2-DM-DOM

vanc 6 2-DM-DOM.svg skin-invert-image 200px Serotonin receptor modulator; Serotonin 5-HT2 receptor modulator; Serotonergic psychedelic; Hallucinogen None 52336-49-9 12611596 23242115 174380 2-O-Desmethyl-DOM; 2-DES-Me-DOM; 2-OH-DOM; 2-Hydroxy-DOM; 2-HMMP; 2-Hydroxy-5-methoxy-4-methylamphetamine 2-(2-aminopropyl)-4-methoxy-5-methylphenol 11 17 1 2 CC1=CC(=C(C=C1OC)CC(C)N)O 1S/C11H17NO2/c1-7-4-10(13)9(5-8(2)12)6-11(7)14-3/h4,6,8,13H,5,12H2,1-3H3 NIRJHEFWNFTPAN-UHFFFAOYSA-N 2-DM-DOM, also known as 2-O-desmethyl-DOM, 2-OH-DOM, or 2-hydroxy-5-methoxy-4-methylamphetamine (2-HMMP), is a psychedelic drug of the phenethylamine and amphetamine families related to the DOx psychedelic DOM (2,5-dimethoxy-4-methylamphetamine; STP). Trachsel D, Lehmann D, Enzensperger C Phenethylamine: von der Struktur zur Funktion Solothurn 813–814 2013 Phenethylamines: From Structure to Function 1 Nachtschatten-Verlag Nachtschatten-Science 978-3-03788-700-4 858805226 https://books.google.com/books?id=-Us1kgEACAAJ de https://web.archive.org/web/20251113135159/https://books.google.com/books?id=-Us1kgEACAAJ 13 November 2025 1 February 2026 live Glennon RA, Young R Role of Stereochemistry in Drug Discrimination Studies Drug Discrimination 129–161 5 August 2011 10.1002/9781118023150.ch4 Wiley 978-0-470-43352-2 https://onlinelibrary.wiley.com/doi/10.1002/9781118023150.ch4 1 February 2026 Examination of 2-HMMP, the 2-desmethyl metabolite of DOM (also called 2-DM DOM), and 5-HMMP, the 5-desmethyl metabolite (also called 5-DM DOM) (Figure 4-5), a positional isomer of 2-HMMP, showed that DOM-stimulus generalization occurred to 2-HMMP (ED50 = 1.71 mg/kg), but that administration of low doses of 5-HMMP produced only saline-like responding followed, at a higher dose, by disruption of the animals’ behavior [7]. With a different training drug [i.e., (+)LSD], pre-session injection interval, and strain of rat (Fischer 344 rather than Sprague-Dawley), the (+)LSD stimulus generalized to both metabolites with the 5-desmethyl metabolite 5-HMMP being approximately twice as potent as its positional isomer [8]. [...] Figure 4-5. Chemical structures of the hallucinogen DOM, [...] its 2-desmethyl analog 2-HMMP (also known as 2-DM-DOM) and its positional isomer 5-HMMP (also known as 5-DM-DOM). 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 Eckler JR Stimulus Control by Hallucinogens: SSRI Interactions 20 December 2002 PhD State University of New York at Buffalo https://isomerdesign.com/bitnest/external/ProQuest/3076476 It has been identified as an active metabolite of DOM in animals. Castagnoli N Drug Metabolism: Review of Principles and the Fate of One-Ring Psychotomimetics Stimulants 335–387 1978 10.1007/978-1-4757-0510-2_7 Springer US Boston, MA 978-1-4757-0512-6 http://link.springer.com/10.1007/978-1-4757-0510-2_7 1 February 2026 https://isomerdesign.com/bitnest/external/10.1007/978-1-4757-0510-2_7 The metabolism of [DOM (111)] has been examined in some detail. [...] FIG. 9. Metabolic pathways for amine 111 (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 drug is one of two possible O-demethylated analogues and metabolites of DOM, the other being 5-DM-DOM (5-O-desmethyl-DOM; 5-OH-DOM; 5-HMMP). Use and effects The properties and effects of 2-DM-DOM in humans have not been reported and are unknown. Shulgin A, Manning T, Daley P The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds Berkeley 1 2011 Transform Press 978-0-9630096-3-0 Pharmacology 2-DM-DOM shows affinity for the serotonin 5-HT2A and 5-HT2C receptors (Ki = 589nM and 770nM, respectively). Its affinity for the serotonin 5-HT2A receptor was about 5-fold lower than that of DOM. In another earlier study, its affinities (Ki) were 1,570nM for the serotonin 5-HT1 receptor and 710nM for the serotonin 5-HT2 receptor, with the latter being about 7-fold lower than that of DOM. Glennon RA, Titeler M, McKenney JD Evidence for 5-HT2 involvement in the mechanism of action of hallucinogenic agents Life Sci 35 25 2505–2511 December 1984 6513725 10.1016/0024-3205(84)90436-3 2-DM-DOM fully generalized to (–)-DOM (the more active psychedelic enantiomer of DOM) and LSD in rodent drug discrimination tests. It produced 99% (–)-DOM-appropriate responding at a dose of 3.0mg/kg and 90% LSD-appropriate responding at a dose of 6.0mg/kg. For comparison, the training dose of (–)-DOM was 0.6mg/kg. The drug's substitution was inhibited by the selective serotonin 5-HT2A receptor antagonist volinanserin (MDL-100907). An earlier study similarly found that 3.0mg/kg 2-DM-DOM fully substituted for racemic DOM at a training dose of 1.0mg/kg. The drug's ED50 median effective dose was 1.71mg/kg and it was 4-fold lower than that of DOM and 8-fold lower than that of (–)-DOM. DOM shows an unusually delayed onset of effects in animals and humans compared to other psychedelics like LSD and mescaline. https://www.erowid.org/library/books_online/pihkal/pihkal068.shtml In rats, DOM produces peak interoceptive effects after 60minutes, whereas LSD and mescaline do so after only 15minutes. This cannot be explained by delayed uptake of DOM into the brain, as maximal brain levels of (–)-DOM in rats occur after 15 to 30minutes. Based on these findings, it was theorized that DOM's delayed onset of effects might be due to formation of active metabolites such as 2-DM-DOM and 5-DM-DOM. 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 The lengthy duration may additionally involve the formation of two active metabolites, 1-(2-hydroxy-5-methoxy4-methylphenyl)propan-2-amine and 1-(5-hydroxy-2-methoxy4-methylphenyl)propan-2-amine.35,36 These have been suggested to have greater effectiveness at behavioral disruption in rats than DOM.35 Their effects would be perceived of as a second intensity peak beginning when a user would typically anticipate a drug to be wearing off. This suggestion may be supported by the metabolism of DOM reported in rats by Zweig and Castagnoli36 and Eckler35 but is presently remains unproven for humans due to scant and inadequate studies of DOM's metabolism in humans. Shulgin also voiced suspicions of DOM producing an active metabolite in humans.4 Snyder observed that only between 5% and 10%34 or 5–20%14 of an administered dose of DOM was excreted unchanged, suggesting that significant levels of metabolism may occur in humans. As a result of their free hydroxyl group and consequent greater polarity, these metabolites are expected to cross the blood–brain barrier more slowly than 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 5824997 Another strategy was to unmask one of the two methoxy groups of DOB to provide a polar phenolic group – phenolic groups being known to decrease BBB permeability. We had already examined the two des-methyl analogs of DOM: 2-des-methyl DOM (2-DM-DOM; 26) and 5-des-methyl DOM (5-DM-DOM; 27) (Figure 8).43 Both compounds displayed affinity at 5-HT2A receptors, their affinities being approximately one-fifth and one-half, respectively, that of DOM. Furthermore, both compounds substituted in R(-)DOM-trained and LSD-trained animals, suggesting agonist action, and stimulus effects were antagonized by pretreatment of the animals with the selective phenylalkylamine-based 5-HT2A receptor antagonist M100907 (MDL-100,907; volinanserin, 28).43 Stimulus generalization was demonstrated to be time-dependent, with the phenolic compounds having a longer onset of action time (decreased ability of the agents to penetrate the BBB?). Both of these agents were potential candidates for further investigation. 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. The hypothesis was tested, but it could not be unequivocally accepted nor rejected. Both metabolites were said to be less potent than DOM itself. In any case, the metabolites showed a delayed time to peak interoceptive effects similarly to DOM in rats. There have been concerns that 2-DM-DOM might be neurotoxic. This is because DOM has been found to undergo bis-demethylation into 2,5-DDM-DOM followed by subsequent oxidation to a reactive alkylating para-quinone and/or cyclic iminoquinone. 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 The properties of the hydroquinone DOM metabolite have been said to parallel those of the monoaminergic neurotoxin 6-hydroxydopamine. Chemistry The predicted log P of 2-DM-DOM is 1.92-(2-Aminopropyl)-4-methoxy-5-methylphenol PubChem https://pubchem.ncbi.nlm.nih.gov/compound/12611596 1 February 2026 and of DOM is 2.2.2,5-Dimethoxy-4-Methylamphetamine PubChem https://pubchem.ncbi.nlm.nih.gov/compound/85875 1 February 2026 History 2-DM-DOM was first described in the scientific literature as a DOM metabolite the mid-1970s. Zwieg JS, Castagnoli N Metabolic O-demethylation of the psychotomimetic amine 1-(2, 5-dimetroxy-4-methylphenyl)-2-aminopropane Psychopharmacology Communications 1 4 359–371 1975 1224005 Zweig JS, Castagnoli N In vitro O-demethylation of the psychotomimetic amine, 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane Journal of Medicinal Chemistry 20 3 414–421 March 1977 845874 10.1021/jm00213a020 Subsequently, its pharmacology was described by Richard Glennon and colleagues in the early-to-mid 1980s Glennon RA, Young R, Rosecrans JA Discriminative stimulus properties of DOM and several molecular modifications Pharmacology, Biochemistry, and Behavior 16 4 553–556 April 1982 7071088 10.1016/0091-3057(82)90413-0 and in the early 2000s. See also DOx (psychedelics) 2,5-DDM-DOM 2-OH-2C-B 5-DM-25B-NBOMe 3-O-Desmethylmescaline 4-O-Desmethylmescaline References External links 2-DM-DOM - Isomer Design Category:Hydroxyarenes Category:Methoxyphenethylamines Category:Methyl compounds Category:Psychedelic drug metabolites Category:Psychedelic phenethylamines Category:Serotonin receptor modulators Category:Substituted amphetamines