From Surf Wiki (app.surf) — the open knowledge base
2,5-Dimethoxy-4-methylamphetamine
| Field | Value | |||
|---|---|---|---|---|
| Verifiedfields | verified | |||
| Watchedfields | verified | |||
| verifiedrevid | 477211718 | |||
| drug_name | DOM | |||
| image | DOM_2D_SKELETAL_FORMULA1.png | |||
| image_class | skin-invert-image | |||
| width | 250px | |||
| image2 | DOM_3D_ball_and_stick.png | |||
| image_class2 | bg-transparent | |||
| width2 | 200px | |||
| routes_of_administration | Oral | |||
| class | Serotonin [5-HT2 receptor](5-ht2-receptor) agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen; Stimulant; Antidepressant; Psychic energizer | |||
| ATC_prefix | None | |||
| legal_AU | S9 | |||
| legal_BR | F2 | |||
| legal_BR_comment | ||||
| legal_CA | Schedule I | |||
| legal_UK | Class A | |||
| legal_US | Schedule I | |||
| metabolism | Demethylation | |||
| metabolites | • 2-DM-DOM | |||
| • 5-DM-DOM | ||||
| onset | 0.5–1.5 hours | |||
| Peak: 2–6 hours | ||||
| duration_of_action | Low doses: 5–8 hours | |||
| Moderate doses: 8–24 hours | ||||
| High doses: possibly up to 3–4days | ||||
| excretion | 5–20% unchanged | |||
| CAS_number | 15588-95-1 | |||
| CAS_number_Ref | ||||
| CAS_supplemental | ||||
| 43061-13-8 ((*R*)-DOM) | ||||
| 43061-14-9 ((*S*)-DOM) | ||||
| PubChem | 11735949 | |||
| ChemSpiderID_Ref | ||||
| ChemSpiderID | 9910656 | |||
| UNII_Ref | ||||
| UNII | UKI9MLD5OI | |||
| KEGG | C22736 | |||
| ChEMBL_Ref | ||||
| ChEMBL | 317634 | |||
| synonyms | 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 | |||
| IUPAC_name | 1-(2,5-dimethoxy-4-methylphenyl)propan-2-amine | |||
| C | 12 | H = 19 | N = 1 | O = 2 |
| SMILES | O(c1cc(c(OC)cc1C[C@H](N)C)C)C | |||
| StdInChI | 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 | |||
| StdInChIKey_Ref | ||||
| StdInChIKey | NTJQREUGJKIARY-SECBINFHSA-N | |||
| melting_point | 61 |
| Drugs.com =
• 5-DM-DOM Peak: 2–6 hours | elimination_half-life = Moderate doses: 8–24 hours High doses: possibly up to 3–4days
43061-13-8 ((R)-DOM) 43061-14-9 ((S)-DOM)
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. 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.
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. 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. 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 overwhlemed or like one is losing control, impairment, pupil dilation, jaw tightness, muscle tremors, feeling sick, no 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. 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
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. 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
| Target | Affinity (Ki, nM) |
|---|---|
| [5-HT1A](5-ht1a-receptor) | 3,656–14,200 (Ki) |
| 12,800–13,900 () | |
| 54–74% () | |
| [5-HT1B](5-ht1b-receptor) | 10,000 |
| [5-HT1D](5-ht1d-receptor) | 209 |
| [5-HT1E](5-ht1e-receptor) | 3,542 |
| [5-HT1F](5-ht1f-receptor) | ND |
| [5-HT2A](5-ht2a-receptor) | 2.1–507 (Ki) |
| 1.1–40 (EC50) | |
| 44–132% (Emax) | |
| [5-HT2B](5-ht2b-receptor) | 12–149 (Ki) |
| 128–688 (EC50) | |
| 85–91% (Emax) | |
| [5-HT2C](5-ht2c-receptor) | 19–3,980 (Ki) |
| 0.23–423 (EC50) | |
| 81–119% (Emax) | |
| [5-HT3](5-ht3-receptor) | 10,000 |
| [5-HT4](5-ht4-receptor) | ND |
| [5-HT5A](5-ht5a-receptor) | 10,000 |
| [5-HT6](5-ht6-receptor) | 8,155 |
| [5-HT7](5-ht7-receptor) | 1,591 |
| α1A | 3,219–7,393 |
| α1B | 10,000 |
| α1D | ND |
| 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 |
| TAAR1 | 30,000 (EC50) |
| I1 | 10,000 |
| σ1, σ2 | 10,000 |
| 100,000 (Ki) | |
| 100,000 () | |
| 100,000 (EC50) | |
| 100,000 (Ki) | |
| 70,000 (IC50) | |
| 100,000 (EC50) | |
| 100,000 (Ki) | |
| 64,000 (IC50) | |
| 42,000 (EC50) | |
| 24,000 (IC50) (rat) | |
| 100,000 (IC50) (rat) | |
| **Notes:** The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. **Refs:** | |
DOM acts as a selective serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptor full agonist. 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.
The drug is inactive as a human trace amine-associated receptor 1 (TAAR1) agonist but is an agonist of the rhesus monkey TAAR1. DOM is inactive as a monoamine reuptake inhibitor and releasing agent. 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).
Effects
DOM produces the head-twitch response in rodents, a behavioral proxy of psychedelic-like effects. 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. Conversely however, DOC has shown reinforcing effects, including conditioned place preference (CPP) and self-administration, in rodents similarly to methamphetamine. 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.
DOM has potent anti-inflammatory effects, which may have medical applications.
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. They might contribute to the delayed onset and long duration of DOM in humans. However, these metabolites might also produce metabolism-dependent neurotoxicity. About 5 to 20% of a dose of DOM is excreted unchanged in humans.
Chemistry
_-_53627337701.jpg)
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).
Properties
The chemical properties of DOM have been described.
Synthesis
The chemical synthesis of DOM has been described.
Analogues and derivatives
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.
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-HT2A 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-HT2A binding.
| File:DOM 2D SKELETAL FORMULA1.png | class1=skin-invert-image | DOM (4-methyl-2,5-DMA) | File:DOB-racemic-skeletal.svg | class2=skin-invert-image | DOB (4-bromo-2,5-DMA) | File:DOI-racemic-skeletal.svg | class3=skin-invert-image | DOI (4-iodo-2,5-DMA) | File:DOET structure.png | class4=skin-invert-image | DOET (Hecate; 4-ethyl-2,5-DMA) | File:DOPR chemical structure.svg | class5=skin-invert-image | DOPR (4-propyl-2,5-DMA) | File:DOiPR structure.png | class6=skin-invert-image | DOIP (4-isopropyl-2,5-DMA) | File:DOBU.svg | class7=skin-invert-image | DOBU (4-butyl-2,5-DMA) | File:DOIB structure.png | class8=skin-invert-image | DOIB (4-isobutyl-2,5-DMA) | File:DOSB structure.png | class9=skin-invert-image | DOSB (4-sec-butyl-2,5-DMA) | File:DOTB structure.png | class10=skin-invert-image | DOTB (4-tert-butyl-2,5-DMA) | File:DOAM.svg | class11=skin-invert-image | DOAM (4-amyl-2,5-DMA) | File:DOHX structure.png | class12=skin-invert-image | DOHx (4-hexyl-2,5-DMA) | File:DOCT structure.png | class13=skin-invert-image | DOCT (4-octyl-2,5-DMA) | File:DOYN structure.png | class14=skin-invert-image | DOYN (4-ethynyl-2,5-DMA) | File:DOBZ structure.png | class15=skin-invert-image | DOBz (4-benzyl-2,5-DMA) | File:4-PhPr-2,5-DMA.svg | class16=skin-invert-image | DOPP (4-PhPr-2,5-DMA) | File:DOTFM.svg | class17=skin-invert-image | DOTFM (4-trifluoromethyl-2,5-DMA) | File:DOAC structure.png | class18=skin-invert-image | DOAc (4-acetyl-2,5-DMA) | File:DOCN structure.png | class19=skin-invert-image | DOCN (4-cyano-2,5-DMA) | File:2C-D 2DACS.svg | class20=skin-invert-image | 2C-D (α-desmethyl-DOM) | File:Ariadne.svg | class21=skin-invert-image | Ariadne | File:Charmian.svg | class22=skin-invert-image | Charmian (α-methyl-DOM) | File:Β-Methyl-DOM.svg | class23=skin-invert-image | β-Methyl-DOM (Daphne/Elvira) | File:Ganesha.svg | class24=skin-invert-image | Ganesha (G, G-0; 3-methyl-DOM) | File:6-methyl-DOM.svg | class25=skin-invert-image | Juno (6-methyl-DOM) | File:DOTMA.svg | class26=skin-invert-image | DOTMA (3,6-dimethyl-DOM) | File:Florence drug.svg | class27=skin-invert-image | Florence (DOM-2EtO) | File:IRIS (psychedelic).svg | class28=skin-invert-image | Iris (DOM-5EtO) | File:3,4-trimethylene-2,5-dimethoxyamphetamine.svg | class29=skin-invert-image | G-3 (3,4-trimethylene-2,5-DMA) | File:3,4-Tetramethylene-2,5-dimethoxyamphetamine.svg | class30=skin-invert-image | G-4 (3,4-tetramethylene-2,5-DMA) | File:3,4-Norbornyl-2,5-dimethoxyamphetamine.svg | class31=skin-invert-image | G-5 (3,4-norbornyl-2,5-DMA) | File:1,4-Dimethoxynaphthyl-2-isopropylamine.svg | class32=skin-invert-image | G-N | File:Beatrice.svg | class33=skin-invert-image | Beatrice (N-methyl-DOM) | File:N-Hydroxy-DOM.svg | class34=skin-invert-image | N-Hydroxy-DOM (DOM-OH) | File:DOM-NBOMe.svg | class35=skin-invert-image | DOM-NBOMe | File:25D-NBOMe2DACS.svg | class36=skin-invert-image | 25D-NBOMe | File:DOM-NDEPA structure.svg | class37=skin-invert-image | DOM-NDEPA | File:25D-NM-NDEAOP chemical structure.svg | class38=skin-invert-image | 25D-NM-NDEAOP | File:DMCPA.svg | class39=skin-invert-image | DMCPA | File:DOM-CR.svg | class40=skin-invert-image | DOM-CR (DOM-THIQ) | File:DOM-AI.svg | class41=skin-invert-image | DOM-AI | File:DOM-AT.svg | class42=skin-invert-image | DOM-AT | File:TFMBOX.svg | class43=skin-invert-image | TFMBOX | File:DEMPDHPCA-2C-D.svg | class44=skin-invert-image | DEMPDHPCA-2C-D | File:Trimethoxyamphetamine.svg | class45=skin-invert-image | TMA (3,4,5-TMA) | File:Mescaline Structural Formulae bondline.svg | class46=skin-invert-image | Mescaline (3,4,5-TMPEA) | File:DESOXY.png | class47=skin-invert-image | Desoxy (4-desoxymescaline) | File:Psi-DOM chemical structure.svg | class48=skin-invert-image | ψ-DOM (psi-DOM) | File:2-TOM.png | class49=skin-invert-image | 2-TOM (2-thio-DOM) | File:5-TOM.png | class50=skin-invert-image | 5-TOM (5-thio-DOM) | File:Bis-TOM.png | class51=skin-invert-image | Bis-TOM (2,5-dithio-DOM) | File:TOMSO.svg | class52=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.
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.
Legal status
Australia
DOM is schedule 9 under the Australia Poisons standard. 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.
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.
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.
References
References
- Anvisa. (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial". [[Diário Oficial da União]].
- (December 2024). "The origin of 2,5-dimethoxy-4-methylamphetamine (DOM, STP)". Drug Test Anal.
- (2011). "[[The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds]]". Transform Press.
- (1991). "PiHKAL: A Chemical Love Story". Transform Press.
- (1 October 2023). "Learning about STP: A Forgotten Psychedelic from the Summer of Love". History of Pharmacy and Pharmaceuticals.
- (9 March 2012). "Medical Toxicology of Drug Abuse: Synthesized Chemicals and Psychoactive Plants". Wiley.
- (1978). "Stimulants". Springer US.
- Shulgin, Alexander T.. (1977). "Profiles of Psychedelic Drugs: 5. STP". Journal of Psychedelic Drugs.
- (August 2003). "Green List: List of Psychotropic Substances Under International Control". [[International Narcotics Control Board]].
- (2003). "Hallucinogens: A Forensic Drug Handbook". Elsevier Science.
- (1994). "Hallucinogens: An Update". National Institute on Drug Abuse.
- (1982). "Indolealkylamine and phenalkylamine hallucinogens: a brief overview". Neurosci Biobehav Rev.
- (November 1967). "2,5-dimethoxy-4-methyl-amphetamine (STP): a new hallucinogenic drug". Science.
- (September 1968). "DOM (STP), a new hallucinogenic drug, and DOET: effects in normal subjects". Am J Psychiatry.
- (1971). "DOM (STP), a new hallucinogenic drug: specific perceptual changes". J Clin Pharmacol New Drugs.
- (1969). "An hallucinogenic amphetamine analog (DOM) in man". Psychopharmacologia.
- (April 1974). "Assessment of tolerance to the hallucinogenic effects of DOM". Psychopharmacologia.
- "PDSP Database".
- Liu, Tiqing. "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".
- (November 2025). "The 4-alkyl chain length of 2,5-dimethoxyamphetamines differentially affects in vitro serotonin receptor actions versus in vivo psychedelic-like effects". Mol Psychiatry.
- (December 2020). "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.
- (1997). "Pharmacochemistry Library". Elsevier.
- (June 2002). "Differences in potency and efficacy of a series of phenylisopropylamine/phenylethylamine pairs at 5-HT(2A) and 5-HT(2C) receptors". Br J Pharmacol.
- (2022). "Monoamine Receptor and Transporter Interaction Profiles of 4-Alkyl-Substituted 2,5-Dimethoxyamphetamines". The FASEB Journal.
- (February 2010). "Psychedelics and the human receptorome". PLOS ONE.
- (March 2014). "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).
- Sanders-Bush, E. (September 1988). "Lysergic acid diethylamide and 2,5-dimethoxy-4-methylamphetamine are partial agonists at serotonin receptors linked to phosphoinositide hydrolysis". [[Journal of Pharmacology and Experimental Therapeutics.
- (December 2011). "Trace amine-associated receptor 1 is a stereoselective binding site for compounds in the amphetamine class". Bioorg Med Chem.
- (December 2018). "Neurochemical pharmacology of psychoactive substituted N-benzylphenethylamines: High potency agonists at 5-HT2A receptors". Biochem Pharmacol.
- (2019). "Amphetamine Derivatives as Monoamine Oxidase Inhibitors". Front Pharmacol.
- (December 1997). "Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives: structure-activity relationships". Biochem Pharmacol.
- (May 2020). "Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species". Neuropharmacology.
- (January 2008). "The behavioral pharmacology of hallucinogens". Biochem Pharmacol.
- (January 2017). "The serotonin 5-HT2C receptor and the non-addictive nature of classic hallucinogens". J Psychopharmacol.
- (June 1986). "Intravenous self-administration of (−)-cathinone and 2-amino-1-(2,5-dimethoxy-4-methyl)phenylpropane in rhesus monkeys". Drug Alcohol Depend.
- (October 2024). "Evaluation of potential punishing effects of 2,5-dimethoxy-4-methylamphetamine (DOM) in rhesus monkeys responding under a choice procedure". Behav Pharmacol.
- (May 2018). "Rewarding and reinforcing effects of 4-chloro-2,5-dimethoxyamphetamine and AH-7921 in rodents". Neurosci Lett.
- (June 2025). "Toxicodynamic insights of 2C and NBOMe drugs - Is there abuse potential?". Toxicol Rep.
- (April 2021). "New designer phenethylamines 2C-C and 2C-P have abuse potential and induce neurotoxicity in rodents". Arch Toxicol.
- (November 2020). "25B-NBOMe, a novel N-2-methoxybenzyl-phenethylamine (NBOMe) derivative, may induce rewarding and reinforcing effects via a dopaminergic mechanism: Evidence of abuse potential". Addict Biol.
- (October 2019). "A novel designer drug, 25N-NBOMe, exhibits abuse potential via the dopaminergic system in rodents". Brain Res Bull.
- (November 2022). "Rewarding and Reinforcing Effects of 25H-NBOMe in Rodents". Brain Sci.
- (August 2023). "Designer Drug, 25D-NBOMe, Has Reinforcing and Rewarding Effects through Change of a Dopaminergic Neurochemical System". ACS Chem Neurosci.
- (April 2024). "The novel psychoactive substance 25E-NBOMe induces reward-related behaviors via dopamine D1 receptor signaling in male rodents". Arch Pharm Res.
- (April 2021). "Structure-Activity Relationship Analysis of Psychedelics in a Rat Model of Asthma Reveals the Anti-Inflammatory Pharmacophore". ACS Pharmacol Transl Sci.
- (April 2017). "The 2014 Philip S. Portoghese Medicinal Chemistry Lectureship: The "Phenylalkylaminome" with a Focus on Selected Drugs of Abuse". J Med Chem.
- (July 2003). "Behavioral characterization of 2-O-desmethyl and 5-O-desmethyl metabolites of the phenylethylamine hallucinogen DOM". Pharmacol Biochem Behav.
- (2017). "Novel Psychoactive Substances-Recent Progress on Neuropharmacological Mechanisms of Action for Selected Drugs". Front Psychiatry.
- (January 2023). "Pharmacological Mechanism of the Non-hallucinogenic 5-HT2A Agonist Ariadne and Analogs". ACS Chemical Neuroscience.
- Braden, Michael Robert. (May 2007). "Towards a Biophysical Basis of Hallucinogen Action". Purdue University.
- Poison Standard https://www.comlaw.gov.au/Details/F2015L01534/Html/Text#_Toc420496379 {{webarchive. link. (2015-12-22)
- "Controlled Drugs and Substances Act".
- (January 2026). "Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026)". U.S. [[Department of Justice]]: [[Drug Enforcement Administration]] (DEA): Diversion Control Division.
This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.
Ask Mako anything about 2,5-Dimethoxy-4-methylamphetamine — get instant answers, deeper analysis, and related topics.
Research with MakoFree with your Surf account
Create a free account to save articles, ask Mako questions, and organize your research.
Sign up freeThis content may have been generated or modified by AI. CloudSurf Software LLC is not responsible for the accuracy, completeness, or reliability of AI-generated content. Always verify important information from primary sources.
Report