|Chemical and physical data|
|Molar mass||155.28 g/mol|
|3D model (JSmol)|
Reports on the "classical" pharmacology of pempidine have been published. 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.
LD50 for the HCl salt of pempidine in mice: 74 mg/kg (i.v.); 125 mg/kg (i.p.); 413 mg/kg (p.o.).
Pempidine is a liquid, b.p. 187–188°; d = 0.858 g/cm3.
Two early syntheses of this compound are those of Leonard and Hauck, and Hall. These are very similar in principle: Leonard and Hauck reacted phorone with ammonia, to produce 2,2,6,6-tetramethyl-4-piperidone, which was then reduced by means of the Wolff–Kishner reduction to 2,2,6,6-tetramethylpiperidine; this secondary amine was then N-methylated using methyl iodide and potassium carbonate.
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.
- A. Spinks and E. H. P. Young (1958) Nat. 181 1397
- G. E. Lee et al. (1958) Nat. 181 1717.
- A. Spinks et al. (1958) Br. J. Pharmacol. Chemother. 13 501-520.
- D. F. Muggleton and H. W.Reading (1959) Br. J. Pharmacol. Chemother. 14 202
- H. K. Hall (1957) J. Am. Chem. Soc. 79 5447-5451.
- N. J. Leonard and F. P. Hauck (1957) J. Am. Chem. Soc. 79 5279-5292.
- The "trivial" name of this compound is triacetonamine.
- The boiling point of 147° given by these authors for their N,2,2,6,6-pentamethylpiperidine (pempidine) is significantly below the range of ~182–188° reported by other chemists.
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