DOM

Clinical data
Other names	2,5-Dimethoxy-4-methylamphetamine; 4-Methyl-2,5-dimethoxyamphetamine; 2,5-Dimethoxy-4-methyl-α-methylphenethylamine; Des-oxy-methyl; DOM; DMMTA; α-Me-2C-D; STP; Serenity, Tranquility, and Peace; Super Terrific Psychedelic; Stop The Police; Too Stupid to Puke;[1] K-61,082[2]
Drug class	Serotonergic psychedelic;Hallucinogen;Serotonin5-HT2 receptoragonist
Legal status
Legal status	AU: S9 (Prohibited substance) BR: Class F2 (Prohibited psychotropics)[3] CA: Schedule I UK: Class A US: Schedule I
Identifiers
IUPAC name 1-(2,5-dimethoxy-4-methylphenyl)propan-2-amine
CAS Number	15588-95-1 Y 43061-13-8 ((R)-DOM) 43061-14-9 ((S)-DOM)
PubChemCID	11735949
ChemSpider	9910656 Y
UNII	UKI9MLD5OI
KEGG	C22736
ChEMBL	ChEMBL317634 Y
CompTox Dashboard(EPA)	DTXSID50860611
Chemical and physical data
Formula	C12H19NO2
Molar mass	209.289 g·mol−1
3D model (JSmol)	Interactive image
Melting point	61 °C (142 °F)
SMILES O(c1cc(c(OC)cc1C[C@H](N)C)C)C
InChI InChI=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/t9-/m1/s1 Key:NTJQREUGJKIARY-SECBINFHSA-N Y
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2,5-Dimethoxy-4-methylamphetamine (DOM), also known asSTP (standing for "Serenity, Tranquility, and Peace" and/or other phrases), is apsychedelicdrug of thephenethylamine,amphetamine, andDOx families.^{[4][5][1][6][7]} It is generally takenorally.^[5][1][6]

DOM was firstsynthesized byAlexander Shulgin, and later described in his bookPiHKAL: A Chemical Love Story (1991).^[1] It is classified as aSchedule Icontrolled substance in theUnited States, and is similarly controlled in other parts of the world.^[1] Internationally, it is a Schedule I drug under theConvention on Psychotropic Substances.^[8]

Effects of this drug include substantial perceptual changes such asblurred vision, multiple images, vibration of objects, visual alterations, distorted shapes, enhancement of details,slowed passage of time, increased sexual drive and pleasure, and increased contrasts. It may causemystical experiences and changes inconsciousness. It may also causepupillary dilation and a rise insystolic blood pressure.^[9]

The effects of DOM were assessed inclinical studies in the late 1960s and early 1970s and by other researchers.^{[2][7][10][11][12]} At low doses, such as 1 to 4 mg, DOM produces effects includingstimulation,euphoria, enhancedself-awareness, and milddose-dependentperceptual disturbances.^[2] At higher doses, of above 5 to 7 mg, DOM produces psychedelic effects.^[2]

Very little is known about thetoxicity of DOM.

DOM acts as aselectiveserotonin5-HT_2A,5-HT_2B, and5-HT_2C receptorfull agonist.^{[16][15][17][18]} Its psychedelic effects are mediated by itsagonistic properties at the 5-HT_2A receptor. Due to its selectivity, DOM is often used inscientific research in studies of the5-HT₂ receptor subfamily. DOM is achiral molecule, andR-(−)-DOM is the more activeenantiomer, functioning as a potent agonist of these receptors.^[25]

The drug is inactive as a humantrace amine-associated receptor 1 (TAAR1) agonist but is an agonist of therhesus monkey TAAR1.^[19] DOM is inactive as amonoamine reuptake inhibitor andreleasing agent.^[18] It is a very weakmonoamine oxidase inhibitor (MAOI), specifically ofmonoamine oxidase A (MAO-A), whereas it was inactive atmonoamine oxidase B (MAO-B).^[23][24]

DOM produces thehead-twitch response in rodents, a behavioral proxy ofpsychedelic-like effects.^[26] It also substitutes forLSD in rodentdrug discrimination tests.^[26] DOM is widely used as a psychedelic training drug in rodent drug discrimination assays and many otherserotonergic psychedelics have been shown to generalize to it.^[26]

In contrast toamphetamines like(−)-cathinone but similarly tomescaline, DOM has shown nostimulant-like orreinforcing effects in rhesus monkeys.^{[27][28][29][30]} Conversely however,DOC has shown reinforcing effects, includingconditioned place preference (CPP) andself-administration, in rodents similarly tomethamphetamine.^[31] This is analogous to other findings in which various2C andNBOMedrugs have been found to producedopaminergic elevations and reinforcing effects in rodents.^{[32][33][34][35][36][37][38]}

According toAlexander Shulgin, the effects of DOM typically last 14 to 20 hours, though other clinical trials indicate a duration of 7 to 8 hours.^[9]

Metabolites of DOM like 2-O-desmethyl-DOM (2-DM-DOM) and 5-O-desmethyl-DOM (5-DM-DOM) arepharmacologically active and showpsychedelic-like effects inanimal studies.^[39][40] They might contribute to the delayedonset and longduration of DOM.^[40][39] However, these metabolites might also producemetabolism-dependentneurotoxicity.^[39]

DOM, also known as 2,5-dimethoxy-4-methylamphetamine or as 2,5-dimethoxy-4-methyl-α-methylphenethylamine, is asubstituted phenethylamine andamphetamine and is a member of theDOx group of drugs.^[4][5][6][7] It isstructurally related to thenaturally occurring phenethylamine psychedelicmescaline (3,4,5-trimethoxyphenethylamine).^[7][41]

Analogues of DOM include other DOx drugs such asDOET,DOB,DOI,DOC, andTMA, among others.^[7] The α-desmethyl or phenethylamine analogue of DOM is2C-D.^[4][5]Ariadne is the α-ethyl orphenylisobutylamine analogue of DOM.^[42][5]

The 2,6-dimethoxy positional isomer of DOM, known asΨ-DOM, is also mentioned inPiHKAL as being active, as is the α-ethyl homologueAriadne. Analogues where the methoxy groups at the 2,5- positions of the aromatic ring have been altered have also been synthesised and tested as part of an effort to identify the binding mode of DOM at the serotonin5-HT_2A receptor. Both the 2- and 5- O-desmethyl derivatives 2-DM-DOM and 5-DM-DOM, and the 2- and 5- ethyl analogues 2-Et-DOM and 5-Et-DOM, have been tested, but in all cases were significantly less potent than the corresponding methoxy compound, showing the importance of the oxygen lone pairs in 5-HT_2A binding.^[40][43]

DOM was first synthesized and tested in 1963 byAlexander Shulgin, who was investigating the effect of 4-position substitutions on psychedelic amphetamines.^[1][5]

In mid-1967, tablets containing 20 mg (later 10 mg) of DOM were widely distributed in theHaight-Ashbury District ofSan Francisco under the name of STP, having been manufactured by underground chemistsOwsley Stanley andTim Scully.^[1] This short-lived appearance of DOM on theblack market proved disastrous for several reasons.^[1] First, the tablets contained an excessively high dose of the chemical.^[1] This, combined with DOM's slowonset of action (which encouraged some users, familiar with drugs that have quicker onsets, such asLSD, to re-dose) and its remarkably longduration, caused many users topanic and sent some to theemergency room.^[1] Second, treatment of suchoverdoses was complicated by the fact that no one at the time knew that the tablets called STP were, in fact, DOM, and there was no effectiveantidote.^[1]

The nameDOM is an acronym of the code name "des-oxy-methyl" coined by the drug's inventorAlexander Shulgin.^[1]

DOM is schedule 9 under the AustraliaPoisons standard.^[44] A schedule 9 substance is a "Substances which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities."^[44]

Listed as aSchedule 1, as it is an analogue of amphetamine.

DOM is aClass A drug in the United Kingdom under theMisuse of Drugs Act 1971.

DOM is Schedule I in the United States. This means it is illegal to manufacture, buy, possess, or distribute (make, trade, own or give) without a DEA license.

• DOx (psychedelics)
• Stimulant § Serotonin 5-HT_2A receptor agonists
• Motivation-enhancing drug § Serotonin 5-HT_2A receptor agonists
• ASR-2001 (2CB-5PrO)

• DOM - Isomer Design
• DOM - PsychonautWiki
• Erowid DOM Vault
• DOM - PiHKAL - Erowid
• DOM - PiHKAL - Isomer Design
• What is DOM? The Serenity Psychedelic - Tripsitter

• 5-HT2A agonists
• 5-HT2B agonists
• 5-HT2C agonists
• Alexander Shulgin
• Anti-inflammatory agents
• Designer drugs
• DOx (psychedelics)
• PiHKAL
• Psychedelic phenethylamines
• TAAR1 agonists

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