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#107 MDHOET

HYDROXYETHYL-MDA; 3,4-METHYLENEDIOXY-N-(2-HYDROXYETHYL)AMPHETAMINE

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 MDMA 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 3x100 mL CH2Cl2 the aqueous phase was made basic with 25% NaOH, and extracted with 4x100 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-hydroxy-ethyl)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.

There was one report that at very high doses some central effects were indeed observed. With quantities in the several hundreds of milligrams a picture emerged of changes in perceived color and depth perception, but without euphoria. It was said to resemble a mild dose of ketamine. This is an interesting comment, in that ketamine has found its major medical use as an anesthetic, and MDHOET is among the most effective of all the N-substituted MDA derivatives assayed in several animal analgesia models.

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