Sarin

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-56 °C, 217 K, -69 °F

158 °C, 431 K, 316 °F

Sarin, or GB is an organophosphorus compound with the formula [(CH3)2CHO]CH3P(O)F. It is a colorless, odorless liquid,[3] which is used as a chemical weapon. It has been classified as a weapon of mass destruction in UN Resolution 687. Production and stockpiling of sarin was outlawed by the Chemical Weapons Convention of 1993 where it is classified as a Schedule 1 substance.

Contents

Production and structure

Sarin is a chiral molecule, with four substituents attached to the tetrahedral phosphorus center.[4] It is prepared from methylphosphonyl difluoride and a mixture of isopropyl alcohol.

Isopropylamine is added to neutralize the hydrogen fluoride generated during this alcoholysis reaction. As a binary chemical weapon, it can be generated in situ by this same reaction.

Biological effects

Its mechanism of action resembles that of some commonly used insecticides, such as malathion. In terms of biological activity, it resembles carbamate insecticides such as sevin and medicines pyridostigmine, neostigmine, and physostigmine. Like other nerve agents, sarin attacks the nervous system.

Specifically, sarin is a potent inhibitor of the enzyme cholinesterase.[5] Sarin acts on cholinesterase by forming a covalent bond with the particular serine residue at the active site. Fluoride is the leaving group, and the resulting phosphoester is robust but biologically inactive.[6][7] With the enzyme inhibited, acetylcholine builds up in the synapse and continues to act so that any nerve impulses are, in effect, continually transmitted. Normally, the acetylcholinesterase breaks down the acetylcholine in the synaptic cleft in order to allow the effector muscle or organ to relax.

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