2,5-Dimethoxy-4-iodoamphetamine

Chemical compound vanc 6 verified verified 477211688 DOI DOI structure.svg skin-invert-image 200px DOI ball-and-stick chemical structure.png bg-transparent 185px Oral Serotonergic psychedelic; Hallucinogen; Serotonin 5-HT2 receptor agonist; Anti-inflammatory agent None F2 Anvisa RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial 2023-07-24 Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 live https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 2023-08-27 2023-08-27 Diário Oficial da União pt-BR 2023-07-25 Schedule I 16–30 hours correct correct 64584-34-5 82864-06-0 ((R)-DOI)99665-04-0 ((S)-DOI)42203-78-1 (HCl) 1229 147 correct chemspider 1192 correct FDA Q2E57V2WS3 correct EBI 6616 DOI; 2,5-Dimethoxy-4-iodoamphetamine; 4-Iodo-2,5-dimethoxyamphetamine 1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine 11 16 1 1 2 IC(C=C1OC)=C(OC)C=C1CC(C)N correct chemspider 1S/C11H16INO2/c1-7(13)4-8-5-11(15-3)9(12)6-10(8)14-2/h5-7H,4,13H2,1-3H3 correct chemspider BGMZUEKZENQUJY-UHFFFAOYSA-N 201.5 (hydrochloride) 10 mg/mL D101 DOI hydrochloride ≥98% (HPLC), solid http://www.sigmaaldrich.com/catalog/search/ProductDetail/SIGMA/D101 13 April 2008 2,5-Dimethoxy-4-iodoamphetamine (DOI) is a psychedelic drug of the phenethylamine, amphetamine, and DOx families. Cameron LP, Jaster AM, Ramos R, Ullman EZ The Utility of DOI For the Study of Serotonin 2A and 2C Receptors Molecular Pharmacology 100093 2025 10.1016/j.molpha.2025.100093 Shulgin A, Shulgin A #67 DOI PiHKAL: A Chemical Love Story 1990 Transform Press https://web.archive.org/web/20141027003157/http://www.erowid.org/library/books_online/PiHKAL/PiHKAL067.shtml 2014-10-27 https://www.erowid.org/library/books_online/PiHKAL/PiHKAL067.shtml 2014-12-17 live Glennon RA, Dukat M 1-(2,5-Dimethoxy-4-iodophenyl)-2-aminopropane (DOI): From an Obscure to Pivotal Member of the DOX Family of Serotonergic Psychedelic Agents - A Review ACS Pharmacology & Translational Science 7 6 1722–1745 June 2024 38898956 11184610 10.1021/acsptsci.4c00157 free Canal CE, Morgan D Head-twitch response in rodents induced by the hallucinogen 2,5-dimethoxy-4-iodoamphetamine: a comprehensive history, a re-evaluation of mechanisms, and its utility as a model Drug Testing and Analysis 4 7–8 556–576 2012 22517680 3722587 10.1002/dta.1333 It is little-used recreationally, but is widely used in scientific research in the study of psychedelics and serotonin receptors. The drug is taken orally. It acts as a potent serotonin 5-HT2 receptor agonist, including of the serotonin 5-HT2A and 5-HT2C receptors. Analogues of DOI include 2C-I, DOB, DOC, DOM, and 25I-NBOMe, among others. DOI was first described in the scientific literature by Ronald Coutts and Jerry Malicky in 1973. Coutts RT, Malicky JL The Synthesis of Some Analogs of the Hallucinogen 1-(2,5-Dimethoxy-4-methylphenyl)-2-aminopropane (DOM) Canadian Journal of Chemistry 51 9 1402–1409 1 May 1973 10.1139/v73-210 0008-4042 https://cdnsciencepub.com/doi/10.1139/v73-210 27 November 2025 Subsequently, it was described in greater detail by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). DOI has been encountered as a novel designer drug. LSD Blotter Acid Mimics (Actually containing 4-IODO-2,5-DIMETHOXYAMPHETAMINE (DOI) and 4-CHLORO-2,5-DIMETHOXYAMPHETAMINE (DOC)) in Lantana, Florida Washington, DC June 2008 DEA Microgram Bulletin Office of Forensic Sciences, Drug Enforcement Administration http://www.usdoj.gov/dea/programs/forensicsci/microgram/mg0608/mg0608.html 12 February 2009 https://web.archive.org/web/20090204025435/http://www.usdoj.gov/dea/programs/forensicsci/microgram/mg0608/mg0608.html 2009-02-04 Owing to their very long and disagreeable durations however, DOI and other DOx drugs have seen very little recreational availability and use. Nichols DE Psychedelics Pharmacological Reviews 68 2 264–355 April 2016 26841800 4813425 10.1124/pr.115.011478 Although studies have appeared that employed psilocybin or LSD or a select few other agents, probably the majority of animal experiments have used the "psychedelic" 5-HT2A agonist DOI. That is another unfortunate consequence of the current drug laws. DOI has never been popular as a recreational drug, nor has any clinical study been carried out to compare its effects with classic drugs such as LSD, mescaline, or psilocybin, and only anecdotal reports of its human psychopharmacology exist (e.g., Shulgin and Shulgin, 1991). Although DOI is quite potent, it likely never became popular as a street drug because of its very prolonged duration of action, so it had never been placed into Schedule I of the Controlled Substances Act (although as of November 2015, there are congressional moves afoot to change that). Therefore, DOI has been commercially available to qualified investigators and did not require a U.S. Drug Enforcement Administration license to work with it. Today P Is the DEA Sabotaging Psychedelic Research? Inside the Push to Schedule DOI and DOC 21 January 2025 Psychedelics Today https://psychedelicstoday.com/2025/01/21/is-the-dea-sabotaging-psychedelic-research-inside-the-push-to-schedule-doi-and-doc/ 6 June 2025 Baggott MJ Learning about STP: A Forgotten Psychedelic from the Summer of Love History of Pharmacy and Pharmaceuticals 65 1 93–116 1 October 2023 10.3368/hopp.65.1.93 2694-3034 free https://hopp.uwpress.org/content/wphopp/65/1/93.full.pdf 27 January 2025 Trout K, Daley PF The origin of 2,5-dimethoxy-4-methylamphetamine (DOM, STP) Drug Testing and Analysis 16 12 1496–1508 December 2024 38419183 10.1002/dta.3667 Unlike many other psychedelic drugs, DOI is not an explicitly controlled substance in the United States. However, in 2023, the Drug Enforcement Administration (DEA) began taking steps to make DOI a controlled substance. As of late 2025, DOI is poised to become a Schedule I controlled substance in the United States. Use and effects In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists DOI's dose as 1.5 to 3mg orally and its duration as 16 to 30hours. The effects of DOI have been reported to include feelings of unreality, strangeness, closed-eye imagery, time dilation, having none of LSD's sparkle, depression and sadness, enhanced eroticism, lightheadedness, and spaciness, among others. It was said to have little or no body load. The (R)-enantiomer, (R)-DOI, was active at doses of 1.0 to 2.3mg orally, whereas the (S)-enantiomer, (S)-DOI, was active at a dose of 6.3mg orally. Interactions Psychedelic drug#Interactions Trip killer#Serotonergic psychedelic antidotes It is unclear whether DOI may interact with monoamine oxidase inhibitors (MAOIs). Rached G, Campana A, Fiani D, Nguyen C, Van den Eynde V, Gillman PK, Barnett BS Safety and Efficacy of Monoamine Oxidase Inhibitors in Patients Who Use Psychoactive Substances: Potential Drug Interactions and Substance Use Disorder Treatment Data CNS Drugs January 2026 41546846 10.1007/s40263-025-01256-7 Pharmacology Pharmacodynamics Actions + DOI activities Target Affinity (Ki, nM) 5-HT1A 2,219–4,177 5-HT1B >10,000 5-HT1D 458 5-HT1E 1,013–2,970 5-HT1F 1,739–2,511 5-HT2A 0.46–165 (Ki)0.42–57 (EC50 half-maximal effective concentration)46–111% (Emax maximal efficacy) 5-HT2B 1.4–336 (Ki)1.4–39 (EC50 half-maximal effective concentration)71–103% (Emax maximal efficacy) 5-HT2C 1.8–48 (Ki)0.14–178 (EC50 half-maximal effective concentration)90–114% (Emax maximal efficacy) 5-HT3 >10,000 5-HT4 ND No data 5-HT5A >10,000 5-HT5B 1,000 (rat) 5-HT6 2,113 5-HT7 5,769 α1A >10,000 α1B >10,000 α1D ND No data α2A 74 α2B 340 α2C 601 β1 591 β2 139 D1 9,688 D2–D5 >10,000 H1 1,757 H2–H4 >10,000 M1 2,720 M2 1,989 M3 1,428 M4 578 M5 2,208 TAAR1 >1,000 I1 >10,000 σ1 8,565 σ2 9,172 SERT Serotonin transporter 685 (Ki) NET Norepinephrine transporter >10,000 (Ki) DAT Dopamine transporter >10,000 (Ki) MAO-A Monoamine oxidase A 37,000 (IC50 half-maximal inhibitory concentration) MAO-B Monoamine oxidase B >200,000 (IC50 half-maximal inhibitory concentration) Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: PDSP Database UNC https://pdsp.unc.edu/databases/pdsp.php?receptorDD=&receptor=&speciesDD=&species=&sourcesDD=&source=&hotLigandDD=&hotLigand=&testLigandDD=&testFreeRadio=testFreeRadio&testLigand=doi&referenceDD=&reference=&KiGreater=&KiLess=&kiAllRadio=all&doQuery=Submit+Query zu 4 February 2025 Liu T BindingDB BDBM28582 1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine::CHEMBL6616::DOI::DOI,(+)::DOI,(-)::US20240166618, Compound DOI::[125I]2,5-dimethoxy-4-iodoamphetamine::[125I]4-iodo-2,5-dimethoxyphenylisopropylamine::[125I]DOI BindingDB https://www.bindingdb.org/rwd/bind/chemsearch/marvin/MolStructure.jsp?monomerid=28582 4 February 2025 van Wijngaarden I, Soudijn W 5-HT2A, 5-HT2B and 5-HT2C receptor ligands Pharmacochemistry Library 27 161–197 1997 10.1016/s0165-7208(97)80013-x Elsevier 978-0-444-82041-9 Reyes-Parada M, Iturriaga-Vasquez P, Cassels BK Amphetamine Derivatives as Monoamine Oxidase Inhibitors Frontiers in Pharmacology 10 2019 32038257 6989591 10.3389/fphar.2019.01590 free 1590 Matsumoto T, Maeno Y, Kato H, Seko-Nakamura Y, Monma-Ohtaki J, Ishiba A, Nagao M, Aoki Y 5-hydroxytryptamine- and dopamine-releasing effects of ring-substituted amphetamines on rat brain: a comparative study using in vivo microdialysis European Neuropsychopharmacology 24 8 1362–1370 August 2014 24862256 10.1016/j.euroneuro.2014.04.009 Rudin D, Luethi D, Hoener MC, Liechti ME Structure-activity Relation of Halogenated 2,5-Dimethoxyamphetamines Compared to their α‑Desmethyl (2C) Analogues The FASEB Journal 36 S1 2022 10.1096/fasebj.2022.36.S1.R2121 fasebj.2022.36.S1.R2121 0892-6638 free https://www.researchgate.net/publication/360423277 Acuña-Castillo C, Villalobos C, Moya PR, Sáez P, Cassels BK, Huidobro-Toro JP Differences in potency and efficacy of a series of phenylisopropylamine/phenylethylamine pairs at 5-HT(2A) and 5-HT(2C) receptors British Journal of Pharmacology 136 4 510–519 June 2002 12055129 1573376 10.1038/sj.bjp.0704747 Hemanth P, Nistala P, Nguyen VT, Eltit JM, Glennon RA, Dukat M Binding and functional structure-activity similarities of 4-substituted 2,5-dimethoxyphenyl isopropylamine analogues at 5-HT2A and 5-HT2B serotonin receptors Frontiers in Pharmacology 14 2023 36762110 9902381 10.3389/fphar.2023.1101290 free 1101290 Wallach J, Cao AB, Calkins MM, Heim AJ, Lanham JK, Bonniwell EM, Hennessey JJ, Bock HA, Anderson EI, Sherwood AM, Morris H, de Klein R, Klein AK, Cuccurazzu B, Gamrat J, Fannana T, Zauhar R, Halberstadt AL, McCorvy JD Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential Nature Communications 14 1 December 2023 38102107 10724237 10.1038/s41467-023-44016-1 free 2023NatCo..14.8221W 8221 DOI is a serotonin 5-HT2A, 5-HT2B and 5-HT2C receptor agonist. Ray TS Psychedelics and the human receptorome PLOS ONE 5 2 February 2010 20126400 2814854 10.1371/journal.pone.0009019 2010PLoSO...5.9019R free e9019 It is said to be approximately 5- to 12-fold selective for the serotonin 5-HT2A receptor over the serotonin 5-HT2C receptor. Poulie CB, Jensen AA, Halberstadt AL, Kristensen JL DARK Classics in Chemical Neuroscience: NBOMes ACS Chemical Neuroscience 11 23 3860–3869 December 2020 31657895 9191638 10.1021/acschemneuro.9b00528 The psychedelic phenethylamines typically exhibit less than 5–10-fold selectivity for 5-HT2A over 5-HT2C receptors.53,54 [...] The reported selectivity of 25CN-NBOH for 5-HT2A over 5-HT2C varies depending on the experimental conditions,49,59,60 but 25CN-NBOH is clearly more selective than DOI, which is only ~5-fold and 12-fold selective for 5-HT2A over 5-HT2C at the human and murine receptors, respectively.93–95 [...] The drug shows biased agonism at the serotonin 5-HT2C receptor. Bonniwell EM, Alabdali R, Hennessey JJ, McKee JL, Cavalco NG, Lammers JC, Moore EJ, Franchini L, Orlandi C, McCorvy JD Serotonin 5-HT2C Receptor Signaling Analysis Reveals Psychedelic Biased Agonism ACS Chemical Neuroscience 16 19 3899–3914 October 2025 40944639 10.1021/acschemneuro.5c00647 12629614 The drug is not a monoamine releasing agent of serotonin or dopamine. DOI is an agonist of the rat trace amine-associated receptor 1 (TAAR1). Bunzow JR, Sonders MS, Arttamangkul S, Harrison LM, Zhang G, Quigley DI, Darland T, Suchland KL, Pasumamula S, Kennedy JL, Olson SB, Magenis RE, Amara SG, Grandy DK Amphetamine, 3,4-methylenedioxymethamphetamine, lysergic acid diethylamide, and metabolites of the catecholamine neurotransmitters are agonists of a rat trace amine receptor Molecular Pharmacology 60 6 1181–1188 December 2001 11723224 10.1124/mol.60.6.1181 The compound has a stereocenter, and R-(−)-DOI is the more active stereoisomer. [125I]-R-(−)-DOI is used as a radioligand and indicator of the presence of serotonin 5-HT2A receptors in studies. Effects (R)-DOI and several other serotonergic psychedelics, including TCB-2, LSD, and LA-SS-Az, have been found to show potent inhibition of tumor necrosis factor alpha (TNFα)-induced inflammation. Miller KJ, Gonzalez HA Serotonin 5-HT2A receptor activation inhibits cytokine-stimulated inducible nitric oxide synthase in C6 glioma cells Annals of the New York Academy of Sciences 861 1 169–173 December 1998 9928254 10.1111/j.1749-6632.1998.tb10188.x 23264746 1998NYASA.861..169M Yu B, Becnel J, Zerfaoui M, Rohatgi R, Boulares AH, Nichols CD Serotonin 5-hydroxytryptamine(2A) receptor activation suppresses tumor necrosis factor-alpha-induced inflammation with extraordinary potency The Journal of Pharmacology and Experimental Therapeutics 327 2 316–323 November 2008 18708586 10.1124/jpet.108.143461 25374241 Pelletier M, Siegel RM Wishing away inflammation? New links between serotonin and TNF signaling Molecular Interventions 9 6 299–301 December 2009 20048135 2861806 10.1124/mi.9.6.5 (R)-DOI was the most active of the assessed drugs and showed extremely high potency that was in the picomolar range and was an order of magnitude more potent than its action as a hallucinogen. TNFα may play a mediating role in the pathophysiology of degenerative inflammatory conditions like rheumatoid arthritis and Alzheimer's disease. (R)-DOI has also been found to block pulmonary inflammation, mucus hyperproduction, airway hyperresponsiveness, and to turn off key genes in pulmonary immune response, effects which block the development of allergic asthma in animal models. LSU Health New Orleans research finds psychedelic drug prevents asthma development in mice http://www.eurekalert.org/pub_releases/2015-02/lsuh-lhn020915.php EurekAlert! These findings could make DOI and other serotonin 5-HT2A agonists novel treatments for inflammatory conditions. Yu B, Becnel J, Zerfaoui M, Rohatgi R, Boulares AH, Nichols CD Serotonin 5-hydroxytryptamine(2A) receptor activation suppresses tumor necrosis factor-alpha-induced inflammation with extraordinary potency The Journal of Pharmacology and Experimental Therapeutics 327 2 316–323 November 2008 18708586 10.1124/jpet.108.143461 25374241 DOI has been shown to induce rapid growth and reorganization of dendritic spines and synaptic connections with other neurons, processes known to underlie neuroplasticity, and hence to be a psychoplastogen. Jones KA, Srivastava DP, Allen JA, Strachan RT, Roth BL, Penzes P Rapid modulation of spine morphology by the 5-HT2A serotonin receptor through kalirin-7 signaling Proceedings of the National Academy of Sciences of the United States of America 106 46 19575–19580 November 2009 19889983 2780750 10.1073/pnas.0905884106 free 2009PNAS..10619575J DOI, along with other psychedelics, has been reported to produce serotonergic neurotoxicity in vitro and in rodents in vivo at high doses given repeatedly. Rudin D, Liechti ME, Luethi D Molecular and clinical aspects of potential neurotoxicity induced by new psychoactive stimulants and psychedelics Exp Neurol 343 113778 September 2021 34090893 10.1016/j.expneurol.2021.113778 free Capela JP, Carmo H, Remião F, Bastos ML, Meisel A, Carvalho F Molecular and cellular mechanisms of ecstasy-induced neurotoxicity: an overview Mol Neurobiol 39 3 210–271 June 2009 19373443 10.1007/s12035-009-8064-1 To further corroborate the fact that MDMA agonistic properties at the 5-HT2A receptor could produce neuronal death, DOI, a prototypical agonist of that receptor was added to cortical neurons [289]. DOI (10 to 100 μM for 24 or 48 h) also induced a dose- and time-dependent apoptotic cortical neuronal apoptosis, which was attenuated by ketanserin and R-96544 [289]. Ketanserin and R-96544 are competitive selective 5-HT2A receptor antagonists and only attenuated MDMA-induced cortical neurodegeneration. However, an antibody raised against the 5-HT2A-receptor, an "irreversible" non-competitive 5-HT2A receptor blocker, prevented almost completely MDMA- and DOI-induced cortical neurotoxicity [289, 290]. Neuronal apoptosis mediated by MDMA is accompanied by activation of caspase 3, which could be blocked by the antibody raised against the 5-HT2A receptor [290]. Therefore, it is likely that DOI- and MDMA-induced neuronal apoptosis arises from direct stimulation of the 5-HT2A receptor [289, 290]. Capela JP, Ruscher K, Lautenschlager M, Freyer D, Dirnagl U, Gaio AR, Bastos ML, Meisel A, Carvalho F Ecstasy-induced cell death in cortical neuronal cultures is serotonin 2A-receptor-dependent and potentiated under hyperthermia Neuroscience 139 3 1069–1081 2006 16504407 10.1016/j.neuroscience.2006.01.007 Custodio RJ, Ortiz DM, Lee HJ, Sayson LV, Kim M, Lee YS, Kim KM, Cheong JH, Kim HJ Serotonin 2C receptors are also important in head-twitch responses in male mice Psychopharmacology (Berl) 242 7 1585–1605 July 2025 37882810 10.1007/s00213-023-06482-9 Capela JP, da Costa Araújo S, Costa VM, Ruscher K, Fernandes E, Bastos Mde L, Dirnagl U, Meisel A, Carvalho F The neurotoxicity of hallucinogenic amphetamines in primary cultures of hippocampal neurons Neurotoxicology 34 254–263 January 2013 22983118 10.1016/j.neuro.2012.09.005 Serotonin 5-HT2A receptor antagonism or knockdown could partially but greatly block this neurotoxicity in vitro. Chemistry DOI, also known as 2,5-dimethoxy-4-iodoamphetamine or as 2,5-dimethoxy-4-iodo-α-methylphenethylamine, is a substituted phenethylamine and amphetamine derivative and a member of the DOx family of drugs. It is structurally related to the naturally occurring phenethylamine psychedelic mescaline (3,4,5-trimethoxyphenethylamine). Synthesis The chemical synthesis of DOI has been described. Analogues Analogues of DOI include 2C-I, 4C-I, DOB, DOC, DOF, and DOM, among many others. Other analogues include N-methyl-DOI, IDNNA (N,N-dimethyl-DOI), DOI-NBOMe, and 25I-NBOMe, among others. History DOI was first described in the scientific literature by Ronald Coutts and Jerry Malicky in 1973. Coutts RT, Malicky JL The Synthesis of Some Analogs of the Hallucinogen 1-(2,5-Dimethoxy-4-methylphenyl)-2-aminopropane (DOM) Canadian Journal of Chemistry 51 9 1402–1409 1 May 1973 10.1139/v73-210 0008-4042 https://cdnsciencepub.com/doi/10.1139/v73-210 27 November 2025 Subsequently, it was described in greater detail by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). The radioactive iodine-125 form of DOI for PET imaging was first developed in the lab of David E. Nichols.November 2025 In January 2007, British police reported that three young men had fallen ill, reportedly, after taking DOI at a rave in Biggleswade, near Milton Keynes, and warned others who had taken it to seek medical attention. This would appear to be the first indication that DOI has found more widespread use as a recreational drug in the United Kingdom. New drug alert as three taken ill 29 January 2007 https://news.bbc.co.uk/2/hi/uk_news/england/beds/bucks/herts/6308895.stm BBC News South Australian man Cody Edwards who brutally murdered Synamin Bell controversially plead guilty to the lesser sentence of manslaughter after attesting that the drug DOI had induced paranoia, and that he had subsequently acted in 'self-defence' when he had beaten the mother-of-three to death with a dumbbell, resulting in over fifty wounds. Man sentenced to prison for manslaughter of partner, as government moves to close 'defence loophole' - ABC News 6 September 2024 https://www.abc.net.au/news/2024-09-06/cody-edwards-11-years-prison-manslaughter-synamin-bell/104319886 2024-09-06 amp.abc.net.au As of late 2025, DOI is expected to become a Schedule I controlled substance in the United States. Society and culture Scientific research DOI is widely used in scientific research to study serotonergic psychedelics and the serotonin 5-HT2 receptors. This is in part due to the fact that it is not a controlled substance in the United States. However, DOI is poised to become a Schedule I controlled substance in this country in the near future, which will greatly restrict access to the drug. A number of alternatives to DOI have been suggested for use in research, including the non-selective serotonin 5-HT2A receptor agonist TCB-2 and the selective serotonin 5-HT2A receptor agonists 25CN-NBOH and LPH-5. Another notable but much more recent compound is TGF-8027, which is a highly selective serotonin 5-HT2A receptor agonist and among the most selective such drugs currently known. Fenske TG, McKee JL, Cavalco NG, Schalk SS, Bonniwell EM, Lammers JC, Shacham N, Cuccurazzu B, Halberstadt AL, McCorvy JD Discovery of Highly Selective 5-HT2A Agonists Using Structure-Guided Design J Med Chem September 2025 acs.jmedchem.5c01855 40997862 10.1021/acs.jmedchem.5c01855 Legal status Australia The Standard for the Uniform Scheduling of Medicines and Poisons (SUSMP) of Australia does not list DOI as a prohibited substance. Gill A POISONS STANDARD 2013 22 July 2013 Therapeutic Goods Administration Australian Government Department of Health and Ageing 4 March 2014 http://www.comlaw.gov.au/Details/F2013L01607/229bdf2e-7014-4379-b751-0b584f55d699 PDF Canada Listed as a Schedule 1 Controlled Drugs and Substances Act: Legislative history · Schedule I · Section 19: Tramadol [Proposed]; Amphetamines http://isomerdesign.com/Cdsa/schedule.php?schedule=1&section=18.5&structure=C isomerdesign.com 2012-11-27 2022-03-31 https://archive.today/20220331223632/http://isomerdesign.com/Cdsa/schedule.php?schedule=1&section=18.5&structure=C as it is an analogue of amphetamine. Controlled Drugs and Substances Act: Definitions and Interpretations http://isomerdesign.com/Cdsa/definitions.php?structure=C isomerdesign.com 2012-11-27 2013-11-10 https://web.archive.org/web/20131110213450/http://isomerdesign.com/Cdsa/definitions.php?structure=C The CDSA was updated as a result of the Safe Streets and Communities Act, changing amphetamines from Schedule 3 to Schedule 1. Backgrounder: The Safe Streets and Communities Act Four Components Coming Into Force http://www.justice.gc.ca/eng/news-nouv/nr-cp/2012/doc_32759.html Department of Justice Government of Canada https://web.archive.org/web/20121018122345/http://www.justice.gc.ca/eng/news-nouv/nr-cp/2012/doc_32759.html 18 October 2012 Denmark Illegal since 8 April 2007. Erowid DOC Vault: Legal Status https://www.erowid.org/chemicals/doc/doc_law.shtml www.erowid.org Finland DOI is classified as a psychoactive substance banned from the consumer market in Finland. FINLEX ® - Ajantasainen lainsäädäntö: Valtioneuvoston asetus kuluttajamarkkinoilta… 1130/2014 https://www.finlex.fi/fi/lainsaadanto/2014/1130 Sweden Sveriges riksdag added DOI to schedule I ("substances, plant materials and fungi which normally do not have medical use") as narcotics in Sweden as of August 30, 2007, published by Medical Products Agency in their regulation LVFS 2007:10 listed as DOI, 4-jod-2,5-dimetoxi-amfetamin. Läkemedelsverkets föreskrifter - LVFS och HSLF-FS | Läkemedelsverket https://badzsoba.com.pl/b/lvfs_2007-10.pdf United States As of 2023, DOI is not scheduled in the United States. PART 1308 - Section 1308.11 Schedule I http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm www.deadiversion.usdoj.gov 2014-12-17 2009-08-27 https://web.archive.org/web/20090827043725/http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm However, DOI may be considered an analog of other controlled DOx drugs like DOB, in which case, sales or possession could be prosecuted under the Federal Analogue Act. The drug's non-controlled status has made it usefully accessible for use in scientific research, which has contributed to its popularity for such uses. In December 2023, the United States Drug Enforcement Administration (DEA) issued a notice of proposed rulemaking that would classify both DOI and DOC as schedule I controlled substances. Schedules of Controlled Substances: Placement of 2,5-dimethoxy-4-iodoamphetamine (DOI) and 2,5-dimethoxy-4-chloroamphetamine (DOC) in Schedule I https://www.regulations.gov/document/DEA-2022-0026-0001/comment www.regulations.gov However, in May 2024, it was reported that the DEA's June 10, 2024 hearing on scheduling of DOI and DOC had been postponed.Hu Jane C. Revisions made to report critical of Lykos's research on MDMA-assisted therapy; Lawsuit postpones hearing for contentious DEA proposal; and former MAPS employees make troubling allegations The Microdose U.C. Berkeley Center for the Science of Psychedelics 17 May 2024 https://themicrodose.substack.com/p/revisions-made-to-report-critical 6 February 2025 Judge Halts DEA's Hearing On Proposed Psychedelics Ban 9 May 2024 Law360 https://www.law360.com/cannabis/articles/1835534/judge-halts-dea-s-hearing-on-proposed-psychedelics-ban 6 February 2025 This followed opposition to the proposal by psychedelic researchers. DOI is frequently used in scientific research due in considerable part to its non-scheduled status, and DOI becoming a controlled substance would cause problems for scientists. In any case, an administrative judge recommended placement of DOI into Schedule I in June 2025, and it is likely that the drug will be scheduled. Palamar JJ, Fitzgerald ND The Epidemiology of Recreational Use and Availability of DOC and DOI in the United States Journal of Psychoactive Drugs 1–10 October 2025 41065346 10.1080/02791072.2025.2570937 12645445 DOI is a Schedule I controlled substance in the state of Florida. Statutes & Constitution :View Statutes: Online Sunshine http://leg.state.fl.us/statutes/index.cfm?App_mode=Display_Statute&URL=0800-0899/0893/0893.html leg.state.fl.us See also DOx (psychedelics) 5-HT2A receptor § Anti-inflammatory effects References External links y DOI - Isomer Design DOI - PsychonautWiki DOI - Erowid DOI - Lycaeum DOI - PiHKAL - Erowid DOI - PiHKAL - Isomer Design DOI - The Shulgin Index The Big & Dandy DOI Thread - Bluelight DOI (2,5-Dimethoxy-4-iodoamphetamine): A Potent & Unique Psychedelic Compound - Tripsitter Category:5-HT2A agonists Category:5-HT2B agonists Category:5-HT2C agonists Category:Anti-inflammatory agents Category:Biased ligands Category:Designer drugs Category:DOx (psychedelics) Category:Iodobenzene derivatives Category:PET radiotracers Category:PiHKAL Category:Psychoplastogens Category:Psychedelic drug research Category:Psychedelic phenethylamines Category:TAAR1 agonists Category:TNF inhibitors