2,5-Dimethoxy-4-methylamphetamine

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2,5-Dimethoxy-4-methylamphetamine (DOM), also known as STP (standing for "Serenity, Tranquility, and Peace" and/or other phrases), is a psychedelic drug of the phenethylamine, amphetamine, and DOx families.<ref name="ShulginManningDaley2011">Template:Cite book</ref><ref name="PiHKAL1991">Template:Cite book</ref><ref name="Baggott2023">Template:Cite journal</ref><ref name="WillsErickson2012">Template:Cite book</ref><ref name="Shulgin1978">Template:Cite book</ref> It is generally taken orally.<ref name="PiHKAL1991" /><ref name="Baggott2023" /><ref name="WillsErickson2012" />

DOM was first synthesized by Alexander Shulgin, and later described in his book PiHKAL: A Chemical Love Story (1991).<ref name="Baggott2023" /> It is classified as a Schedule I controlled substance in the United States, and is similarly controlled in other parts of the world.<ref name="Baggott2023" /> Internationally, it is a Schedule I drug under the Convention on Psychotropic Substances.<ref name="INCB2003">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

Effects

Effects of this drug include substantial perceptual changes such as blurred 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 cause mystical experiences and changes in consciousness. It may also cause pupillary dilation and a rise in systolic blood pressure.<ref name="Snyder">Template:Cite journal</ref>

The effects of DOM were assessed in clinical studies in the late 1960s and early 1970s and by other researchers.<ref name="TroutDaley2024" /><ref name="Shulgin1978">Template:Cite book</ref><ref name="SnyderFaillaceHollister1967">Template:Cite journal</ref><ref name="SnyderFaillaceWeingartner1968">Template:Cite journal</ref><ref name="WeingartnerSnyderFaillace1971">Template:Cite journal</ref> At low doses, such as 1 to 4Template:Nbspmg, DOM produces effects including stimulation, euphoria, enhanced self-awareness, and mild dose-dependent perceptual disturbances.<ref name="TroutDaley2024" /> At higher doses, of above 5 to 7Template:Nbspmg, DOM produces psychedelic effects.<ref name="TroutDaley2024" />

Side effects

Very little is known about the toxicity of DOM.

Pharmacology

Pharmacodynamics

Actions

Template:Nowrap

Target	Affinity (Ki, nM)
5-HT1A	3,656–14,200 (Ki) 12,800–13,900 (Template:Abbrlink) 54–74% (Template:Abbrlink)
5-HT1B	>10,000
5-HT1D	209
5-HT1E	3,542
5-HT1F	Template:Abbr
5-HT2A	2.1–507 (Ki) 1.1–40 (Template:Abbr) 44–132% (Template:Abbr)
5-HT2B	12–41 (Ki) 128–145 (Template:Abbr) 85% (Template:Abbr)
5-HT2C	19–3,980 (Ki) 0.23–423 (Template:Abbr) 81–119% (Template:Abbr)
5-HT3	>10,000
5-HT4	Template:Abbr
5-HT5A	>10,000
5-HT6	8,155
5-HT7	1,591
α1A	3,219
α1B	>10,000
α1D	Template:Abbr
α2A	580
α2B	874
α2C	921
β1	>10,000
β2	49
D1–D5	>10,000
H1–H4	>10,000
M1, M2, M5	>10,000
M3, M4	Template:Abbr
TAAR1	>10,000 (Template:Abbr)
I1	>10,000
σ1, σ2	>10,000
Template:Abbrlink	>100,000 (Ki) >100,000 (Template:Abbrlink) >100,000 (Template:Abbr)
Template:Abbrlink	>100,000 (Ki) >70,000 (Template:Abbr) >100,000 (Template:Abbr)
Template:Abbrlink	>100,000 (Ki) 64,000 (Template:Abbr) >42,000 (Template:Abbr)
Template:Abbrlink	24,000 (Template:Abbr) (rat)
Template:Abbrlink	>100,000 (Template:Abbr) (rat)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: <ref name="PDSPKiDatabase">{{#invoke:citation/CS1|citation		CitationClass=web }}</ref><ref name="BindingDB">{{#invoke:citation/CS1|citation	CitationClass=web }}</ref><ref name="Ray2010" /><ref name="LuethiRudinHoener2022" /><ref name="EshlemanForsterWolfrum2014" /><ref name="EshlemanWolfrumReed2018" /><ref name="LewinMillerGilmour2011" /><ref name="ÅstrandGuerrieriVikingsson2020">Template:Cite journal</ref><ref name="vanWijngaardenSoudijn1997">Template:Cite book</ref><ref name="Acuña-CastilloVillalobosMoya2002">Template:Cite journal</ref><ref name="Reyes-ParadaIturriaga-VasquezCassels2019" /><ref name="ScorzaCarrauSilveira1997" />

DOM acts as a selective serotonin 5-HT_2A, 5-HT_2B, and 5-HT_2C receptor full agonist.<ref name="LuethiRudinHoener2022">Template:Cite journal</ref><ref name="Ray2010">Template:Cite journal</ref><ref name="EshlemanForsterWolfrum2014">Template:Cite journal</ref><ref name="EshlemanWolfrumReed2018" /> Its psychedelic effects are mediated by its agonistic properties at the 5-HT_2A receptor. Due to its selectivity, DOM is often used in scientific research in studies of the 5-HT₂ receptor subfamily. DOM is a chiral molecule, and R-(−)-DOM is the more active enantiomer, functioning as a potent agonist of these receptors.<ref>Template:Cite journal</ref>

The drug is inactive as a human trace amine-associated receptor 1 (TAAR1) agonist but is an agonist of the rhesus monkey TAAR1.<ref name="LewinMillerGilmour2011">Template:Cite journal</ref> DOM is inactive as a monoamine reuptake inhibitor and releasing agent.<ref name="EshlemanWolfrumReed2018">Template:Cite journal</ref> It is a very weak monoamine oxidase inhibitor (MAOI), specifically of monoamine oxidase A (MAO-A), whereas it was inactive at monoamine oxidase B (MAO-B).<ref name="Reyes-ParadaIturriaga-VasquezCassels2019">Template:Cite journal</ref><ref name="ScorzaCarrauSilveira1997">Template:Cite journal</ref>

Effects

DOM produces the head-twitch response in rodents, a behavioral proxy of psychedelic-like effects.<ref name="HalberstadtChathaKlein2020">Template:Cite journal</ref> It also substitutes for LSD in rodent drug discrimination tests.<ref name="HalberstadtChathaKlein2020" /> DOM is widely used as a psychedelic training drug in rodent drug discrimination assays and many other serotonergic psychedelics have been shown to generalize to it.<ref name="HalberstadtChathaKlein2020" />

In contrast to amphetamines like (–)-cathinone but similarly to mescaline, DOM has shown no stimulant-like or reinforcing effects in rhesus monkeys.<ref name="FantegrossiMurnaneReissig2008">Template:Cite journal</ref><ref name="CanalMurnane2017">Template:Cite journal</ref><ref name="Yanagita1986">Template:Cite journal</ref><ref name="Maguire2024">Template:Cite journal</ref> Conversely however, DOC has shown reinforcing effects, including conditioned place preference (CPP) and self-administration, in rodents similarly to methamphetamine.<ref name="ChaJeonJang2018">Template:Cite journal</ref> This is analogous to other findings in which various 2C and NBOMe drugs have been found to produce dopaminergic elevations and reinforcing effects in rodents.<ref name="Gil-MartinsBarbosaBorges2025">Template:Cite journal</ref><ref name="KimMaHur2021">Template:Cite journal</ref><ref name="CustodioSaysonBotanas2020">Template:Cite journal</ref><ref name="SeoHurKo2019">Template:Cite journal</ref><ref name="JoJooYoun2022">Template:Cite journal</ref><ref name="LeeHurHwang2023">Template:Cite journal</ref><ref name="KimKookMa2024">Template:Cite journal</ref>

Pharmacokinetics

According to Alexander Shulgin, the effects of DOM typically last 14 to 20 hours, though other clinical trials indicate a duration of 7 to 8 hours.<ref name=Snyder />

Metabolites of DOM like 2-O-desmethyl-DOM (2-DM-DOM) and 5-O-desmethyl-DOM (5-DM-DOM) are pharmacologically active and show psychedelic-like effects in animal studies.<ref name="Glennon2017">Template:Cite journal</ref><ref name="EcklerChang-FongRabin2003">Template:Cite journal</ref> They might contribute to the delayed onset and long duration of DOM.<ref name="EcklerChang-FongRabin2003" /><ref name="Glennon2017" /> However, these metabolites might also produce metabolism-dependent neurotoxicity.<ref name="Glennon2017" />

Chemistry

File:DOM, STP (Serenity, Tranquillity & Peace) - 53627337701.jpg

Sample of DOM.

DOM, also known as 2,5-dimethoxy-4-methylamphetamine or as 2,5-dimethoxy-4-methyl-α-methylphenethylamine, is a substituted phenethylamine and amphetamine and is a member of the DOx group of drugs.<ref name="ShulginManningDaley2011" /><ref name="PiHKAL1991" /><ref name="WillsErickson2012" /><ref name="Shulgin1978" /> It is structurally related to the naturally occurring phenethylamine psychedelic mescaline (3,4,5-trimethoxyphenethylamine).<ref name="Shulgin1978" /><ref name="HassanBoschSingh2017">Template:Cite journal</ref> Analogues of DOM include other DOx drugs such as DOET, DOB, DOI, DOC, and TMA, among others.<ref name="Shulgin1978" /> The α-desmethyl or phenethylamine analogue of DOM is 2C-D.<ref name="ShulginManningDaley2011" /><ref name="PiHKAL1991" /> Ariadne is the α-ethyl or phenylisobutylamine analogue of DOM.<ref name="CunninghamBockSerrano2023">Template:Cite journal</ref><ref name="PiHKAL1991" />

File:DOM-25-varients.png

Chemical structures of some DOM variants

The 2,6-dimethoxy positional isomer of DOM, known as Ψ-DOM, is also mentioned in PiHKAL as being active, as is the α-ethyl homologue Ariadne. 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 serotonin 5-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.<ref name="EcklerChang-FongRabin2003" /><ref name="Braden2007">Template:Cite thesis</ref>

History

STP was first synthesized and tested in 1963 by Alexander Shulgin, who was investigating the effect of 4-position substitutions on psychedelic amphetamines.<ref name="Baggott2023" /><ref name="PiHKAL1991" />

In mid-1967, tablets containing 20Template:Nbspmg (later 10Template:Nbspmg) of STP were widely distributed in the Haight-Ashbury District of San Francisco under the name of STP, having been manufactured by underground chemists Owsley Stanley and Tim Scully.<ref name="Baggott2023" /> This short-lived appearance of STP on the black market proved disastrous for several reasons.<ref name="Baggott2023" /> First, the tablets contained an excessively high dose of the chemical.<ref name="Baggott2023" /> This, combined with DOM's slow onset of action (which encouraged some users, familiar with drugs that have quicker onsets, such as LSD, to re-dose) and its remarkably long duration, caused many users to panic and sent some to the emergency room.<ref name="Baggott2023" /> Second, treatment of such overdoses 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 effective antidote.<ref name="Baggott2023" />

Society and culture

Legal status

Australia

DOM is schedule 9 under the Australia Poisons standard.<ref name="Poisons Standard">Poison Standard https://www.comlaw.gov.au/Details/F2015L01534/Html/Text#_Toc420496379 Template:Webarchive</ref> 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."<ref name="Poisons Standard" />

Canada

Listed as a Schedule 1, as it is an analogue of amphetamine.

United Kingdom

DOM is a Class A drug in the United Kingdom under the Misuse of Drugs Act 1971.

United States

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.

See also

• ASR-2001

External links

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

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