N., Taga, T., Hirano, T., Kishimoto, T., Saxon, A. J. Immunol. (1991) [Pubmed]
  21. The Cold and Menthol Receptor TRPM8 Contains a Functionally Important Double Cysteine Motif. Dragoni, I., Guida, E., McIntyre, P. J. Biol. Chem. (2006) [Pubmed]
  22. Disposition kinetics and effects of menthol. Gelal, A., Jacob, P., Yu, L., Benowitz, N.L. Clin. Pharmacol. Ther. (1999) [Pubmed]
  23. Specificity of cold thermotransduction is determined by differential ionic channel expression. Viana, F., de la Peña, E., Belmonte, C. Nat. Neurosci. (2002) [Pubmed]
  24. TRPM8-independent Menthol-induced Ca2+ Release from Endoplasmic Reticulum and Golgi. Mahieu, F., Owsianik, G., Verbert, L., Janssens, A., De Smedt, H., Nilius, B., Voets, T. J. Biol. Chem. (2007) [Pubmed]
  25. The mechanism of cyclic monoterpene inhibition of hepatic 3-hydroxy-3-methylglutaryl coenzyme A reductase in vivo in the rat. Clegg, R.J., Middleton, B., Bell, G.D., White, D.A. J. Biol. Chem. (1982) [Pubmed]
  26. Noxious cold ion channel TRPA1 is activated by pungent compounds and bradykinin. Bandell, M., Story, G.M., Hwang, S.W., Viswanath, V., Eid, S.R., Petrus, M.J., Earley, T.J., Patapoutian, A. Neuron (2004) [Pubmed]
  27. Selectivity of lingual nerve fibers to chemical stimuli. Wang, Y., Erickson, R.P., Simon, S.A. J. Gen. Physiol. (1993) [Pubmed]
  28. Flavor release measurement by atmospheric pressure chemical ionization ion trap mass spectrometry, construction of interface and mathematical modeling of release profiles. Haahr, A.M., Madsen, H., Smedsgaard, J., Bredie, W.L., Stahnke, L.H., Refsgaard, H.H. Anal. Chem. (2003) [Pubmed]
  29. Interconversion between apolipoprotein A-I-containing lipoproteins of pre-beta and alpha electrophoretic mobilities. Kunitake, S.T., Mendel, C.M., Hennessy, L.K. J. Lipid Res. (1992) [Pubmed]
  30. The super-cooling agent icilin reveals a mechanism of coincidence detection by a temperature-sensitive TRP channel. Chuang, H.H., Neuhausser, W.M., Julius, D. Neuron (2004) [Pubmed]
  31. Characterization of the mouse cold-menthol receptor TRPM8 and vanilloid receptor type-1 VR1 using a fluorometric imaging plate reader (FLIPR) assay. Behrendt, H.J., Germann, T., Gillen, C., Hatt, H., Jostock, R. Br. J. Pharmacol. (2004) [Pubmed]
  32. ATP signaling is crucial for communication from taste buds to gustatory nerves. Finger, T.E., Danilova, V., Barrows, J., Bartel, D.L., Vigers, A.J., Stone, L., Hellekant, G., Kinnamon, S.C. Science (2005) [Pubmed]
  33. Photochemical gating of heterologous ion channels: remote control over genetically designated populations of neurons. Zemelman, B.V., Nesnas, N., Lee, G.A., Miesenbock, G. Proc. Natl. Acad. Sci. U.S.A. (2003) [Pubmed]
  34. Menthol cigarettes and risk of lung cancer. Brooks, D.R., Palmer, J.R., Strom, B.L., Rosenberg, L. Am. J. Epidemiol. (2003) [Pubmed]
  35. Evidence of cold receptors in the human bladder: effect of menthol on the bladder cooling reflex. Geirsson, G. J. Urol. (1993) [Pubmed]
  36. Topical mononitrate treatment in patients with anal fissure. Tankova, L., Yoncheva, K., Muhtarov, M., Kadyan, H., Draganov, V. Aliment. Pharmacol. Ther. (2002) [Pubmed]
  37. Little evidence that "denicotinized" menthol cigarettes have pharmacological effects: an EEG/heart-rate/sujective-response study. Pritchard, W.S., Houlihan, M.E., Guy, T.D., Robinson, J.H. Psychopharmacology (Berl.) (1999) [Pubmed]
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