2,5-Dimethoxy-4-butylamphetamine

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. 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

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, and DOAM, 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 1991 book PiHKAL (Phenethylamines I Have Known and Loved).

Society and culture

Legal status

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.

References

References

1. Shulgin, Alexander T.. (1978). "Stimulants". Springer US.
2. (November 2025). "The 4-alkyl chain length of 2,5-dimethoxyamphetamines differentially affects in vitro serotonin receptor actions versus in vivo psychedelic-like effects". Mol Psychiatry.
3. {{CitePiHKAL
4. (1978). "Mescaline analogs: substitutions at the 4-position". NIDA Res Monogr.
5. (2022). "Monoamine Receptor and Transporter Interaction Profiles of 4-Alkyl-Substituted 2,5-Dimethoxyamphetamines". The FASEB Journal.
6. (December 2023). "Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential". Nat Commun.
7. (April 1982). "A comparison of the behavioral effects of DOM homologs". Pharmacol Biochem Behav.
8. (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.
9. (1989). "Stimulus properties of hallucinogenic phenalkylamines and related designer drugs: formulation of structure-activity relationships". NIDA Res Monogr.
10. (May 2020). "Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species". Neuropharmacology.
11. (1984). "Hallucinogens: Neurochemical, Behavioral, and Clinical Perspectives". Raven Press.
12. (1994). "Structure-activity relationships of the classic hallucinogens and their analogs". NIDA Res Monogr.
13. (2003). "Hallucinogens: A Forensic Drug Handbook". Elsevier Science.
14. (14 July 1969). "phenethylamines and their pharmacologically-acceptable salts".
15. "Controlled Drugs and Substances Act".
16. (January 2026). "Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026)". U.S. [[Department of Justice]]: [[Drug Enforcement Administration]] (DEA): Diversion Control Division.