DOM (2,5-Dimethoxy-4-methylamphetamine)

Overview

DOM (also known as STP, “Serenity, Tranquility, and Peace”) is a synthetic psychedelic compound belonging to the substituted amphetamine / phenethylamine family. It is chemically related to mescaline and the 2,5-dimethoxy substituted phenethylamines explored extensively by Alexander Shulgin.

• IUPAC name: 1-(2,5-dimethoxy-4-methylphenyl)propan-2-amine
• Molecular formula: C₁₂H₁₉NO₂
• Molecular weight: ~209.29 g/mol
• CAS Number: 15588-95-1
• Class: Psychedelic phenethylamine; 5-HT₂A receptor agonist

History & Origin

DOM was first synthesized and characterized in the 1960s. It appeared briefly on the U.S. street market around 1967–1968 under the name “STP,” promoted as a longer-lasting alternative to LSD. Reports of unexpectedly long duration and uncomfortable reactions led to its rapid disappearance from the recreational market. The compound later became a reference point in Shulgin’s PiHKAL (1991), where its synthesis, dosage, and human effects are documented.

Pharmacology

DOM acts primarily as a potent agonist at the serotonin 5-HT₂A and 5-HT₂C receptors, which is the mechanism shared by classic psychedelics. It also shows activity at adrenergic receptors and is a monoamine releasing agent.

• Receptor binding: Strong partial agonist at 5-HT₂A; significant activity at 5-HT₂B and 5-HT₂C
• Onset: 1–2 hours (oral)
• Duration: 14–20 hours (notably long for its dose)
• Active oral dose range: ~3–10 mg

Documented Effects (Shulgin, PiHKAL)

At common doses, effects include:

• Visual alterations (closed-eye imagery, color enhancement, pattern distortions)
• Altered perception of time and space
• Euphoria and emotional openness
• Introspective, meditative state
• Mild to moderate stimulation

At higher doses, effects intensify significantly and may include:

• Strong confusion or anxiety
• Nausea and body load
• Sleep difficulty after the experience

Safety & Harm Considerations

• Long duration makes setting/dosing errors difficult to correct.
• Risk of psychological distress, especially at high doses or in unprepared users.
• Serotonergic activity (5-HT₂B agonism in particular) raises theoretical concerns for cardiac valvulopathy with repeated use.
• May interact dangerously with SSRIs, MAOIs, and other serotonergic medications.
• Tolerance develops rapidly and resets within roughly 3–4 days.