2,5-Dimethoxy-4-isobutylamphetamine

2,5-Dimethoxy-4-isobutylamphetamine (DOIB or DOiBu) is a serotonin 5-HT_2A receptor agonist, serotonergic psychedelic, and anti-inflammatory drug of the phenethylamine, amphetamine, and DOx families.^{[1][2][3][4][5]} 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.^[4]

2,5-Dimethoxy-4-isobutylamphetamine

Clinical data
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
Identifiers
IUPAC name 1-[2,5-dimethoxy-4-(2-methylpropyl)phenyl]propan-2-amine
CAS Number	89556-64-9
PubChem CID	44374984
ChemSpider	23231800
ChEMBL	ChEMBL161299
Chemical and physical data
Formula	C15H25NO2
Molar mass	251.370 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(C)CC1=CC(=C(C=C1OC)CC(C)N)OC
InChI InChI=1S/C15H25NO2/c1-10(2)6-12-8-15(18-5)13(7-11(3)16)9-14(12)17-4/h8-11H,6-7,16H2,1-5H3 Key:ZLESHKOTWSWEGW-UHFFFAOYSA-N

The drug is a full agonist of the serotonin 5-HT_2A receptor, with an EC₅₀Tooltip half-maximal effective concentration of 12.6 nM and an E_maxTooltip maximal efficacy of 98.8%, both for calcium mobilization.^[5] It is about one-third as potent as DOM in rodent drug discrimination tests and also substitutes for LSD in these tests.^[3][6][1][2] 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.^{[2][3][7][8][9]}

In addition to its psychedelic effects, DOIB has highly potent anti-inflammatory effects in preclinical research.^[5] It was more potent than almost any other tested psychedelic.^[5] The drug was notably more potent than (R)-DOI, but was less potent than 2C-I (the most potent assessed compound).^[5]

Some other notable analogues of DOIB include DOBU (n-butyl), DOSB (sec-butyl), and DOTB (tert-butyl).^{[1][2][7][8][9]}

DOIB, DOSB, and DOTB.^{[1][2][7][8][9]}

See also

• 2C-iBu (ELE-02)
• Anti-inflammatory § Serotonergic psychedelics