2,5-Dimethoxy-4-butylamphetamine

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2,5-Dimethoxy-4-butylamphetamine
DOBU.svg
Clinical data
Other namesDOBU; 2,5-Dimethoxy-4-butylamphetamine; 4-Butyl-2,5-dimethoxyamphetamine
Routes of
administration 		Oral [1] [2]
Drug class Serotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen
Identifiers
  • 1-(4-butyl-2,5-dimethoxyphenyl)propan-2-amine
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)
  • 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 Yes check.svgY
  • Key:NGVDYAULSQKEGW-UHFFFAOYSA-N Yes check.svgY
   (verify)

2,5-Dimethoxy-4-butylamphetamine (DOBU) is a lesser-known serotonin receptor agonist and serotonergic psychedelic of the amphetamine and DOx families. [2] [1]

Contents

Effects

DOBU was first synthesized by Alexander Shulgin. [1] [2] In his book PiHKAL (Phenethylamines i Have Known And Loved) and other publications, he and colleagues stated that doses of 1 to 3 mg orally produced clear threshold effects and it was active at a dosage 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 on the qualitative effects of DOAM. [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]

Pharmacology

Compared to shorter chain homologues such as DOM, DOET, and DOPR which are all potent hallucinogens, DOBU has an even higher serotonin 5-HT2 receptor affinity. [4] It has been found to act as a potent full agonist of the serotonin 5-HT2A and 5-HT2C receptors. [5] [6] Findings are mixed with regard to the serotonin 5-HT2B receptor, with DOBU reported to act as a potent and high-efficacy partial agonist of this receptor [6] or to be inactive as an agonist of the receptor. [5]

DOBU fully substitutes for DOM in rodent drug discrimination tests, albeit several-fold less potently than DOET or DOPR. [7] [4] [8] [9] 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, and DOC. [8] The doses at which DOBU produces peak head twitches are similar to those of DOM and DOET. [8]

Chemistry

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. [10] [11] [12] All are significantly less potent than DOBU, with DOIB being active at around 10–15 mg, and DOSB at 25–30 mg. [10] The most highly branched isomer DOTB was completely inactive in both animal and human trials. [10] However, it was also reported that DOTB and DOAM partially generalized to DOM in animal drug discrimination tests. [7]

DOIB, DOSB, and DOTB. DOIB,DOSBandDOTB.png
DOIB, DOSB, and DOTB.

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 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 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 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.
  5. 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.
  6. 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.
  7. 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.
  8. 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.
  9. ↑ 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.
  10. 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.
  11. 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.
  12. 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.


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