Helional (1 g) was dissolved in ethanol (2 ml) in a 50 mL beaker with stirring. Hydroxylamine hydrochloride (1 ml, 50% w/v in water) was added. An aqueous solution of sodium carbonate (1 ml, 40% w/v) was added dropwise with stirring and the mixture was stirred at room temperature for 19 hours. A light brown coloured gel was formed and the solvent was evaporated by standing at room temperature for 1-2 days. The resultant aldoxime compound was used directly in the subsequent procedure without purification.

The aldoxime product (described above) and nickel acetate (0.02 g) were dissolved in xylene (3 ml) with stirring. The mixture was refluxed for 5 hours at 140°C in an oil bath. A dark brown solid precipitated and was collected by filtration and dried in air.

Sodium hypochlorite solution (1.25 ml, 4.2%) and sodium hydroxide solution (1 ml, 5%) was added to the solid amide (0.1 g). In reflux set-up the mixture was stirred, and the heat slowly increased to 80°C and held there for 30 minutes. After being allowed to cool a liquid-liquid extraction was performed with diethyl ether. Sodium sulfate was added to remove any residual water and then filtered back out. The ether solution was evaporated off leaving the amine base in the form of a dark brown oil. The method for this step was reported by Monk and Mohan 1999 (61). MDA HCl synthesis The amine base was dissolved into dry diethyl ether (2 ml) and HCl in diethyl ether (1 ml) was added to precipitate the amine salt. Then the solution was evaporated off. The amine salt was then washed with cold acetone and dried resulting in an off-white crystalline solid.