2,5-Dimethoxy-4-tert-butylamphetamine

Pharmacodynamics

DOTB binds with high affinity to the serotonin 5-HT₂ receptors, including to the serotonin 5-HT_2A and 5-HT_2C receptors and, to about a 10-fold lesser extent, to the serotonin 5-HT_2B receptor.^{[9][10][11][12]} It has been found to act as a partial agonist of the serotonin 5-HT_2A receptor, with an intrinsic efficacy of about 30% for phosphatidylinositol hydrolysis and about half of the efficacy of (R)-DOB.^[13][14] DOTB has also been assessed and found to act as a partial agonist of the serotonin 5-HT_2B receptor (E_maxTooltip maximal efficacy = 69%).^[10]

The drug appeared to be inactive in animals in the conditioned avoidance test in rodents.^[3][15] DOTB only partially substituted for DOM in rodent drug discrimination tests (up to 70% responding, followed by disruption at higher doses) and with much lower potency than other DOx drugs.^[16][17] In combination with DOM, DOTB produced some antagonism of the stimulus generalization of DOM, suggesting action as a lower-efficacy partial agonist of the serotonin 5-HT_2A receptor.^[12] Unlike DOM but similarly to DOAM, DOTB did not substitute for 5-MeO-DMT in rodent drug discrimination tests.^[5] It also did not affect locomotor activity in rodents, again in contrast to other DOx drugs, though there were non-significant increases in locomotion at the highest assessed doses.^[14] It did still produce hyperthermia in rabbits similarly to other DOx drugs, albeit with dramatically reduced potency.^[18][15][5]

Synthesis

The chemical synthesis of DOTB has been described.^[3]

Analogues

DOTB 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][9][5]

Some other notable analogues of DOTB include DOBU (n-butyl), DOIB (iso-butyl), and DOSB (sec-butyl).^{[1][2][7][8][6]}

Legal status