2,5-Dimethoxy-4-butylamphetamine (DOBU) is a lesser-known psychedelic drug and a substituted amphetamine. DOBU was first synthesized by Alexander Shulgin. In his book PiHKAL (Phenethylamines i Have Known And Loved), only low dosages of 2 to 3 mg were tested, with the duration simply listed as "very long". DOBU produces paresthesia and difficulty sleeping, but with few other effects.
 | |
| Names | |
|---|---|
| Preferred IUPAC name
1-(4-Butyl-2,5-dimethoxyphenyl)propan-2-amine | |
| Other names
2,5-Dimethoxy-4-butyl-amphetamine
2,5-Dimethoxy-4-butyl-1-ethyl-(alpha-methyl)amine | |
| Identifiers | |
3D model (JSmol)
|
|
| ChEMBL | |
| ChemSpider | |
PubChem CID
|
|
| UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
| Properties | |
| C15H25NO2 | |
| Molar mass | 251.37 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Compared to shorter chain homologues such as DOM, DOET, and DOPR which are all potent hallucinogens, DOBU has an even stronger serotonin 5-HT2 receptor affinity, but fails to substitute for hallucinogens in animal drug discrimination tests or produce hallucinogenic effects in humans.[1] These findings suggest that it has low efficacy and is thus an antagonist or weak partial agonist at the serotonin 5-HT2A receptor. However, DOBU has since been found to act as a full agonist of the serotonin 5-HT2A receptor.[2] Hence, the reasons for the lack of psychedelic effects with DOBU remain unknown.[2] DOBU is inactive as an agonist of the serotonin 5-HT2B receptor though still shows affinity for the serotonin 5-HT2C receptor.[2]
Isomers
editAlternative 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.[3][4][5] All are significantly less potent than DOBU, with DOIB being active at around 10–15 mg, and DOSB at 25–30 mg.[3] The most highly branched isomer DOTB was completely inactive in both animal and human trials.[3] However, it was also reported that DOTB and DOAM partially generalized to DOM in animal drug discrimination tests.[6]
See also
editReferences
edit- ^ Seggel MR, Yousif MY, Lyon RA, Titeler M, Roth BL, Suba EA, Glennon RA (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.
- ^ a b c Luethi, Dino; Rudin, Deborah; Hoener, Marius C.; Liechti, Matthias E. (2022). "Monoamine Receptor and Transporter Interaction Profiles of 4-Alkyl-Substituted 2,5-Dimethoxyamphetamines" (PDF). The FASEB Journal. 36 (S1). doi:10.1096/fasebj.2022.36.S1.R2691. ISSN 0892-6638.
- ^ a b c d 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.
- ^ a b Jacob P, Shulgin AT (1994). "Structure-activity relationships of the classic hallucinogens and their analogs" (PDF). NIDA Res Monogr. 146: 74–91. PMID 8742795.
- ^ a b Shulgin, Alexander T. (2003). "Basic Pharmacology and Effects". In Laing, Richard R. (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.
- ^ 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.
External links
edit