34433-31-3 Usage
Chemical Properties
Off-White Solid
Uses
Cholinesterase reactivator. A potential antidote for organophosphate poisoning
General Description
HI-6 functions as an antidote for treating intoxication caused by nerve agents. It acts as a potent drug in radiation protection and suppresses oxidative stress. HI-6 prevents the toxicity of the antineoplastic drug irinotecan.
Biological Activity
asoxime, also known as hi-6, is an asymmetric bis-pyridinium aldoxime and reactivates ache via nucleophilic attack of oximate anions on organophosphate-ache conjugates.ache, one of the primary targets of organophosphates, is inactivated by organophosphates via reacting covalently with the active center serine, which blocks the hydrolyzation of acetylcholine at peripheral and central synapses. additionally, the accumulation of acetylcholine leads to an over-stimulation of cholinergic receptors, which disrupts a variety of biological functions.
Biochem/physiol Actions
HI-6 is an efficient oxime cholinesterase reactivator that is used as an antidote for organophosphates (Ops) exposure.
in vitro
hi-6 showed a bacteriostatic effect on francisella tularensis (f. tularensis) and inhibited the growth of f. tularensis when treated with 100 mm hi-6 [1].
in vivo
female balb/c mice, infected by f. tularensis, were administrated subcutaneously with 100 μl hi-6 for ten days. the lower dose of hi-6 yielded in different symptoms and mortality. compared to mice injected only with tularemia, groups of mice exposed to the lower dose of hi-6 showed a decline in mortality, which can be explained via higher efficacy of bacteriostatic effect while the toxic effect was decreased [1]. female wistar rats were treated intramuscularly with hi-6 at a dose of 15.6 or 156 mg/kg for one day. the level of thiobarbituric acid reactive substances was increased, which was triggered by hi-62 [2].
IC 50
8.9 μm: blocks ache in human; 126 μm: inhibits acetylcholinesterase (ache) in bovine; 160 μm: blocks muscarinic acetylcholine receptor m1, m2, m3 and m4 in mouse.
references
[1]. pohanka, m., pavli, o., pikula, j., treml, f., & kuca, k. modulation of tularemia disease progress by the bisquaternary pyridinium oxime hi-6. acta veterinaria brno. 2010; 79(3): 443-448.[2]. pohanka, m., sobotka, j., svobodova, h., & stetina, r. sulfur mustard induced oxidative stress and its alteration using asoxime (hi-6). interdisciplinary toxicology. 2013; 6(4).
Check Digit Verification of cas no
The CAS Registry Mumber 34433-31-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,4,4,3 and 3 respectively; the second part has 2 digits, 3 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 34433-31:
(7*3)+(6*4)+(5*4)+(4*3)+(3*3)+(2*3)+(1*1)=93
93 % 10 = 3
So 34433-31-3 is a valid CAS Registry Number.
InChI:InChI=1/C14H14N4O3.2ClH/c15-14(19)12-4-7-17(8-5-12)10-21-11-18-6-2-1-3-13(18)9-16-20;;/h1-9H,10-11H2,(H-,15,19);2*1H/b13-9-;;
34433-31-3Relevant articles and documents
Process for halomethyl ethers of hydroxyiminomethyl quaternary pyridinium salts
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Page/Page column 7, (2008/06/13)
A halide salt of a 1-(hydroxyiminomethyl-1-pyridino)-3-(halomethyl)-2-oxapropane is prepared by adding a pyridinealdoxime to a bis-halomethylether in such a manner that the bis-halomethylether is maintained in excess throughout the addition. This procedure produces the halide salt of a 1-(hydroxyiminomethyl-1-pyridino)-3-(halomethyl)-2-oxapropane in high yield and purity, which facilitates its use as an intermediate in the manufacture of an asymmetrically substituted 1,3-di (1-pyridino)-2-oxapropane, a class of compounds that are generally useful antidotes to various toxic agents. A prominent member of the class is the dimethylsulfonate salt of 1-(2-hydroxyiminomethyl-1-pyridino)-3-(4-carbamoyl-1-pyridino)-2-oxapropane. The use of mercaptoalkyl-functionalized polymers is disclosed as a preferred metal ion scavenger for a final purification step in the manufacture of these compounds.
