5-MeO-DALT
5-methoxy-N,N-diallyltryptamine
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5-MeO-DALT (5-methoxy-N,N-diallyltryptamine) — also known as Foxtrot — is a synthetic psychedelic of the tryptamine class. It is a close relative of 5-MeO-DMT with a notably muted visual profile. 5-MeO-DALT is a dual 5-HT₁A and 5-HT₂A receptor agonist, producing its effects through serotonin activation where strong 5-HT₁A engagement buffers the hallucinogenic response.[1]
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Synthesized by Alexander Shulgin in May 2004, 5-MeO-DALT reached online research chemical markets within weeks of its initial disclosure.[2] It became one of the earliest designer tryptamines sold on the internet, prompting European drug monitoring reports by 2007 and a WHO review in 2020. The compound remains under WHO surveillance without international scheduling.[3]
Subjective effects include euphoria, sensory enhancement, physical stimulation, and mild visual alterations.[4] The experience is predominantly somatic — a buzzing physical activation and wakefulness that distinguishes it from the deeply visual or introspective states of classical tryptamines like DMT or psilocybin.[1] Agitation, rapid heart rate, and nausea are characteristic unsought effects.
No physical dependence has been documented, and no lethal dose has been established in any species.[3] Serious adverse events — delirium, muscle breakdown, and cyclic involuntary movements — appear in case reports,[5][6][7] and one indirect fatality occurred when an intoxicated individual was struck by a vehicle.[2] The evidence base is thin: no clinical trials exist, and current understanding rests on animal pharmacology, metabolic studies, and a handful of emergency presentations.[8]
History[edit]
Discovery
5-MeO-DALT was first synthesized by Alexander Shulgin in May 2004 and shared with a research associate known by the pseudonym "Murple".[2] Shulgin's self-experimentation indicated oral psychoactivity at 12–20 mg, with effects lasting 2–4 hours and characterized by positive emotional changes, closed-eye visuals, and enhanced appreciation of music.[9] Reports appeared on Erowid.org by August 2004, and Chinese laboratories began commercial production by approximately June 2004, making 5-MeO-DALT one of the first designer tryptamines to reach the online market.
Emergence and monitoring
5-MeO-DALT entered European drug monitoring when Finland reported it to the EMCDDA in 2007; by 2015, fourteen countries had identified the compound in seizures or surveillance data.[2] The first reported death involving the compound occurred in mid-2010 in the United Kingdom, when a man in his mid-20s was struck by a vehicle while intoxicated — an indirect fatality attributed to behavioral impairment rather than drug toxicity.[2]
Regulatory review
The WHO Expert Committee on Drug Dependence reviewed 5-MeO-DALT at its 43rd meeting in October 2020 and concluded that insufficient evidence existed to recommend international scheduling under the 1971 Convention on Psychotropic Substances. The compound was placed under surveillance.[3]
The abbreviation "DALT" derives from N,N-diallyltryptamine, referring to the two allyl groups on the molecule's nitrogen atom. The compound was marketed commercially as "Foxtrot," a fumarate salt formulation developed for improved water solubility.[3] Brandt et al. (2017) provided the first comprehensive forensic reference data for 5-MeO-DALT, establishing NMR, GC-MS, and LC-MS/MS identification benchmarks for the compound and 16 other DALT analogs.[10]
Chemistry[edit]
Structural class
5-MeO-DALT belongs to the substituted tryptamine family, sharing the indole-ethylamine backbone common to DMT, psilocin, and 5-MeO-DMT. Two structural modifications define it: a methoxy group at the 5-position of the indole ring and two allyl groups on the terminal nitrogen. The allyl substituents — each containing an unsaturated carbon-carbon double bond — introduce conformational flexibility and alter how the molecule fits into receptor binding sites compared to saturated analogs like N,N-dipropyltryptamine.
The molecule contains no stereogenic centers and is therefore achiral.[11]
Molecular properties
| Molecular formula | C₁₇H₂₂N₂O |
| Molecular weight | 270.37 g/mol |
Physical properties
The freebase appears as a white to off-white crystalline powder, though forensic samples have been described as grey, light brown, or tan. Compressed tablets in yellow, purple, and green have been seized.[3]
The freebase is poorly water-soluble; the fumarate salt (marketed as "Foxtrot") was developed specifically for aqueous solubility.[3]
Synthesis
5-MeO-DALT is prepared via the Speeter–Anthony tryptamine synthesis. A microwave-accelerated variant of this route was used to prepare reference standards for 17 DALT analogs, providing the first comprehensive spectral characterization of the series.[10]
Pharmacology[edit]
Mechanism of action
5-MeO-DALT acts on multiple serotonin receptor subtypes simultaneously, with no single dominant target.[3] Its psychedelic effects arise primarily through 5-HT₂A receptor activation, but unusually strong concurrent 5-HT₁A activation appears to dampen the hallucinogenic response.[1]
This dual mechanism explains the compound's characteristically muted visual profile. In rodent behavioral studies, 5-HT₂A binding predicted hallucinogenic behavior while 5-HT₁A binding negatively modulated it — a buffering effect confirmed across the DALT series.[1] The compound also binds to several additional serotonin receptor subtypes and adrenergic receptors.[9]
Functional assays confirm full agonist activity at its primary serotonin targets.[12] Drug discrimination studies show that 5-MeO-DALT does not substitute for MDMA in trained animals,[13] indicating different dominant mechanisms than entactogens.
Pharmacokinetics
No controlled pharmacokinetic studies have been conducted in humans. The only human plasma datapoint comes from a case report: a measurable blood concentration was detected 8 hours after oral ingestion of approximately 10.7 mg.[8] Basic parameters — peak blood levels, half-life, and oral bioavailability — remain unknown.
Metabolic studies in rat and human liver tissue have mapped the compound's breakdown pathways, which include hydroxylation, removal of allyl groups, and addition of water-soluble tags for excretion.[14]
5-MeO-DALT is not detected by standard immunoassay drug screens.[8][5] Confirmed identification requires specialized laboratory analysis such as LC-MS/MS.[15][16]
Neuroscience[edit]
Where it acts
No direct brain imaging or electrophysiology studies have been conducted with 5-MeO-DALT. As a confirmed serotonin 2A receptor agonist,[1][13] it is expected to activate serotonin receptors on neurons in the prefrontal cortex, disrupting the brain's default filtering of sensory and cognitive information and increasing neural connectivity.
Its unusually strong 5-HT₁A activity[12] may dampen the excitatory cascades that typically produce vivid hallucinations, potentially explaining why the experience is more physical than visual.[4]
Theoretical context
The REBUS model predicts that 5-HT₂A psychedelics increase the brain's information entropy, loosening rigid patterns of thought and perception. 5-MeO-DALT partially conforms: it produces confirmed psychedelic activity but with attenuated perceptual effects. If 5-HT₁A agonism truly buffers entropic disruption, the compound would preserve more cognitive coherence at peak effect than pure 5-HT₂A agonists — a hypothesis that remains untested by neuroimaging.
Whether 5-MeO-DALT promotes structural brain changes (neuroplasticity) via the same pathways as DMT or psilocybin has not been investigated.
Key unanswered questions include whether 5-MeO-DALT promotes neuroplasticity as other psychedelics do, what its brain imaging signature looks like under conditions of dual 5-HT₁A/5-HT₂A activation, and whether its stimulant-to-sedative dose-response shift reflects changing dominance between receptor systems at different doses.
Subjective Effects[edit]
The 5-MeO-DALT experience is fundamentally somatic. Where classical tryptamines like psilocybin or DMT center on visual and introspective transformation, 5-MeO-DALT delivers buzzing physical stimulation, wakefulness, and sensory sharpening as its dominant features.[1] Emotional tone varies with set and setting, but the physical character — stimulation, body awareness, alertness — persists across contexts. At lower doses effects are mild and stimulant-like; higher doses introduce more noticeable perceptual shifts without reaching the visual intensity of classical psychedelics.[4]
The closest experiential comparison may be low-dose 5-MeO-DMT in terms of somatic emphasis, though 5-MeO-DALT lacks its dimethyl cousin's intensity and ego dissolution potential. The smoked route compresses the arc into a brief, sharper peak; oral administration spreads the experience over a longer, more gradual timeline.[9]
Effect Grid
At common doses, the full 5-MeO-DALT experience manifests. Emotional enhancement is pronounced — appreciation of music, social warmth, and aesthetic sensitivity increase substantially. Thought acceleration and thought connectivity are prominent cognitive features, with analysis enhancement and conceptual thinking becoming accessible. Visual effects remain moderate compared to classical psychedelics: color enhancement, visual drifting, symmetrical texture repetition, and visual acuity enhancement are present but rarely overwhelming.
Stimulation is marked and distinguishes the experience from DMT or psilocybin. Spontaneous body sensations pervade, and sexual arousal enhancement is frequently reported. Pupil dilation, mild tachycardia, and temperature dysregulation occur. Time alteration becomes noticeable.
Functional impairment is moderate. Sleep is unlikely for 3–4 hours post-ingestion. Total duration is typically 2–4 hours.
Modeled from the effect's dose-dependence curve — not per-substance measurements.
Brightness alteration · Geometry · Light sensitivity · Visual breathing · Touch enhancement · Symmetrical texture repetition · Auditory distortion · Auditory enhancement · Depth perception distortion · Environmental patterning · Holotropic state · Peripheral vision distortion · Perspective distortion · Sound sensitivity · Spatial disorientation · Visual haze / noise · Visual acuity enhancement · Visual morphing · After-images · Auditory misinterpretation · Dreaming enhancement · Proprioceptive distortion · Synesthesia · Vestibular distortion · Visual diffraction · Visual processing acceleration · Visual magnification · Visual melting · External hallucinations · Internal hallucinations · Object transformations · Auditory hallucinations · Object activation · Perspective hallucinations · Visual recursion
Touch enhancement · Symmetrical texture repetition · Auditory distortion · Auditory enhancement · Depth perception distortion · Environmental patterning · Holotropic state · Peripheral vision distortion · Perspective distortion · Sound sensitivity · Spatial disorientation · Visual haze / noise · Visual acuity enhancement · Visual morphing · After-images · Auditory misinterpretation · Dreaming enhancement · Proprioceptive distortion · Synesthesia · Vestibular distortion · Visual diffraction · Visual processing acceleration · Visual magnification · Visual melting · External hallucinations · Internal hallucinations · Object transformations · Auditory hallucinations · Object activation · Perspective hallucinations · Visual recursion
Sexual arousal enhancement · Wakefulness · Body high · Dizziness · Heart rate perception changes · Nausea · Restlessness · Tingling / electric sensations · Vibrations / buzzing · Appetite suppression · Bodily lightness · Breathing alteration · Excessive sweating · Insomnia · Laughter fits · Muscle tension · Physical fatigue · Tactile euphoria · Abnormal heartbeat · Body schema distortion · Involuntary body movements · Kundalini-like energy · Respiratory stimulation · Trembling · Vomiting · Yawning · Bodily dissociation
Dizziness · Heart rate perception changes · Nausea · Restlessness · Tingling / electric sensations · Vibrations / buzzing · Appetite suppression · Bodily lightness · Breathing alteration · Excessive sweating · Insomnia · Laughter fits · Muscle tension · Physical fatigue · Tactile euphoria · Body schema distortion · Involuntary body movements · Kundalini-like energy · Respiratory stimulation · Trembling · Vomiting · Yawning · Bodily dissociation
Pattern recognition enhancement · Conceptual thinking · Thought connectivity · Cognitive euphoria · Cognitive flexibility · Cognitive impairment · Immersion enhancement · Introspection enhancement · Multiple thought streams · Openness enhancement · Analysis enhancement · Creativity enhancement · Humor enhancement · Memory suppression · Confusion · Focus suppression · Increased nature relatedness · Information processing suppression · Memory fragmentation · Synchronicity · Thought disorganization · Thought loops · Cognitive dysphoria · Memory replays · Motivation enhancement
Cognitive flexibility · Cognitive impairment · Immersion enhancement · Introspection enhancement · Multiple thought streams · Openness enhancement · Analysis enhancement · Creativity enhancement · Humor enhancement · Memory suppression · Confusion · Focus suppression · Increased nature relatedness · Information processing suppression · Memory fragmentation · Synchronicity · Thought disorganization · Thought loops · Cognitive dysphoria · Memory replays · Motivation enhancement
Empathy enhancement · Catharsis · Simultaneous emotions · Dysphoria · Irritability
Irritability
Social connection · Trust enhancement · Communication enhancement · Sociability enhancement · Flow state · Boundary dissolution · Ego dissolution · Identity alteration · Cognitive disconnection · Telepathic feelings
Flow state · Boundary dissolution · Ego dissolution · Identity alteration · Cognitive disconnection · Telepathic feelings
Time cessation
Transpersonal visions · Death-rebirth sequence · Non-dual awareness · Voidness
Lucidity enhancement · Recursive awareness
Timeline
First alerts appear as a subtle shift in body awareness — mild warmth, slight increase in wakefulness, and a faint sense of something changing.
Stimulation builds noticeably. Emotional coloring shifts toward positivity, sensory acuity increases, and mild visual changes (color brightening, slight drifting) begin to emerge.
Maximum intensity of all effect domains. Stimulation is pronounced, emotional enhancement peaks, thought connectivity and acceleration are at their strongest. Visual effects — color enhancement, symmetrical texture repetition, tracers — reach their ceiling, though remain moderate compared to classical tryptamines.
Effects gradually recede. Stimulation diminishes first, followed by cognitive and visual effects. A gentle baseline mood returns, though mild sensory enhancement may linger.
Residual wakefulness and mild mood elevation may persist for several hours. Some users report lingering body stimulation.
⚠ Do not drive or operate machinery for the remainder of the day following oral ingestion.
Safety[edit]
- Acute toxicity
- Moderate
- Chronic toxicity
- Low
- Withdrawal
- None
- Tolerance buildup
- rapid
- Tolerance reset
- 7 days
- Physical
- None
- Psychological
- Negligible
- Compulsive redosing
- Negligible
- Dose escalation
- Negligible
- Cross-tol.
- LSD · psilo · mesc
Toxicity
Lethal dose
No lethal dose has been established for 5-MeO-DALT in any species.[3] No deaths directly caused by the drug's pharmacological effects — cardiac arrest, respiratory failure, or organ failure — have been published.
One indirect fatality occurred in the United Kingdom in mid-2010 when a man in his mid-20s was struck by a vehicle while intoxicated; the coroner attributed death to behavioral impairment, not drug toxicity.[2]
Acute toxicity
Across four published case reports,[5][6][7][8] serious adverse presentations include:
- Neurological: delirium, loss of consciousness, hallucinations, cyclic involuntary movements, brain dysfunction
- Cardiovascular: Rapid heart rate (no reported arrhythmias or cardiac arrest)
- Autonomic: Profuse sweating, combativeness, extreme agitation
- Musculoskeletal: Muscle breakdown with secondary risk of kidney injury[6]
These features overlap with stimulant toxicity and are consistent with serotonin excess, though the full serotonin syndrome triad has not been formally diagnosed in published cases.
Detection gap
5-MeO-DALT is not detected by standard drug screening tests.[8][5] Emergency physicians should consider synthetic tryptamines when patients present with unexplained stimulant-like or serotonergic symptoms and negative routine screens.[17]
Product purity
Online products have shown extreme inconsistency: one confirmed case found only 11% purity in tablets marketed as 5-MeO-DALT, with each tablet containing approximately 3.6 mg of active compound in a 32.5 mg tablet.[8] Users may consume far larger quantities to compensate for weak products, then encounter higher-purity material with the same dosing habits.
Psychological Risks
No controlled studies of psychological adverse effects have been conducted. Acute psychosis, delirium, and severe agitation appear in case reports.[5][8] Long-term risks — including HPPD (HPPD), psychosis precipitation, or psychiatric destabilization — are entirely unstudied.
As a serotonergic psychedelic, 5-MeO-DALT carries the class-level risk of triggering or worsening psychotic disorders in predisposed individuals.inferred
Tolerance & Dependence
No human tolerance studies specific to 5-MeO-DALT have been published. The WHO noted anecdotal reports of tolerance with daily use.[3]
Tolerance is expected to develop rapidly through 5-HT₂A downregulation, the standard mechanism for psychedelic tachyphylaxis.[18] Cross-tolerance with LSD, psilocybin, mescaline, and DMT is expected based on shared 5-HT₂A mechanism.
No evidence of physical dependence or withdrawal exists. Anecdotal reports do not suggest compulsive use patterns.[3]
Drug Interactions
The primary pharmacodynamic risk is serotonin syndrome — a potentially life-threatening condition caused by excess serotonin activity. As a direct 5-HT₁A and 5-HT₂A agonist, 5-MeO-DALT carries significant interaction risk when combined with other serotonergic agents.
MAO inhibitors represent the highest-risk combination. Monoamine oxidase inhibition would reduce 5-MeO-DALT clearance while simultaneously increasing serotonin availability, compounding both pharmacokinetic and pharmacodynamic exposure.[14]safety citation needed
SSRIs, SNRIs, and tramadol carry serotonin syndrome risk through combined serotonin elevation. Tramadol additionally lowers seizure threshold, compounding risk given the documented involuntary movements.[7]
Stimulants (cocaine, amphetamines) would be expected to heighten cardiovascular strain — rapid heart rate, elevated blood pressure, and overheating.
Pharmacokinetic interactions: Medications that inhibit the liver enzymes responsible for breaking down 5-MeO-DALT — including fluoxetine, paroxetine, fluvoxamine, and certain antifungals — could slow clearance and intensify effects.[14] Individuals who are genetically slow metabolizers of CYP2D6 may have inherently elevated exposure.
Contraindications
No substance-specific contraindication studies exist. The following are inferred from pharmacological class and documented adverse events:
- Psychotic disorders or family history of psychosis: Class-level risk of triggering or worsening psychotic episodesinferred
- Conditions predisposing to muscle breakdown: Given the documented case,[6] individuals with muscle disorders face elevated risk
- Heart conditions: Rapid heart rate is documented across case reports;[5][8] pre-existing cardiac problems increase risk from cardiovascular stress
- Concurrent serotonergic medication: MAOIs, SSRIs, SNRIs, tramadol, and triptans compound serotonin syndrome risk
- Seizure disorders: Cyclic involuntary movements have been documented;[7] individuals with epilepsy or lowered seizure threshold face additional risk
- Liver impairment: 5-MeO-DALT is extensively processed by the liver;[14] significant liver disease could reduce clearance and prolong or intensify effects
- Pregnancy: No reproductive safety data exist; use during pregnancy is contraindicated
Harm Reduction[edit]
Forms & Identification
5-MeO-DALT circulates as powder (white, off-white, grey, or tan) and as pressed tablets in various colors. Product purity has been documented as low as 11%,[8] meaning the active dose in any given product is unpredictable without testing. Standard drug screening tests cannot detect this compound,[8][5] so reagent testing is the only accessible pre-use verification — though reagent kits can only confirm the presence of a tryptamine, not the exact compound or purity.
Weigh every dose with a milligram-precision scale; volume-based estimation is unreliable at this potency range.
Guidelines
- Test all material with reagent kits before use
- Weigh doses with a milligram-precision scale — never estimate
- Start with a low dose on first use to assess individual response and product potency
- Remain in a safe, familiar environment with a sober companion present
- Stay hydrated but avoid excessive water intake
- Do not redose within the duration window — effects may still be building
- Avoid intense physical exertion during the experience; muscle breakdown has been documented at high doses[6]
- Allow at least 24 hours between experiences to account for acute tolerance
Set & Setting
5-MeO-DALT's predominantly physical and stimulating character makes environmental factors important. A familiar, calm environment with minimal external demands reduces the risk of agitation-related harm. The compound's short duration and relatively mild cognitive effects mean that set and setting shape emotional tone more than perceptual content.
A trusted sitter is recommended for first experiences, particularly given the unpredictability of unregulated products.
Aftercare & integration. The short duration and predominantly physical character of 5-MeO-DALT typically produce less psychological disruption than longer-acting psychedelics. Post-experience fatigue, mild headache, or residual stimulation may persist for several hours. Eat a light meal, hydrate, and rest.
If the experience produced unexpected psychological intensity — anxiety, confusion, or disturbing thoughts — allow time for processing. Journaling, conversation with a trusted person, or a structured integration session can help contextualize the experience. Seek professional support if distress persists beyond a few days.
Recovery & Support
5-MeO-DALT does not produce physical dependence, and compulsive use patterns have not been reported.[3] If use has become a pattern of avoidance or escalation, support resources include psychedelic integration therapists, harm reduction organizations, and peer support communities. The Fireside Project (62-FIRESIDE) offers psychedelic-specific crisis support.
Recovery resources, crisis lines, and support pathways → View all
Emergency Response
Recognizing an emergency: Uncomfortable physical stimulation and mild anxiety are common and typically self-limiting. Seek immediate help if any of the following occur: loss of consciousness, seizure-like movements or repetitive muscle jerking, extreme confusion or delirium, chest pain, or dangerously high body temperature (skin hot to the touch).
Immediate steps:
- Call emergency services immediately
- If the person is unconscious but breathing, place them on their side (recovery position)
- Do not restrain them unless they are in immediate danger of harming themselves
- Remove hazards from the environment — the documented fatality involved a person wandering into traffic[2]
- Monitor breathing and body temperature while waiting for help
What to tell the dispatcher: Name the substance (5-MeO-DALT or "a synthetic tryptamine"), 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 emergency.
No reversal agent exists for 5-MeO-DALT. Treatment is supportive.
Legal Status[edit]
5-MeO-DALT is not scheduled under the United Nations 1971 Convention on Psychotropic Substances. The WHO Expert Committee on Drug Dependence reviewed the compound in October 2020 and placed it under surveillance, concluding that insufficient evidence existed to recommend international control.[3]
National scheduling varies widely. Several jurisdictions have enacted specific or blanket controls, while the compound remains unscheduled at the federal level in the United States — where the Federal Analogue Act may apply when intended for human consumption. The earliest national-level control was enacted by Sweden in May 2007.
| Jurisdiction | Classification | Key provisions |
|---|---|---|
| United States (federal) | Unscheduled | Federal Analogue Act may apply if sold for human consumption as an analog of scheduled tryptamines[19] |
| Florida (US) | Schedule I | State-level controlled substance[19] |
| Louisiana (US) | Schedule I | Controlled since June 2013[19] |
| Virginia (US) | Schedule I | Controlled since July 1, 2012[19] |
| United Kingdom | Class A (Misuse of Drugs Act 1971) | Under tryptamine blanket ban, effective January 7, 2015[19] |
| Sweden | Controlled | Since May 1, 2007 — earliest national control[19] |
| China | Category I psychotropic | Controlled since September 2010[19] |
| Japan | Designated Substance | Under Pharmaceutical Affairs Law[19] |
| Finland | Banned | Included in mass-scheduling of 100+ compounds, December 2014[19] |
| Singapore | Fifth Schedule (Misuse of Drugs Act) | Controlled since May 2015citation needed |
| Canada | Not explicitly listed | Not specifically listed in CDSA schedules; may fall under tryptamine analog provisionscitation needed |
| Australia | Unconfirmed | No specific scheduling found; status under Poisons Standard unconfirmedcitation needed |
references
- [1]
- [2]
- [3]
- [4]
- [5]
- [6]