2,5-Dimethoxy-4-methylamphetamine

vanc 6 verified verified 477211718 DOM 2,5-dimethoxy-4-methylamphetamine.svg skin-invert-image 200px DOM 3D ball and stick.png bg-transparent 200px Oral Serotonin 5-HT2 receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen; Stimulant; Antidepressant; Psychic energizer None S9 F2 Anvisa 2023-07-24 RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial pt-BR Diário Oficial da União https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 2023-08-27 2023-08-27 https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 Brazilian Health Regulatory Agency Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control live 2023-07-25 Schedule I Class A Schedule I Demethylation • 2-DM-DOM• 5-DM-DOM• 2,5-DDM-DOM 0.5–1.5 hoursPeak: 2–6 hours Low doses: 5–8 hoursModerate doses: 8–24 hoursHigh doses: possibly up to 3–4days 5–20% unchanged 15588-95-1 correct CAS 43061-13-8 ((R)-DOM)43061-14-9 ((S)-DOM) 85875 DB01528 correct chemspider 77462 correct FDA UKI9MLD5OI C22736 correct EBI 8600 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; K-61,082 Trout K, Daley PF The origin of 2,5-dimethoxy-4-methylamphetamine (DOM, STP) Drug Testing and Analysis 16 12 1496–1508 December 2024 38419183 10.1002/dta.3667 https://shulginresearch.net/wp-content/uploads/2024/03/The-origin-of-25-dimethoxy-4-methylamphetamine-DOM-STP.-Trout.-Drug-Test.-Anal.-DOI-10.1002-dta.3667-2024.pdf 1-(2,5-dimethoxy-4-methylphenyl)propan-2-amine 12 19 1 2 CC1=CC(=C(C=C1OC)CC(C)N)OC 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 correct chemspider NTJQREUGJKIARY-UHFFFAOYSA-N 61 2,5-Dimethoxy-4-methylamphetamine (DOM), also known as STP (standing for "Serenity, Tranquility, and Peace" and other phrases), is a psychedelic drug of the phenethylamine, amphetamine, and DOx families. Shulgin A, Manning T, Daley PF 2011 #60. DOM The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds Berkeley, CA Transform Press 1 118–129 978-0-9630096-3-0 https://archive.org/details/shulgin-index-vol-1/page/118/mode/1up 709667010 1991 #68 DOM; STP; 2,5-DIMETHOXY-4-METHYLAMPHETAMINE PiHKAL: A Chemical Love Story Berkeley, CA Transform Press 1st 637–642 978-0-9630096-0-9 https://books.google.com/books?id=O8AdHBGybpcC Alexander T. Shulgin Ann Shulgin https://erowid.org/library/books_online/pihkal/pihkal068.shtml 25627628 Baggott MJ Learning about STP: A Forgotten Psychedelic from the Summer of Love History of Pharmacy and Pharmaceuticals 65 1 1 October 2023 2694-3034 10.3368/hopp.65.1.93 free 93–116 https://hopp.uwpress.org/content/wphopp/65/1/93.full.pdf 26 January 2025 Wills B, Erickson T 9 March 2012 Barceloux DG Psychoactive Phenethylamine, Piperazine, and Pyrrolidinophenone Derivatives Medical Toxicology of Drug Abuse: Synthesized Chemicals and Psychoactive Plants Wiley 156–192 978-0-471-72760-6 10.1002/9781118105955.ch10 Shulgin AT 1978 Iversen LL, Iversen SD, Snyder SH Psychotomimetic Drugs: Structure-Activity Relationships Stimulants Springer US 243–333 978-1-4757-0512-6 10.1007/978-1-4757-0510-2_6 Boston, MA https://bitnest.netfirms.com/external/10.1007/978-1-4757-0510-2_6 Shulgin AT Profiles of Psychedelic Drugs: 5. STP Journal of Psychedelic Drugs 9 2 171–172 1977 10.1080/02791072.1977.10472044 https://bibliography.maps.org/resources/download/9495 2025-07-12 https://web.archive.org/web/20250712225853/https://bibliography.maps.org/resources/download/9495 0022-393X It has stimulant and antidepressant-like effects at low doses and hallucinogenic effects at higher doses. The drug can have a very slow onset and long duration, with its duration possibly being up to a few days at high doses. It is usually taken orally. Side effects of DOM include amphetamine-like effects, among others. The drug acts as a serotonin 5-HT2 receptor agonist, including of the serotonin 5-HT2A receptor. Analogues of DOM include mescaline, 2C-D, DOET, DOB, DOI, and Ariadne (4C-D), among others. DOM was first synthesized and tested by Alexander Shulgin in 1963 and was later further described in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). The drug caused a small public health crisis in San Francisco in 1967 when it was introduced as a substitute for LSD, which was due to the tablets containing high doses and causing intense and very long-lived effects. DOM is classified as a Schedule I controlled substance in the United States, and is similarly controlled in other parts of the world. Internationally, it is a Schedule I drug under the Convention on Psychotropic Substances.http://www.incb.org/documents/Psychotropics/green_lists/Green_list_ENG_2014_85222_GHB.pdf Green List: List of Psychotropic Substances Under International Control August 2003 23rd International Narcotics Control Board 4 22 February 2014 dead https://web.archive.org/web/20131219071757/http://www.incb.org/documents/Psychotropics/green_lists/Green_list_ENG_2014_85222_GHB.pdf 19 December 2013 Use and effects In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists DOM's dose as 3 to 10mg orally and its duration as 14 to 24hours. Shulgin AT 2003 Laing RR Basic Pharmacology and Effects Hallucinogens: A Forensic Drug Handbook Forensic Drug Handbook Series Elsevier Science 67–137 978-0-12-433951-4 https://books.google.com/books?id=l1DrqgobbcwC 13 July 2025 https://web.archive.org/web/20250713013624/https://bibliography.maps.org/resources/download/12634 https://bibliography.maps.org/resources/download/12634 Jacob P, Shulgin AT 1994 Lin GC, Glennon RA Structure-Activity Relationships of the Classic Hallucinogens and Their Analogs Hallucinogens: An Update National Institute on Drug Abuse Research Monograph Series National Institute on Drug Abuse 146 74–91 8742795 https://archives.nida.nih.gov/sites/default/files/monograph146.pdf 13 July 2025 https://web.archive.org/web/20250713011914/https://bibliography.maps.org/resources/download/11534 https://bibliography.maps.org/resources/download/11534 An estimated typical dose is about 6mg. The (R)-enantiomer, (R)-DOM, was active at a dose of 0.5mg, whereas DOM itself produces threshold effects only at 1mg. The (S)-enantiomer, (S)-DOM, showed no psychoactive effects at doses of up to 2.6mg. As such, the activity of DOM appears to reside in (R)-DOM, with this enantiomer appearing to be roughly twice as potent as racemic DOM. In a review by Richard Glennon and colleagues, the approximate hallucinogenic dose was listed as 2 to 5mg for racemic DOM, 1.0 to 2.5mg for (R)-DOM, and greater than 4mg for (S)-DOM, with no known active level of the latter enantiomer. Glennon RA, Rosecrans JA Indolealkylamine and phenalkylamine hallucinogens: a brief overview Neuroscience and Biobehavioral Reviews 6 4 489–497 1982 6757811 10.1016/0149-7634(82)90030-6 DOM is said by Shulgin to have a slow build-up, with an onset of 30 to 60minutes and a peak of 2 to 6hours. It may also have a very long duration of up to 3 or 4days when taken in excessively high doses such as 14 to 30mg. However, it is unclear the extent to which this is actually true or may just be exaggeration. DOM is about 50- to 150-fold as potent as mescaline and around 30- to 60-fold less potent than LSD. The effects of DOM were reported by Shulgin to include feeling strange, color enhancement, closed-eye imagery, visuals, introspection and insights, fantasy, depersonalization, music and erotic enhancement, time dilation, emotional changes, mood elevation, increased empathy, stimulation, mood swings, tension, discomfort, feeling overwhelmed or like one is losing control, impairment, pupil dilation, jaw tightness, muscle tremors, feeling sick (but without nausea), other burdensome physical side effects, insomnia, and sleep disturbances. It has also been observed that DOM produces similar effects to LSD but causes less disorientation, impairment, and ego dissolution. The effects of DOM are highly dependent on set and setting, as with psychedelics in general. At lower doses of 2 to 5mg, DOM is said to produce few or no physiological effects, no perceptual distortion, and more subtle visual, cognitive, and affective changes, but as not producing hallucinogenic effects at such doses. The drug was one of Shulgin's "magical half-dozen" psychedelic compounds in PiHKAL. The effects of DOM were formally assessed in clinical studies by Solomon H. Snyder and Leo Hollister and colleagues in the late 1960s and early 1970s. Snyder SH, Faillace L, Hollister L 2,5-dimethoxy-4-methyl-amphetamine (STP): a new hallucinogenic drug Science New York, N.Y. 158 3801 669–670 November 1967 4860952 10.1126/science.158.3801.669 1967Sci...158..669S 24065654 Snyder SH, Faillace LA, Weingartner H DOM (STP), a new hallucinogenic drug, and DOET: effects in normal subjects The American Journal of Psychiatry 125 3 113–120 September 1968 4385937 10.1176/ajp.125.3.357 Weingartner H, Snyder SH, Faillace LA DOM (STP), a new hallucinogenic drug: specific perceptual changes The Journal of Clinical Pharmacology and New Drugs 11 2 103–111 1971 5206471 10.1177/009127007101100205 Hollister LE, Macnicol MF, Gillespie HK An hallucinogenic amphetamine analog (DOM) in man Psychopharmacologia 14 1 62–73 1969 5351858 10.1007/BF00401535 At low doses, such as 1 to 4mg, DOM produced effects including stimulation, euphoria, enhanced self-awareness, and mild dose-dependent perceptual disturbances. At higher doses, of above 5 to 7mg, DOM produces marked and full psychedelic effects. Hallucinogenic effects were said to start at doses of more than 3 to 5mg. Other effects of the drug were also described. Although Shulgin described the effects of DOM as typically lasting 14 to 20hours, clinical studies with low doses reported a duration of only 5 to 8hours, but with a lack of an unexpectedly long duration even at doses of up to 14mg. Another source listed the average duration as only 8 to 15hours at doses of 5 or 10mg. The reasons for these discrepancies are unclear. The onset was 0.5 to 1.5hours and peak effects occurred after 3 to 5hours. Low doses of DOM have been used as a stimulant, such as by the Grateful Dead. This may be the first known instance of psychedelic microdosing. The related drug DOET is also implicated as having stimulant and "psychic energizer" effects at low doses, which notably greatly impressed Shulgin. Interactions Psychedelic drug#Interactions Trip killer#Serotonergic psychedelic antidotes The typical antipsychotic and serotonin 5-HT2A receptor antagonist chlorpromazine has been reported to partially reduce the effects of DOM. Side effects Side effects of DOM include sweating, muscle tremors, and large increases in heart rate. These are said to be worrisome and not seen with other psychedelics like LSD. (S)-DOM produces increased heart rate and blood pressure but no psychoactive effects, in contrast to (R)-DOM. It may be importantly involved in the physical side effects of DOM, such that enantiopure (R)-DOM might be better-tolerated. Tolerance Repeated administration of DOM results in rapid tolerance development. Angrist B, Rotrosen J, Gershon S Assessment of tolerance to the hallucinogenic effects of DOM Psychopharmacologia 36 3 203–207 April 1974 4844244 10.1007/BF00421802 In one study, in which five people were given 6mg DOM for 3days, there were "extremely intense" effects the first day, but diminished effects on the third day, ranging from "moderately strong" to "felt absolutely nothing". In another study, in which two people were given gradually increasing doses from 1 to 12mg over 8days, there was development of marked partial tolerance to the effects of DOM. Tolerance developed to both the psychoactive and physiological effects of the drug. Overdose Overdose of DOM can have a very long duration and result in an amphetamine psychosis-like state. It is said to have pronounced hallucinogenic effects as well as amphetamine-like side effects in overdose. Pharmacology Pharmacodynamics Actions + DOM activities Target Affinity (Ki, nM) 5-HT1A 3,656–14,200 (Ki)12,800–13,900 (EC50 half-maximal effective concentration)54–74% (Emax maximal efficacy) 5-HT1B >10,000 5-HT1D 209 5-HT1E 3,542 5-HT1F ND No data 5-HT2A 2.1–507 (Ki)1.1–40 (EC50 half-maximal effective concentration)44–132% (Emax maximal efficacy) 5-HT2B 12–149 (Ki)128–688 (EC50 half-maximal effective concentration)85–91% (Emax maximal efficacy) 5-HT2C 19–3,980 (Ki)0.23–423 (EC50 half-maximal effective concentration)81–119% (Emax maximal efficacy) 5-HT3 >10,000 5-HT4 ND No data 5-HT5A >10,000 5-HT6 8,155 5-HT7 1,591 α1A 3,219–7,393 α1B >10,000 α1D ND No data α2A 580–>4,970 α2B 874 α2C 921 β1 >10,000 β2 49 D1–D5 >10,000 H1–H4 >10,000 M1, M2, M5 >10,000 M3, M4 ND No data TAAR1 >30,000 (EC50 half-maximal effective concentration) I1 >10,000 σ1, σ2 >10,000 SERT Serotonin transporter >100,000 (Ki)>100,000 (IC50 half-maximal inhibitory concentration)>100,000 (EC50 half-maximal inhibitory concentration) NET Norepinephrine transporter >100,000 (Ki)>70,000 (IC50 half-maximal inhibitory concentration)>100,000 (EC50 half-maximal inhibitory concentration) DAT Dopamine transporter >100,000 (Ki)64,000 (IC50 half-maximal inhibitory concentration)>42,000 (EC50 half-maximal inhibitory concentration) MAO-A Monoamine oxidase A 24,000 (IC50 half-maximal inhibitory concentration) (rat) MAO-B Monoamine oxidase B >100,000 (IC50 half-maximal inhibitory concentration) (rat) Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: PDSP Database UNC https://pdsp.unc.edu/databases/pdsp.php?receptorDD=&receptor=&speciesDD=&species=&sourcesDD=&source=&hotLigandDD=&hotLigand=&testLigandDD=&testFreeRadio=testFreeRadio&testLigand=DOM&referenceDD=&reference=&KiGreater=&KiLess=&kiAllRadio=all&doQuery=Submit+Query zu 1 February 2025 Liu T BindingDB BDBM50005265 (+/-)2-(2,5-Dimethoxy-4-methyl-phenyl)-1-methyl-ethylamine::(-)2-(2,5-Dimethoxy-4-methyl-phenyl)-1-methyl-ethylamine::(Rec)2-(2,5-Dimethoxy-4-methyl-phenyl)-1-methyl-ethylamine; compound with 2-(2,5-dimethoxy-4-methyl-phenyl)-1-methyl-ethylamine::2-(2,5-Dimethoxy-4-methyl-phenyl)-1-methyl-ethylamine::2-(2,5-Dimethoxy-4-methyl-phenyl)-1-methyl-ethylamine((R)-(-)-DOM)::2-(2,5-Dimethoxy-4-methyl-phenyl)-1-methyl-ethylamine(DOM)::CHEMBL8600::DOM::DOM,R(-)::Racemic DOM BindingDB https://www.bindingdb.org/rwd/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50005265 1 February 2025 Luethi D, Glatfelter GC, Pottie E, Sellitti F, Maitland AD, Gonzalez NR, Kryszak LA, Jackson SN, Hoener MC, Stove CP, Liechti ME, Smieško M, Baumann MH, Simmler LD, Rudin D The 4-alkyl chain length of 2,5-dimethoxyamphetamines differentially affects in vitro serotonin receptor actions versus in vivo psychedelic-like effects Molecular Psychiatry 31 3 1799–1809 November 2025 41193673 10.1038/s41380-025-03325-1 12916490 https://www.nature.com/articles/s41380-025-03325-1.pdf Åstrand A, Guerrieri D, Vikingsson S, Kronstrand R, Green H In vitro characterization of new psychoactive substances at the μ-opioid, CB1, 5HT1A, and 5-HT2A receptors-On-target receptor potency and efficacy, and off-target effects Forensic Science International 317 110553 December 2020 33160102 10.1016/j.forsciint.2020.110553 free van Wijngaarden I, Soudijn W 1997 5-HT2A, 5-HT2B and 5-HT2C receptor ligands Pharmacochemistry Library Elsevier 27 161–197 978-0-444-82041-9 10.1016/s0165-7208(97)80013-x Acuña-Castillo C, Villalobos C, Moya PR, Sáez P, Cassels BK, Huidobro-Toro JP Differences in potency and efficacy of a series of phenylisopropylamine/phenylethylamine pairs at 5-HT(2A) and 5-HT(2C) receptors British Journal of Pharmacology 136 4 510–519 June 2002 12055129 1573376 10.1038/sj.bjp.0704747 DOM acts as a selective serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptor full agonist. Luethi D, Rudin D, Hoener MC, Liechti ME Monoamine Receptor and Transporter Interaction Profiles of 4-Alkyl-Substituted 2,5-Dimethoxyamphetamines The FASEB Journal 36 S1 fasebj.2022.36.S1.R2691 2022 10.1096/fasebj.2022.36.S1.R2691 free 0892-6638 Ray TS Psychedelics and the human receptorome PLOS ONE 5 2 e9019 February 2010 20126400 2814854 10.1371/journal.pone.0009019 free 2010PLoSO...5.9019R Eshleman AJ, Forster MJ, Wolfrum KM, Johnson RA, Janowsky A, Gatch MB Behavioral and neurochemical pharmacology of six psychoactive substituted phenethylamines: mouse locomotion, rat drug discrimination and in vitro receptor and transporter binding and function Psychopharmacology Berl 231 5 875–888 March 2014 24142203 3945162 10.1007/s00213-013-3303-6 Its psychedelic effects are thought to be mediated by its agonistic properties at the serotonin 5-HT2A 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. Sanders-Bush E, Burris KD, Knoth K Lysergic acid diethylamide and 2,5-dimethoxy-4-methylamphetamine are partial agonists at serotonin receptors linked to phosphoinositide hydrolysis The Journal of Pharmacology and Experimental Therapeutics 246 3 924–928 September 1988 2843634 10.1016/S0022-3565(25)22189-9 The drug is inactive as a human trace amine-associated receptor 1 (TAAR1) agonist but is an agonist of the rhesus monkey TAAR1. Lewin AH, Miller GM, Gilmour B Trace amine-associated receptor 1 is a stereoselective binding site for compounds in the amphetamine class Bioorganic & Medicinal Chemistry 19 23 7044–7048 December 2011 22037049 3236098 10.1016/j.bmc.2011.10.007 DOM is inactive as a monoamine reuptake inhibitor and releasing agent. Eshleman AJ, Wolfrum KM, Reed JF, Kim SO, Johnson RA, Janowsky A Neurochemical pharmacology of psychoactive substituted N-benzylphenethylamines: High potency agonists at 5-HT2A receptors Biochemical Pharmacology 158 27–34 December 2018 30261175 6298744 10.1016/j.bcp.2018.09.024 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). Reyes-Parada M, Iturriaga-Vasquez P, Cassels BK Amphetamine Derivatives as Monoamine Oxidase Inhibitors Frontiers in Pharmacology 10 1590 2019 32038257 6989591 10.3389/fphar.2019.01590 free Scorza MC, Carrau C, Silveira R, Zapata-Torres G, Cassels BK, Reyes-Parada M Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives: structure-activity relationships Biochemical Pharmacology 54 12 1361–1369 December 1997 9393679 10.1016/s0006-2952(97)00405-x https://repositorio.uchile.cl/handle/2250/157599 Effects DOM produces the head-twitch response in rodents, a behavioral proxy of psychedelic-like effects. Halberstadt AL, Chatha M, Klein AK, Wallach J, Brandt SD Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species Neuropharmacology 167 107933 May 2020 31917152 9191653 10.1016/j.neuropharm.2019.107933 http://usdbiology.com/cliff/Courses/Advanced%20Seminars%20in%20Neuroendocrinology/Serotonergic%20Psychedelics%2020/Halberstadt%2020%20Neuropharm%20potency%20of%20hallucinogens%20%20head-twitch.pdf 2025-03-26 2025-03-27 https://web.archive.org/web/20250326111621/http://usdbiology.com/cliff/Courses/Advanced%20Seminars%20in%20Neuroendocrinology/Serotonergic%20Psychedelics%2020/Halberstadt%2020%20Neuropharm%20potency%20of%20hallucinogens%20%20head-twitch.pdf dead The head-twitch response produced by DOM is robust. It also substitutes for LSD in rodent drug discrimination tests. 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. Other effects of DOM in rodents include hyperlocomotion at lower doses, hypolocomotion at higher doses, and hypothermia at high doses. In contrast to amphetamines like (−)-cathinone but similarly to mescaline, DOM has shown no stimulant-like or reinforcing effects in rhesus monkeys. Fantegrossi WE, Murnane KS, Reissig CJ The behavioral pharmacology of hallucinogens Biochemical Pharmacology 75 1 17–33 January 2008 17977517 2247373 10.1016/j.bcp.2007.07.018 Despite the reasonably constant recreational use of hallucinogens since at least the early 1970s [44], the reinforcing effects of hallucinogens have not been widely investigated in laboratory animals. Indeed, one of the earliest studies on the reinforcing effects of drugs using the intravenous self-administration procedure in rhesus monkeys found that no animal initiated self-injection of mescaline either spontaneously or after one month of programmed administration [45]. Likewise, the phenethylamine hallucinogen 2,5-dimethoxy-4-methylamphetamine (DOM) was not effective in maintaining self-administration in rhesus monkeys [46]. Nevertheless, the hallucinogen-like phenethylamine 3,4-methylenedioxymethamphetamine (MDMA) has been shown to act as a reinforcer in intravenous self-administration paradigms in baboons [47], rhesus monkeys [48 – 50], rats [51] and mice [52]. Canal CE, Murnane KS The serotonin 5-HT2C receptor and the non-addictive nature of classic hallucinogens Journal of Psychopharmacology Oxford, England 31 1 127–143 January 2017 27903793 10.1177/0269881116677104 5445387 One of the earliest studies on the reinforcing effects of drugs using the intravenous self-administration procedure in rhesus monkeys found that no animal initiated self-injection of mescaline either spontaneously or after one month of programmed administration, [...] (Deneau et al., 1969). The lack of mescaline self-administration stood in contrast to positive findings of self-administration of morphine, codeine, cocaine, amphetamine, pentobarbital, ethanol, and caffeine. A subsequent study with rhesus monkeys using 2,5-dimethoxy-4-methylamphetamine (DOM; Yanagita, 1986) provided similar results as the mescaline study. These findings have withstood the test of time, as the primary literature is virtually devoid of any accounts of self-administration of [classical hallucinogens (CH)], suggesting that there are very limited conditions under which laboratory animals voluntarily consume CH. Yanagita T Intravenous self-administration of (−)-cathinone and 2-amino-1-(2,5-dimethoxy-4-methyl)phenylpropane in rhesus monkeys Drug and Alcohol Dependence 17 2–3 135–141 June 1986 3743404 10.1016/0376-8716(86)90004-9 Maguire DR Evaluation of potential punishing effects of 2,5-dimethoxy-4-methylamphetamine (DOM) in rhesus monkeys responding under a choice procedure Behavioural Pharmacology 35 7 378–385 October 2024 39052019 10.1097/FBP.0000000000000787 11398979 Conversely however, DOC has shown reinforcing effects, including conditioned place preference (CPP) and self-administration, in rodents similarly to methamphetamine. Cha HJ, Jeon SY, Jang HJ, Shin J, Kim YH, Suh SK Rewarding and reinforcing effects of 4-chloro-2,5-dimethoxyamphetamine and AH-7921 in rodents Neuroscience Letters 676 66–70 May 2018 29626650 10.1016/j.neulet.2018.04.009 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. Gil-Martins E, Barbosa DJ, Borges F, Remião F, Silva R Toxicodynamic insights of 2C and NBOMe drugs - Is there abuse potential? Toxicology Reports 14 101890 June 2025 39867514 10.1016/j.toxrep.2025.101890 11762925 2025ToxR...1401890G Kim YJ, Ma SX, Hur KH, Lee Y, Ko YH, Lee BR, Kim SK, Sung SJ, Kim KM, Kim HC, Lee SY, Jang CG New designer phenethylamines 2C-C and 2C-P have abuse potential and induce neurotoxicity in rodents Archives of Toxicology 95 4 1413–1429 April 2021 33515270 10.1007/s00204-021-02980-x 2021ArTox..95.1413K Custodio RJ, Sayson LV, Botanas CJ, Abiero A, You KY, Kim M, Lee HJ, Yoo SY, Lee KW, Lee YS, Seo JW, Ryu IS, Kim HJ, Cheong JH 25B-NBOMe, a novel N-2-methoxybenzyl-phenethylamine (NBOMe) derivative, may induce rewarding and reinforcing effects via a dopaminergic mechanism: Evidence of abuse potential Addiction Biology 25 6 e12850 November 2020 31749223 10.1111/adb.12850 free Seo JY, Hur KH, Ko YH, Kim K, Lee BR, Kim YJ, Kim SK, Kim SE, Lee YS, Kim HC, Lee SY, Jang CG A novel designer drug, 25N-NBOMe, exhibits abuse potential via the dopaminergic system in rodents Brain Research Bulletin 152 19–26 October 2019 31279579 10.1016/j.brainresbull.2019.07.002 Jo C, Joo H, Youn DH, Kim JM, Hong YK, Lim NY, Kim KS, Park SJ, Choi SO Rewarding and Reinforcing Effects of 25H-NBOMe in Rodents Brain Sciences 12 11 November 2022 1490 36358416 9688077 10.3390/brainsci12111490 free Lee JG, Hur KH, Hwang SB, Lee S, Lee SY, Jang CG Designer Drug, 25D-NBOMe, Has Reinforcing and Rewarding Effects through Change of a Dopaminergic Neurochemical System ACS Chemical Neuroscience 14 15 2658–2666 August 2023 37463338 10.1021/acschemneuro.3c00196 Kim YJ, Kook WA, Ma SX, Lee BR, Ko YH, Kim SK, Lee Y, Lee JG, Lee S, Kim KM, Lee SY, Jang CG The novel psychoactive substance 25E-NBOMe induces reward-related behaviors via dopamine D1 receptor signaling in male rodents Archives of Pharmacal Research 47 4 360–376 April 2024 38551761 10.1007/s12272-024-01491-4 DOM has potent anti-inflammatory effects, which may have medical applications. Flanagan TW, Billac GB, Landry AN, Sebastian MN, Cormier SA, Nichols CD Structure-Activity Relationship Analysis of Psychedelics in a Rat Model of Asthma Reveals the Anti-Inflammatory Pharmacophore ACS Pharmacology & Translational Science 4 2 488–502 April 2021 33860179 8033619 10.1021/acsptsci.0c00063 Pharmacokinetics The pharmacokinetics of DOM, including in humans, have been very limitedly studied. The drug crosses the blood–brain barrier in rodents. 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. Eckler JR, Chang-Fong J, Rabin RA, Smith C, Teitler M, Glennon RA, Winter JC Behavioral characterization of 2-O-desmethyl and 5-O-desmethyl metabolites of the phenylethylamine hallucinogen DOM Pharmacology, Biochemistry, and Behavior 75 4 845–852 July 2003 12957227 10.1016/s0091-3057(03)00159-x They might contribute to the delayed onset and long duration of DOM in humans. However, these metabolites might also produce metabolism-dependent neurotoxicity via conversion into 2,5-DDM-DOM and subsequent transformation. 2,5-DDM-DOM is similar in chemical structure to 6-hydroxydopamine (6-OHDA) and has likewise been found to be a potent neurotoxin. Shulgin AT 1980 Burger A, Wolf ME Hallucinogens Burger's Medicinal Chemistry New York Wiley 4 3 1109–1137 978-0-471-01572-7 https://books.google.com/books?id=2b3wAAAAMAAJ https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6ac0c892ee380436f614d3aae0686ef617b2e0c5 219960627 The third principal metabolic route common to the hallucinogenic drugs is oxidation. Benzylic oxidation had been reported with both DOM (60.22aa) and DOET (60.22bb) (61, 62). Of greater theoretical interest is oxidative cyclization to form an indole species, reminiscent of the conversion of epinephrine to adrenochrome. Many of the hallucinogens are in fact indoles, and since the phenethylamine chain has the exact atom composition of indole itself, there has been frequent speculation that there might be some metabolic conversion from one family to the other. It has been shown (63) that one of the metabolites of DOM (2,5-dihydroxy[-4-methyl]phenylisopropylamine, 60.17), which bears a close chemical and pharmacological resemblance to the potent neurodegenerative agent 6-hydroxydopamine (60.18) (64), can undergo a facile oxidative cyclization to form a 5-hydroxyindole. The intermediate iminoquinone is potentially very reactive with nucleophilic agents found in normal body chemistry, and may be important in any explanation of biological activity. Castagnoli N Stimulants Drug Metabolism: Review of Principles and the Fate of One-Ring Psychotomimetics Springer US Boston, MA 1978 978-1-4757-0512-6 10.1007/978-1-4757-0510-2_7 http://link.springer.com/10.1007/978-1-4757-0510-2_7 3 February 2026 335–387 FIG. 9. Metabolic pathways for amine III (DOM). [...] The third general metabolic pathway for 111 is oxidative O-demethylation of the methyl phenyl ether groups. All three possible O-demethylated metabolites, compounds 118-120, have been characterized in rabbit liver homogenates (Zweig and Castagnoli, 1975, 1977). The p-hydroquinone 120 is an analog of the sympatholytic agent 6-hydroxydopamine (107) and has been shown to possess some of the neurodegenerative properties of 6-hydroxydopamine (Butcher, 1975). Similar to 6-hydroxydopamine (Blank et ai., 1972), hydroquinone 120 undergoes facile oxidation to form the quinone 129 (Fig. 10), which cyclizes to the iminoquinone 130 (Zweig and Castagnoli, 1974). In the absence of nucleophiles, 130 is relatively stable at pH 7.4. As the pH is raised, however, proton rearrangements take place, eventually leading to the indole 132 via the indolinine 131. In view of the ease with which the hydroquinone 120 undergoes oxidation at pH 7.4, it is somewhat surprising that this compound survives the one hour pH 7.4 incubation. This stabilization may be analogous to the inhibition by liver constituents of hydroxylamine auto-oxidation. It should prove of interest to determine the nature and significance of the protection of these substances from air oxidation. [...] FIG. 10. Oxidative cyclization of p-hydroquinone metabolite derived from DOM. [...] Glennon RA The 2014 Philip S. Portoghese Medicinal Chemistry Lectureship: The "Phenylalkylaminome" with a Focus on Selected Drugs of Abuse Journal of Medicinal Chemistry 60 7 2605–2628 April 2017 28244748 10.1021/acs.jmedchem.7b00085 However, there was some concern that 2-DM-DOM and 5-DM-DOM might undergo further O-demethylation in vivo to a hydroquinone. It had been shown years earlier that DOM can undergo metabolic bis-demethylation to a hydroquinone, and that the hydroquinone undergoes oxidation to a para-quinone (and/or a cyclic iminoquinone) that reacts irreversibly with various proteins.44 As a consequence, this approach was not pursued because of potential risks of neurotoxicity. [...] 44. Jacob P. 3rd; Kline, T., Castagnoli, N. Jr. Chemical and biological studies of 1-(2,5-dihydroxy-4- methylphenyl)-2-aminopropane, an analogue of 6-hydroxydopamine. J Med Chem. 1979; 22:662– 671. [PubMed: 458821] 5824997 Jacob P, Kline T, Castagnoli N Chemical and biological studies of 1-(2,5-dihydroxy-4-methylphenyl)-2-aminopropane, an analogue of 6-hydroxydopamine Journal of Medicinal Chemistry 22 6 662–671 June 1979 458821 10.1021/jm00192a011 Butcher LL Degenerative processes after punctate intracerebral administration of 6-hydroxydopamine Journal of Neural Transmission 37 3 189–203 1975 1185165 10.1007/BF01670128 Similarly, 1-(2,5-dihydroxy-4-methylphenyl)-2-aminopropane was not a more potent cytotoxin than 6-OHDA even though this new neurotoxin has a propane side chain which renders it immune to monoamine oxidase. [...] The neurotoxin 1-(2,5-dihydroxy-4-methylphenyl)-2-aminopropane-HC1 (DIMPAP) was synthesized by Dr. Nell Castagnoli, University of California Medical Center, San Francisco, CA, U.S.A. [...] Fig. 28. Chemical structure of 1-(2, 5-dihydroxy-4-methylphenyl)-2-aminopropaneHC1 (DIMPAP) [...] The extent of zone-3 damage: after intrastriatal infusion of various doses of DIMPAP is depicted in figures 29–33. No significant difference exists between the non-selective damage produced by DIMPAP and similar doses of 6-OHDA (e.g., compare Figs. 29–33 with Figs. 25–30 in Butcher et al., 1974). Furthermore, nialamide pre-treatment does not alter the destructive potency of either 6-OHDA or DIMPAP (compare Figs. 34–38 with Figs. 39–43 and Figs. 44–47). About 5 to 20% of a dose of DOM is excreted unchanged in humans. Chemistry thumb|left|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. It is structurally related to the naturally occurring phenethylamine psychedelic mescaline (3,4,5-trimethoxyphenethylamine). Hassan Z, Bosch OG, Singh D, Narayanan S, Kasinather BV, Seifritz E, Kornhuber J, Quednow BB, Müller CP Novel Psychoactive Substances-Recent Progress on Neuropharmacological Mechanisms of Action for Selected Drugs Frontiers in Psychiatry 8 152 2017 28868040 5563308 10.3389/fpsyt.2017.00152 free The next, even though less accidental, producer of NPS hallucinogens was Alexander T. Shulgin, who synthesized hundreds of novel hallucinogenic tryptamines and phenylethylamines in his home laboratory. He described the synthesis of these compounds and also their psychotomimetic effects experienced in self-experiments in detail in his books PIHKAL and TIHKAL (199, 200). He created several dimethoxy-substituted phenylethylamines, such as DOM, 2,5-dimethoxy-4-bromoamphetamine (DOB), 2,5-dimethoxy-4-iodoamphetamine (DOI), and 2,5-dimethoxy-4-ethylamphetamine (DOET), which all display strong hallucinogenic properties. These drugs usually have much longer durations of action (12–30 h) and are much more potent agonists at 5-HT2A-Rs (50- to 175-fold) compared to their related phenylethylamine derivative mescaline (duration of action: 4–8 h) (189, 199, 200). Properties The chemical properties of DOM have been described. Synthesis The chemical synthesis of DOM has been described. Analogues and derivatives DOx (psychedelics) PiHKAL#Ten classic ladies Analogues of DOM include other DOx drugs such as DOET, DOB, DOI, DOC, and TMA, among others. The α-desmethyl or phenethylamine analogue of DOM is 2C-D. Ariadne is the α-ethyl or phenylisobutylamine homologue of DOM. Cunningham MJ, Bock HA, Serrano IC, Bechand B, Vidyadhara DJ, Bonniwell EM, Lankri D, Duggan P, Nazarova AL, Cao AB, Calkins MM, Khirsariya P, Hwu C, Katritch V, Chandra SS, McCorvy JD, Sames D Pharmacological Mechanism of the Non-hallucinogenic 5-HT2A Agonist Ariadne and Analogs ACS Chemical Neuroscience 14 1 119–135 January 2023 36521179 10147382 10.1021/acschemneuro.2c00597 DOM analogues with the 2- and/or 5-methoxy groups replaced have been studied, for instance 2-DM-DOM (2-OH-DOM), 5-DM-DOM (5-OH-DOM), 2,5-DDM-DOM, 2-TOM (2-thio-DOM), 5-TOM (5-thio-TOM), bis-TOM (2,5-dithio-TOM), TOMSO (5-TOM-sulfoxide), and others. Braden MR May 2007 Towards a Biophysical Basis of Hallucinogen Action Purdue University https://books.google.com/books?id=sz4zbKBniZQC 28 February 2012 703618147 Chemical structures of DOM analogues and derivatives 120 180 File:2,5-dimethoxy-4-methylamphetamine.svg skin-invert-image DOM (4-methyl-2,5-DMA) File:DOB-racemic-skeletal.svg skin-invert-image DOB (4-bromo-2,5-DMA) File:DOI structure.svg skin-invert-image DOI (4-iodo-2,5-DMA) File:DOET structure.svg skin-invert-image DOET (Hecate; 4-ethyl-2,5-DMA) File:DOPR chemical structure.svg skin-invert-image DOPR (4-propyl-2,5-DMA) File:DOiP structure.svg skin-invert-image DOIP (4-isopropyl-2,5-DMA) File:DOBU.svg skin-invert-image DOBU (4-butyl-2,5-DMA) File:DOiB structure.svg skin-invert-image DOIB (4-isobutyl-2,5-DMA) File:DOsB structure.svg skin-invert-image DOSB (4-sec-butyl-2,5-DMA) File:DOtB structure.svg skin-invert-image DOTB (4-tert-butyl-2,5-DMA) File:DOAM.svg skin-invert-image DOAM (4-amyl-2,5-DMA) File:DOHx structure.svg skin-invert-image DOHx (4-hexyl-2,5-DMA) File:DOCT structure.svg skin-invert-image DOCT (4-octyl-2,5-DMA) File:DOYN structure.svg skin-invert-image DOYN (4-ethynyl-2,5-DMA) File:DOBz structure.svg skin-invert-image DOBz (4-benzyl-2,5-DMA) File:4-PhPr-2,5-DMA.svg skin-invert-image DOPP (4-PhPr-2,5-DMA) File:DOTFM.svg skin-invert-image DOTFM (4-trifluoromethyl-2,5-DMA) File:DOAc structure.svg skin-invert-image DOAc (4-acetyl-2,5-DMA) File:DOCN structure.svg skin-invert-image DOCN (4-cyano-2,5-DMA) File:2C-D 2DACS.svg skin-invert-image 2C-D (α-desmethyl-DOM) File:Ariadne.svg skin-invert-image Ariadne 95% (4C-D, BL-3912, Dimoxamine) File:Charmian structure.svg skin-invert-image Charmian (α-methyl-DOM) File:Β-Methyl-DOM structure.svg skin-invert-image β-Methyl-DOM (Daphne/Elvira) File:Ganesha.svg skin-invert-image Ganesha (G, G-0; 3-methyl-DOM) File:Juno structure.svg skin-invert-image Juno (6-methyl-DOM) File:DOTMA structure.svg skin-invert-image DOTMA (3,6-dimethyl-DOM) File:Florence structure.svg skin-invert-image Florence (DOM-2EtO) File:Iris structure.svg skin-invert-image Iris (DOM-5EtO) File:3,4-trimethylene-2,5-dimethoxyamphetamine.svg skin-invert-image G-3 (3,4-trimethylene-2,5-DMA) File:3,4-Tetramethylene-2,5-dimethoxyamphetamine.svg skin-invert-image G-4 (3,4-tetramethylene-2,5-DMA) File:3,4-Norbornyl-2,5-dimethoxyamphetamine.svg skin-invert-image G-5 (3,4-norbornyl-2,5-DMA) File:1,4-Dimethoxynaphthyl-2-isopropylamine.svg skin-invert-image G-N File:Beatrice.svg skin-invert-image Beatrice (N-methyl-DOM) File:N-Hydroxy-DOM.svg skin-invert-image N-Hydroxy-DOM (DOM-OH) File:DOM-NBOMe.svg skin-invert-image DOM-NBOMe File:25D-NBOMe2DACS.svg skin-invert-image 25D-NBOMe File:DOM-NDEPA.svg skin-invert-image DOM-NDEPA File:25D-NM-NDEAOP chemical structure.svg skin-invert-image 25D-NM-NDEAOP 95% (25D-NM-NDEPA) File:DMCPA structure.svg skin-invert-image DMCPA File:DOM-CR.svg skin-invert-image DOM-CR (DOM-THIQ) File:DOM-AI.svg skin-invert-image DOM-AI File:DOM-AT structure.svg skin-invert-image DOM-AT File:TFMBOX.svg skin-invert-image TFMBOX File:UCD0120-2C-D (DEMPDHPCA-2C-D).svg skin-invert-image DEMPDHPCA-2C-D File:Trimethoxyamphetamine.svg skin-invert-image TMA (3,4,5-TMA) File:Mescaline Structural Formulae bondline.svg skin-invert-image Mescaline (3,4,5-TMPEA) File:4-Desoxymescaline.svg skin-invert-image Desoxy (4-desoxymescaline) File:Psi-DOM chemical structure.svg skin-invert-image ψ-DOM (psi-DOM) File:2-DM-DOM.svg skin-invert-image 2-DM-DOM (2-OH-DOM) File:5-DM-DOM.svg skin-invert-image 5-DM-DOM (5-OH-DOM) File:2,5-DDM-DOM.svg skin-invert-image 2,5-DDM-DOM (2,5-diOH-DOM) File:2-TOM.svg skin-invert-image 2-TOM (2-thio-DOM) File:5-TOM.svg skin-invert-image 5-TOM (5-thio-DOM) File:Bis-TOM structure.svg skin-invert-image Bis-TOM (2,5-dithio-DOM) File:TOMSO structure.svg skin-invert-image TOMSO (5-TOM-sulfoxide) History DOM was first synthesized and tested in 1963 by Alexander Shulgin, who was investigating the effect of 4-position substitutions on psychedelic amphetamines. His 15-year-old son Theodore "Ted" Shulgin assisted in the synthesis of DOM by performing the first step of the synthesis at Dow Chemical Company on June 22, 1963 during a brief period when he was interested in chemistry. Later, Alexander Shulgin completed the synthesis on November 30, 1963. He initially discovered the effects of DOM on January 4, 1964, when he ingested a 1mg dose orally. The hallucinogenic effects of DOM were discovered on February 3, 1964 by Shulgin's colleague Thornton W. Sargent when he ingested 2.3mg. The first clearly psychedelic experience occurred with a dose of 4.1mg on November 6, 1964. Shulgin hoped that Dow Chemical Company would develop DOM for medical purposes. In mid-1967, tablets containing 20mg and later 10mg of DOM 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. This short-lived appearance of DOM on the black market proved disastrous for several reasons. First, the tablets contained an excessively high dose of the chemical. This, combined with DOM's slow onset (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. 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. Many people with DOM intoxication were treated by David E. Smith and colleagues at the Haight Ashbury Free Clinic as well as at San Francisco General Hospital. Meyers FH, Rose AJ, Smith DE Incidents Involving the Haight-Ashbury Population and Some Uncommonly Used Drugs Journal of Psychedelic Drugs 1 2 139–146 1968 10.1080/02791072.1968.10524531 0022-393X Smith DE The Psychotomimetic Amphetamines with Special Reference to DOM (STP) Toxicity Journal of Psychedelic Drugs 2 2 37–41 1969 10.1080/02791072.1969.10524413 0022-393X Society and culture Names The name DOM is an acronym of the code name "des-oxy-methyl" coined by the drug's inventor Alexander Shulgin. The drug was also initially known by the code name K-61,082 and is widely known by its nickname STP. The STP name has been said to stand for various acronyms, including Serenity, Tranquility, and Peace, Super Terrific Psychedelic, Stop The Police, and Too Stupid to Puke, among others. Popular culture DOM (STP) was featured in the 1968 psychedelic film Psych-Out. Markert J 23 May 2013 Hooked in Film: Substance Abuse on the Big Screen Bloomsbury Publishing USA 224– 979-8-216-22555-3 https://books.google.com/books?id=pziAEQAAQBAJ&pg=PA224 12 February 2026 Psych-Out (1968) is thematically similar to The Trip, but with a more evolved storyline. Its primary "educational” value was to warn the viewer that while LSD is fine, one should at all costs avoid STP: "Don't get near that stuff. [You] don't know what's in it. They say it's LSD, cocaine, and methadrine." Another character chimes in: “It's like driving a Ferrari with the gas pedal strapped to the floor. It's nothing to play with." To drive home the admonition, Strasberg's character shortly thereafter is given some STP and freaks out: she sees fireballs in her mind's eye and attempts to flee them by running across a San Francisco bridge while cars careen around her. This was a critical warning to audiences when the film was released. In 1967, tablets containing DOM (2.5-Dimethoxy-4-methylamphetamine) were widely distributed in the Haight-Ashbury district of San Francisco under the name STP, which stood for Serenity-Tranquility-Peace. The short-lived appearance of DOM proved disastrous for several reasons. [...] Legal status Australia DOM is schedule 9 under the Australia Poisons standard.Poison Standard https://www.comlaw.gov.au/Details/F2015L01534/Html/Text#_Toc420496379 https://web.archive.org/web/20151222222450/https://www.comlaw.gov.au/Details/F2015L01534/Html/Text 2015-12-22 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." Canada DOM is a Schedule I controlled substance in Canada.Controlled Drugs and Substances Act Department of Justice Canada https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html 19 January 2026 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. Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) January 2026 U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division United States https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf This means it is illegal to manufacture, buy, possess, or distribute (make, trade, own or give) without a DEA license. Research DOM, along with DOET, was of interest in the potential treatment of psychiatric disorders such as depression in the 1960s. Subsequently, the related compound Ariadne (4C-D; BL-3912; Dimoxamine) was investigated in the 1970s, but was not marketed either. See also DOx (psychedelics) Stimulant § Serotonin 5-HT2A receptor agonists Motivation-enhancing drug § Serotonin 5-HT2A receptor agonists ASR-2001 (2CB-5PrO) References External links DOM - Isomer Design DOM - PsychonautWiki DOM - Erowid DOM - PiHKAL - Erowid DOM - PiHKAL - Isomer Design DOM - The Shulgin Index The Big & Dandy DOM Thread - Bluelight What is DOM? The Serenity Psychedelic - Tripsitter Category:5-HT2A agonists Category:5-HT2B agonists Category:5-HT2C agonists Category:Alexander Shulgin Category:Antidepressants Category:Anti-inflammatory agents Category:Designer drugs Category:DOx (psychedelics) Category:Methyl compounds Category:PiHKAL Category:Psychedelic phenethylamines Category:Stimulants Category:TAAR1 agonists