SYNTHESIS: A solution of 10.5 g propargylamine hydrochloride in 40 mL
MeOH was treated with 2.0 g 3,4-methylenedioxyphenylacetone (see under
MDMA for its preparation) followed by 0.55 g sodium cyanoborohydride.
Concentrated HCl was added as needed, to keep the pH constant at about
6. The reaction seemed to progress very slowly. After about five
days, the reaction mixture was added to 400 of H2O, acidified with
HCl, and extracted with 3x100 mL CH2Cl2. The aqueous phase was made
basic with 25% NaOH, and extracted with 3x100 mL CH2Cl2. Evaporation
of the solvent from these extracts yielded 1.6 g of a clear amber,
strong smelling oil which, on distillation at 105-110 °C at 0.2 mm/Hg,
yielded 1.0 g of an almost colorless oil. This was dissolved in 20 mL
IPA, neutralized with about 10 drops of concentrated HCl, and the
spontaneously formed crystals were diluted with 50 mL anhydrous Et2O.
After filtration, Et2O washing and air drying, there was obtained 1.1
g white crystals of 3,4-methylenedioxy-N-propargylamphetamine
hydrochloride (MDPL) with a mp of 189-190 °C. Anal. (C13H16ClNO2) N.
DOSAGE: greater than 150 mg.
DURATION: unknown.
EXTENSIONS AND COMMENTARY: There is a continuing uncertainty about the
name for the three-carbon radical that contains a triple bond. The
hydrocarbon is propyne, although it has been referred to as
methylacetylene in the older literature. The adjective, going from
the triple bond out to the point of attachment, is called propargyl,
as in propargyl chloride. When the adjective must be built on the
parent hydrocarbon, the double bond is on the outside and one reads
away from it, as in 2-propynyl something. However, when the
hydrocarbon is essentially the entire structure, then things get named
going towards the triple bond, as in 3-chloro-1-propyne. Wait. I'm
not done yet! When the actual hydrocarbon name becomes distorted into
the derivative, then the triple bond is again at the high end of the
numbering scheme. Propynol is 2-propyn-1-ol, which is, of course, the
same as 3-hydroxypropyne, or propargyl alcohol. The code MDPL takes
the first and last letter of the two of them, both propargyl and
propynyl.
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