2,5-Dimethoxy-4-isobutylamphetamine
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| Other names | 2,5-Dimethoxy-4-isobutylamphetamine; 4-Isobutyl-2,5-dimethoxyamphetamine; DOIB; DOiBu; 2,5-Dimethoxy-4-(2-methylpropyl)amphetamine |
| Routes of administration | Oral |
| Drug class | Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen; Anti-inflammatory drug |
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| Formula | C15H25NO2 |
| Molar mass | 251.370 g·mol−1 |
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2,5-Dimethoxy-4-isobutylamphetamine (DOIB or DOiBu) is a serotonin 5-HT2A receptor agonist, serotonergic psychedelic, and anti-inflammatory drug of the phenethylamine, amphetamine, and DOx families. It is part of the series of straight-chain and branched-chain 4-alkylated DOx drugs that also includes DOM, DOET, DOPR, DOBU, DOAM, and DOHx, among others.
The drug is a full agonist of the serotonin 5-HT2A receptor, with an EC50 of 12.6 nM and an Emax of 98.8%, both for calcium mobilization. It is about one-third as potent as DOM in rodent drug discrimination tests and also substitutes for LSD in these tests. In humans, DOIB is active at doses of 10 to 15 mg orally, and hence is also about one-third as potent as DOM in humans as in rodents.
In addition to its psychedelic effects, DOIB has highly potent anti-inflammatory effects in preclinical research. It was more potent than almost any other tested psychedelic. The drug was notably more potent than (R)-DOI, but was less potent than 2C-I (the most potent assessed compound).
Some other notable analogues of DOIB include DOBU (n-butyl), DOSB (sec-butyl), and DOTB (tert-butyl).