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| Other names | DOBU; 2,5-Dimethoxy-4-butylamphetamine; 4-Butyl-2,5-dimethoxyamphetamine |
| Routes of administration | Oral[1][2][3] |
| Drug class | Serotonin5-HT2 receptoragonist;Serotonin 5-HT2A receptor agonist;Serotonergic psychedelic;Hallucinogen |
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| Pharmacokinetic data | |
| Duration of action | "Very long"[2] |
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| Chemical and physical data | |
| Formula | C15H25NO2 |
| Molar mass | 251.370 g·mol−1 |
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2,5-Dimethoxy-4-butylamphetamine (DOBU) is apsychedelic drug of thephenethylamine,amphetamine, andDOx families related toDOM.[2][1][4] It is thederivative of DOM in which themethyl group at the 4 position has been replaced with abutyl group.[2] The drug is takenorally.[1][2][3]
It acts as aserotonin receptor agonist, including of theserotonin5-HT2A receptor.[4] The drug produces psychedelic-like effects in animals.[4]
DOBU was first described in the literature byAlexander Shulgin in 1970.[5] Subsequently, it was described in greater detail by Shulgin in his 1991 bookPiHKAL (Phenethylamines I Have Known and Loved).[2]
In his bookPiHKAL (Phenethylamines I Have Known and Loved) and other publications,Alexander Shulgin and colleagues stated that doses of 1 to 3 mgorally produced clear threshold effects and that it was active at a dose of slightly more than twice that ofDOM.[1][2][3] It was stated that 10 mg DOBU was required to produce hallucinogenic effects.[3] The drug'sduration was listed as "very long".[2] There was limited investigation of its qualitative effects.[1] However, inPiHKAL, at the assessed doses of 2.2 mg and 2.8 mg, it was described as producingparesthesia and difficultysleeping with few other effects.[2] The effects of higher doses of DOBU have not been described beyond them producing hallucinogenic effects.[2][3]
Compared to shorter-chainhomologues such asDOM,DOET, andDOPR, which are allpotentpsychedelics, DOBU has even higheraffinity for theserotonin5-HT2A receptor.[4][6] It has been found to act as apotentfull agonist of the serotonin5-HT2A and5-HT2C receptors.[4][7][8] The drug is also a serotonin5-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 rodentdrug discrimination tests, albeit several-fold less potently than DOET or DOPR.[9][6][10][11] 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, DOPR, andDOC.[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 includehyperlocomotion at lower doses,hypolocomotion at higher doses, andhypothermia at higher doses.[4]
DOBU crosses theblood–brain barrier in rodents.[4]
Thechemical synthesis of DOBU has been described.[2]
Analogues of DOBU include2,5-dimethoxyamphetamine (2,5-DMA),DOM,DOET,DOPR, andDOAM, among others.[2][4]
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.[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 andDOAM partially generalized to DOM in animaldrug discrimination tests.[9]
DOBU was first described in the literature byAlexander Shulgin in 1970.[5] Subsequently, it was described in greater detail by Shulgin in his 1991 bookPiHKAL (Phenethylamines I Have Known and Loved).[2]
DOBU is acontrolled substance inCanada under phenethylamine blanket-ban language.[15]
DOBU is not an explicitlycontrolled substance in theUnited States.[16] However, it could be considered a controlled substance under theFederal Analogue Act if intended for human consumption.
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.
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.
