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    TMA-2 molecular structure

    TMA-2 Stats & Data

    Domeo 2,5-dimethoxy-4-methoxyamphetamine
    NPS DataHub
    MW261.75
    FormulaC12H20ClNO3
    CAS15995-72-9
    IUPAC1-(2,4,5-trimethoxyphenyl)propan-2-amine hydrochloride
    SMILES[Cl-].COc1cc(CC(C)N)c(OC)cc1OC.[H+]
    InChIKeyJHYCECCYAFOEDA-UHFFFAOYSA-N
    Phenethylamines; 2020/1. Von 2-Phenethylamin abgeleitete Verbindungen; 2021/1. Von 2-Phenethylamin abgeleitete Verbindungen; 2022/1. Von 2-Phenethylamin abgeleitete Verbindungen
    Chemical Class Amphetamine
    Psychoactive Class Psychedelic / Stimulant
    Half-Life Unknown in humans; effect duration is ~8–12 hours, but pharmacokinetics have not been characterized.

    Receptor Profile

    Receptor Actions

    Agonists
    5-HT2A receptor agonist (partial)
    5-HT2B receptor agonist
    5-HT2C receptor agonist (weak)

    History & Culture

    TMA-2 was first synthesized by Hungarian chemist Viktor Bruckner in 1933, but its psychoactive properties remained unrecognized for nearly three decades. Alexander Shulgin independently synthesized the compound in 1962 and conducted the first documented self-experiments to evaluate its effects. His 1964 publication described the experience as bearing similarities to mescaline, though notably lacking in chromatic visual phenomena, producing less gastrointestinal distress, and demonstrating a tendency to provoke anxiety and restlessness. The discovery of TMA-2's potency proved pivotal in the development of psychedelic phenethylamine research. Shulgin noted that simply relocating a single methoxy group from the original TMA configuration to the 2,4,5-arrangement produced an unexpected tenfold increase in effectiveness. This finding prompted systematic exploration of all six possible trimethoxy arrangements on the amphetamine backbone, yielding the compounds subsequently designated TMA-3 through TMA-6. The 2,4,5-methoxy pattern also occurs naturally in certain essential oils, with structural parallels found in the asarone compounds—α-asarone, β-asarone, and γ-asarone (also called euasarone)—establishing TMA-2 as one of the "essential amphetamines" with botanical connections. Despite its early synthesis, TMA-2 saw only minimal human use throughout the 20th century. Scattered references in early 1970s counter-culture publications describe the compound as rarely manufactured and considerably more expensive than LSD, suggesting extremely limited availability. The 1991 publication of Shulgin's comprehensive work PiHKAL brought renewed attention to the compound, yet it has remained something of an obscurity within the psychedelic community—occasionally sought as a novelty rather than a substance of particular interest. In contemporary contexts, TMA-2 is seldom encountered through conventional illicit markets and is primarily obtained through online vendors offering grey-area research chemicals.

    Effect Profile

    Curated + 32 Reports
    Psychedelic 8.8

    Strong visuals, headspace, auditory effects, and body load

    Visual Intensity×3
    1010
    Headspace Depth×3
    107.8
    Auditory Effects×1
    1010
    Body Load / Somatic Effects×1
    1010
    Catalog Erowid
    Stimulant 7.0

    Strong stimulation, anxiety/jitters, and focus with mild euphoria

    Stimulation / Energy×3
    1010
    Euphoria / Mood Lift×2
    54.2
    Focus / Productivity×2
    85.6
    Anxiety / Jitters×1
    109.8
    Catalog Erowid

    Tolerance & Pharmacokinetics

    drugs.wiki
    Half-Life
    Unknown in humans; effect duration is ~8–12 hours, but pharmacokinetics have not been characterized.
    Addiction Potential
    Low; not considered habit-forming or physically addictive, though psychological habituation from frequent use is possible.

    Tolerance Decay

    Full tolerance 6h Half tolerance 3d Baseline ~7d

    Acute tolerance develops within hours like other serotonergic psychedelics; functional tolerance typically halves over ~3 days and largely resolves within ~7–14 days. Cross‑tolerance with other classical psychedelics is expected via 5‑HT2A downregulation; ratios are rough heuristic values from general psychedelic literature, not TMA‑2 specific measurements.

    Cross-Tolerances

    LSD
    50% ●○○
    Mescaline
    50% ●○○
    2C-x phenethylamines
    40% ●○○

    Experience Report Analysis

    Erowid
    32 Reports
    2000–2024 Date Range
    13 With Age Data
    28 Effects Detected

    Demographics

    Gender Distribution

    Age Distribution

    Reports Over Time

    Effect Analysis

    Erowid

    Effects aggregated from 32 experience reports (32 Erowid)

    32 Reports
    28 Effects Detected
    9 Positive
    11 Adverse
    8 Neutral

    Effect Sentiment Distribution

    Confidence Distribution

    Positive Effects 9

    Stimulation 59.4% 70%
    Color Enhancement 56.2% 70%
    Music Enhancement 56.2% 70%
    Tactile Enhancement 31.2% 70%
    Euphoria 28.1% 70%
    Empathy 28.1% 70%
    Focus Enhancement 28.1% 70%
    Introspection 25.0% 70%
    Body High 18.8% 70%

    Adverse Effects 11

    Nausea 50.0% 70%
    Anxiety 37.5% 70%
    Muscle Tension 34.4% 70%
    Pupil Dilation 18.8% 70%
    Confusion 15.6% 70%
    Increased Heart Rate 12.5% 70%
    Headache 9.4% 70%
    Sweating 9.4% 70%
    Psychosis 9.4% 70%
    Jaw Clenching 9.4% 70%
    Motor Impairment 9.4% 70%

    Dose-Response Correlation

    How effect frequency changes across dose levels

    View data table
    Effect Common (n=12)
    Visual Distortions 91.7%
    Sedation 66.7%
    Music Enhancement 66.7%
    Nausea 58.3%
    Stimulation 58.3%
    Color Enhancement 41.7%
    Anxiety 41.7%
    Closed-Eye Visuals 33.3%
    Euphoria 33.3%
    Tactile Enhancement 33.3%
    Introspection 33.3%
    Empathy 25.0%
    Focus Enhancement 25.0%
    Body High 25.0%
    Pupil Dilation 25.0%

    Dose–Effect Mapping

    Experience Reports

    How reported effects shift across dose tiers, based on 32 experience reports.

    Limited tier coverage — most reports fall within the Common range. Effects at other dose levels may not be represented.

    Oral dose range: 25.0–50.0 mg (median 35.0 mg)
    Effect Common (n=12)
    visual distortions
    92%
    sedation
    67%
    music enhancement
    67%
    nausea
    58%
    stimulation
    58%
    color enhancement
    42%
    anxiety
    42%
    closed-eye visuals
    33%
    euphoria
    33%
    tactile enhancement
    33%
    introspection
    33%
    empathy
    25%
    focus enhancement
    25%
    body high
    25%
    pupil dilation
    25%
    auditory effects
    25%
    muscle tension
    17%
    open-eye visuals
    17%
    ego dissolution
    17%
    confusion
    17%

    Showing top 20 of 23 effects

    Dosage Distribution

    Dose distribution from experience reports

    Median: 35.0 mg IQR: 25.0–50.0 mg n=20

    Real-World Dose Distribution

    62K Doses

    From 45 individual dose entries

    Oral (n=36)

    Median: 35.0mg 25th: 25.0mg 75th: 41.25mg 90th: 57.5mg
    mg/kg median: 0.504 mg/kg 75th: 0.608

    Insufflated (n=6)

    Median: 21.25mg 25th: 6.88mg 75th: 33.75mg 90th: 62.5mg
    mg/kg median: 0.272 mg/kg 75th: 0.447

    Common Combinations

    Most co-occurring substances in experience reports

    Form / Preparation

    Most common forms and preparations reported

    Body-Weight Dosing

    Dose relative to body weight from reports with weight data

    Median: 0.504 mg/kg IQR: 0.435–0.596 mg/kg n=18

    Redose Patterns

    Redosing behavior across 26 reports

    26.9% Redosed
    1.3 Avg Doses
    50m Median Interval

    Legal Status

    UN Convention on Psychotropic Substances 1971 (Schedule I) EU Council Decision (December 2003) - requiring member states to implement control measures within 90 days
    Country Status Notes
    Austria Illegal (SMG) Prohibited under the Suchtmittelgesetz (Narcotics Act). Possession, production, and sale are illegal.
    Belgium Illegal Added to the list of illegal psychotropic substances on November 8, 2004.
    Canada Schedule III (CDSA) Listed as 2,4,5-trimethoxyamphetamine in Schedule III of the Controlled Drugs and Substances Act. Possession and sale are prohibited.
    Finland Controlled Classified as a controlled substance under Finnish drug legislation.
    Germany Anlage I BtMG Controlled under Anlage I of the Betäubungsmittelgesetz (Narcotics Act) since October 10, 1999. Manufacturing, possession, import, export, purchase, sale, procurement, and dispensing without a license are illegal.
    Greece Controlled Became a controlled substance on February 18, 2003.
    Ireland Schedule 1 Controlled as a positional isomer of TMA (a UN-listed substance) under the Misuse of Drugs Act, similar to UK scheduling.
    Italy Tabella I Added to Tabella I (list of prohibited plants and substances) by Ministry of Health decree on January 11, 2005.
    Portugal Controlled Control measures enacted in January 2005 alongside 2C-I, 2C-T-2, and 2C-T-7.
    Slovakia Grade 2 Added to Grade 2 (corresponding to Schedule II of the 1971 UN Convention on Psychotropic Substances) in October 2009.
    Sweden Class I Placed into Class I (most restrictive category) as of March 16, 2004.
    Switzerland Controlled (Verzeichnis D) Specifically named as a controlled substance under Verzeichnis D of Swiss controlled substances legislation.
    Turkey Illegal Classified as a controlled drug under Turkish law. Possession, production, supply, and import are prohibited.
    United Kingdom Class A Controlled as a Class A drug under the Misuse of Drugs Act 1971. Covered by the generic phenethylamine definition as a positional isomer of the UN-controlled drug TMA. Class A classification carries the most severe penalties.
    United States Schedule I Controlled as a positional isomer of TMA, which is explicitly listed as a Schedule I hallucinogen under the Controlled Substances Act. Manufacturing, possession, and distribution are prohibited.

    Harm Reduction

    drugs.wiki

    Potency and margin: PiHKAL and Erowid note active oral range roughly 20–40 mg with some users sensitive at ~10–20 mg; Shulgin cautioned the psychoactive-to-adverse dose margin may be relatively narrow, so conservative titration is prudent. Effects duration is long (often 8–12 h) with residual stimulation or difficulty sleeping for some users, so plan set/setting and sleep accordingly. Qualitative reports mention GI upset, tremor, peripheral tingling/numbness, and occasional light-headedness; at 40 mg some noted intestinal cramps/diarrhea and sleep difficulty later in the day—avoid strenuous activity early in the come-up and stay hydrated. Animal data cited by Erowid describe bradycardia and hypothermia at high doses, so people with cardiovascular or thermoregulation vulnerabilities should be extra cautious. Cross-tolerance is expected with other 5‑HT2A psychedelics (e.g., LSD, mescaline), reducing effect intensity if taken again within days; spacing experiences by at least one to two weeks minimizes tolerance and psychological strain. Combining with MAOIs can unpredictably intensify and prolong effects and has a poor safety margin; lithium with serotonergic psychedelics has credible reports of seizures and severe adverse reactions—do not combine. Because TMA-2 is rare in current markets and has occasionally been confused with other phenethylamines, use multi-reagent testing; Project Response color testing has reported green→brown shifts—use Marquis/Mandelin/Mecke and a lab if possible. Use an accurate scale; for fine measurement or sub-milligram precision, use volumetric dosing to avoid weighing error. Legal controls vary; EU Council (2003) urged Member States to control TMA‑2, and many countries have scheduled it or control it as a TMA isomer—check local law before possession, ordering, or travel.

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