2,5-Dimethoxy-4-butylamphetamine
 | |
| Clinical data | |
|---|---|
| Other names | DOBU; 2,5-Dimethoxy-4-butylamphetamine; 4-Butyl-2,5-dimethoxyamphetamine |
| Routes of administration | Oral[1][2][3] |
| Drug class | Serotonin 5-HT2 receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen |
| ATC code |
|
| Pharmacokinetic data | |
| Duration of action | "Very long"[2] |
| Identifiers | |
| |
| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| UNII | |
| ChEMBL | |
| CompTox Dashboard (EPA) | |
| Chemical and physical data | |
| Formula | C15H25NO2 |
| Molar mass | 251.370 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
| (verify) | |
2,5-Dimethoxy-4-butylamphetamine (DOBU) is a psychedelic drug of the phenethylamine, amphetamine, and DOx families related to DOM.[2][1][4] It is the derivative of DOM in which the methyl group at the 4 position has been replaced with a butyl group.[2] The drug is taken orally.[1][2][3]
It acts as a serotonin receptor agonist, including of the serotonin 5-HT2A receptor.[4] The drug produces psychedelic-like effects in animals.[4]
DOBU was first described in the literature by Alexander Shulgin in 1970.[5] Subsequently, it was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).[2]
Use and effects
[edit]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.[1][2][3] It was stated that 10 mg DOBU was required to produce hallucinogenic effects.[3] The drug's duration was listed as "very long".[2] There was limited investigation of its qualitative effects.[1] 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.[2] The effects of higher doses of DOBU have not been described beyond them producing hallucinogenic effects.[2][3]
Interactions
[edit]Pharmacology
[edit]Pharmacodynamics
[edit]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.[4][6] It has been found to act as a potent full agonist of the serotonin 5-HT2A and 5-HT2C receptors.[4][7][8] The drug is also a serotonin 5-HT2B receptor full agonist but with far lower potency.[4][8][7] Additional receptor interactions have also been described.[4]
DOBU fully substitutes for DOM in rodent drug discrimination tests, albeit several-fold less potently than DOET or DOPR.[9][6][10][11] 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.[4][10] The doses at which DOBU produces peak head twitches are similar to those of DOM and DOET.[10][4]
Other effects of DOBU in rodents include hyperlocomotion at lower doses, hypolocomotion at higher doses, and hypothermia at higher doses.[4]
Pharmacokinetics
[edit]DOBU crosses the blood–brain barrier in rodents.[4]
Chemistry
[edit]Synthesis
[edit]The chemical synthesis of DOBU has been described.[2]
Analogues
[edit]Analogues of DOBU include 2,5-dimethoxyamphetamine (2,5-DMA), DOM, DOET, DOPR, DOAM, DOHx, and 2C-Bu, among others.[2][4]
Isomers
[edit]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.[12][13][14] All are significantly less potent than DOBU, with DOIB being active at around 10–15 mg, and DOSB at 25–30 mg.[12] The most highly branched isomer DOTB was completely inactive in both animal and human trials.[12] However, it was also reported that DOTB and DOAM partially generalized to DOM in animal drug discrimination tests.[9]
History
[edit]DOBU was first described in the literature by Alexander Shulgin in 1970.[5] Subsequently, it was described in greater detail by Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved) in 1991.[2]
Society and culture
[edit]Legal status
[edit]Canada
[edit]DOBU is a controlled substance in Canada under phenethylamine blanket-ban language.[15]
United States
[edit]DOBU is not an explicitly controlled substance in the United States.[16] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.
See also
[edit]References
[edit]- 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.
- 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.
- 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.
- 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.
- 1 2 "phenethylamines and their pharmacologically-acceptable salts". Google Patents. 14 July 1969. Retrieved 30 November 2025.
- 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.
- 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.
- 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.
- 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.
- 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.
- ↑ 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.
- 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.
- 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.
- 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.
- ↑ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
- ↑ 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