SYNTHESIS: To a well stirred solution of 25 g ethanolamine hydrochloride in 75 mL MeOH there was added 4.45 g of 3,4-methylenedioxyphenylacetone (see under for its preparation) followed by 1.1 g sodium cyanoborohydride. Concentrated HCl in MeOH was added as required, over the next few days, to maintain the pH at about 6 as determined with external, dampened universal pH paper. The reaction mixture was added to 300 mL H₂O and made strongly acidic with an excess of HCl. After washing with 3×100 mL CH₂Cl₂ the aqueous phase was made basic with 25% NaOH, and extracted with 4×100 mL CH₂Cl₂. Removal of the solvent under vacuum yielded 3.5 g of a viscous off-white oil that was distilled at 160 °C at 1.3 mm/Hg to give 2.0 g of a white viscous oil. The pot residue remained fluid, but was discarded. This distillate was dissolved in 8.0 mL IPA to give, eventually, a clear solution. This was neutralized with concentrated HCl and diluted with 100 mL anhydrous Et₂O. The loose white crystals of 3,4-methylenedioxy-N-(2-hydroxyethyl)amphetamine hydrochloride (MDHOET) that formed were removed by filtration, washed with Et₂O, and air dried. These weighed 2.3 g, and had a mp of 147–148 °C. Anal. (C₁₂H₁₈ClNO₃) N.

DOSAGE: greater than 50 mg.

DURATION: unknown.

EXTENSIONS AND COMMENTARY: Most compounds with bare, exposed polar groups like hydroxyls are not centrally active, as they simply do not have any way of getting into the brain. MDHOET is certainly not very active, if it is active at all.