{"Abbreviation":"DOI","Aliases":["4-DOI","4-Iodo-2,5-dimethoxyphenylisopropylamine","2,5-Dimethoxy-4-iodophenylisopropylamine","1-(2,5-Dimethoxy-4-iodophenyl)-2-aminopropane","1-(4-Iodo-2,5-dimethoxyphenyl)-2-aminopropane","DOI-P","4-Iodo-2,5-dimethoxy-α-methylbenzeneethanamine","DOI cpd","DOI","4-Iodo-2,5-dimethoxyamphetamine","2-(4-iodo-2,5-dimethoxyphenyl)-1-methylethylamine","1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane","Racemic DOI","82830-53-3","1-(4-Iodo-2,5-dimethoxyphenyl)-2-propanamine","Lopac0_000466","GTPL147","Benzeneethanamine, 4-iodo-2,5-dimethoxy-α-methyl-","2,5-dimethoxy 4-iodoamphetamine","Bgmzuekzenqujy-uhfffaoysa-","DOI,(+)","PCA58434","Pdsp1_001383","Pdsp2_001367","CCG-204558"],"CAS":"64584-34-5","ChEBI":"CHEBI:64629","ChEMBL":"CHEMBL6616","ChemicalClasses":["2,5-dimethoxyamphetamine"],"Chirality":"racemic","Classes":["Psychedelic"],"Erowid Experience Reports":[],"Esters":[],"Formating":[],"HMDB ID":"HMDB0243794","HeavyAtomCount":15,"IUPACName":"1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine","InChI":"InChI=1S/C11H16INO2/c1-7(13)4-8-5-11(15-3)9(12)6-10(8)14-2/h5-7H,4,13H2,1-3H3","InChIKey":"BGMZUEKZENQUJY-UHFFFAOYSA-N","MeSH Pharmacological Classification":"Drugs capable of inducing illusions, hallucinations, delusions, paranoid ideations, and other alterations of mood and thinking. Despite the name, the feature that distinguishes these agents from other classes of drugs is their capacity to induce states of altered perception, thought, and feeling that are not experienced otherwise. (See all compounds classified as Hallucinogens.)","MolecularFormula":"C\u003csub\u003e11\u003c/sub\u003eH\u003csub\u003e16\u003c/sub\u003eINO\u003csub\u003e2\u003c/sub\u003e","MolecularWeight":"321.15 g/mol","Opticalactivity":"( + / - )","PubChemId":1229,"Record Description":["2,5-Dimethoxy-4-iodoamphetamine (DOI) is a psychedelic drug and a substituted amphetamine. Unlike other substituted amphetamines, however, it is not a stimulant.[2] DOI has a stereocenter and R-(\u0026#8722;)-DOI is the more active stereoisomer. In neuroscience research, [125I]-R-(\u0026#8722;)-DOI is used as a radioligand and indicator of the presence of 5-HT2A serotonin receptors. DOI's effects have been compared to LSD, although there are differences that experienced users can distinguish. Besides the longer duration, the trip tends to be more energetic than an LSD trip, with more body load and a different subjective visual experience.","Wikipedia|List of designer drugs|Psychedelics|Dox","Wikipedia|PiHKAL|Phenethylamines"],"RefCount":3,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/2,5-Dimethoxy-4-iodoamphetamine","Name":"2,5-Dimethoxy-4-iodoamphetamine","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/1229","Name":"2,5-Dimethoxy-4-iodoamphetamine","Sub":false}]},{"Name":"ChEMBL","Urls":[{"Link":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL6616","Name":"2,5-Dimethoxy-4-iodoamphetamine","Sub":false}]},{"Name":"ChEBI","Urls":[{"Link":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:64629","Name":"2,5-Dimethoxy-4-iodoamphetamine","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=64584-34-5","Name":"2,5-Dimethoxy-4-iodoamphetamine","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0243794","Name":"2,5-Dimethoxy-4-iodoamphetamine","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/OOM10GW9UE","Name":"2,5-Dimethoxy-4-iodoamphetamine","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID7040520","Name":"2,5-Dimethoxy-4-iodoamphetamine","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 1229, 2,5-Dimethoxy-4-iodoamphetamine. Accessed July 13, 2025. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/1229\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/1229\u003c/a\u003e","U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. 2,5-Dimethoxy-4-iodoamphetamine. UNII: OOM10GW9UE. Global Substance Registration System. Accessed July 13, 2025. \u003ca href=https://gsrs.ncats.nih.gov/ginas/app/beta/substances/OOM10GW9UE\u003ehttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/OOM10GW9UE\u003c/a\u003e"],"SMILES":"CC(CC1=CC(=C(C=C1OC)I)OC)N","SaltData":[{"AcidCount":1,"AmineCount":1,"Formula":"Cl","Name":"hydrochloride","Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 112.871 78.276\"\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=\"#3050f8\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".7\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h113v79H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath d=\"m67.456 46.754-.003-15.24M67.453 31.514l-13.199-7.618M54.254 23.896l-13.197 7.622\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"M41.057 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