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March 31, 1951


JAMA. 1951;145(13):967-972. doi:10.1001/jama.1951.02920310023006

The use of alkyl phosphate anticholinesterase agents in the treatment of myasthenia gravis has caused considerable interest in the last few years. Diisopropyl fluorophosphate,1 hexaethyl tetraphosphate2 and tetraethyl pyrophosphate3 have all been used. While tetraethyl pyrophosphate proved to be the most effective, it had two disadvantages. Toxic manifestations were frequent, and it was rapidly hydrolyzed when exposed to moisture. These disadvantages seem to be characteristic of cholinergic phosphates, in which all the alkyl groups in the molecule are linked to phosphorus by means of oxygen atoms.

Octamethyl pyrophosphoramide, which lacks the alkyl-oxy-phosphate linkage, has the following chemical structure.

It is a colorless liquid with a faint taste similar to that of black pepper and a specific gravity of 1.137. It is soluble in water and in most organic solvents. The molecular weight is 286, and it has a relatively low volatility. This compound was first synthesized by

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