DOBU was first synthesized byAlexander Shulgin.[1][2] In his bookPiHKAL (Phenethylamines i Have Known And Loved) and other publications, he and colleagues stated that doses of 1 to 3mgorally produced clear threshold effects and it was active at a dosage of slightly more than twice that ofDOM.[1][2][3] It was stated that 10mg DOBU was required to produce hallucinogenic effects.[3] The drug'sduration was listed as "very long".[2] There was limited investigation on the qualitative effects of DOAM.[1] However, inPiHKAL, at the assessed doses of 2.2mg and 2.8mg, it was described as producingparesthesia and difficultysleeping with few other effects.[2]
DOBU fully substitutes forDOM in rodentdrug discrimination tests, albeit several-fold less potently thanDOET orDOPR.[7][4][8][9] In addition, DOBU robustly induces thehead-twitch response, a behavioral proxy ofpsychedelic-like effects, in rodents, and maximally does so about as strongly as other DOx drugs like DOM, DOET, andDOC.[8] The doses at which DOBU produces peak head twitches are similar to those of DOM and DOET.[8]
Alternativeskeletal 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, theiso-butyl,sec-butyl andtert-butyl compounds being calledDOIB,DOSB, andDOTB, 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 andDOAM partially generalized to DOM in animaldrug discrimination tests.[7]
^abcdeShulgin 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.ISBN978-1-4757-0512-6.3.4.10. 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.
^abBraun U, Braun G, Jacob P, Nichols DE, Shulgin AT (1978)."Mescaline analogs: substitutions at the 4-position"(PDF).NIDA Res Monogr (22):27–37.PMID101882. Archived fromthe 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.
^abSeggel 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.PMID2308135.
^abGlennon 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.PMID7071089.
