Phosphorus-Nitrogen Compounds. 26. Phosphaminimides. 2. 2,2'-Phosphinylidenebis(1,1,1-trimethylhydrazinium) Iodide Inner Salts as Agents Affecting Ganglionic Transmission

The N-2 atoms of phosphorus 2,2-dimethylhydrazides, contrary to a previous report, can be methylated by iodomethane. Treatment of the resulting dihydrazinium iodides with aqueous sodium hydroxide results in mono- instead of didehydroiodination, apparently due to resonance stabilization of the inner...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1985-05, Vol.28 (5), p.595-597
Main Authors: Cates, Lindley A, Li, Ven-Shun, Saddawi, Bashir H, Alkadhi, Karim A
Format: Article
Language:English
Subjects:
Animals
Artemia
Ganglia, Sympathetic - drug effects
Ganglionic Blockers - chemical synthesis
Hydrazines - chemical synthesis
Hydrazines - pharmacology
Hydrazines - toxicity
In Vitro Techniques
Lethal Dose 50
Organophosphorus Compounds - chemical synthesis
Organophosphorus Compounds - pharmacology
Organophosphorus Compounds - toxicity
Rats
Rats, Inbred Strains
Structure-Activity Relationship
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Summary:The N-2 atoms of phosphorus 2,2-dimethylhydrazides, contrary to a previous report, can be methylated by iodomethane. Treatment of the resulting dihydrazinium iodides with aqueous sodium hydroxide results in mono- instead of didehydroiodination, apparently due to resonance stabilization of the inner salt form. The phosphaminimide products and their hydrazinium iodide precursors blocked sympathetic ganglionic transmission while one dihydrazide intermediate produced potentiation. Brine shrimp testing indicated that conversion of a hydrazinium iodide to an aminimide moiety results in decreased toxicity.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm50001a010