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Substance Name: Tabun
RN: 77-81-6
UNII: S45M750QSH
InChIKey: PJVJTCIRVMBVIA-UHFFFAOYSA-N

Note

  • Proposed as military nerve gas and exptl cholinesterase inhibitor; extremely poisonous.

Molecular Formula

  • C5-H11-N2-O2-P

Molecular Weight

  • 162.128
 

Classification Codes

Classification Codes

  • Chemical Warfare Agents
  • Cholinergic Agents
  • Cholinesterase Inhibitors
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Human Data
  • Neurotransmitter Agents
  • Noxae
  • Poisons

Superlist Classification Code

  • Threshold Planning Quantity (TPQ) = 10 lb
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Names and Synonyms

Name of Substance

  • Tabun

Synonyms

  • 4-04-00-00275 (Beilstein Handbook Reference)
  • BRN 1769395
  • CCRIS 3421
  • Dimethylamidoethoxyphosphoryl cyanide
  • Dimethylaminocyanphosphorsaeureaethylester
  • Dimethylaminocyanphosphorsaeureaethylester [German]
  • Dimethylphosphoramidocyanidic acid, ethyl ester
  • EA 1205
  • Ethyl dimethylamidocyanophosphate
  • Ethyl dimethylphosphoramido cyanidate
  • Ethyl dimethylphosphoramidocyanidate
  • Ethyl N,N-dimethylphosphoramidocyanidate
  • Ethyl N-dimethylphosphoramidocyanidate
  • Ethyl phosphorodimethylamidocyanidate
  • Ethylester-dimethylamid kyseliny kyanfosfonove
  • Ethylester-dimethylamid kyseliny kyanfosfonove [Czech]
  • GA [Chemical Warfare Agent]
  • Gelan I
  • HSDB 6378
  • Le-100
  • Nerve agent
  • O-Ethyl N,N-dimethylphosphoramidocyanidate
  • T-2104
  • Taboon A
  • Tabun
  • TL 1578
  • Trilon 83
  • UNII-S45M750QSH

Systematic Names

  • Dimethylphosphoramidocyanidic acid, ethyl ester
  • Phosphoramidocyanidic acid, dimethyl-, ethyl ester
  • Phosphoramidocyanidic acid, N,N-dimethyl-, ethyl ester
  • Tabun

Superlist Name

  • Tabun

Registry Numbers

CAS Registry Number

  • 77-81-6

FDA UNII

  • S45M750QSH

Other Registry Number

  • 102490-55-1

System Generated Number

  • 0000077816

Structure Descriptors

InChI

1S/C5H11N2O2P/c1-4-9-10(8,5-6)7(2)3/h4H2,1-3H3

InChIKey

PJVJTCIRVMBVIA-UHFFFAOYSA-N

Smiles

O([P@@](N(C)C)(C#N)=O)CC

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 intravenous 47ug/kg (0.047mg/kg)   Neurotoxicology. Vol. 7, Pg. 225, 1986.
chicken LD50 intramuscular 118ug/kg (0.118mg/kg)   Toxicology. Vol. 72, Pg. 117, 1992.
chicken LD50 subcutaneous 98911ug/kg (98.911mg/kg)   Archives of Toxicology. Vol. 52, Pg. 71, 1983.
dog LD50 intravenous 84ug/kg (0.084mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 132, Pg. 50, 1961.
dog LD50 oral 200ug/kg (0.2mg/kg)   Deutsche Gesundheitswesen. Vol. 15, Pg. 2179, 1960.
dog LD50 skin 30mg/kg (30mg/kg)   National Technical Information Service. Vol. PB158-508,
dog LD50 subcutaneous 284ug/kg (0.284mg/kg)   Fundamental and Applied Toxicology. Vol. 4, Pg. S106, 1984.
domestic animals - goat/sheep LD50 skin 1100ug/kg (1.1mg/kg)   National Technical Information Service. Vol. PB158-508,
guinea pig LD50 skin 35mg/kg (35mg/kg) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: COMA
National Technical Information Service. Vol. PB158-508,
guinea pig LD50 subcutaneous 120ug/kg (0.12mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Toxicology and Applied Pharmacology. Vol. 40, Pg. 109, 1977.
hamster LD50 subcutaneous 245ug/kg (0.245mg/kg)   Canadian Journal of Physiology and Pharmacology. Vol. 44, Pg. 745, 1966.
human LCLo inhalation 150mg/m3 (150mg/m3) SENSE ORGANS AND SPECIAL SENSES: MIOSIS (PUPILLARY CONSTRICTION): EYE

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE
Science Journal. Vol. 3(4), Pg. 33, 1967.
human LDLo intravenous 14ug/kg (0.014mg/kg) SENSE ORGANS AND SPECIAL SENSES: MIOSIS (PUPILLARY CONSTRICTION): EYE

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE
Science Journal. Vol. 3(4), Pg. 33, 1967.
human LDLo skin 23mg/kg (23mg/kg) SENSE ORGANS AND SPECIAL SENSES: MIOSIS (PUPILLARY CONSTRICTION): EYE

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE
Science Journal. Vol. 3(4), Pg. 33, 1967.
monkey LD50 intramuscular 34ug/kg (0.034mg/kg)   Archives of Toxicology. Vol. 63, Pg. 144, 1989.
monkey LD50 intravenous 50ug/kg (0.05mg/kg)   Journal of Toxicology and Environmental Health, Part A. Vol. 59, Pg. 439, 2000.
monkey LD50 skin 9300ug/kg (9.3mg/kg)   National Technical Information Service. Vol. PB158-508,
monkey LD50 subcutaneous 70ug/kg (0.07mg/kg)   Archives of Toxicology. Vol. 63, Pg. 144, 1989.
mouse LC50 inhalation 15mg/m3/30M (15mg/m3)   Deutsche Gesundheitswesen. Vol. 15, Pg. 2179, 1960.
mouse LD50 intramuscular 440ug/kg (0.44mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 204, Pg. 110, 1973.
mouse LD50 intraperitoneal 604ug/kg (0.604mg/kg)   "Fluorine Chemistry, Volume III. Biological Effects of Organic Fluorides," Simons, J.H., ed., New York, Academic Press, Inc., 1963Vol. 3, Pg. 69, 1963.
mouse LD50 intravenous 150ug/kg (0.15mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

BEHAVIORAL: COMA
National Technical Information Service. Vol. PB158-508,
mouse LD50 skin 1mg/kg (1mg/kg) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: COMA
National Technical Information Service. Vol. PB158-508,
mouse LD50 subcutaneous 250ug/kg (0.25mg/kg)   Acta Pharmaceutica Jugoslavica. Vol. 30, Pg. 151, 1980.
rabbit LD50 intravenous 63ug/kg (0.063mg/kg)   National Technical Information Service. Vol. PB158-508,
rabbit LD50 oral 16300ug/kg (16.3mg/kg)   National Technical Information Service. Vol. PB158-508,
rabbit LD50 skin 2500ug/kg (2.5mg/kg)   National Technical Information Service. Vol. PB158-508,
rabbit LD50 subcutaneous 375ug/kg (0.375mg/kg)   Canadian Journal of Physiology and Pharmacology. Vol. 46, Pg. 109, 1968.
rat LD50 intramuscular 800ug/kg (0.8mg/kg)   Journal of Clinical Investigation. Vol. 37, Pg. 350, 1958.
rat LD50 intraperitoneal 490ug/kg (0.49mg/kg)   Pharmacology and Toxicology Vol. 65, Pg. 181, 1989.
rat LD50 intravenous 66ug/kg (0.066mg/kg) BEHAVIORAL: COMA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS
National Technical Information Service. Vol. PB158-508,
rat LD50 oral 3700ug/kg (3.7mg/kg) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: COMA
National Technical Information Service. Vol. PB158-508,
rat LD50 skin 18mg/kg (18mg/kg)   National Technical Information Service. Vol. PB158-508,
rat LD50 subcutaneous 162ug/kg (0.162mg/kg)   Pharmacology and Toxicology Vol. 65, Pg. 181, 1989.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point -5.00E+01 deg C   EXP
Boiling Point 240 deg C   EXP
log P (octanol-water) 0.38 (none)   EXP
Water Solubility 9.80E+04 mg/L 25 EXP
Vapor Pressure 0.07 mm Hg 25 EXP
Henry's Law Constant 1.52E-07 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 8.03E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.