Pempidine is a
ganglion-blocking drug, first reported in 1958 by two research groups working independently, and introduced as an oral treatment for
hypertension.[1]
Pharmacology
Reports on the "classical" pharmacology of pempidine have been published.[2][3] The Spinks group, at
ICI, compared pempidine, its N-ethyl analogue, and
mecamylamine in considerable detail, with additional data related to several structurally simpler compounds.[2]
Hall's method involved reacting
acetone with ammonia in the presence of
calcium chloride to give 2,2,6,6-tetramethyl-4-piperidone, which was then reduced under Wolff–Kishner conditions, followed by N-methylation of the resulting 2,2,6,6-tetramethylpiperidine with
methyl p-toluenesulfonate.
^
abHall HK (1957). "Steric Effects on the Base Strengths of Cyclic Amines". Journal of the American Chemical Society. 79 (20): 5444–5447.
doi:
10.1021/ja01577a031.
^Leonard NJ, Hauck Jr FP (October 1957). "Unsaturated amines. X. The mercuric acetate route to substituted piperidines, Δ2-tetrahydropyridines and Δ2-tetrahydroanabasines". Journal of the American Chemical Society. 79 (19): 5279–5292.
doi:
10.1021/ja01576a056.
^The boiling point of 147 °C given by these authors for their 1,2,2,6,6-pentamethylpiperidine is significantly below the range of approximately 182–188 °C reported by other chemists.