2,5-Dimethoxy-4-butylamphetamine

{{Short description|Substituted amphetamine psychedelic drug}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{Other uses|Dobu (disambiguation)}} {{Infobox drug | Verifiedfields = verified | verifiedrevid = 477211590 | drug_name = DOBU | image = DOBU.svg | image_class = skin-invert-image | width = 250px | caption =

| legal_status =

| CAS_number_Ref = {{cascite|correct|CAS}} | CAS_number = 63779-89-5 | CAS_supplemental = | PubChem = 10060720 | PubChemSubstance = | IUPHAR_ligand = | DrugBank = | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 8236274 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 6ARH6DPN4N | KEGG = | ChEBI = | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 8214 | NIAID_ChemDB = | PDB_ligand = | synonyms = DOBU; 2,5-Dimethoxy-4-butylamphetamine; 4-Butyl-2,5-dimethoxyamphetamine

| IUPAC_name = 1-(4-butyl-2,5-dimethoxyphenyl)propan-2-amine | C=15 | H=25 | N=1 | O=2 | SMILES = C1(=CC(=C(C=C1CC(C)N)OC)CCCC)OC | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = NGVDYAULSQKEGW-UHFFFAOYSA-N }}

'''2,5-Dimethoxy-4-butylamphetamine''' ('''DOBU''') is a psychedelic drug of the phenethylamine, amphetamine, and DOx families related to DOM.<ref name="PiHKAL" /><ref name="Shulgin1978">{{cite book | veditors = Iversen LL, Iversen SD, Snyder SH | last=Shulgin | first=Alexander T. | title=Stimulants | chapter=Psychotomimetic Drugs: Structure-Activity Relationships | publisher=Springer US | publication-place=Boston, MA | date=1978 | isbn=978-1-4757-0512-6 | doi=10.1007/978-1-4757-0510-2_6 | pages=243–333 | chapter-url=https://bitnest.netfirms.com/external/10.1007/978-1-4757-0510-2_6 | url=https://books.google.com/books?id=h0_uBwAAQBAJ&pg=PA261 | quote=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.}}</ref><ref name="LuethiGlatfelterPottie2025">{{cite journal | vauthors = 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 | title = The 4-alkyl chain length of 2,5-dimethoxyamphetamines differentially affects in vitro serotonin receptor actions versus in vivo psychedelic-like effects | journal = Mol Psychiatry | volume = | issue = | pages = | date = November 2025 | pmid = 41193673 | doi = 10.1038/s41380-025-03325-1 | url = https://www.nature.com/articles/s41380-025-03325-1.pdf}}</ref> It is the derivative of DOM in which the methyl group at the 4 position has been replaced with a butyl group.<ref name="PiHKAL" /> The drug is taken orally.<ref name="Shulgin1978" /><ref name="PiHKAL" /><ref name="BraunBraunJacob1978" />

It acts as a serotonin receptor agonist, including of the serotonin 5-HT2A receptor.<ref name="LuethiGlatfelterPottie2025" /> The drug produces psychedelic-like effects in animals.<ref name="LuethiGlatfelterPottie2025" />

DOBU was first described in the literature by Alexander Shulgin in 1970.<ref name="US3547999" /> Subsequently, it was described in greater detail by Shulgin in his 1991 book ''PiHKAL'' (''Phenethylamines I Have Known and Loved'').<ref name="PiHKAL" />

==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 3{{nbsp}}mg orally produced clear threshold effects and that it was active at a dose of slightly more than twice that of DOM.<ref name="Shulgin1978" /><ref name="PiHKAL">{{CitePiHKAL}}</ref><ref name="BraunBraunJacob1978">{{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 | archive-url = https://web.archive.org/web/20230805004421/https://archives.nida.nih.gov/sites/default/files/monograph22.pdf#page=38 | url-status = dead | archive-date = August 5, 2023 | 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.}}</ref> It was stated that 10{{nbsp}}mg DOBU was required to produce hallucinogenic effects.<ref name="BraunBraunJacob1978" /> The drug's duration was listed as "very long".<ref name="PiHKAL" /> There was limited investigation of its qualitative effects.<ref name="Shulgin1978" /> 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.<ref name="PiHKAL" /> The effects of higher doses of DOBU have not been described beyond them producing hallucinogenic effects.<ref name="PiHKAL" /><ref name="BraunBraunJacob1978" />

==Interactions== {{See also|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.<ref name="LuethiGlatfelterPottie2025" /><ref name="SeggelYousifLyon1990" /> It has been found to act as a potent full agonist of the serotonin 5-HT2A and 5-HT2C receptors.<ref name="LuethiGlatfelterPottie2025" /><ref name="LuethiRudinHoener2022">{{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 | article-number=fasebj.2022.36.S1.R2691 | doi-access=free | url=https://www.researchgate.net/publication/360369275 }}</ref><ref name="WallachCaoCalkins2023">{{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 | article-number = 8221 | date = December 2023 | pmid = 38102107 | pmc = 10724237 | doi = 10.1038/s41467-023-44016-1 | bibcode = 2023NatCo..14.8221W }}</ref> The drug is also a serotonin 5-HT2B receptor full agonist but with far lower potency.<ref name="LuethiGlatfelterPottie2025" /><ref name="WallachCaoCalkins2023" /><ref name="LuethiRudinHoener2022" /> Additional receptor interactions have also been described.<ref name="LuethiGlatfelterPottie2025" />

DOBU fully substitutes for DOM in rodent drug discrimination tests, albeit several-fold less potently than DOET or DOPR.<ref name="GlennonYoungRosecrans1982">{{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 = }}</ref><ref name="SeggelYousifLyon1990">{{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}}</ref><ref name="HalberstadtChathaKlein2020" /><ref name="Glennon1989">{{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| archive-url = https://web.archive.org/web/20230511144224/https://archives.nida.nih.gov/sites/default/files/monograph94.pdf#page=54| url-status = dead| archive-date = May 11, 2023}}</ref> 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.<ref name="LuethiGlatfelterPottie2025" /><ref name="HalberstadtChathaKlein2020">{{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 = | article-number = 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}}</ref> The doses at which DOBU produces peak head twitches are similar to those of DOM and DOET.<ref name="HalberstadtChathaKlein2020" /><ref name="LuethiGlatfelterPottie2025" />

Other effects of DOBU in rodents include hyperlocomotion at lower doses, hypolocomotion at higher doses, and hypothermia at higher doses.<ref name="LuethiGlatfelterPottie2025" />

===Pharmacokinetics=== DOBU crosses the blood–brain barrier in rodents.<ref name="LuethiGlatfelterPottie2025" />

==Chemistry== ===Synthesis=== The chemical synthesis of DOBU has been described.<ref name="PiHKAL" />

===Analogues=== Analogues of DOBU include 2,5-dimethoxyamphetamine (2,5-DMA), DOM, DOET, DOPR, DOAM, DOHx, and 2C-Bu, among others.<ref name="PiHKAL" /><ref name="LuethiGlatfelterPottie2025" />

====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.<ref name="NicholsGlennon1984">{{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 }}</ref><ref name="JacobShulgin1994">{{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 | archive-url = https://web.archive.org/web/20230805004551/https://archives.nida.nih.gov/sites/default/files/monograph146.pdf#page=79 | url-status = dead | archive-date = August 5, 2023 }}</ref><ref name="Shulgin2003">{{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}}</ref> All are significantly less potent than DOBU, with DOIB being active at around 10–15 mg, and DOSB at 25–30 mg.<ref name="NicholsGlennon1984" /> The most highly branched isomer DOTB was completely inactive in both animal and human trials.<ref name="NicholsGlennon1984" /> However, it was also reported that DOTB and DOAM partially generalized to DOM in animal drug discrimination tests.<ref name="GlennonYoungRosecrans1982">{{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 = }}</ref>

{{Gallery | title = Chemical structures of DOBU and its skeletal isomers<ref name="NicholsGlennon1984" /><ref name="JacobShulgin1994" /><ref name="Shulgin2003" /> | height = 130 | width = 195 | File:DOBU.svg | class1=skin-invert-image | DOBU | File:DOiB structure.svg | class2=skin-invert-image | DOiB | File:DOsB structure.svg | class3=skin-invert-image | DOsB | File:DOtB structure.svg | class4=skin-invert-image | DOtB }}

==History== DOBU was first described in the literature by Alexander Shulgin in 1970.<ref name="US3547999">{{cite web | title=phenethylamines and their pharmacologically-acceptable salts | website=Google Patents | date=14 July 1969 | url=https://patents.google.com/patent/US3547999 | access-date=30 November 2025}}</ref> Subsequently, it was described in greater detail by Shulgin in his book ''PiHKAL'' (''Phenethylamines I Have Known and Loved'') in 1991.<ref name="PiHKAL" />

==Society and culture== ===Legal status=== ====Canada==== DOBU is a controlled substance in Canada under phenethylamine blanket-ban language.<ref name="CDSA">{{cite web | title=Controlled Drugs and Substances Act | website=Department of Justice Canada | url=https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html | access-date=19 January 2026}}</ref>

====United States==== DOBU is not an explicitly controlled substance in the United States.<ref name="OrangeBook2026">{{citation | title = Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) | date = January 2026 | publisher = U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division | location = United States | url = https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf}}</ref> However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.

== See also == * DOx (psychedelics)

==References== {{Reflist}}

== External links == * [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]

Category:5-HT2A agonists Category:5-HT2B agonists Category:5-HT2C agonists Category:DOx (psychedelics) Category:PiHKAL Category:Psychedelic phenethylamines Category:Serotonin receptor agonists