DOM

1-(2,5-dimethoxy-4-methylphenyl)propan-2-amine

Overview

DOM belongs to Psychedelics / Phenethylamines.

Key safety note: DOM ("STP") is a cautionary example: it is potent (active at a few milligrams), comes on slowly (often 1–2+ hours), and lasts a very long time (~12–20 hours, longer at high doses).[5][2]
Effects
Subjective effects vary. What a substance feels like depends on dose, individual physiology, mindset, and setting. The points below describe commonly reported effects, not guaranteed, uniform, or desirable outcomes.
  • Strongly stimulating with a heavy body load and a fairly neutral, analytical headspace
  • Pronounced visual geometry and internal/external hallucinations, though sometimes described as less visually complex than other psychedelics at moderate doses
  • A slow build and an exceptionally long plateau, with cardiovascular effects (racing heart, sweating, tremor) that can be uncomfortable
Dosing & duration
Harm-reduction note: These are commonly cited reference ranges, not a recommendation or a “safe” dose. Potency, purity, body chemistry, tolerance, and drug combinations vary widely. Start low, go slow, wait for full effects before redosing, and never assume an unknown product matches these figures. Missing data is not evidence of safety.

Oral. DOM is potent and very long-acting with a slow onset, which historically led people to redose and overdose (the 1967 'STP' emergencies). Common oral doses are only a few milligrams. Start low, and, crucially, do not redose because it 'hasn't come up yet'. Volumetric dosing of a solution is recommended for accuracy.

Dose ranges

Threshold

~0.5–1 mg

Light

1–3 mg

Common

3–5 mg

Strong

5–10 mg

Duration

onset

1–2 h (slow)

peak

6–8 h

total

12–20 h (longer at high doses)

Chemical & Physical Properties
FormulaC12H19NO2
Molar mass209.28 g/mol
StateNot reported
Melting point60.5 to 60.1 °C
Boiling pointNot reported
DensityNot reported
Vapor pressureNot reported
pKaNot reported
LogP2.24
SolubilityNot reported
Refractive indexNot reported
Identifiers & Synonyms
CAS15588-95-1
CAS (enantiomer)
PubChem CID85875
InChIKeyNTJQREUGJKIARY-UHFFFAOYSA-N
InChIInChI=1S/C12H19NO2/c1-8-5-12(15-4)10(6-9(2)13)7-11(8)14-3/h5,7,9H,6,13H2,1-4H3
SMILESCC1=CC(=C(C=C1OC)CC(C)N)OC

Synonyms

  • STP
  • 2,5-Dimethoxy-4-methylamphetamine
  • 4-Methyl-2,5-dimethoxyamphetamine
  • α-Methyl-2C-D
  • DOM
Pharmacodynamics & Biochemistry

A potent, long-acting psychedelic phenethylamine of the DOx (amphetamine) series: the α-methyl homologue of 2C-D. It acts as a selective full agonist at the serotonin 5-HT2A, 5-HT2B and 5-HT2C receptors, with the psychedelic effects mediated mainly by 5-HT2A. It is roughly 50–150× as potent as mescaline and about 30–60× less potent than LSD. (R)-(−)-DOM is the active enantiomer (eutomer). Notably, the inactive (S)-enantiomer still raises heart rate and blood pressure without psychoactivity: a reminder that DOM's cardiovascular load is not simply a function of its 'trip'. It is metabolised to the pharmacologically active demethyl metabolites 2-DM-DOM and 5-DM-DOM, which likely contribute to its slow onset and very long duration. A further metabolite (2,5-DDM-DOM) resembles the neurotoxin 6-hydroxydopamine and is a potential source of metabolism-dependent neurotoxicity.

Biological targets

  • 5-HT2A
  • 5-HT2B
  • 5-HT2C

Binding & functional measurements

TargetMeasurementSpecies
5-HT2A receptorKi 66 nMHuman
5-HT2B receptorKi 149 nMHuman
5-HT2C receptorKi 404 nMHuman
β2-adrenoceptorKi 49 nMHuman
5-HT1D receptorKi 209 nMHuman
α2A-adrenoceptorKi 580 nMHuman
α2B-adrenoceptorKi 874 nMHuman
α2C-adrenoceptorKi 921 nMHuman
5-HT7 receptorKi 1,591 nMHuman
α1A-adrenoceptorKi 3,219 nMHuman
5-HT1E receptorKi 3,542 nMHuman
5-HT1A receptorKi 7,238 nMHuman
5-HT6 receptorKi 8,155 nMHuman
5-HT2A receptorEC50 21 nM
Emax 92%		Human
5-HT2B receptorEC50 688 nM
Emax 91%		Human
5-HT2C receptorEC50 3.2 nM
Emax 98%		Human
Pharmacokinetics
BioavailabilityNot reported
TmaxNot reported
Half-lifeNot established in humans, onset is slow and effects are very long (≈12–20 h, longer at high doses)
VdNot reported
Protein bindingNot reported
MetabolismHepatic O-demethylation to the pharmacologically active metabolites 2-DM-DOM and 5-DM-DOM, which likely contribute to the slow onset and long duration. About 5–20% is excreted unchanged. A further metabolite, 2,5-DDM-DOM, structurally similar to the neurotoxin 6-hydroxydopamine, is a potential source of metabolism-dependent neurotoxicity
ExcretionNot reported
Toxicology & Safety
Harm-reduction note: Toxicity and risk depend on dose, route, purity, combinations, setting, and individual health factors. Missing harms should never be interpreted as evidence of safety.

Not reported

DOM ("STP") is a cautionary example: it is potent (active at a few milligrams), comes on slowly (often 1–2+ hours), and lasts a very long time (~12–20 hours, longer at high doses). In 1967 tablets containing 10–20 mg were sold as 'STP' in San Francisco. The high dose, slow onset (which led LSD-experienced users to redose) and long duration sent many people to emergency rooms. It also causes a pronounced cardiovascular load, tachycardia, sweating and muscle tremor more marked than with LSD, and vasoconstriction at higher doses. The (S)-enantiomer raises heart rate and blood pressure even without psychoactive effects. Tolerance builds rapidly with repeated dosing. Never redose because it 'hasn't come up yet'. Limited human data must never be read as evidence of safety.[5][2]

Legal Status
Legal note: Legal status can change over time and may vary by country, region, formulation, analogue status, prescription context, and enforcement practice. Always confirm with current official sources before relying on this section.
Interactions & Contraindications

Drug interactions

Stimulants (amphetamines, cocaine) Add cardiovascular strain, anxiety, panic and thought loops, a particular concern given DOM's own strong cardiovascular load and long duration.
Lithium, Tramadol Raise the risk of seizures and psychosis with psychedelics.
SSRIs, SNRIs, MAOIs Add to serotonergic load. MAOIs may unpredictably intensify and prolong effects.
Cannabis Can intensify effects and increase anxiety or panic.

Contraindications

Cardiovascular disease, hypertension or arrhythmia DOM causes marked tachycardia and vasoconstriction.
Personal or family history of psychosis, schizophrenia or bipolar disorder
Concurrent MAOI, SSRI/SNRI or other serotonergic medication includes MAO inhibitors, and avoid concurrent stimulants or vasoconstrictors.
Settings where impairment or dissociation risks injury (driving, water, heights) slow onset, extreme potency and ~12-20 h duration.
Usage & Context
  • Research.
  • Recreational.
Sources & Evidence

Further Information