2,5-Dimethoxy-4-amylamphetamine

vanc 6 verified verified 477211551 DOAM DOAM.svg skin-invert-image 250px 2,5-Dimethoxy-4-amylamphetamine-3D-spacefill.png bg-transparent 200px Oral Serotonin 5-HT2 receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen None Unknown correct CAS 63779-90-8 12262512 correct chemspider 10440619 correct FDA N80EWL36CB correct EBI 161416 DOAM; 2,5-Dimethoxy-4-amylamphetamine; 4-Amyl-2,5-dimethoxyamphetamine; 2,5-Dimethoxy-4-pentylamphetamine; 4-Pentyl-2,5-dimethoxyamphetamine 1-(2,5-dimethoxy-4-pentylphenyl)propan-2-amine 16 27 1 2 CCCCCC1=CC(OC)=C(CC(C)N)C=C1OC correct chemspider 1S/C16H27NO2/c1-5-6-7-8-13-10-16(19-4)14(9-12(2)17)11-15(13)18-3/h10-12H,5-9,17H2,1-4H3 correct chemspider VLJORLCVOAUUKM-UHFFFAOYSA-N 2,5-Dimethoxy-4-amylamphetamine (DOAM), also known as 2,5-dimethoxy-4-pentylamphetamine, is a psychedelic drug of the phenethylamine, amphetamine, and DOx families related to DOM. 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 Mol Psychiatry November 2025 41193673 10.1038/s41380-025-03325-1 https://www.nature.com/articles/s41380-025-03325-1.pdf It is the derivative of DOM in which the methyl group at the 4 position has been replaced with an amyl (pentyl) group. The drug is taken orally. It is a serotonin receptor agonist, including of the serotonin 5-HT2A receptor. The drug produces weak and mixed psychedelic-like effects in animals. DOAM was first described in the scientific literature by Alexander Shulgin and colleagues in 1975. Subsequently, it was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). Use and effects In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists the dose of DOAM as greater than 10mg orally and its duration as unknown. DOAM was reported to produce a bare threshold and tenseness. In other publications however, DOAM has been said to produce threshold effects at 5 to 10mg orally and to be hallucinogenic at a dose of 40mg orally, with about 10-fold higher potency than mescaline. Braun U, Braun G, Jacob P, Nichols DE, Shulgin AT Mescaline analogs: substitutions at the 4-position NIDA Res Monogr 22 27–37 1978 101882 https://archives.nida.nih.gov/sites/default/files/monograph22.pdf#page=38 https://web.archive.org/web/20230805004421/https://archives.nida.nih.gov/sites/default/files/monograph22.pdf#page=38 dead August 5, 2023 TABLE II RELATIVE POSTENCIES IN MAN OF DIMETHOXYPHENYLISOPROPYLAMINE PSYCHOTOMIMETICS WITH VARIOUS SUBSTITUENTS ON THE 4-POSITION [...] Name: DOBU. Potency (total dose mg/man): 10 mg (e). Name: DOTB. Potency (total dose mg/man): >25 mg (d,f). Name: DOAM. Potency (total dose mg/man): 40 mg (e). [...] REFERENCES FOR TABLE II: [...] d. Shulgin, A.T., and Nichols, D.E. In: Stillman, R., and Willette, R. eds. Psychopharmacology of Hallucinogens. New York: Pergamon Press, 1978. e. Shulgin, A.T., and Dyer, D.C. J Med Chem, 18:1201, 1975. f. A > symbol indicates the absence of any activity at the stated dosage. Shulgin AT, Dyer DC Psychotomimetic phenylisopropylamines. 5. 4-Alkyl-2,5-dimethoxyphenylisopropylamines J Med Chem 18 12 1201–1204 December 1975 1195275 10.1021/jm00246a006 https://bitnest.netfirms.com/external/10.1021/jm00246a006 subscription In any case, it shows far lower psychedelic potency than other DOx drugs such as DOM. Iversen LL, Iversen SD, Snyder SH Shulgin Alexander T. Stimulants Psychotomimetic Drugs: Structure-Activity Relationships Springer US Boston, MA 1978 978-1-4757-0512-6 10.1007/978-1-4757-0510-2_6 243–333 https://bitnest.netfirms.com/external/10.1007/978-1-4757-0510-2_6 https://books.google.com/books?id=h0_uBwAAQBAJ&pg=PA261 3.4.11. 2,5-Dimethoxy-4-amylphenylisopropylamine: The last member of this series of homologs is 2,5-dimethoxy-4-amylphenylisopropylamine (77, DOAM). As will be seen below, it has been studied both in behavioral tests and in biochemical systems, and in both it appears to be of substantially reduced potency compared with its two immediately lower homologs. Limited human evaluation has provided the same results. Threshold effects are noticed at levels of 5-10 mg orally, and the compound has a stated effective potency of only 10 times that of mescaline (Shulgin and Dyer, 1975). No qualitative description of its intoxication syndrome at effective levels can be made from the limited experimental data available. [...] No qualitative description of its effects at hallucinogenic doses is available. Interactions Psychedelic drug#Interactions Trip killer#Serotonergic psychedelic antidotes Pharmacology Pharmacodynamics DOAM has been found to be a moderate- to high-efficacy partial agonist of the serotonin 5-HT2A receptor. 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 2022 0892-6638 10.1096/fasebj.2022.36.S1.R2691 fasebj.2022.36.S1.R2691 free https://www.researchgate.net/publication/360369275 It also shows lower affinity for the serotonin 5-HT2B and 5-HT2C receptors, whereas it has very low affinity for the serotonin 5-HT1A receptor. The drug is a full agonist of the serotonin 5-HT2B and 5-HT2C receptors. It is most potent as a serotonin 5-HT2C receptor agonist, whereas it shows far lower potency as an agonist of the serotonin 5-HT2B receptor than as an agonist of the serotonin 5-HT2A and 5-HT2C receptors. DOAM shows very low potency as a human trace amine-associated receptor 1 (TAAR1) agonist. It does not bind to the monoamine transporters. Other receptor interactions have also been described. The drug produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents. However, it produces only a weak head-twitch response and is less potent and much less efficacious than DOM in this regard. In addition, DOAM fails to substitute for DOM in rodent drug discrimination tests, producing up to 35% responding followed up behavioral disruption at higher doses. Glennon RA, Young R, Rosecrans JA A comparison of the behavioral effects of DOM homologs Pharmacol Biochem Behav 16 4 557–559 April 1982 7071089 10.1016/0091-3057(82)90414-2 https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=08722eb1322400803893f721407308f48f0404cd subscription Glennon RA Stimulus properties of hallucinogenic phenalkylamines and related designer drugs: formulation of structure-activity relationships NIDA Res Monogr 94 43–67 1989 2575229 https://archives.nida.nih.gov/sites/default/files/monograph94.pdf#page=54 https://web.archive.org/web/20230511144224/https://archives.nida.nih.gov/sites/default/files/monograph94.pdf#page=54 dead May 11, 2023 It was also unable to antagonize the DOM stimulus at the assessed doses, and behavioral disruption at higher doses prevented further assessment. Glennon RA, Seggel MR Interaction of Phenylisopropylamines with Central 5-HT2 Receptors: Analysis by Quantitative Structure—Activity Relationships Probing Bioactive Mechanisms American Chemical Society Washington, DC 413 14 November 1989 978-0-8412-1702-7 10.1021/bk-1989-0413.ch018 264–280 https://bitnest.netfirms.com/external/10.1021/bk-1989-0413.ch018 Other effects of DOAM in rodents include hyperlocomotion at lower doses, hypolocomotion at higher doses, and hypothermia at higher doses. As the 4-alkyl chain length in DOx is increased from shorter homologues such as DOM, DOET and DOPR which are all potent hallucinogens, the serotonin 5-HT2 receptor binding affinity increases, rising to a maximum with DOHx before falling again with even longer chains. Compounds with sufficiently long chains, such as DOAM, or with bulky groups such as DOTB, have reduced or absent psychedelic-type effects in animals and/or humans, suggesting that they may have reduced agonistic activity at the serotonin 5-HT2A receptor.Bryan Roth Seggel MR, Yousif MY, Lyon RA, Titeler M, Roth BL, Suba EA, Glennon RA A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors Journal of Medicinal Chemistry 33 3 1032–6 March 1990 2308135 10.1021/jm00165a023 For example, using rats trained to discriminate DOM from saline, ED,, values for stimulus generalization are significantly correlated with 5-HT2 affinity. However, some of the compounds included in the present study (e.g., In and Io) possess a high affinity for the 5-HT2 sites but do not result in stimulus generalization.Dowd CS, Herrick-Davis K, Egan C, DuPre A, Smith C, Teitler M, Glennon RA 1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT(2A) partial agonists Journal of Medicinal Chemistry 43 16 3074–84 August 2000 10956215 10.1021/jm9906062Patentscope. PHENALKYLAMINES AND METHODS OF MAKING AND USING THE SAME. Patent WO2022192781. Retrieved 2026-06-18 Chemistry Synthesis The chemical synthesis of DOAM has been described. Analogues Analogues of DOAM include 2,5-dimethoxyamphetamine (2,5-DMA), DOM, DOET, DOPR, DOBU, and DOHx, among others. History DOAM was first described in the scientific literature by Alexander Shulgin and colleagues in 1975. Subsequently, it was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). Society and culture Legal status Canada DOAM is a controlled substance in Canada under phenethylamine blanket-ban language.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 See also DOx (psychedelics) 2,5-Dimethoxy-4-butylamphetamine (DOBU) 2,5-Dimethoxy-4-hexylamphetamine (DOHx) References External links DOAM - Isomer Design DOAM - PiHKAL - Erowid DOAM - PiHKAL - Isomer Design DOAM - The Shulgin Index DOAM: What Do We Know About This Mysterious Psychedelic? - Tripsitter Category:5-HT2A agonists Category:5-HT2B agonists Category:5-HT2C agonists Category:DOx (psychedelics) Category:Pentyl compounds Category:PiHKAL Category:Psychedelic phenethylamines