Linked Life Data

3827594

Source:http://linkedlifedata.com/resource/pubmed/id/3827594

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
4
pubmed:dateCreated
1987-4-15
pubmed:abstractText
HI 6 has been shown to be efficacious in soman intoxication of laboratory animals by reactivation of acetylcholinesterase. To assess possible risks involved in the administration of HI 6 its degradation products were analyzed at pH 2.0, 4.0, 7.4, and 9.0. At pH 2.0, where HI 6 in aqueous solution has its maximal stability, attack on the aminal-acetal bond of the "ether bridge" predominates, with formation of formaldehyde, isonicotinamide, and pyridine-2-aldoxime. Besides, HI 6 decomposes at the oxime group yielding 2-cyanopyridine. Liberation of hydrocyanic acid at pH 2.0 is below 5%. At pH 7.4, primary attack is on the oxime group, resulting in formation of the corresponding pyridone via an intermediate nitrile. The pyridone has been isolated and identified as 2-pyridinone, 1-[(4-carbamoylpyridinio)methoxy)methyl)formate. This major metabolite deaminates further to the 2-pyridinone, 1-[(4-carboxypyridinio)methoxy)methyl) derivative, which ultimately decomposes into formaldehyde, isonicotinic acid, and 2-pyridone. Hydrolysis of the acid amide group probably also occurs with HI 6 itself. Significant amounts of free hydrocyanic acid were only detected in the presence of an alkali trap; otherwise hydrocyanic acid reacts with formaldehyde to yield hydroxyacetonitrile from which hydrocyanic acid can be liberated again. Up to 0.6 equivalents of hydrocyanic acid were evolved at pH 7.4. After repetitive administration and impaired renal elimination of HI 6, e.g. during renal shock, there might be some risk of cyanide intoxication.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Dec
pubmed:issn
0340-5761
pubmed:author
pubmed:issnType
Print
pubmed:volume
59
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
266-71
pubmed:dateRevised
2010-11-18
pubmed:meshHeading
pubmed:year
1986
pubmed:articleTitle
Studies on the decomposition of the oxime HI 6 in aqueous solution.
pubmed:publicationType
Journal Article