EA-1699

EA-1699
Names
Preferred IUPAC name
2-[ethoxy(methyl)phosphoryl]sulfanyl-N,N-dimethylethanamine
Other names
S-(2-(Dimethylamino)ethyl) O-ethyl P-methylphosphonothioate
IIVX
Medemo
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C7H18NO2PS/c1-5-10-11(4,9)12-7-6-8(2)3/h5-7H2,1-4H3
    Key: PKDYQTANBZBIRM-UHFFFAOYSA-N
  • CCOP(C)(=O)SCCN(C)C
Properties
C7H18NO2PS
Molar mass 211.26 g·mol−1
Density 1.06 g/ml[1]
Boiling point 200 °C to 250 °C[2]
248 g/L[2]
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
4
1
1
Lethal dose or concentration (LD, LC):
17 μg/kg (intravenous, rat)[3]
23.6 μg/kg (intramuscular, rat)[3]
54.5 μg/kg (intraperitoneal, rat)[3]
121.9 μg/kg (oral, rat)[3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

EA-1699, also known as IIVX,[2] is an extremely toxic synthetic chemical compound in the organophosphorus class, specifically, a thiophosphonate. It was derived from the more widely known nerve agent VX and can be seen as the dimethyl analogue of it.[2]

Indicators of EA-1699 have been detected at a Syrian chemical weapons production facility.[4][5]

Synthesis

The synthesis of EA-1699 is analogous to that of VX with the N,N-diisopropylaminoethanol being replaced with N,N-dimethylaminoethanol.[2]

The B in the following diagram denotes a base with diethylaniline being described as a suitable one in literature.[2]

References

  1. ↑ Pampalakis, Georgios; Kostoudi, Stavroula (2023-05-11). "Chemical, Physical, and Toxicological Properties of V-Agents". International Journal of Molecular Sciences. 24 (10). MDPI AG: 8600. doi:10.3390/ijms24108600. ISSN 1422-0067. PMC 10218410. PMID 37239944.
  2. 1 2 3 4 5 6 Ledgard, Jared B. (2006). The Laboratory History of Chemical Warfare Agents. Paranoid Publications Group. p. 227. ISBN 978-1-4116-9432-3.
  3. 1 2 3 4 J, Bajgar; J, Fusek; J, Patocka (1978). "Toxicities and the rates of penetration of O-ethyl-S-(2-dimethylaminoethyl)-methylphosphonothioate into the blood following different routes of intoxication". Acta Biologica et Medica Germanica. 37 (4). Acta Biol Med Ger: 633–636. ISSN 0001-5318. PMID 735630.
  4. ↑ "Statement by H.E. Ambassador SHINO Mitsuko, Deputy Permanent Representative of Japan to the United Nations, at the Security Council Briefing on "the situation in the Middle East (Syria chemical weapons)"". 国際連合（国連）日本政府代表部. Retrieved September 24, 2025.
  5. ↑ "Two New Outstanding Issues with Syria's Chemical Weapon Declarations 'Extremely Worrying', United Nations Official Tells Security Council". Meetings Coverage and Press Releases. September 5, 2024. Retrieved September 24, 2025.
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