2,5-Dimethoxy-4-butylamphetamine

Substituted amphetamine psychedelic drug vanc 6 Dobu (disambiguation) verified 477211590 DOBU DOBU.svg skin-invert-image 250px Oral Serotonin 5-HT2 receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen None "Very long" correct CAS 63779-89-5 10060720 correct chemspider 8236274 correct FDA 6ARH6DPN4N correct EBI 8214 DOBU; 2,5-Dimethoxy-4-butylamphetamine; 4-Butyl-2,5-dimethoxyamphetamine 1-(4-butyl-2,5-dimethoxyphenyl)propan-2-amine 15 25 1 2 C1(=CC(=C(C=C1CC(C)N)OC)CCCC)OC correct chemspider 1S/C15H25NO2/c1-5-6-7-12-9-15(18-4)13(8-11(2)16)10-14(12)17-3/h9-11H,5-8,16H2,1-4H3 correct chemspider NGVDYAULSQKEGW-UHFFFAOYSA-N 2,5-Dimethoxy-4-butylamphetamine (DOBU) is a psychedelic drug of the phenethylamine, amphetamine, and DOx families related to 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 3.4.10. 2,5-Dimethoxy-4-butylphenylisopropylamine The four-carbon homolog in this series, 2,5-dimethoxy-4-butylphenylisopropylamine (76, DOBU), appears in the animal behavior tests (see DOAM, 77) to be a highly potent compound, although somewhat less active than the three-carbon counterpart. The compound shows clear threshold effects in man in the 1-2 mg area, acutely and orally, and is effective at dosage levels slightly more than twice those required for DOM (69). It has been assigned (Shulgin and Dyer, 1975) a relative potency 36 times that of mescaline, although the qualitative nature has not yet been adequately investigated. As with the 4-propyl counterpart (75) there seems to be a sympathomimetic stimulatory component associated with the effective dosage. 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 a butyl group. The drug is taken orally. It acts as a serotonin receptor agonist, including of the serotonin 5-HT2A receptor. The drug produces psychedelic-like effects in animals. DOBU was first described in the literature by Alexander Shulgin in 1970. 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) and other publications, Alexander Shulgin and colleagues stated that doses of 1 to 3mg orally produced clear threshold effects and that it was active at a dose of slightly more than twice that of DOM. 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. It was stated that 10mg DOBU was required to produce hallucinogenic effects. The drug's duration was listed as "very long". There was limited investigation of its qualitative effects. However, in PiHKAL, at the assessed doses of 2.2mg and 2.8mg, it was described as producing paresthesia and difficulty sleeping with few other effects. The effects of higher doses of DOBU have not been described beyond them producing hallucinogenic effects. Interactions Psychedelic drug#Interactions Trip killer#Serotonergic psychedelic antidotes Pharmacology Pharmacodynamics Compared to shorter-chain homologues such as DOM, DOET, and DOPR, which are all potent psychedelics, DOBU has even higher affinity for the serotonin 5-HT2A receptor. It has been found to act as a potent full agonist of the serotonin 5-HT2A and 5-HT2C receptors. 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 Wallach J, Cao AB, Calkins MM, Heim AJ, Lanham JK, Bonniwell EM, Hennessey JJ, Bock HA, Anderson EI, Sherwood AM, Morris H, de Klein R, Klein AK, Cuccurazzu B, Gamrat J, Fannana T, Zauhar R, Halberstadt AL, McCorvy JD Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential Nat Commun 14 1 8221 December 2023 38102107 10724237 10.1038/s41467-023-44016-1 free 2023NatCo..14.8221W The drug is also a serotonin 5-HT2B receptor full agonist but with far lower potency. Additional receptor interactions have also been described. DOBU fully substitutes for DOM in rodent drug discrimination tests, albeit several-fold less potently than DOET or DOPR. 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 Seggel MR, Yousif MY, Lyon RA, Titeler M, Roth BL, Suba EA, Glennon RA Bryan Roth 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 1032–1036 March 1990 2308135 10.1021/jm00165a023 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 In addition, DOBU robustly induces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents, and maximally does so about as strongly as other DOx drugs like DOM, DOET, DOPR, and DOC. 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 doses at which DOBU produces peak head twitches are similar to those of DOM and DOET. Other effects of DOBU in rodents include hyperlocomotion at lower doses, hypolocomotion at higher doses, and hypothermia at higher doses. Pharmacokinetics DOBU crosses the blood–brain barrier in rodents. Chemistry Synthesis The chemical synthesis of DOBU has been described. Analogues Analogues of DOBU include 2,5-dimethoxyamphetamine (2,5-DMA), DOM, DOET, DOPR, DOAM, DOHx, and 2C-Bu, among others. Isomers Alternative skeletal isomers of DOBU can also be produced, where the 4-(n-butyl) group of DOBU is replaced with any of the three other butyl isomers, the iso-butyl, sec-butyl and tert-butyl compounds being called DOIB, DOSB, and DOTB, respectively. Nichols DE, Glennon RA 1984 Medicinal Chemistry and Structure-Activity Relationships of Hallucinogens Jacobs BL Hallucinogens: Neurochemical, Behavioral, and Clinical Perspectives 95–142 Raven Press New York 978-0-89004-990-7 10324237 https://books.google.com/books?id=EdpsAAAAMAAJ&pg=PA95 https://bitnest.netfirms.com/external/Books/HallucinogensNBCP95 Jacob P, Shulgin AT Structure-activity relationships of the classic hallucinogens and their analogs NIDA Res Monogr 146 74–91 1994 8742795 https://archives.nida.nih.gov/sites/default/files/monograph146.pdf#page=79 https://web.archive.org/web/20230805004551/https://archives.nida.nih.gov/sites/default/files/monograph146.pdf#page=79 dead August 5, 2023 Shulgin AT Basic Pharmacology and Effects 67–137 Laing RR Hallucinogens: A Forensic Drug Handbook Elsevier Science Forensic Drug Handbook Series 2003 978-0-12-433951-4 https://books.google.com/books?id=l1DrqgobbcwC https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6bb3a7499da8e9852b39cd4db16891147c83f5c6 1 February 2025 All are significantly less potent than DOBU, with DOIB being active at around 10–15 mg, and DOSB at 25–30 mg. The most highly branched isomer DOTB was completely inactive in both animal and human trials. However, it was also reported that DOTB and DOAM partially generalized to DOM in animal drug discrimination tests. Chemical structures of DOBU and its skeletal isomers 130 195 File:DOBU.svg skin-invert-image DOBU File:DOiB structure.svg skin-invert-image DOiB File:DOsB structure.svg skin-invert-image DOsB File:DOtB structure.svg skin-invert-image DOtB History DOBU was first described in the literature by Alexander Shulgin in 1970.phenethylamines and their pharmacologically-acceptable salts Google Patents 14 July 1969 https://patents.google.com/patent/US3547999 30 November 2025 Subsequently, it was described in greater detail by Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved) in 1991. Society and culture Legal status Canada DOBU 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 United States DOBU is not an explicitly controlled substance 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 However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption. See also DOx (psychedelics) References External links DOBU - Isomer Design DOBU - PiHKAL - Erowid DOBU - PiHKAL - Isomer Design DOBU - The Shulgin Index Here’s What We Know About The Psychedelic DOBU - Tripsitter Category:5-HT2A agonists Category:5-HT2B agonists Category:5-HT2C agonists Category:DOx (psychedelics) Category:PiHKAL Category:Psychedelic phenethylamines Category:Serotonin receptor agonists