Demeton

Demeton
Names
	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;
	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[1]
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[2]
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)[3]
LCLo (lowest published)	15 mg/m3 (rat, 4 hr); 15 mg/m3 (cat, 4 hr)[3]
	US health exposure limits (NIOSH):
PEL (Permissible)	TWA 0.1 mg/m3 [skin][1]
REL (Recommended)	TWA 0.1 mg/m3 [skin][1]
IDLH (Immediate danger)	10 mg/m3[1]
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 was a phosphorothioate insecticide with the chemical formula C₈H₁₉O₃PS₂. While it was previously used as an insecticide, it is now largely obsolete due to its relatively high toxicity to humans. 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]

References

1 2 3 4 "NIOSH Pocket Guide to Chemical Hazards #0177". National Institute for Occupational Safety and Health (NIOSH).
↑ "Demeton_msds".
1 2 "Demeton". Immediately Dangerous to Life and 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.

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[PGCH-1] 1 2 3 4 "NIOSH Pocket Guide to Chemical Hazards #0177". National Institute for Occupational Safety and Health (NIOSH).

[chemsrc-2] "Demeton_msds".

[IDLH-3] 1 2 "Demeton". Immediately Dangerous to Life and 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.

Demeton

See also

References