4-HO-DiPT
4-hydroxy-N,N-diisopropyltryptamine
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4-HO-DiPT (4-hydroxy-N,N-diisopropyltryptamine) is a synthetic psychedelic of the tryptamine class. It is a close structural analog of psilocin, the primary psychoactive molecule in psilocybin mushrooms. It activates serotonin receptors in the brain and also slows serotonin reuptake,[1] producing the visual and cognitive shifts characteristic of classical psychedelics.[2]
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First synthesized in 1977 as part of a systematic study of psilocin analogs,[3] 4-HO-DiPT was documented for human use by Alexander Shulgin in TiHKAL in 1997.[4] A pharmaceutical company later developed it into the prodrug luvesilocin (RE104),[5] which received FDA Breakthrough Therapy Designation for postpartum depression in February 2026.[6] It remains unscheduled at the US federal level, though several countries control it under broad psychoactive substance laws.
Subjective effects include color enhancement, mild visual distortion, introspective thought, time compression, and heightened body awareness. The experience is defined by its brevity — a full psychedelic state that arrives fast and ends well before a psilocybin trip would peak, with lighter visuals and closer in character to smoked DMT than to oral mushrooms. Leg tremors, muscle tension, nausea, and elevated heart rate are characteristic unwanted effects.[7]
4-HO-DiPT does not produce physical dependence, and no lethal dose has been established.safety citation needed The primary danger is the steep dose-response curve — a modest increase in dose can shift the experience from mild to overwhelming, making precise measurement critical;[4] combining it with MAOIs or tramadol risks dangerous overloading of the serotonin system. What is known comes from preclinical studies, one prodrug clinical trial, and user reports — controlled human toxicity data for the free compound do not exist.safety citation needed
History[edit]
Discovery
4-HO-DiPT was first synthesized in 1977 by David Repke and colleagues as part of a systematic study of psilocin analogs.[3] No human testing followed the original publication. Alexander Shulgin documented the compound's human effects twenty years later as entry #17 in TiHKAL (1997), describing it as unmatched among oral psychedelics for speed and brevity.[4]
Clinical development
Reunion Neuroscience developed luvesilocin (RE104), a subcutaneous prodrug form of 4-HO-DiPT designed for controlled clinical use.[5] A Phase 2 trial in 84 patients with postpartum depression met its primary endpoint.[8] The FDA granted Breakthrough Therapy Designation in February 2026.[6]
Regulatory history
The DEA proposed placing 4-HO-DiPT in Schedule I in January 2022, then withdrew the proposal in July 2022 pending further scientific review from the Department of Health and Human Services.[9] The compound remains unscheduled federally but may be prosecuted as a structural analog of Psilocin under the Federal Analogue Act.
The name iprocin — a contraction of "isopropyl" and "psilocin" — follows the Shulgin-era naming convention for tryptamine analogs. 4-HO-DiPT first appeared on European research chemical markets around 2005,[10] earning a niche reputation for its unusually short duration, though it never achieved the recognition of psilocybin or LSD.
Chemistry[edit]
4-HO-DiPT belongs to the tryptamine family — the same chemical class as psilocin, DMT, and serotonin itself. It is a direct structural analog of psilocin, with the nitrogen-methyl groups replaced by bulkier isopropyl groups — a change that shifts receptor binding while preserving psychedelic activity.[11]
Its molecular formula is C₁₆H₂₄N₂O. It is also the active compound released when the pharmaceutical prodrug luvesilocin (RE104) is metabolized in the body.[5]
Pharmacology[edit]
Mechanism of action
4-HO-DiPT produces psychedelic effects primarily by activating serotonin receptors. Blocking this activation eliminates psychedelic-like behavior in animals.[11][2] It also slows the brain's serotonin reuptake process,[1] placing its pharmacological profile closer to psilocin than to LSD or mescaline.
Pharmacokinetics
No human pharmacokinetic study has been published for oral 4-HO-DiPT. In rats given the prodrug RE104, the compound had a plasma half-life of roughly 40 minutes, with blood concentration tracking directly with behavioral intensity.[5] This short half-life is consistent with the brief total duration reported in human accounts.[4]
Metabolism
Most metabolic data come from studies of 4-AcO-DiPT, which rapidly converts to 4-HO-DiPT in the body.[12] The primary breakdown enzyme is CYP2D6.[13][14] People who metabolize drugs slowly through this enzyme may experience stronger or more prolonged effects.[15]
Neuroscience[edit]
Where it acts
4-HO-DiPT activates serotonin receptors[2] and is expected to trigger activity in frontal brain regions — disrupting the normal filtering of sensory information and producing the characteristic expansion of awareness.inferred Preclinical work also shows it activates inhibitory neurons in the amygdala — the brain's fear-processing center — dampening conditioned fear responses.[2]
Why it matters
Despite its brief duration, 4-HO-DiPT produced antidepressant-like effects in animals that lasted a week after a single dose.[5] The RECONNECT clinical trial showed sustained improvement at four weeks from a single short session.[6] This supports the idea that psychedelics trigger structural brain changes — new connections, new growth — that outlast the drug itself.[16]
Key unknowns include whether 4-HO-DiPT promotes neuroplasticity through pathways independent of serotonin receptors (as psilocin does via the TrkB/BDNF pathway[16]), whether its short duration limits or preserves therapeutic benefit compared to longer-acting psychedelics, and how genetic variation in CYP2D6 metabolism affects both the experience and the therapeutic response.
Subjective Effects[edit]
The 4-HO-DiPT experience is defined by compression. A full psychedelic state arrives quickly and recedes within a couple of hours — intense, direct, and physically grounded. Characteristic leg tremors and a heightened sense of the body run throughout, anchoring an otherwise perceptual experience.
Compared to psilocybin, the experience is faster, shorter, and visually lighter, with a more prominent body load. Relative to smoked DMT, it is more navigable — similar in intensity but gentler in entry and long enough to orient.
Effect Grid
At common doses (15–20 mg oral), the full psychedelic experience unfolds rapidly. Colour enhancement becomes pronounced, objects may exhibit mild drifting and morphing, and rainbow halos or tracers appear around light sources. Closed-eye visuals remain modest compared to psilocin. Thought connectivity increases significantly, often producing introspective insights and novel personal perspectives. Cognitive euphoria ranges from mild to strong.
Physically, leg tremors, muscle loosening, mild stimulation, and elevated heart rate are commonly reported. A vague body malaise and chill-like sensations may occur. Nausea is possible but less prominent than with psilocybin.
The experience peaks within 20–30 minutes of onset and resolves to baseline within approximately 2–3 hours. The steep dose-response curve means that 15 mg produces a mild-to-moderate experience while 20 mg can reach full intensity.
Modeled from the effect's dose-dependence curve — not per-substance measurements.
Color enhancement · Geometry · Brightness alteration · Music enhancement · Holotropic state · Visual morphing · Symmetrical texture repetition · Tracers · Auditory enhancement · Auditory misinterpretation · Environmental patterning · Light sensitivity · Sound sensitivity · Touch enhancement · Vestibular distortion · Visual haze / noise · Visual melting · Depth perception distortion · Perspective distortion · After-images · Ganzfeld effect · Peripheral vision distortion · Proprioceptive distortion · Spatial disorientation · Visual acuity enhancement · Synesthesia · Visual diffraction · Dreaming enhancement · Peripheral misidentification · Tinnitus · Visual acuity suppression · Visual magnification · Visual processing acceleration · Flashbacks · Object transformations · Internal hallucinations · Visual recursion · Auditory hallucinations · Environmental orbism / cubism · External hallucinations · Object activation · Perspective hallucinations · Shadow people · Persisting hallucinations
Holotropic state · Visual morphing · Symmetrical texture repetition · Tracers · Auditory enhancement · Auditory misinterpretation · Environmental patterning · Light sensitivity · Sound sensitivity · Touch enhancement · Vestibular distortion · Visual haze / noise · Visual melting · Depth perception distortion · Perspective distortion · After-images · Ganzfeld effect · Peripheral vision distortion · Proprioceptive distortion · Spatial disorientation · Visual acuity enhancement · Synesthesia · Visual diffraction · Dreaming enhancement · Peripheral misidentification · Tinnitus · Visual acuity suppression · Visual magnification · Visual processing acceleration · Flashbacks · Object transformations · Internal hallucinations · Visual recursion · Auditory hallucinations · Environmental orbism / cubism · External hallucinations · Object activation · Perspective hallucinations · Shadow people · Persisting hallucinations
Spontaneous body sensations · Appetite suppression · Stimulation · Physical fatigue · Tactile euphoria · Tingling / electric sensations · Wakefulness · Bodily heaviness · Bodily pressures · Body schema distortion · Breathing alteration · Dizziness · Dry mouth · Heart rate perception changes · Insomnia · Nausea · Laughter fits · Muscle tension · Vibrations / buzzing · Bodily lightness · Excessive sweating · Headache · Muscle relaxation · Restlessness · Dehydration sensation · Diarrhea · Involuntary body movements · Abnormal heartbeat · Pain suppression · Respiratory stimulation · Sedation · Sexual arousal enhancement · Trembling · Vasoconstriction · Yawning · Nystagmus (eye wobbles) · Vomiting · Bodily dissociation · Tactile hallucination
Physical fatigue · Tactile euphoria · Tingling / electric sensations · Wakefulness · Bodily heaviness · Bodily pressures · Body schema distortion · Breathing alteration · Dizziness · Dry mouth · Heart rate perception changes · Insomnia · Nausea · Laughter fits · Muscle tension · Vibrations / buzzing · Bodily lightness · Excessive sweating · Headache · Muscle relaxation · Restlessness · Dehydration sensation · Diarrhea · Involuntary body movements · Pain suppression · Respiratory stimulation · Sedation · Sexual arousal enhancement · Trembling · Vasoconstriction · Yawning · Nystagmus (eye wobbles) · Vomiting · Bodily dissociation · Tactile hallucination
Introspection enhancement · Openness enhancement · Pattern recognition enhancement · Cognitive euphoria · Immersion enhancement · Cognitive flexibility · Increased nature relatedness · Thought connectivity · Creativity enhancement · Memory suppression · Thought loops · Cognitive fatigue · Cognitive impairment · Focus suppression · Information processing suppression · Memory fragmentation · Multiple thought streams · Thought acceleration · Analysis enhancement · Humor enhancement · Analysis suppression · Confusion · Motivation suppression · Synchronicity · Thought disorganization · Information processing enhancement · Motivation enhancement · Cognitive dysphoria · Language suppression · Memory replays · Focus enhancement · Language enhancement · Thought organization · Memory enhancement · Delusions
Cognitive euphoria · Immersion enhancement · Cognitive flexibility · Increased nature relatedness · Thought connectivity · Creativity enhancement · Memory suppression · Thought loops · Cognitive fatigue · Cognitive impairment · Focus suppression · Information processing suppression · Memory fragmentation · Multiple thought streams · Thought acceleration · Analysis enhancement · Humor enhancement · Analysis suppression · Confusion · Motivation suppression · Synchronicity · Thought disorganization · Information processing enhancement · Motivation enhancement · Cognitive dysphoria · Language suppression · Memory replays · Focus enhancement · Language enhancement · Thought organization · Memory enhancement
Anxiety · Empathy enhancement · Catharsis · Anxiety suppression · Dysphoria · Irritability
Dysphoria · Irritability
Trust enhancement · Sociability enhancement · Communication enhancement · Flow state · Automaticity · Communication suppression · Sociability suppression · Social disconnection · Boundary dissolution · Ego dissolution · Cognitive disconnection · Identity alteration · Telepathic feelings
Automaticity · Communication suppression · Sociability suppression · Social disconnection · Boundary dissolution · Ego dissolution · Cognitive disconnection · Identity alteration · Telepathic feelings
Time cessation
Transpersonal visions · Entity contact · Transpersonal memory access · Cessation · Death-rebirth sequence · Near-death experience · Voidness
Death-rebirth sequence · Near-death experience · Voidness
Recursive awareness
Timeline
First alerts within 10–20 minutes: subtle mood shift, mild visual brightening, and a growing sense of bodily awareness. The rapid onset is a defining feature of 4-HO-DiPT.
Effects build quickly over 10–20 minutes. Colour enhancement sharpens, body load manifests as leg restlessness or tremor, and thought patterns begin to shift. The transition from first alerts to approaching peak can feel abrupt.
Full psychedelic intensity lasts 45–90 minutes. Visual effects, introspective cognition, and emotional amplification reach maximum. The steep dose-response curve means peak intensity is highly dose-sensitive.
Effects diminish steadily over 30–60 minutes. Visual distortion fades, cognitive clarity returns, and body load eases. Most users feel substantially baseline by this phase.
Mild residual mood elevation and subtle sensory enhancement may persist for 1–3 hours after primary effects resolve. Cognitive function is largely restored but subtle perceptual shifts remain.
⚠ Do not drive or operate machinery for the remainder of the day following a 4-HO-DiPT experience.
Safety[edit]
- Acute toxicity
- Low
- Chronic toxicity
- Negligible
- Withdrawal
- None
- Tolerance buildup
- rapid
- Tolerance reset
- 7 days
- Physical
- None
- Psychological
- Negligible
- Compulsive redosing
- Negligible
- Dose escalation
- Negligible
- Cross-tol.
- psilo · psilocin · lsd
Toxicity
Acute toxicity
No lethal dose has been established in any species, and no hospitalization or death has been reported from the compound.safety citation needed In a Phase 2 trial of the prodrug luvesilocin (84 patients, subcutaneous — not directly comparable to oral free base), the most common side effects were nausea (43.9%) and headache (34.1%), both mild to moderate.[8] No serious adverse events occurred, and preclinical studies showed no organ toxicity.[5]
User reports describe leg tremors, muscle tension, body malaise, and elevated heart rate, though none have been measured under controlled conditions.[7]
Chronic toxicity
No chronic toxicity data exist. The compound is used episodically, and no repeat-dosing studies have been published.
Dose-response sensitivity
The steep dose-response curve is the primary substance-specific safety concern.[4] At 15 mg oral, effects are mild; at 20 mg, they reach full psychedelic intensity — a roughly 30% dose increase that produces a disproportionate intensity jump. Without precise weighing equipment, accidental overdose is a real risk.
Psychological risks
As a serotonergic psychedelic, 4-HO-DiPT can produce acute anxiety, panic, paranoia, dysphoria, and perceptual disturbance. The steep dose-response curve amplifies this — small weighing errors can shift the experience from mild to overwhelming.
The short duration means adverse effects resolve faster than with psilocybin or LSD. Cannabis co-administration can unpredictably amplify effects, increasing panic and paranoia risk.[7] No compound-specific data exist on persistent perceptual disturbance or psychosis precipitation, though both are recognized risks of the serotonergic psychedelic class.inferred
Tolerance and dependence
4-HO-DiPT is not habit-forming. Tolerance develops rapidly after a single dose through downregulation — the same mechanism shared by all serotonergic psychedelics. Cross-tolerance exists with psilocin, LSD, DMT, and mescaline,inferred and sensitivity is estimated to reset within approximately 7 days.inferred
Drug interactions
Serotonergic interactions
4-HO-DiPT both activates serotonin receptors and slows serotonin reuptake,[1] making it unusually vulnerable to serotonin overload when combined with other serotonergic agents.
Tramadol adds further serotonin activity on top of 4-HO-DiPT's own load, creating a dangerous additive effect.[17][18]
MAO inhibitors block the enzymatic breakdown of serotonin. Combined with a substance that both activates serotonin receptors and slows reuptake, this can trigger severe serotonin syndrome — a potentially life-threatening response involving high fever, muscle rigidity, and seizures.[15][19]
SSRIs and SNRIs may blunt psychedelic effects through chronic receptor adaptation, while acute combination risks serotonin toxicity.inferred
Other interactions
Cannabis can unpredictably amplify psychedelic effects, significantly increasing the risk of adverse psychological reactions.[7]
Lithium carries a class-based seizure risk when combined with serotonergic psychedelics.safety citation needed
4-HO-DiPT inhibits the liver enzyme CYP2D6,[13] which may affect the breakdown of drugs processed by this enzyme — including codeine, tamoxifen, and many antidepressants. Clinical significance at typical doses has not been studied.
Contraindications
Absolute contraindications
- Concurrent MAOI use — severe serotonin toxicity risk[19]
- Concurrent tramadol use — dangerous additive serotonergic mechanism[17]
Relative contraindications
- Personal or family history of psychotic disorders — serotonergic psychedelics can trigger or worsen psychosis in vulnerable individualsinferred
- Bipolar disorder with psychotic features — risk of manic or psychotic episodeinferred
- Concurrent lithium use — seizure risksafety citation needed
- Concurrent SSRI/SNRI use — blunted efficacy or serotonin toxicity riskinferred
- Pregnancy and breastfeeding — no reproductive toxicity data existsafety citation needed
Harm Reduction[edit]
Forms & Identification
4-HO-DiPT is sold primarily as a powder — free base or hydrochloride salt — and occasionally as pellets. Established reagent test profiles for this compound are limited, making visual identification unreliable.
A milligram-precision scale (0.001 g) is essential. The steep dose-response curve means 2–3 mg of error can dramatically alter the experience. Volumetric dosing — dissolving a weighed amount in a measured volume of liquid — offers the most reliable accuracy at low doses.
Guidelines
- Start at the low end of the dose range (15 mg or below). Do not redose — the experience will end naturally within a few hours.
- Use a milligram-precision scale. Volumetric dosing is strongly recommended for doses under 20 mg.
- Set up the environment fully before dosing: music, lighting, water, blankets, phone silenced.
- Have a sober sitter present, especially for first experiences or doses above 15 mg.
- Avoid a heavy meal within 2 hours of dosing to reduce nausea.
- Wait at least 7 days between experiences to allow full sensitivity reset.
Set & Setting
The fast onset leaves little transition time between baseline and full effect. The environment should be fully arranged before dosing — music, lighting, water, and a clear physical space all in place.
A calm, familiar, private setting with a sober sitter present is strongly recommended, especially for first experiences or higher doses. The short total duration makes structured sessions practical, but the speed of onset can catch an unprepared person off guard.
Aftercare & integration. The return to baseline is rapid, but the psychological content of the experience can still carry weight. Allow the rest of the day for quiet recovery — avoid demanding tasks or social obligations.
Journaling within the first few hours captures insights before they fade. If the experience was emotionally intense or disturbing, discussing it with a trusted person or integration-trained therapist within the first week supports processing. Persistent anxiety, mood changes, or intrusive thoughts lasting more than a few days warrant professional consultation.
Recovery & Support
4-HO-DiPT does not produce physical dependence, and compulsive use is rare across the psychedelic class. If psychedelic use is becoming avoidance rather than engagement, or if experiences are causing more distress than insight, a pause and professional support are warranted. Resources include the Fireside Project (psychedelic peer support line), MAPS integration therapist directory, and local harm reduction organisations.
Recovery resources, crisis lines, and support pathways → View all
Emergency Response
Recognizing an emergency: Most uncomfortable experiences resolve within a few hours without medical intervention. Seek immediate help if the person shows signs of self-harm intent, complete disconnection from reality (unable to recognize people or surroundings), seizure activity, severe chest pain, or loss of consciousness.
Immediate steps:
- Stay with the person. Speak in calm, short sentences.
- If conscious and distressed, move to a quiet, low-stimulation space.
- If unconscious or seizing, place in the recovery position (on their side, airway clear) and call emergency services immediately.
- Do not restrain unless there is immediate danger of self-harm or harm to others.
- Do not attempt to induce vomiting.
What to tell the dispatcher: Name the substance (4-HO-DiPT, a tryptamine psychedelic), the approximate amount taken, the time of ingestion, and current symptoms. Good Samaritan laws in many jurisdictions protect people who call for help during a drug-related emergency.
Legal Status[edit]
As of April 2026, 4-HO-DiPT is unscheduled at the US federal level but occupies legally ambiguous territory in most countries — its structural similarity to psilocin exposes it to structural analog drug laws in jurisdictions that employ them.
| Jurisdiction | Classification | Key provisions |
|---|---|---|
| United States (federal) | Not scheduled | DEA proposed Schedule I placement Jan 2022; withdrew proposal Jul 2022 pending HHS re-evaluation.[9] May be prosecuted under Federal Analogue Act as a structural analog of psilocin. |
| United States (Florida) | Schedule I | Specifically scheduled at state level.[7] |
| United Kingdom | Class A | Controlled under Misuse of Drugs Act 1971 via generic tryptamine clause. Possession: up to 7 years; supply/production: up to life imprisonment.[7] |
| Canada | Not controlled | Not listed in the Controlled Drugs and Substances Act as of 2025.[7] |
| Germany | NpSG | Controlled under the Neue-Psychoaktive-Stoffe-Gesetz (New Psychoactive Substances Act). Use permitted only for industrial and scientific purposes.[7] |
| Australia | Uncertain | Not explicitly listed in the Poisons Standard. May be captured as an analog of psilocin under Criminal Code Regulations.citation needed |
Legal status changes frequently and varies by jurisdiction. This information is not legal advice. Always verify current local law before relying on it.
Analog and prodrug considerations
The Federal Analogue Act potentially applies to 4-HO-DiPT as a structural analog of Psilocin, provided it is intended for human consumption. The clinical prodrug luvesilocin (RE104) is under FDA Investigational New Drug authorization, which covers the clinical trial but does not change the scheduling status of the parent compound.
references
- [1] ^abcRickli A, Moning OD, Hoener MC, Liechti ME (2016) Receptor interaction profiles of novel psychoactive tryptamines compared with classic hallucinogens — European Neuropsychopharmacology doi:10.1016/j.euroneuro.2016.05.001
- [2] ^abcdKelly TJ, Bonniwell EM, Mu L, Liu X, Hu Y, Friedman V, Yu H, Su W, McCorvy JD, Liu QS (2024) Psilocybin analog 4-OH-DiPT enhances fear extinction and GABAergic inhibition of principal neurons in the basolateral amygdala — Neuropsychopharmacology doi:10.1038/s41386-023-01744-8
- [3] ^abRepke D, Ferguson W, Bates D (1977) Psilocin analogs. 1. Synthesis of 3-[2-(dialkylamino)ethyl]-and 3-[2-(cycloalkylamino)ethyl] indol-4-ols — Journal of Heterocyclic Chemistry doi:10.1002/jhet.5570140113
- [4]
- [5]
- [6]