2,5-Dimethoxy-4-butylamphetamine
Substituted amphetamine psychedelic drug
From Wikipedia, the free encyclopedia
2,5-Dimethoxy-4-butylamphetamine (DOBU) is a psychedelic drug of the phenethylamine, amphetamine, and DOx families related to DOM.[2][1][4] It is the derivative of DOM in which the methyl group at the 4 position has been replaced with a butyl group.[2] The drug is taken orally.[1][2][3]
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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 | Serotonin 5-HT2 receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen |
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| Duration of action | "Very long"[2] |
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| Formula | C15H25NO2 |
| Molar mass | 251.370 g·mol−1 |
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It acts as a serotonin receptor agonist, including of the serotonin 5-HT2A receptor.[4] The drug produces psychedelic-like effects in animals.[4]
DOBU was first described in the literature by Alexander Shulgin in 1970.[5] Subsequently, it was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).[2]
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 3 mg orally produced clear threshold effects and that it was active at a dose 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 of its qualitative effects.[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] The effects of higher doses of DOBU have not been described beyond them producing hallucinogenic effects.[2][3]
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.[4][6] It has been found to act as a potent full agonist of the serotonin 5-HT2A and 5-HT2C receptors.[4][7][8] The drug is also a serotonin 5-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 rodent drug discrimination tests, albeit several-fold less potently than DOET or DOPR.[9][6][10][11] 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.[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 include hyperlocomotion at lower doses, hypolocomotion at higher doses, and hypothermia at higher doses.[4]
Pharmacokinetics
DOBU crosses the blood–brain barrier in rodents.[4]
Chemistry
Synthesis
The chemical synthesis of DOBU has been described.[2]
Analogues
Analogues of DOBU include 2,5-dimethoxyamphetamine (2,5-DMA), DOM, DOET, DOPR, DOAM, DOHx, and 2C-Bu, among others.[2][4]
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.[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 and DOAM partially generalized to DOM in animal drug discrimination tests.[9]
History
DOBU was first described in the literature by Alexander Shulgin in 1970.[5] Subsequently, it was described in greater detail by Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved) in 1991.[2]
Society and culture
Legal status
Canada
DOBU is a controlled substance in Canada under phenethylamine blanket-ban language.[15]
United States
DOBU is not an explicitly controlled substance in the United States.[16] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.