Description and references

Strong organic base existing primarily as guanidinium ion at physiological pH. Found in turnip juice, mushrooms, corn germ, rice hulls, mussels, earthworms. Prepn of nitrate from dicyanodiamide + ammonium nitrate: Smith et al., Ind. Eng. Chem. 23, 1124 (1931); Davis, Org. Synth. coll. vol. I (2nd ed., 1941) p 302; from SO₂, CO₂, + NH₃: Boivin, US 2762843 (1956); from urea: Mackay, US 2590257 (1952 to Am. Cyanamid); Craig, Minor, US 3009949 (1961 to Deere); Shaver, US 3108999 (1963 to Monsanto); from ammonium thiocyanate or thiourea + ammonia: Watt, Makosky, Ind. Eng. Chem. 46, 2599 (1954). Pharmacology as muscle stimulant: A. I. Podlesnaya, Bull. Exp. Biol. Med. 61, 291 (1966). Clinical evaluation with pyridostigmine in Lambert-Eaton myasthenic syndrome: S. J. Oh et al., Muscle Nerve 20, 1146 (1997). Review of mode of action: D. R. Tershak et al., “Guanidine” in Handbook of Experimental Pharmacology Vol. 61, G. V. R. Born et al., Eds. entitled “Chemotherapy of Viral Infections” P. E. Came, L. A. Caliguiri, Eds. (Springer-Verlag, New York, 1982) pp 343-375. Review of structure activity studies: F. Davidoff, N. Engl. J. Med. 289, 141-146 (1973). General reviews: M. Schenck, Pharmazie 3, 5 (1948); G. Schaefer, “Guanidines and Biguanidines” in International Encyclopedia of Pharmacology and Therapeutics 107, M. Erecinska, Ed. (Pergamon, Oxford 1981) pp 165-185.

Properties

Derivative

Derivative