2,5-Dimethoxy-4-butylamphetamine

DOBU
Clinical data
Other namesDOBU; 2,5-Dimethoxy-4-butylamphetamine; 4-Butyl-2,5-dimethoxyamphetamine
Routes of
administration		Oral
Drug classSerotonin 5-HT2 receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Duration of action"Very long"
Identifiers
  • 1-(4-butyl-2,5-dimethoxyphenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H25NO2
Molar mass251.370 g·mol−1
3D model (JSmol)
  • C1(=CC(=C(C=C1CC(C)N)OC)CCCC)OC
  • InChI=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 checkY
  • Key:NGVDYAULSQKEGW-UHFFFAOYSA-N checkY
  (verify)

2,5-Dimethoxy-4-butylamphetamine (DOBU) is a psychedelic drug of the phenethylamine, amphetamine, and DOx families related to DOM. 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 3 mg orally produced clear threshold effects and that it was active at a dose of slightly more than twice that of DOM. It was stated that 10 mg 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 2.2 mg and 2.8 mg, 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

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. 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. 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. 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. 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.

History

DOBU was first described in the literature by Alexander Shulgin in 1970. Subsequently, it was described in greater detail by Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved) in 1991.

Society and culture

Canada

DOBU is a controlled substance in Canada under phenethylamine blanket-ban language.

United States

DOBU is not an explicitly controlled substance in the United States. However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.

See also

References

  1. 1 2 3 4 5 Shulgin AT (1978). "Psychotomimetic Drugs: Structure-Activity Relationships". In Iversen LL, Iversen SD, Snyder SH (eds.). Stimulants. Boston, MA: Springer US. pp. 243–333. doi:10.1007/978-1-4757-0510-2_6. ISBN 978-1-4757-0512-6. 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.
  2. 1 2 3 4 5 6 7 8 9 10 11 12 13 Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
  3. 1 2 3 4 5 Braun U, Braun G, Jacob P, Nichols DE, Shulgin AT (1978). "Mescaline analogs: substitutions at the 4-position" (PDF). NIDA Res Monogr (22): 27–37. PMID 101882. Archived from the original (PDF) on 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.
  4. 1 2 3 4 5 6 7 8 9 10 11 12 Luethi D, Glatfelter GC, Pottie E, Sellitti F, Maitland AD, Gonzalez NR, et al. (November 2025). "The 4-alkyl chain length of 2,5-dimethoxyamphetamines differentially affects in vitro serotonin receptor actions versus in vivo psychedelic-like effects" (PDF). Mol Psychiatry. doi:10.1038/s41380-025-03325-1. PMID 41193673.
  5. 1 2 "phenethylamines and their pharmacologically-acceptable salts". Google Patents. 14 July 1969. Retrieved 30 November 2025.
  6. 1 2 Seggel MR, Yousif MY, Lyon RA, Titeler M, Roth BL, Suba EA, et al. (March 1990). "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. doi:10.1021/jm00165a023. PMID 2308135.
  7. 1 2 Luethi D, Rudin D, Hoener MC, Liechti ME (2022). "Monoamine Receptor and Transporter Interaction Profiles of 4-Alkyl-Substituted 2,5-Dimethoxyamphetamines". The FASEB Journal. 36 (S1) fasebj.2022.36.S1.R2691. doi:10.1096/fasebj.2022.36.S1.R2691. ISSN 0892-6638.
  8. 1 2 Wallach J, Cao AB, Calkins MM, Heim AJ, Lanham JK, Bonniwell EM, et al. (December 2023). "Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential". Nat Commun. 14 (1) 8221. Bibcode:2023NatCo..14.8221W. doi:10.1038/s41467-023-44016-1. PMC 10724237. PMID 38102107.
  9. 1 2 Glennon RA, Young R, Rosecrans JA (April 1982). "A comparison of the behavioral effects of DOM homologs". Pharmacol Biochem Behav. 16 (4): 557–559. doi:10.1016/0091-3057(82)90414-2. PMID 7071089.
  10. 1 2 3 Halberstadt AL, Chatha M, Klein AK, Wallach J, Brandt SD (May 2020). "Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species" (PDF). Neuropharmacology. 167 107933. doi:10.1016/j.neuropharm.2019.107933. PMC 9191653. PMID 31917152. Archived from the original (PDF) on 2025-03-26. Retrieved 2025-03-27.
  11. ↑ Glennon RA (1989). "Stimulus properties of hallucinogenic phenalkylamines and related designer drugs: formulation of structure-activity relationships" (PDF). NIDA Res Monogr. 94: 43–67. PMID 2575229. Archived from the original (PDF) on May 11, 2023.
  12. 1 2 3 4 Nichols DE, Glennon RA (1984). "Medicinal Chemistry and Structure-Activity Relationships of Hallucinogens". In Jacobs BL (ed.). Hallucinogens: Neurochemical, Behavioral, and Clinical Perspectives. New York: Raven Press. pp. 95–142. ISBN 978-0-89004-990-7. OCLC 10324237.
  13. 1 2 Jacob P, Shulgin AT (1994). "Structure-activity relationships of the classic hallucinogens and their analogs" (PDF). NIDA Res Monogr. 146: 74–91. PMID 8742795. Archived from the original (PDF) on August 5, 2023.
  14. 1 2 Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Retrieved 1 February 2025.
  15. ↑ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
  16. ↑ Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) (PDF), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026