2,5-Dimethoxy-4-butylamphetamine

DOBU was first synthesized by Alexander Shulgin. In his book PiHKAL (Phenethylamines i Have Known And Loved) and other publications, he and colleagues stated that doses of 1 to 3{{nbsp}}mg orally produced clear threshold effects and it was active at a dosage of slightly more than twice that of DOM.{{CitePiHKAL}}{{cite journal | vauthors = Braun U, Braun G, Jacob P, Nichols DE, Shulgin AT | title = Mescaline analogs: substitutions at the 4-position | journal = NIDA Res Monogr | volume = | issue = 22 | pages = 27–37 | date = 1978 | pmid = 101882 | doi = | url = https://archives.nida.nih.gov/sites/default/files/monograph22.pdf#page=38 | quote = 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 10{{nbsp}}mg DOBU was required to produce hallucinogenic effects. The drug's duration was listed as "very long". There was limited investigation on the qualitative effects of DOAM. However, in PiHKAL, at the assessed doses of 2.2{{nbsp}}mg and 2.8{{nbsp}}mg, it was described as producing paresthesia and difficulty sleeping with few other effects.

Compared to shorter chain homologues such as DOM, DOET, and DOPR which are all potent hallucinogens, DOBU has an even higher serotonin 5-HT₂ receptor affinity. It has been found to act as a potent full agonist of the serotonin 5-HT_2A and 5-HT_2C receptors.{{cite journal | vauthors = Luethi D, Rudin D, Hoener MC, Liechti ME | title=Monoamine Receptor and Transporter Interaction Profiles of 4-Alkyl-Substituted 2,5-Dimethoxyamphetamines | journal=The FASEB Journal | volume=36 | issue=S1 | date=2022 | issn=0892-6638 | doi=10.1096/fasebj.2022.36.S1.R2691 | page= | doi-access=free | url=https://www.researchgate.net/profile/Dino-Luethi/publication/360369275_Monoamine_Receptor_and_Transporter_Interaction_Profiles_of_4-Alkyl-Substituted_25-Dimethoxyamphetamines/links/627531dc107cae29198ee5f2/Monoamine-Receptor-and-Transporter-Interaction-Profiles-of-4-Alkyl-Substituted-2-5-Dimethoxyamphetamines.pdf }}{{cite journal | vauthors = 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 | title = Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential | journal = Nat Commun | volume = 14 | issue = 1 | pages = 8221 | date = December 2023 | pmid = 38102107 | pmc = 10724237 | doi = 10.1038/s41467-023-44016-1 | url = https://bitnest.netfirms.com/external/10.1038/s41467-023-44016-1}} Findings are mixed with regard to the serotonin 5-HT_2B receptor, with DOBU reported to act as a potent and high-efficacy partial agonist of this receptor or to be inactive as an agonist of the receptor.

DOBU fully substitutes for DOM in rodent drug discrimination tests, albeit several-fold less potently than DOET or DOPR.{{cite journal | vauthors = Glennon RA, Young R, Rosecrans JA | title = A comparison of the behavioral effects of DOM homologs | journal = Pharmacol Biochem Behav | volume = 16 | issue = 4 | pages = 557–559 | date = April 1982 | pmid = 7071089 | doi = 10.1016/0091-3057(82)90414-2 | url = }}{{cite journal |vauthors=Seggel MR, Yousif MY, Lyon RA, Titeler M, Roth BL, Suba EA, Glennon RA|author5-link=Bryan Roth |title=A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors |journal=Journal of Medicinal Chemistry |volume=33 |issue=3 |pages=1032–1036 |date=March 1990 |pmid=2308135 |doi=10.1021/jm00165a023}}{{cite journal | vauthors = Glennon RA | title = Stimulus properties of hallucinogenic phenalkylamines and related designer drugs: formulation of structure-activity relationships | journal = NIDA Res Monogr | volume = 94 | issue = | pages = 43–67 | date = 1989 | pmid = 2575229 | doi = | url = https://archives.nida.nih.gov/sites/default/files/monograph94.pdf#page=54}} 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, and DOC.{{cite journal | vauthors = Halberstadt AL, Chatha M, Klein AK, Wallach J, Brandt SD | title = Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species | journal = Neuropharmacology | volume = 167 | issue = | pages = 107933 | date = May 2020 | pmid = 31917152 | pmc = 9191653 | doi = 10.1016/j.neuropharm.2019.107933 | url = http://usdbiology.com/cliff/Courses/Advanced%20Seminars%20in%20Neuroendocrinology/Serotonergic%20Psychedelics%2020/Halberstadt%2020%20Neuropharm%20potency%20of%20hallucinogens%20%20head-twitch.pdf}} The doses at which DOBU produces peak head twitches are similar to those of DOM and DOET.

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.{{cite book | vauthors = Nichols DE, Glennon RA | date = 1984 | chapter = Medicinal Chemistry and Structure-Activity Relationships of Hallucinogens | veditors = Jacobs BL | title = Hallucinogens: Neurochemical, Behavioral, and Clinical Perspectives | pages = 95–142 | publisher = Raven Press | location = New York | isbn = 978-0-89004-990-7 | oclc = 10324237 | url = https://books.google.com/books?id=EdpsAAAAMAAJ&pg=PA95 | chapter-url = https://bitnest.netfirms.com/external/Books/HallucinogensNBCP95 }}{{cite journal | vauthors = Jacob P, Shulgin AT | title = Structure-activity relationships of the classic hallucinogens and their analogs | journal = NIDA Res Monogr | volume = 146 | issue = | pages = 74–91 | date = 1994 | pmid = 8742795 | doi = | url = https://archives.nida.nih.gov/sites/default/files/monograph146.pdf#page=79 }}{{cite book | vauthors = Shulgin AT | chapter=Basic Pharmacology and Effects | pages=67–137 | veditors = Laing RR | title=Hallucinogens: A Forensic Drug Handbook | publisher=Elsevier Science | series=Forensic Drug Handbook Series | year=2003 | isbn=978-0-12-433951-4 | url=https://books.google.com/books?id=l1DrqgobbcwC | chapter-url=https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6bb3a7499da8e9852b39cd4db16891147c83f5c6 | access-date=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.{{cite journal | vauthors = Glennon RA, Young R, Rosecrans JA | title = A comparison of the behavioral effects of DOM homologs | journal = Pharmacol Biochem Behav | volume = 16 | issue = 4 | pages = 557–559 | date = April 1982 | pmid = 7071089 | doi = 10.1016/0091-3057(82)90414-2 | url = }}

Image:DOIB,DOSBandDOTB.png, DOSB, and DOTB.]]

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• 2,5-Dimethoxy-4-amylamphetamine (DOAM)
• 2,5-Dimethoxy-4-butylphenethylamine (2C-Bu)

{{Reflist}}

• [https://isomerdesign.com/pihkal/explore/63 DOBU - Isomer Design]
• [http://www.erowid.org/library/books_online/pihkal/pihkal063.shtml DOBU - PiHKAL - Erowid]
• [http://pihkal.info/read.php?domain=pk&id=63 DOBU - PiHKAL - Isomer Design]
• [https://tripsitter.com/dobu/ Here’s What We Know About The Psychedelic DOBU - Tripsitter]

{{Psychedelics}}

{{Serotonin receptor modulators}}

{{Phenethylamines}}

Category:5-HT2A agonists

Category:5-HT2B agonists

Category:5-HT2C agonists

Category:DOx (psychedelics)

Category:Psychedelic phenethylamines

Category:Serotonin receptor agonists