2986. 3,4-Diaminopyridine

Nomenclature

CAS number: 54-96-6
3,4-Pyridinediamine; 3,4-DAP.
C5H7N3; mol wt 109.13.
C 55.03%, H 6.47%, N 38.50%.

Description and references

Potassium channel blocker; antagonizes non-depolarizing neuromuscular blockade. Prepn: O. Bremer, Ann. 518, 274 (1935); J. W. Clark-Lewis, R. P. Singh, J. Chem. Soc. 1962, 2379; J. B. Campbell et al., J. Heterocycl. Chem. 23, 669 (1986). HPLC determn in serum: J. Leslie, C. T. Bever, J. Chromatogr. 496, 214 (1989). Acute toxicity: P. Lechat et al., Ann. Pharm. Fr. 26, 345 (1968). Effect on neuromuscular transmission: J. Molgo et al., Eur. J. Pharmacol. 61, 25 (1980); R. H. Thomsen, D. F. Wilson, J. Pharmacol. Exp. Ther. 227, 260 (1983). Evaluation in human botulism: A. P. Ball et al., Q. J. Med. 48, 473 (1979). Clinical evaluations in myasthenic syndromes: K. M. McEvoy et al., N. Engl. J. Med. 321, 1567 (1989); J. Palace et al., J. Neurol. Neurosurg. Psychiatry 54, 1069 (1991); in multiple sclerosis: C. T. Bever, Jr. et al., Ann. Neurol. 27, 421 (1990); idem, ibid. 36, S118 (1994).

Chemical structure

Properties

Needles from water, mp 220° (Clark-Lewis, Singh); also reported as white to beige crystals from water, mp 218-219° (Campbell). Readily sol in water, alcohol; slightly sol in ether. LD50 i.v. in mice: 13 mg/kg (Lechat).

Use

Intermediate in synthesis of heterocyclic compds.