{"ATC Code":["QR - Respiratory system","QR06 - Antihistamines for systemic use","QR06A - Antihistamines for systemic use","QR06AA - Aminoalkyl ethers","QR06AA09 - Doxylamine","R - Respiratory system","R06 - Antihistamines for systemic use","R06A - Antihistamines for systemic use","R06AA - Aminoalkyl ethers","R06AA09 - Doxylamine"],"Absorption, Distribution and Excretion":"Readily absorbed via the gastrointestinal tract.","Adverse Effects":"Because doxylamine is available over the counter, the risk of overdose is a concern. Adverse effects due to hypersensitivity to the drug include hypotension, urticaria, and decreased oxygen saturation. Common adverse effects include impaired vigilance, atropine-like effects, impaired coordination, and drowsiness during the day—all of which could pose problems for high-risk fall patients and those operating heavy machinery or who drive a vehicle.","Aliases":["Dossilamina","Doxylaminum","Doxilminio","doxilamina","2-Dimethylaminoethoxyphenylmethyl-2-picoline","N,N-Dimethyl-2-(1-phenyl-1-(2-pyridinyl)ethoxy)ethanamine","Phenyl-2-pyridylmethyl-β-N,N-dimethylaminoethyl ether","dimethyl({2-[1-phenyl-1-(pyridin-2-yl)ethoxy]ethyl})amine","2-(α-(2-(Dimethylamino)ethoxy)-α-methylbenzyl)pyridine","Ethanamine, N,N-dimethyl-2-(1-phenyl-1-(2-pyridinyl)ethoxy)-","Dtxsid1022970","Chebi:51380","Pyridine, 2-(α-(2-(dimethylamino)ethoxy)-α-methylbenzyl)-","Ethanamine, N,N-dimethyl-2-[1-phenyl-1-(2-pyridinyl)ethoxy]-","dimethyl((2-(1-phenyl-1-(pyridin-2-yl)ethoxy)ethyl))amine","Dtxcid102970","R06AA09","207-414-2","S-Doxylamine","NCI C60684","Doxylaminephenyl-d5","Alsadorm","Decapryn","Pyridine, 2-[α-[2-(dimethylamino)ethoxy]-α-methylbenzyl]-","HSDB 5184","Einecs 207-414-2","Unii-95qb77jkpl","Brn 0230379","()-Doxylamine","N,N-Dimethyl-2-[(1S)-1-phenyl-1-(2-pyridinyl)ethoxy]ethanamine; (S)-N,N-Dimethyl-2-(1-phenyl-1-(pyridin-2-yl)ethoxy)ethanamine","Spectrum_001014","Prestwick0_000027","Prestwick1_000027","Prestwick2_000027","Prestwick3_000027","Spectrum2_000115","Spectrum3_000409","Spectrum4_000528","Spectrum5_000949","Ec 207-414-2","Schembl4709","CHEMBL1004","Lopac0_000348","BSPBio_000093","BSPBio_001938","KBioGR_001135","KBioSS_001494","5-21-03-00508","DivK1c_000841","SPBio_000130","SPBio_002014","BPBio1_000103","GTPL7171","Schembl30702275","KBio1_000841","KBio2_001494","KBio2_004062","KBio2_006630","KBio3_001158","MSK2841","Ninds_000841","HMS3604L05","N,N-dimethyl-2-[(1-phenyl-1-pyridin-2-ylethyl)oxy]ethanamine","RFC84933","EBC-06825","Mfcd00599469","Akos005657227","CCG-204443","DB00366","Sdccgsbi-0050336.p005","Idi1_000841","( inverted exclamation markA)-Doxylamine","Ncgc00021147-02","Ncgc00021147-03","Ncgc00021147-04","Ncgc00021147-05","Ncgc00021147-06","Ncgc00021147-08","Ncgc00021147-09","Ncgc00021147-13","Ncgc00021147-21","Ncgc00089789-02","Ncgc00089789-04","Ncgc00089789-05","AC-15949","Sbi-0050336.p004","DB-051407","AB00053466","NS00000474","D07878","En300-123421","Ab00053466-18","Ab00053466_19","Ab00053466_20","α-Dimethylaminoethoxyphenylmethyl-2-picoline","L001076","Brd-a44008656-036-05-0","Brd-a44008656-036-15-9","Brd-a44008656-036-24-1","Brd-a44008656-036-25-8","Z2242151271","N,N-dimethyl-2-[1-phenyl-1-(2-pyridyl)ethoxy]ethanamine","N,N-Dimethyl-2-[1-phenyl-1-(2-pyridinyl)ethoxy]ethanamine #","N,N-Dimethyl-2-[1-phenyl-1-(pyridin-2-yl)ethoxy]ethan-1-amine","2-(α(2-(Dimethylamino)ethoxy)-α-methylbenzyl)pyridine"],"Biological Half-Life":"10 hours","Boiling Point":"279 to 286 °F at 0.5 mmHg (NTP, 1992)","CAS":"469-21-6","ChemicalClasses":["phenylethanolamine"],"Chirality":"racemic","Color/Form":"LIQ","Drug Classes":["Breast Feeding","Lactation","Milk, Human","Antihistamines","Antiemetics","Gastrointestinal Agents"],"Drug Indication":"Used alone as a short-term sleep aid, in combination with other drugs as a night-time cold and allergy relief drug. Also used in combination with Vitamin B6 (pyridoxine) to prevent morning sickness in pregnant women.","Drug Warnings":"PERSONS TAKING ANTIHISTAMINES SHOULD BE ALERTED TO THEIR SEDATIVE EFFECTS \u0026 SHOULD BE CAUTIONED NOT TO DRIVE AUTOMOBILE, FLY AIRPLANE, OR OPERATE HAZARDOUS MACHINERY... /ANTIHISTAMINES/","EliminationHalfLife":"10 – 12 hours (range 7 – 15 hours)","Erowid Experience Reports":[{"Author":"Tara","Id":13717,"Title":"Oh My God the Worst Trip Ever!"},{"Author":"Anonymous","Id":38886,"Title":"Good Sleep Aid"},{"Author":"Mingus","Id":80363,"Title":"Mindless Euphoria"},{"Author":"M.F. Luder","Id":106441,"Title":"Daytime Quick Onset Sedation Use"},{"Author":"Dionysus Zane","Id":114529,"Title":"Lack of Sedation"},{"Author":"KommandantBucky","Id":115157,"Title":"From Fascinating to Somewhat Eerie"},{"Author":"Owen","Id":96878,"Title":"Unpleasant But Somewhat Helpful"},{"Author":"Xcel7","Id":113356,"Title":"Euphoria and the Perpetual Nod"},{"Author":"f*cking idiot","Id":17620,"Title":"If You Plan To Trip, Hide Your Sh*t"}],"Esters":[],"European Community (EC) Number":"207-414-2","FDA Pharmacological Classification":[{"Name":"FDA UNII","ReferenceNumber":25,"Value":{"StringWithMarkup":[{"String":"95QB77JKPL"}]}},{"Name":"Active Moiety","ReferenceNumber":25,"Value":{"StringWithMarkup":[{"String":"DOXYLAMINE"}]}},{"Name":"Pharmacological Classes","ReferenceNumber":25,"Value":{"StringWithMarkup":[{"String":"Established Pharmacologic Class [EPC] - Antihistamine"}]}},{"Name":"Pharmacological Classes","ReferenceNumber":25,"Value":{"StringWithMarkup":[{"Markup":[{"Extra":"CID-774","Length":9,"Start":29,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Histamine"}],"String":"Mechanisms of Action [MoA] - Histamine Receptor Antagonists"}]}},{"Name":"FDA Pharmacology Summary","ReferenceNumber":25,"Value":{"StringWithMarkup":[{"Markup":[{"Extra":"CID-3162","Length":10,"Start":0,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Doxylamine"},{"Extra":"CID-3162","Length":10,"Start":59,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/doxylamine"},{"Extra":"CID-774","Length":9,"Start":78,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Histamine"}],"String":"Doxylamine is an Antihistamine. The mechanism of action of doxylamine is as a Histamine Receptor Antagonist."}]}}],"Formating":[],"HMDB ID":"HMDB0001936","HeavyAtomCount":20,"Human Drugs":"Breast Feeding; Lactation; Milk, Human; Antihistamines; Antiemetics; Gastrointestinal Agents","IUPACName":"N,N-dimethyl-2-(1-phenyl-1-pyridin-2-ylethoxy)ethanamine","InChI":"InChI=1S/C17H22N2O/c1-17(20-14-13-19(2)3,15-9-5-4-6-10-15)16-11-7-8-12-18-16/h4-12H,13-14H2,1-3H3","InChIKey":"HCFDWZZGGLSKEP-UHFFFAOYSA-N","Interactions":"Concurrent use may potentiate the CNS depressant effects of either these medications /alcohol or other CNS depression-producing medications/ or antihistamines; also, concurrent use of maprotiline or tricyclic antidepressants may potentiate the anticholinergic effects of either antihistamines or these medications. /Antihistamines/","KEGG Entries":[{"Id":"D02327","Interactions":[],"Synonyms":["Doxylamine succinate","Decapryn"]},{"Id":"D07878","Interactions":[],"Synonyms":["Doxylamine"]}],"MeSH Headers":[{"Id":"M0006795","Link":"https://id.nlm.nih.gov/mesh/M0006795.html","Name":"Doxylamine","Ref":84},{"Id":"DescTree","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":"MeSH Tree","Ref":86},{"Id":"PubMed from MeSH","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":null,"Ref":112},{"Id":"M0001391","Link":"https://id.nlm.nih.gov/mesh/M0001391.html","Name":"Antiemetics","Ref":113},{"Id":"M0010395","Link":"https://id.nlm.nih.gov/mesh/M0010395.html","Name":"Histamine H1 Antagonists","Ref":114}],"MeSH Pharmacological Classification":[{"Id":"M0001391","Link":"https://id.nlm.nih.gov/mesh/M0001391.html","Name":"Antiemetic","Ref":113},{"Id":"M0010395","Link":"https://id.nlm.nih.gov/mesh/M0010395.html","Name":"Histamine H1 Antagonist","Ref":114}],"Mechanism of Action":"Like other antihistamines, doxylamine acts by competitively inhibiting histamine at H1\u0026nbsp;receptors. It also has substantial sedative and anticholinergic effects.","Melting Point":"\u003c 25 °C","Metabolism/Metabolites":"Hepatic.","MolecularFormula":"C\u003csub\u003e17\u003c/sub\u003eH\u003csub\u003e22\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eO","MolecularWeight":"270.37 g/mol","Opticalactivity":"( + / - )","Pharmacodynamics":"Doxylamine is an antihistamine commonly used as a sleep aid. This drug is also used to relieve symptoms of hay fever (allergic rhinitis), hives (rash or itching), and other allergic reactions. Doxylamine is a member of the ethanolamine class of antihistamines and has anti-allergy power far superior to virtually every other antihistamine on the market, with the exception of diphenhydramine (Benadryl). It is also the most powerful over-the-counter sedative available in the United States, and more sedating than many prescription hypnotics. In a study, it was found to be superior to even the barbiturate, phenobarbital for use as a sedative. Doxylamine is also a potent anticholinergic.","Physical Description":"Doxylamine is a clear colorless liquid. (NTP, 1992)","PubChemId":3162,"Record Description":["LiverTox|CNS|Sedative/Hypnotic|Antihistamine"],"Records":{"UNII":{"Impurities":[]}},"RefChem":"55070","RefCount":3,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Doxylamine","Name":"Doxylamine","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q423390","Name":"Doxylamine","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/DB00366","Name":"Doxylamine","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/3162","Name":"Doxylamine","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=469-21-6","Name":"Doxylamine","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0001936","Name":"Doxylamine","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/D07878","Name":"Doxylamine","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/95QB77JKPL","Name":"Doxylamine","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID1022970","Name":"Doxylamine","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 3162, doxylamine. Accessed May 11, 2026. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/3162\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/3162\u003c/a\u003e","U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. Doxylamine. UNII: 95QB77JKPL. Global Substance Registration System. Accessed May 11, 2026. \u003ca href=https://gsrs.ncats.nih.gov/ginas/app/beta/substances/95QB77JKPL\u003ehttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/95QB77JKPL\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). /SUCCINATE/","SMILES":"CC(C1=CC=CC=C1)(C2=CC=CC=N2)OCCN(C)C","SaltData":[{"AcidCount":1,"Amine":"Doxylamine","AmineCount":1,"Formula":"C(CC(=O)O)C(=O)O","Name":"succinate","RName":"succinate","Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 175.051 93.397\"\u003e\u003crect width=\"100%\" height=\"100%\" fill=\"#fff\"/\u003e\u003cdesc\u003eGenerated by the Chemistry Development Kit (http://github.com/cdk)\u003c/desc\u003e\u003cg fill=\"#ff0d0d\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".7\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 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1.221.529.839 0 1.22-.529.387-.536.387-1.459 0-.929-.387-1.452-.381-.524-1.208-.524-.834 0-1.227.524-.393.523-.393 1.452\" class=\"atom\"/\u003e\u003cpath stroke=\"none\" d=\"M16.182 18.6h-.72l-2.62-4.066h-.029l.029.595q.024.357.024.732V18.6h-.565v-4.9h.714l2.607 4.054h.03l-.018-.327q-.012-.22-.023-.476-.006-.262-.006-.482V13.7h.577z\" class=\"atom\"/\u003e\u003cpath stroke=\"#3050f8\" d=\"m62.609 67.519-3.482-4.148\" class=\"hi\"/\u003e\u003cpath stroke=\"#ff0d0d\" d=\"M40.638 50.551v5.659M37.354 44.734l-4.957-2.862\" class=\"hi\"/\u003e\u003cpath stroke=\"#3050f8\" d=\"m17.395 17.971 5.023 2.899M14.241 12.3V6.605M11.088 17.971 6.065 20.87\" class=\"hi\"/\u003e\u003c/g\u003e\u003c/g\u003e\u003c/svg\u003e","Therapeutic Uses":"Anti-Allergic Agents; Antiemetics; Antitussive Agents; Histamine H1 Antagonists; Sedatives, Nonbarbiturate","Title":"Doxylamine","UNII":"95QB77JKPL","Wikidata":"Q423390","Wikipedia":"Doxylamine","XLogP":2.5}