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Tabun
Sign in to saveAlso known as ethyl dimethylamidocyanophosphate, O-Ethyl N,N-dimethylphosphoramidocyanidate, EA-1205, TL-1578
nerve agent
OverviewAI-generated
Tabun is a chemical compound with the formula C₅H₁₁N₂O₂P. Its canonical SMILES notation is CCOP(=O)(C#N)N(C)C. The substance has a mass of 162.055814222 and a weight of 162.13.
Chemical properties include an xlogp value of 0.1 and a topological polar surface area of 53.3. The molecule contains zero hydrogen bond donors and four hydrogen bond acceptors, with a charge of 0. It is associated with a PubMed query count of 651 and is referenced by 537 other encyclopedia articles.
Synthesized by Vinony from 16 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Chemical data
- Formula
- C5H11N2O2P
- Molecular weight
- 162.13 g/mol
- IUPAC name
- [dimethylamino(ethoxy)phosphoryl]formonitrile
- SMILES
- CCOP(=O)(C#N)N(C)C
- InChIKey
- PJVJTCIRVMBVIA-UHFFFAOYSA-N
- XLogP
- 0.1
- Polar surface area
- 53.3 Ų
- H-bond donors
- 0
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Research
651 papers- The development of new oximes and the evaluation of their reactivating, therapeutic and neuroprotective efficacy against tabun.Mini reviews in medicinal chemistry · 2008
- Reversal of Tabun Toxicity Enabled by a Triazole-Annulated Oxime Library-Reactivators of Acetylcholinesterase.Chemistry (Weinheim an der Bergstrasse, Germany) · 2019
- Cholinergic Crisis.2026
- Counteracting tabun inhibition by reactivation by pyridinium aldoximes that interact with active center gorge mutants of acetylcholinesterase.Toxicology and applied pharmacology · 2019
- Therapeutic and neuroprotective efficacy of pharmacological pretreatment and antidotal treatment of acute tabun or soman poisoning with the emphasis on pretreatment drug PANPAL.Arhiv za higijenu rada i toksikologiju · 2006
via PubMed
~15 min read
Encyclopedic overview
Tabun (NATO designation GA) is an extremely toxic compound and nerve agent chemical weapon of the organophosphate family. It is not present in nature. At room temperature, the pure compound is a clear and viscous liquid. However, impurities imparted during its manufacture are almost always present, turning it yellow or brown. Exposed to environs, it slowly evaporates into the atmosphere, with the vapor having a slight fruity or almond-like odor. As the compound has a much higher molecular mass (162 g/mol) compared to air, tabun gas tends to accumulate in low-lying areas.
It is a potent inhibitor of acetylcholinesterase, a key enzyme within the human body as well as in other animals. Acetylcholinesterase is responsible for breaking down acetylcholine, a neurotransmitter released into the synaptic cleft by motor neurons. The presence of acetylcholine within the cleft signals the post-synaptic (downstream) motor neuron to contract the neuron's associated muscle fibers, and vice versa. By irreversibly phosphorylating the enzyme, tabun accomplishes a constant and involuntary contraction of the affected muscles, as the acetylcholine is not recycled and continues to build up within the cleft. Death of the organism ensues when respiratory muscles, such as the diaphragm and intercostals, become exhausted and paralyzed from constant contraction, leading to loss of respiratory functions.
Excerpted from Wikipedia’s “Tabun” article, available under the CC BY-SA 4.0 licence.