DOI
2,5-Dimethoxy-4-iodoamphetamine
DOI is a psychedelic amphetamine of the DOx family. First described in the scientific literature in 1973, it was later documented in detail by Alexander Shulgin in PiHKAL (1991). DOI is among the most potent phenethylamine psychedelics and is notable for its exceptionally long duration, which can prevent sleep for 24 hours or more. It is widely used in scientific research as a radioligand for mapping serotonin 5-HT2A receptors in the brain.12
Contents
Dosage & Duration
Dosage
Threshold~0.5 mg
Light0.5-1 mg
Moderate1-2 mg
Strong2-3 mg
Heavy3+ mg
Residual stimulation and insomnia are frequently reported effects that may extend well beyond the primary experience, sometimes lasting into the following day or longer depending on the dose taken and when it was administered.
Duration
Onset60-120 minutes
Come Up90-180 minutes
After Effects1-24 hours
Total16-24 hours
Subjective Effects
Effects vary widely by individual, dose, and context.
Physical
Cognitive
Visual
Hallucinatory States
Auditory
Reagent Testing
Loading reagent data
Expected colorimetric results are being prepared.
Pharmacology
Pharmacodynamics
DOI acts as a potent agonist at serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors1, with approximately 5- to 12-fold selectivity for 5-HT2A over 5-HT2C3 and biased agonism at 5-HT2C3. Despite its amphetamine backbone, DOI does not function as a monoamine releasing agent of serotonin or dopamine4. It is also an agonist at the rat trace amine-associated receptor 1 (TAAR1)5, and the R-(−) enantiomer is the more pharmacologically active stereoisomer1. DOI has additionally been found to potently inhibit tumor necrosis factor alpha (TNFα)-induced inflammation at picomolar concentrations6 and to promote neuroplasticity through rapid dendritic spine growth and reorganization78, classifying it as a psychoplastogen8.
Pharmacokinetics
Absorption & half-lifenot documented yetMetabolitesnone documented yet
Dangerous
Highest riskThese combinations are considered extremely harmful and should always be avoided. Reactions to these drugs taken in combination are highly unpredictable and have a potential to cause death.
Unsafe
AvoidThere is considerable risk of physical harm when taking these combinations, they should be avoided where possible.
Caution
Use cautionThese combinations are not usually physically harmful, but may produce undesirable effects, such as physical discomfort or overstimulation. Extreme use may cause physical health issues. Synergistic effects may be unpredictable. Care should be taken when choosing to use this combination.
Tolerance
Full Tolerance
Tolerance to the effects of DOI develops almost immediately after ingestion.
Baseline Reset
10-14 days in the absence of further consumption
Half Tolerance
5-7 days
Cross Tolerance
Psychedelics (all serotonergic psychedelics will have reduced effect following DOI consumption)
Harm Potential
Addiction & Dependence
Psychological
Extremely LowDOI is not habit-forming, and the desire to use it can actually decrease with use. It is most often self-regulating.
Physical
No documented physical dependence or withdrawal symptoms have been reported.
Toxicity
Cardiovascular
Cardiovascular effects including elevated blood pressure, increased heart rate, and vasoconstriction have been reported, particularly at higher doses; severe vasoconstriction may develop several hours into intoxication and in extreme overdose cases may require medical intervention to prevent hypertensive emergency.9
Psychosis Risk
At high doses, psychosis, bizarre delusional behavior, and paranoia may occur. Frequent use carries risk of reality distortion which may manifest as anxiety states or schizophrenic traits. DOI can trigger latent psychoses. The extended duration contributes to sleep deprivation, and stimulant psychosis symptoms may surface during the comedown, particularly around the 16-24 hour mark.
Seizure Risk
Seizures are rarely observed but may occur in those predisposed to them, especially in physically taxing conditions such as dehydration, undernourishment, overheating, or fatigue. At appropriately high doses, seizure risk increases.
History & Culture
Discovery and Synthesis
DOI was first synthesized and described in the scientific literature by Ronald Coutts and Jerry Malicky in 1973.10 The compound later received more detailed documentation, including its psychoactive effects in humans, when Alexander Shulgin included it in his 1991…
Legality
International
DOI is not listed under the 1961 Single Convention on Narcotic Drugs, the 1971 Convention on Psychotropic Substances, or the 1988 Convention against Illicit Traffic in Narcotic Drugs and Psychotropic Substances.
By Country
United StatesIllegal (analog/blanket ban)Analogue Act
Not federally scheduled. However, it would likely be considered an analog of DOB, meaning sales for human consumption or possession with intent to ingest could be prosecuted under the Federal Analogue Act. DOI is regularly used in animal and in vitro research, which has been cited as a reason against scheduling.
By state
Across the 50 states, D.C., and the permanent territories, most jurisdictions treat DOI consistently with federal control; listed entries record independently verified differences in state classification or coverage.
ArizonaIllegalDangerous drug
District of ColumbiaIllegalSchedule I
FloridaIllegalSchedule I
IdahoIllegalSchedule I
IllinoisIllegalSchedule I
MaineIllegalSchedule W
MinnesotaIllegalSchedule I
NebraskaIllegalSchedule I
North CarolinaIllegalSchedule I
North DakotaIllegalSchedule I controlled substance
Northern Mariana IslandsNot schedulednot-listed-in-commonwealth-schedule-i
OklahomaIllegalSchedule I
South DakotaIllegalSchedule I controlled substance
VermontIllegal (analog/blanket ban)Stimulant analog
West VirginiaNot schedulednot-listed-in-schedules
AustraliaControlled (disputed)Citation needed
Reported Australian status is inconsistent. One account treats DOI as controlled and notes it has appeared on blotter sold as LSD; another says DOI is absent from the SUSMP poison-scheduling standard.
BelgiumIllegal (analog/blanket ban)Bijlage IVA
Koninklijk besluit van 6 september 2017 houdende regeling van verdovende middelen, psychotrope stoffen1819
DOI is covered as an amphetamine derivative in Annex IVA of the Royal Decree of 6 September 2017. Annex IVA covers derivatives of 1-phenylpropan-2-amine with permitted phenyl-ring substituents including alkoxy groups and halogens, and permits multiple such substitutions; DOI has 2,5-dimethoxy and 4-iodo substitutions. The decree requires a prior activity licence for import, export, transport, manufacture, production, possession, sale, supply, delivery, or acquisition, and restricts that licence to scientific or medical purposes.
CanadaIllegal (analog/blanket ban)Schedule III
Controlled Drugs and Substances Act, Schedule III23
Controlled as of October 12, 2016 under a broad definition covering 2,5-dimethoxyphenethylamine derivatives. This includes most 2C compounds, DOx series, and related phenethylamines.
DenmarkIllegalBilag 1
Bekendtgørelse om euforiserende stoffer27
Added to the list of Schedule I controlled substances on April 8, 2007, alongside 2C-E, 2C-P, and DOC.
GermanyIllegalAnlage II
DOI is expressly listed in Anlage II of Germany's Betäubungsmittelgesetz as 2,5-Dimethoxy-4-iodamfetamin. Anlage II contains marketable but non-prescribable narcotics; unlicensed manufacture, trade, import, export, acquisition, and possession are criminal offences under the Act.
JapanIllegal指定薬物
Controlled under the Pharmaceutical Affairs Law as a Designated Substance. Possession and sale are prohibited.
NetherlandsIllegal (analog/blanket ban)Lijst IA
Since 1 July 2025, DOI (2,5-dimethoxy-4-iodoamphetamine) falls within the 2-fenethylamine substance group in List IA of the Netherlands' Opiumwet: its phenyl ring and 2-aminoethyl side chain match the statutory scaffold and permitted iodine, methoxy, and methyl substitutions. Article 2a prohibits importing, exporting, preparing, processing, selling, supplying, transporting, possessing, or manufacturing a substance in a List IA group, subject to the statutory exemptions.
NorwayRestrictedNarkotikalisten
DOI is listed in the Narkotikalisten as 2,5-dimetoksy-4-jodamfetamin. Under the Medicines Act, its manufacture, import, wholesale and retail supply require express authorization; sale, dispensing and dispatch are limited to medical and scientific use. Possession and use without lawful access are prohibited.
South AfricaIllegal (analog/blanket ban)Part III
Schedule 2 Part III, Drugs and Drug Trafficking Act 140 of 199247
DOI is covered by Schedule 2 Part III's homologue provision because it is chemically related to the listed 2,5-dimethoxyamphetamine and incorporates its amphetamine structural fragment. Part III classifies it as an undesirable dependence-producing substance; unauthorised possession, use, manufacture, supply, sale, import, or export is prohibited under the Drugs and Drug Trafficking Act. The current Schedule 2 text has applied since 14 December 2022; contravening the possession or use prohibition carries a maximum of 15 years' imprisonment, while dealing carries a maximum of 25 years.
SpainNot scheduled
Real Decreto 2829/1977, Anexo 151
DOI (2,5-dimetoxi-4-yodoanfetamina) is not included in the current Lista I of Annex 1 to Real Decreto 2829/1977, Spain's controlled psychotropic schedule. The annex separately lists the related 2C-I (2,5-dimetoxi-4-iodofenetilamina) and DOC (2,5-dimetoxi-4-cloroanfetamina), but not DOI; the decree subjects only the substances referred to in Lists I–IV and their preparations to its controls.
SwitzerlandIllegal (analog/blanket ban)Verzeichnis e
Considered a controlled substance as a defined derivative of α-Methylphenethylamine under Verzeichnis E point 130. Legal when used for scientific or industrial purposes.
UkraineIllegalСписок № 2
Ukraine places DOI (2,5-dimethoxy-4-iodoamphetamine) in Table I, List No. 2 of the national controlled-substances list; that list is for especially dangerous psychotropic substances whose circulation is prohibited. Resolution No. 1129 of 5 December 2012 added DOI to that list. The statutory regime defines circulation to include production, manufacture, storage, transport, acquisition, sale, import, and export, and permits Table I List No. 2 substances only for the purposes and grounds specified by law.
ArgentinaIllegalAnexo I
DOI (4-yodo-2,5-dimetoxianfetamina) is listed in Annex I to Decree 560/2019, as substituted by Decree 122/2026, and is therefore an estupefaciente under article 77 of the Criminal Code. The current Annex I took effect on 3 March 2026. Law 23.737 criminalizes unauthorized production, manufacture, preparation, distribution, storage, transport, commercial dealing, and possession of estupefacientes.
AustriaIllegal (analog/blanket ban)Phenethylamin-Verbindungen
Prohibited under the Neue-Psychoaktive-Substanzen-Gesetz (New Psychoactive Substances Act). Possession, production, and sale are illegal.
BrazilIllegalLista F2
Resolução da Diretoria Colegiada Anvisa nº 1.036, de 9 de julho de 2026, Anexo I da Portaria SVS/MS nº 344/19982021
Listed as a controlled substance on Portaria SVS/MS nº 344.22 Possession, production, and sale are prohibited.
Czech RepublicIllegalList 4
Since 1 October 2015, the Czech Republic has listed DOI (2,5-dimethoxy-4-iodoamphetamine) in List 4 of Government Regulation No. 463/2013 Coll., on lists of addictive substances. Under the Addictive Substances Act, List 4 substances may be used only for limited research, scientific, or very limited therapeutic purposes specified in a handling permit; handling includes production, storage, supply, purchase, and sale.
FinlandRestricted1130/2014
Valtioneuvoston asetus kuluttajamarkkinoilta kielletyistä psykoaktiivisista aineista 1130/201428
Finland’s Government Decree 1130/2014 places DOI on the list of psychoactive substances prohibited from the consumer market. The restriction prohibits making the substance available to consumers under the Psychoactive Substances Act framework; it is distinct from narcotics scheduling.
IrelandIllegal (analog/blanket ban)Schedule 1
DOI is covered by the Schedule 1 provision for substances structurally derived from alpha-methylphenethylamine with alkoxy or halo ring substitutions. Unauthorised possession of a controlled drug is an offence under the Misuse of Drugs Act 1977, and the 2017 Regulations prohibit its production, supply, importation and exportation except as authorised.
LatviaIllegal (analog/blanket ban)Schedule I
Cabinet Regulation No. 847, Annex 137
Classified as a Schedule I controlled substance under national drug legislation.
New ZealandIllegal (analog/blanket ban)Class C
Misuse of Drugs Act 1975, Schedule 340
Controlled under the catch-all Analogues section in Schedule 3 (Class C) of New Zealand's drug laws, which covers structural analogs of scheduled substances.41
PolandIllegal (analog/blanket ban)grupa I-NPS
Rozporządzenie Ministra Zdrowia z dnia 17 sierpnia 2018 r. w sprawie wykazu substancji psychotropowych, środków odurzających oraz nowych substancji psychoaktywnych444546
Poland's Group I-NPS catch-all covers DOI as a 2-phenylethylamine derivative bearing iodine and alkoxy substituents on the phenyl ring and a methyl substituent on the side chain. The Group I-NPS provision has applied since 21 August 2018. Under the Act on Counteracting Drug Addiction, possession of a new psychoactive substance is punishable by a fine, while possession of a significant quantity can be punished by a fine, restriction of liberty, or imprisonment for up to three years; supplying it for financial or personal benefit is punishable by imprisonment from one to ten years.
South KoreaIllegal별표 3
DOI is listed as a Schedule 3 psychotropic substance in Appendix 3 to the Enforcement Decree of the Narcotics Control Act, effective 7 February 2025. South Korea prohibits possession, ownership, use, management, import, export, manufacture, sale, solicitation or arrangement of sales, and transfer of Article 2(3)(a) psychotropic substances, except with approval from the Ministry of Food and Drug Safety as provided by decree.
SwedenIllegalFörteckning I
Classified as a Schedule I substance as of August 30, 2007, published by the Medical Products Agency in regulation LVFS 2007:10.
TurkeyIllegal
Classified as a controlled drug. Possession, production, supply, and import are prohibited.
United KingdomIllegal (analog/blanket ban)Class A
DOI is a Class A controlled drug under the phenethylamine-derivative provision in Schedule 2 Part I to the Misuse of Drugs Act 1971. The provision covers alpha-methylphenethylamine derivatives with alkoxy and halide ring substitutions, which includes 2,5-dimethoxy-4-iodoamphetamine. Unless authorised under the statutory regime, possession, production, supply, and importation or exportation are offences or prohibited under the Act.
References
Source Pages
Citations
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