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    DOI molecular structure

    DOI Stats & Data

    PubChem
    MW321.15
    FormulaC11H16INO2
    LogP2.5
    IUPAC1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine
    InChIKeyBGMZUEKZENQUJY-UHFFFAOYSA-N
    Chemical Class Substituted amphetamine
    Psychoactive Class Psychedelic / Stimulant

    Receptor Profile

    Receptor Actions

    Agonists
    5-HT2A receptor agonist (full)
    5-HT2B receptor agonist (full)
    5-HT2C receptor agonist (full)

    Receptor Binding

    5-HT 2A agonist

    Measured Affinities

    Guide to PHARMACOLOGY

    Measured binding and functional data for DOI, curated by the IUPHAR/BPS Guide to PHARMACOLOGY. Each row cites the paper it came from. Lower concentrations mean tighter binding — a value in the sub-nanomolar range indicates a very potent interaction.

    Target Action Measure Value Concentration Species Source
    5-HT2B receptor Htr2b Full agonist pKi 7.6 25.12 nM Rat —
    5-HT2A receptor Htr2a Full agonist pKi 7.1 79.43 nM Rat PMID 11040033
    5-HT1F receptor HTR1F Full agonist pKi 5.8 1,585 nM Human PMID 8380639
    5-HT2A receptor HTR2A Full agonist pKi — — Human —
    5-HT2B receptor HTR2B Full agonist pKi — — Human —
    5-HT2C receptor HTR2C Full agonist pKi — — Human —
    5-ht1e receptor HTR1E Full agonist pKi — — Human —

    Reading this. pKi, pEC50 and pIC50 are negative log molar values, so a higher number means a tighter interaction; the concentration column converts them for you. Values from non-human species are laboratory measurements and do not translate directly to human effect. Receptor affinity is not a dose — it describes what a molecule binds, not how much of it is safe to take.

    Receptor data from the IUPHAR/BPS Guide to PHARMACOLOGY (v2026.2), licensed CC BY-SA 4.0. Matched to this substance by InChIKey.

    History & Culture

    1973–1991

    DOI was first synthesized and described in the scientific literature by Ronald Coutts and Jerry Malicky in 1973. The compound later received more detailed documentation, including its psychoactive effects in humans, when Alexander Shulgin included it in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). Among the psychedelic amphetamines, DOI shares with DOB the distinction of being one of the most potent compounds in its class.

    DOI has become an important tool in neuroscience research, particularly for studying serotonergic systems. The compound can be synthesized with various radioactive iodine isotopes, making it valuable for mapping the distribution of serotonin 5-HT2A receptors in the brain. The radioactive iodine-125 form used in PET imaging was developed in the laboratory of David E. Nichols. The fact that DOI remained unscheduled at the federal level in the United States significantly facilitated its widespread adoption in research settings. At least one neurochemical research company on the East Coast began offering DOI commercially for experimental purposes, though the company appeared aware of the compound's psychedelic properties—at one point nearly doubling its price and adding restrictions against telephone orders. Beyond its utility as a research ligand, DOI has demonstrated unexpected pharmacological properties in laboratory studies. Cell research has shown the compound to be an extremely potent inhibitor of tumour necrosis factor-alpha inflammation at picomolar concentrations. TNF-alpha is a significant target in research on degenerative conditions including rheumatoid arthritis and Alzheimer's disease.

    2007–present

    In January 2007, British police reported that three young men had fallen ill after reportedly consuming DOI at a rave in Biggleswade, near Milton Keynes. Authorities issued warnings for others who may have taken the substance to seek medical attention. This incident represented an early indication that DOI had begun circulating as a recreational drug in the United Kingdom. A notable criminal case in South Australia involved a man named Cody Edwards, who was convicted in the killing of Synamin Bell. Edwards pleaded guilty to manslaughter rather than murder after claiming that DOI had induced paranoia, leading him to act in what he characterized as self-defence when he fatally beat the mother of three with a dumbbell. The case drew attention due to the controversial reduced charge.

    Subjective Effects

    Physical
    • Spontaneous tactile sensations
    • Euphoria
    • Stimulation
    • Nausea
    • Bodily control enhancement
    • Tactile enhancement
    • Temperature regulation loss
    • Increased heart rate
    • Pupil dilation
    Cognitive
    • Empathy, love and sociability enhancement
    • Analysis enhancement
    • Time distortion
    • Novelty enhancement
    • Emotion enhancement
    • Immersion enhancement
    • Memory suppression
    • Ego death
    • Unity and interconnectedness
    • Wakefulness
    • Increased libido
    Sensory
    Auditory
    • Enhancements
    • Distortions
    • Hallucinations
    Visual · Distortions
    • Drifting: (melting, flowing, breathing and morphing)
    • Tracers
    • Symmetrical texture repetition
    • Colour shifting
    • Scenery slicing
    Visual · Enhancements
    • Acuity enhancement
    • Colour enhancement
    • Pattern recognition enhancement
    Visual · Hallucinatory States
    • Transformations
    • Internal hallucinations: (autonomous entities; settings, sceneries, and landscapes; alterations in perspective and scenarios and plots)

    Forked from Subjective Effect Documentation work by Josie Kins, August 2016. Via dose.wiki (CC0).

    Toxicity

    PsychonautWiki

    The toxicity and long-term health effects of recreational DOI do not seem to have been studied in any scientific context and the exact toxic dose is unknown. This is because DOI is a research chemical with very little history of human usage. Anecdotal reports from users suggests that there are no negative health effects attributed to simply trying it by itself at low to moderate doses and using it very sparingly (but nothing can be completely guaranteed). Independent research should always be done to ensure that a combination of two or more substances is safe before consumption. It is strongly recommended that one use harm reduction practices when using this substance.

    Effect Profile

    Curated + 42 Reports
    Psychedelic 8.5

    Strong visuals, headspace, and auditory effects with strong body load

    Visual Intensity×3
    10104.0
    Headspace Depth×3
    106.31.6
    Auditory Effects×1
    8102.4
    Body Load / Somatic Effects×1
    106.63.7
    Catalog Erowid BlueLight
    Stimulant 6.8

    Strong stimulation and euphoria with strong anxiety/jitters, low focus

    Stimulation / Energy×3
    1010
    Euphoria / Mood Lift×2
    96.0
    Focus / Productivity×2
    32.4
    Anxiety / Jitters×1
    107.2
    Catalog Erowid

    Community Effects

    TripSit
    Positive
    visual enhancement euphoria stimulation
    Negative
    vasoconstriction body load nausea

    Tolerance & Pharmacokinetics

    drugs.wiki

    Tolerance Decay

    Full tolerance 1h Half tolerance 10d Baseline ~14d

    Cross-Tolerances

    LSD
    Psilocybin
    Psilocin
    Mescaline
    DMT
    5-MeO-DMT
    2C-B
    2C-E

    Experience Report Analysis

    Erowid BlueLight
    42 Reports
    25 Single-substance
    2002–2012 Date Range
    9 With Age Data
    21 Effects Detected

    Demographics

    Gender Distribution

    Age Distribution

    Reports Over Time

    Effect Analysis

    Erowid + Bluelight

    Effects aggregated from 42 experience reports (25 single-substance Erowid + 17 Bluelight)

    42 Reports
    91 Effects Detected
    45 Positive
    38 Adverse
    8 Neutral

    Effect Sentiment Distribution

    Confidence Distribution

    Each bar is the share of reports mentioning the effect; its whisker, and the band on the rows below, is the 95% interval: where the share could plausibly be with other reports of the same kind.

    Rows resting on fewer than 20 reports show a count (“3 of 7”) instead of a bar. Why 20?

    Positive Effects 45

    Stimulation 50.0% (95% interval 36 to 64 percent) 82%
    Visual Distortions 42.9% (95% interval 29 to 58 percent) 80%
    Euphoria 33.3% (95% interval 21 to 48 percent) 86%
    Color Enhancement 23.8% (95% interval 14 to 38 percent) 86%
    Closed-Eye Visuals 23.8% (95% interval 14 to 38 percent) 92%
    Music Enhancement 21.4% (95% interval 12 to 36 percent) 80%
    Open-Eye Visuals 21.4% (95% interval 12 to 36 percent) 88%
    Body High 16.7% (95% interval 8 to 31 percent) 79%
    Empathy 16.0% (95% interval 6 to 35 percent) 70%
    Introspection 14.3% (95% interval 7 to 28 percent) 85%
    Focus Enhancement 14.3% (95% interval 7 to 28 percent) 85%
    Tactile Enhancement 9.5% (95% interval 4 to 22 percent) 85%
    Patterning 4 of 17 90%
    Brightness Enhancement 4 of 17 82%
    Entity Imagery 4 of 17 85%
    Pareidolia 3 of 17 82%
    Thought Acceleration 3 of 17 83%
    Geometric Imagery 3 of 17 88%
    Contentment 3 of 17 82%
    Depth Distortion 2 of 17 82%

    Adverse Effects 38

    Anxiety 28.6% (95% interval 17 to 44 percent) 88%
    Confusion 21.4% (95% interval 12 to 36 percent) 80%
    Muscle Tension 20.0% (95% interval 9 to 39 percent) 70%
    Nausea 19.0% (95% interval 10 to 33 percent) 85%
    Pupil Dilation 11.9% (95% interval 5 to 25 percent) 85%
    Body Load 5 of 17 86%
    Restlessness 4 of 17 78%
    Dry Mouth 3 of 17 87%
    Paranoid Ideation 2 of 17 85%
    Jaw Clenching 2 of 17 80%
    Thought Disorganization 2 of 17 88%
    Fear 2 of 17 88%
    Insomnia 2 of 17 88%
    Time Dilation 2 of 17 75%
    Ataxia 2 of 17 78%
    Irritability 2 of 17 82%
    Vomiting 2 of 17 85%
    Tremor 2 of 17 82%
    Emotional Lability 2 of 17 80%
    Tension 1 of 17 80%
    ⚠ Chest Pain 1 of 17 85%
    Show 17 more adverse effects
    Dizziness 1 of 17 75%
    Surface Breathing 1 of 17 90%
    Numbness 1 of 17 85%
    Muscle Aches 1 of 17 90%
    Urinary Retention 1 of 17 75%
    Panic 1 of 17 90%
    Paranoia 1 of 17 85%
    Crying 1 of 17 85%
    Temporal Disorientation 1 of 17 75%
    Vasoconstriction 1 of 17 90%
    Pressure 1 of 17 80%
    Sweating 1 of 17 75%
    Chills 1 of 17 90%
    Heaviness 1 of 17 80%
    Body Temperature Change 1 of 17 85%
    Dysphoria 1 of 17 90%
    Itching 1 of 17 75%
    Show 8 neutral or unclassified mentions
    Auditory Effects 19.1% (95% interval 10 to 33 percent)
    Hospital 12.0% (95% interval 4 to 30 percent)
    Ego Dissolution 9.5% (95% interval 4 to 22 percent)
    Sedation 9.5% (95% interval 4 to 22 percent)
    Appetite Suppression 1 of 17
    Hypersomnia 1 of 17
    Blurred Vision 1 of 17
    Frequent Urination 1 of 17

    Also reported in combinations. In the 17 DOI reports where another drug was taken too, 3 mention hospital, emergency services or an overdose, 0 a seizure and 1 psychosis (too few reports for percentages). In the 25 single-substance reports: 12.0%, 0.0% and 8.0%. These are not in the figures above: they cannot be put down to DOI alone, and a mention is not always something that happened to the writer.

    Dosage Distribution

    Dose distribution from experience reports, one dose per report (the first listed). Doses above Q3 + 3×IQR, far above what people typically take, are left out of the median and range and listed under each route: most are real heavy doses or overdoses, not mistakes.

    Median: 3.0 mg IQR: 2.0–3.6 mg n=11

    1 report gave a dose above the typical range (15.9 mg), so it is not in the figures above. Listing a dose here does not mean it is safe.

    Show the report

    Real-World Dose Distribution

    Erowid

    From 31 of 51 recorded dose entries: those that state a weight (mg, g or µg), in routes with at least five of them. Values above Q3 + 3×IQR, far above what people typically take, are left out; they can include real heavy doses and overdoses, not only mistakes.

    Oral (n=29)

    Median: 3.0mg 25th: 2.0mg 75th: 4.0mg 90th: 5.6mg

    Common Combinations

    Most co-occurring substances, as a share of all 42 reports filed under DOI; whiskers are 95% intervals

    Form / Preparation

    Most common forms and preparations, as a share of the 27 reports that give one; whiskers are 95% intervals

    Body-Weight Dosing

    Dose per kg of body weight, one dose per report (the first listed), from reports giving a weight of 30–250 kg. Doses above Q3 + 3×IQR, far above what people typically take, are left out of the median and range and listed under each route.

    Median: 0.04 mg/kg IQR: 0.028–0.053 mg/kg n=11

    1 report gave a dose above the typical range (0.265 mg/kg), so it is not in the figures above. Listing a dose here does not mean it is safe.

    Show the report

    Redose Patterns

    Redosing behavior across 29 reports

    13.8% (95% interval 6 to 31 percent) Redosed
    1.1 Avg Doses

    Legal Status

    Country Status Notes
    Australia Controlled (disputed) Sources conflict on current status. One source indicates DOI is controlled, noting it has been found on blotter sold as LSD. Another source states it is not listed in the Standard for the Uniform Scheduling of Medicines and Poisons (SUSMP). Caution advised regarding current legal status.
    Austria Illegal (NPSG) Prohibited under the Neue-Psychoaktive-Substanzen-Gesetz (New Psychoactive Substances Act). Possession, production, and sale are illegal.
    Brazil Illegal Listed as a controlled substance on Portaria SVS/MS nº 344. Possession, production, and sale are prohibited.
    Canada Schedule III CDSA 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.
    Denmark Schedule I Added to the list of Schedule I controlled substances on April 8, 2007, alongside 2C-E, 2C-P, and DOC.
    Germany Anlage II BtMG Controlled under Anlage II of the Betäubungsmittelgesetz (Narcotics Act, Schedule II) as of December 13, 2014. Manufacturing, possession, import, export, purchase, sale, procurement, or dispensing without a license is illegal.
    Japan Designated Substance (Shitei-Yakubutsu) Controlled under the Pharmaceutical Affairs Law as a Designated Substance. Possession and sale are prohibited.
    Latvia Schedule I Classified as a Schedule I controlled substance under national drug legislation.
    New Zealand Schedule 3 / Class C 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.
    Sweden Schedule I Classified as a Schedule I substance as of August 30, 2007, published by the Medical Products Agency in regulation LVFS 2007:10.
    Switzerland Controlled (with research exemption) Considered a controlled substance as a defined derivative of α-Methylphenethylamine under Verzeichnis E point 130. Legal when used for scientific or industrial purposes.
    Turkey Illegal Classified as a controlled drug. Possession, production, supply, and import are prohibited.
    United Kingdom Illegal (Psychoactive Substances Act) Prohibited under the Psychoactive Substances Act 2016, which came into effect on May 26, 2016. Production, supply, and import are illegal.
    United States Unscheduled (Federal Analogue Act may apply) 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.
    United States - Florida Schedule I Controlled as a Schedule I substance under Florida state law, separate from federal scheduling.
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