Amiton

Title: Amiton
CAS Registry Number: 78-53-5
CAS Name: S-[2-(Diethylamino)ethyl]phosphorothioic acid O,O-diethyl ester
Additional Names: O,O-diethyl S-(b-diethylamino)ethyl phosphorothiolate
Trademarks: Inferno; Metramac; Tetram
Molecular Formula: C10H24NO3PS
Molecular Weight: 269.34
Percent Composition: C 44.59%, H 8.98%, N 5.20%, O 17.82%, P 11.50%, S 11.91%
Literature References: Prepn: Ghosh, Newman, Chem. Ind. (London) 1955, 118; Fukuto, Stafford, J. Am. Chem. Soc. 79, 6083 (1957); Lorenz, Schrader, US 3082240 (1963 to Bayer). Toxicity studies: Shaffer, West, Toxicol. Appl. Pharmacol. 2, 1 (1960); Frawley et al., ibid. 5, 605 (1963).
Properties: Liquid. bp0.01 76°; bp0.2 110°. nD27 1.4655. LD50 orally in rats: 5.4 mg/kg (Frawley).
Boiling point: bp0.01 76°; bp0.2 110°
Index of refraction: nD27 1.4655
Toxicity data: LD50 orally in rats: 5.4 mg/kg (Frawley)
Derivative Type: Acid oxalate (hydrogen oxalate)
Molecular Formula: C10H24NO3PS.C2H2O4
Molecular Weight: 359.38
Percent Composition: C 40.10%, H 7.29%, N 3.90%, O 31.16%, P 8.62%, S 8.92%
Properties: Crystals from isopropanol + ether, mp 98-99°. LD50 orally in male albino rats: 9 mg/kg (Shaffer, West).
Melting point: mp 98-99°
Toxicity data: LD50 orally in male albino rats: 9 mg/kg (Shaffer, West)
CAUTION: Cholinesterase inhibitor.
Use: Contact insecticide, miticide.
Status: This monograph has been retired and is no longer subject to revision or update.
Amitriptyline Amitriptylinoxide Amitrole Amixetrine Amlexanox

VG (nerve agent)
Skeletal formula of VG
Ball-and-stick model of VG
Identifiers
CAS number 78-53-5 N
PubChem 6542
ChemSpider 6294 YesY
Jmol-3D images Image 1
Properties
Molecular formula C10H24NO3PS
Molar mass 269.34 g mol−1
Boiling point 110 °C @ 0.2 mmHg
Vapor pressure 0.01 mmHg @ 80 °C
Hazards
NFPA 704
NFPA 704.svg
2
4
1
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

VG (IUPAC name: O,O-diethyl S-[2-(diethylamino)ethyl] phosphorothioate) (also called Amiton or Tetram) is a "V-series" nerve agent chemically similar to the better-known VX nerve agent. Tetram is the common Russian name for the substance. Amiton was the trade name for the substance when it was marketed as an insecticide by ICI in the mid-1950s.

With a toxicity of about 1/10 that of VX, i.e. similar to that of sarin,[1] it is now considered too dangerous for use in agriculture[2] but unlike other nerve agents it is classified under Schedule 2 of the Chemical Weapons Convention rather than the more restrictive Schedule 1. It is thought that North Korea may have military stockpiles of this chemical .[3]

During the early 1950s at least three chemical companies working on organo-phosphorus insecticides independently discovered the amazing toxicity of these chemicals.[4] In 1952, Dr. Ranajit Ghosh, a chemist working for ICI at their Plant Protection Laboratories was investigating the potential of organophosphate esters of substituted aminoethanethiols for use as pesticides. Like the earlier German investigators of organophosphates in the late 1930s who had discovered the G-series nerve agents, Dr. Ghosh discovered that their action on cholinesterase made them effective pesticides. One of them, Amiton, was described in a 1955 paper by Ghosh and another chemist, J. F. Newman, as being particularly effective against mites.[4] It was brought to market as an insecticide by the company in 1954 but was subsequently withdrawn as too toxic.[5]

The toxicity of these substances had not passed unnoticed by the British Government, as some of the compounds had already been sent to their research facility at Porton Down for evaluation. Some of the chemicals from this class of compounds formed a new group of nerve agents called V Agents. The British Government unilaterally renounced chemical and biological weapons in 1956, although in 1958 traded their research on VX technology with the United States Government in exchange for information on thermonuclear weapons. The US then went into production of large amounts of the chemically similar, but much more toxic VX in 1961.[6]