Diampromide was develloped at the American Cyanamid Company, by some chemists who modified the methadone molecule a bit.
Preliminary clinical results indicate that the potency of diampromide lies between that of meperidine and morphine.
Synthesis:A benzene solution of N-methylphenethylamine
(1) and 2-bromopropionanilide
(2) was heated under reflux to give 2-(N-methylphenethylamino)-propionanilide in 81 % yield (M.P.: 65- 67 °C). The reduction of 2-(N-methylphenethylamino)-propionanilide with LiAlH
4in THF afforded 80 % of N
2-methyl-N
2-phenethyl-N
1-phenyl-1,2-propanediamine (B.P.: 138 - 144 °C / 0.2 mm Hg). When N
2-methyl-N
2-phenethyl-N
1-phenyl-1,2-propanediamine was acylated with propionic anhydride N-[2-(methyl-phenethylamino)-propyl]-propionanilide was obtained in 83 % yield (B.P.: 174 - 178 °C / 0.5 mm Hg). The sulphate salt crystallized from EtOH - Et
2O in 85 % yield (M.P.: 110 - 111 °C).
Precursors:
(1) J. Chem. Soc. (1910) p 2253
(2) Ber. (1892) vol 25 p 2919
Ref.: JACS (1959) vol 81 p 1518 - 1519
A comparison between diampromide, 2,3-seco-fentanyl and fentanyl can be found at:
http://www.ch.ic.ac.uk/ectoc/echet98/pub/028/index.htm
Diampromide seems to be 167 times less potent than fentanyl. Hence, I
estimate that the dose would be 4 - 8 mg.