{"Abbreviation":"","Aliases":["l-Menthol","Levomenthol","l-(-)-Menthol","Menthomenthol","(1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol","Menthacamphor","Peppermint camphor","(1r,2s,5r)-(-)-menthol","Levomentholum","Racementhol"],"Boiling Point":"421 °","CAS":"2216-51-5","ChEBI":"CHEBI:15409","ChEMBL":"CHEMBL470670","ChemicalClasses":[],"Chirality":"racemic","Classes":null,"Color/Form":"Crystals or granules","Decomposition":"When heated to decomposition it emits acrid smoke and irritating fumes.","Density":"0.904 at 59 °F (NTP, 1992) - Less dense than water; will float g/cm\u003csup\u003e3\u003c/sup\u003e","Drug Indication":"Used to treat occasional minor irritation, pain, sore mouth, and sore throat as well as cough associated with a cold or inhaled irritants.","Drug Warnings":"\"COOLING\" EFFECT OF L-MENTHOL WAS FOUND...TO BE SUPERIOR TO THAT PRODUCED BY OTHER ISOMERS; ODOR AND TASTE, TOO OF L-MENTHOL WERE SUPERIOR, WITH SOME OF THE ISOMERS PRODUCING SHARP, IRRITATING AND DISAGREEABLE PERCEPTIONS.","DrugClasses":[],"EINECS":"201-939-0","Erowid Experience Reports":[],"Esters":["acetate"],"European Community (EC) Number":"201-939-0","Flash Point":"196 °F (NTP, 1992)","HMDB ID":"HMDB0003352","HeavyAtomCount":11,"Human Drugs":"Human drug -\u003e Active ingredient (MENTHOL)","IUPACName":"(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexan-1-ol","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","InChIKey":"NOOLISFMXDJSKH-KXUCPTDWSA-N","MeSH Pharmacological Classification":"Agents, usually topical, that relieve itching (pruritus). (See all compounds classified as Antipruritics.)","Melting Point":"100 °","MolecularFormula":"C\u003csub\u003e10\u003c/sub\u003eH\u003csub\u003e20\u003c/sub\u003eO","MolecularWeight":"156.26 g/mol","Odor":"Peppermint odor","Opticalactivity":"( + / - )","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.","Physical Description":"D,l-menthol is a white crystalline solid with a peppermint odor and taste. (NTP, 1992)","PrevSalts":[],"PubChemId":16666,"Record Description":["D,l-menthol is a white crystalline solid with a peppermint odor and taste. (NTP, 1992)","(-)-menthol is a p-menthan-3-ol which has (1R,2S,5R)-stereochemistry. It is the most common naturally occurring enantiomer. It has a role as an antipruritic drug, an antitussive and an antispasmodic drug. It is an enantiomer of a (+)-menthol.","Menthol is a covalent organic compound made synthetically or obtained from peppermint or other mint oils. Forming clear or white waxy, crystalline substance, menthol is typically solid at room temperature. (-)-Menthol is the naturally-occurring and main form of menthol, and is assigned the (1R,2S,5R) configuration. Menthol mediates anesthetic properties and anti-irritating properties locally, thus it is widely used to relieve minor throat irritations.","l-Menthol has been reported in Citrus reticulata, Punica granatum, and other organisms with data available.","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.","LEVOMENTHOL is a small molecule drug with a maximum clinical trial phase of III and has 1 investigational indication.","Menthol is an alcohol produced from mint oils or prepared synthetically. 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.","See also: Menthol (annotation moved to).","(-)-menthol is a p-menthan-3-ol which has (1R,2S,5R)-stereochemistry. It is the most common naturally occurring enantiomer. It has a role as an antipruritic drug, an antitussive and an antispasmodic drug. It is an enantiomer of a (+)-menthol."],"RefCount":3,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Menthol","Name":"Menthol","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q407418","Name":"Menthol","Sub":false},{"Link":"https://www.wikidata.org/wiki/Q27084428","Name":"(+)-Menthol","Sub":true}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/drugs/DB00825","Name":"Menthol","Sub":false},{"Link":"https://go.drugbank.com/drugs/DB11344","Name":"(+)-Menthol","Sub":true}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/16666","Name":"Menthol","Sub":false},{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/165675","Name":"(+)-Menthol","Sub":true}]},{"Name":"ChEMBL","Urls":[{"Link":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL470670","Name":"Menthol","Sub":false},{"Link":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL2106989","Name":"(+)-Menthol","Sub":true}]},{"Name":"ChEBI","Urls":[{"Link":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:15409","Name":"Menthol","Sub":false},{"Link":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:76306","Name":"(+)-Menthol","Sub":true}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=2216-51-5","Name":"Menthol","Sub":false},{"Link":"https://commonchemistry.cas.org/detail?cas_rn=89-78-1","Name":"(+)-Menthol","Sub":true}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0003352","Name":"Menthol","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/C00400","Name":"Menthol","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/YS08XHA860","Name":"Menthol","Sub":false},{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/C6B1OE8P3W","Name":"(+)-Menthol","Sub":true}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID1020805","Name":"Menthol","Sub":false},{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID8029733","Name":"(+)-Menthol","Sub":true}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 16666, Menthol. Accessed June 28, 2025. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/16666\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/16666\u003c/a\u003e","U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. Menthol. UNII: YS08XHA860. Global Substance Registration System. Accessed June 28, 2025. \u003ca href=https://gsrs.ncats.nih.gov/ginas/app/beta/substances/YS08XHA860\u003ehttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/YS08XHA860\u003c/a\u003e"],"Reported Fatal Dose":"4. 4= Very toxic: probable oral lethal dose (human) 50-500 mg/kg, between 1 teaspoon \u0026 1 oz for 70 kg person (150 lb).","SMILES":"C[C@@H]1CC[C@H]([C@@H](C1)O)C(C)C","Solubility":"less than 1 mg/mL at 70 °F (NTP, 1992)","Stability/Shelf Life":"Stable under recommended storage conditions.","StereoisomerRacemic":"(RS)-Menthol","Stereoisomers":["(+)-Menthol"],"StereoisomersUNII":["C6B1OE8P3W"],"StoreUNII":["BZ1R15MTK7"],"StructureBase64":"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","Subjective Effects":null,"Taste":"Peppermint taste","Therapeutic Uses":"INHALERS CONTAINING MENTHOL COMPRESSED INTO BLOCKS OR CONES ARE COMMONLY USED FOR THE RELIEF OF NASAL CONGESTION, HEADACHE, AND NEURALGIA. IT IS NOW RARELY ADMINISTERED INTERNALLY. /MENTHOL/","Title":"Menthol","UNII":"YS08XHA860","Wikidata":"Q407418","Wikipedia":"Menthol","XLogP":3}