Demeton

Demeton
Names
	Preferred IUPAC name O,O-Diethyl S-[2-(ethylsulfanyl)ethyl] phosphorothioate
	Other names Demeton thiol; Izosystox
Identifiers
CAS Number	126-75-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	23115 ;
ECHA InfoCard	100.004.366
PubChem CID	24723;
UNII	3UQ7N6O63K ;
CompTox Dashboard (EPA)	DTXSID9037535 ;
	InChI InChI=1S/C8H19O3PS2/c1-4-10-12(9,11-5-2)14-8-7-13-6-3/h4-8H2,1-3H3 Key: GRPRVIYRYGLIJU-UHFFFAOYSA-N ; InChI=1/C8H19O3PS2/c1-4-10-12(9,11-5-2)14-8-7-13-6-3/h4-8H2,1-3H3 Key: GRPRVIYRYGLIJU-UHFFFAOYAI;
	SMILES O=P(OCC)(SCCSCC)OCC;
Properties
Chemical formula	C8H19O3PS2
Molar mass	258.3384 g/mol
Appearance	colorless to amber oily liquid
Odor	sulfurous
Density	1.146 g/cm3
Boiling point	128 °C (262 °F; 401 K)
Solubility in water	2.0 g/100 mL
log P	2.38
Refractive index (nD)	1.5
Hazards
Flash point	147.6 °C (297.7 °F; 420.8 K)
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	1.5 mg/kg (oral, rat)
LDLo (lowest published)	5 mg/kg (rabbit, oral); 7.85 mg/kg (mouse, oral); 1.7 mg/kg (rat, oral)
LCLo (lowest published)	15 mg/m3 (rat, 4 hr); 15 mg/m3 (cat, 4 hr)
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 0.1 mg/m3 [skin]
REL (Recommended)	TWA 0.1 mg/m3 [skin]
IDLH (Immediate danger)	10 mg/m3
Related compounds
Related Organothiophosphate insecticides	Demeton-S-methyl
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Demeton, sold as an amber oily liquid with a sulphur like odour under the name Systox, is an organophosphate derivative causing irritability and shortness of breath to individuals repeatedly exposed. It was used as a phosphorothioate insecticide and acaricide and has the chemical formula C₈H₁₉O₃PS₂. Although it was previously used as an insecticide, it is now largely obsolete due to its relatively high toxicity to humans. Demeton consists of two components, demeton-S and demeton-O in a ratio of approximately 2:1 respectively. The chemical structure of demeton is closely related to military nerve agents such as VX and a derivative with one of the ethoxy groups replaced by methyl was investigated by both the US and Soviet chemical-weapons programs under the names V-sub x and GD-7.^[4]^[5]

^ ^a ^b ^c ^d NIOSH Pocket Guide to Chemical Hazards. "#0177". National Institute for Occupational Safety and Health (NIOSH).
^ "Demeton_msds".
^ ^a ^b "Demeton". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^ Ledgard J. A laboratory history of chemical warfare agents (2nd, 2006). pp 230-233. ISBN 978-0-6151-3645-5
^ Kulieva AM, Dalimov DN, Dorenskaya GM, et al. Biochemical investigation of cholinesterases and carboxylesterases from the cotton bollworm Heliothis armigera. Chem Nat Compd 1994 Jan; 30(1): 116-120. Kulieva, A. M; Dalimov, D. N; Dorenskaya, G. M; Charieva, O. V; Rozengart, V. I; Kugusheva, L. I; Moralev, S. N; Babaev, B. N; Abduvakhabov, A. A (1994). "Biochemical investigation of cholinesterases and carboxylesterases from the cotton bollworm Heliothis armigera". Chemistry of Natural Compounds. 30: 116–120. doi:10.1007/BF00638435. S2CID 20331774.

[PGCH-1] NIOSH Pocket Guide to Chemical Hazards. "#0177". National Institute for Occupational Safety and Health (NIOSH).

[chemsrc-2] "Demeton_msds".

[IDLH-3] "Demeton". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[4] Ledgard J. A laboratory history of chemical warfare agents (2nd, 2006). pp 230-233. ISBN 978-0-6151-3645-5

[5] Kulieva AM, Dalimov DN, Dorenskaya GM, et al. Biochemical investigation of cholinesterases and carboxylesterases from the cotton bollworm Heliothis armigera. Chem Nat Compd 1994 Jan; 30(1): 116-120. Kulieva, A. M; Dalimov, D. N; Dorenskaya, G. M; Charieva, O. V; Rozengart, V. I; Kugusheva, L. I; Moralev, S. N; Babaev, B. N; Abduvakhabov, A. A (1994). "Biochemical investigation of cholinesterases and carboxylesterases from the cotton bollworm Heliothis armigera". Chemistry of Natural Compounds. 30: 116–120. doi:10.1007/BF00638435. S2CID 20331774.

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