Sarin
Sarin, also designated GB, is a synthetic organophosphorus compound classified as a nerve agent and one of the most toxic substances developed for chemical warfare.[1][2] It exists as a colorless, odorless, and tasteless volatile liquid at room temperature, with the chemical formula C₄H₁₀FO₂P and a molecular weight of 140.09 g/mol.[1][2] Sarin is highly soluble in water and organic solvents, boils at 147°C, and has a density of 1.10 g/mL, enabling rapid dispersal as a vapor or aerosol.[2] The agent's lethality stems from its irreversible inhibition of the enzyme acetylcholinesterase (AChE), which normally hydrolyzes the neurotransmitter acetylcholine at cholinergic synapses.[3][4] This inhibition causes acetylcholine accumulation, resulting in continuous stimulation of muscles, glands, and the central nervous system, manifesting as miosis, salivation, convulsions, respiratory failure, and death within minutes at lethal doses.[3][4] Sarin's potency is extreme, with an estimated human lethal dose via inhalation as low as 0.01 mg/kg or less, far surpassing many conventional toxins.[1][3] Originally synthesized in 1937 by German chemist Gerhard Schrader during organophosphate pesticide research, sarin was identified for its potent toxicity and weaponized by Nazi Germany, though not deployed in World War II.[3][5] It is produced via the reaction of methylphosphonyl difluoride with isopropanol under controlled conditions, a process requiring anhydrous inert atmospheres due to its reactivity.[6] Post-war, sarin was stockpiled by major powers but banned under the 1993 Chemical Weapons Convention as a Schedule 1 substance, with verified destruction programs ongoing.[3] Despite prohibitions, its use in terrorist attacks, such as the 1995 Tokyo subway incident, and alleged state deployments in conflicts highlight persistent proliferation risks and challenges in detection and decontamination.[3][4]
Chemical Properties
Molecular Structure and Formula
Sarin possesses the molecular formula C₄H₁₀FO₂P and a molecular mass of 140.0932 Da.[1]7-8(3%2C5)6/h4H%2C1-3H3) Its IUPAC name is propan-2-yl methylphosphono-fluoridate, commonly referred to as O-isopropyl methylphosphonofluoridate.[1][7] The structure consists of a central phosphorus(V) atom tetrahedrally coordinated to a methyl group (CH₃-), a fluorine atom (F-), an isopropoxy group (-O-CH(CH₃)₂), and a double-bonded oxygen (=O), rendering the phosphorus center chiral with two enantiomers.[1]7-8(3%2C5)6/h4H%2C1-3H3) The SMILES notation is CC(C)OP(=O)(C)F, and the InChI is InChI=1S/C4H10FO2P/c1-4(2)7-8(3,5)6/h4H,1-3H3.[1]7-8(3%2C5)6/h4H%2C1-3H3)Physical Characteristics
Sarin is a colorless, odorless, and tasteless liquid at standard room temperature and pressure.[8][1] In its pure form, it exhibits no perceptible odor, though trace impurities from synthesis can introduce a faint fruity smell in some preparations.[9] As one of the most volatile nerve agents, sarin readily evaporates from liquid to vapor, facilitating rapid dispersal in air, with a vapor pressure of 2.9 mm Hg at 25 °C.[10][11] Key thermophysical properties include a boiling point of 147 °C (297 °F) at atmospheric pressure and a melting point of -57 °C (-71 °F), rendering it a low-viscosity liquid that remains fluid across a wide temperature range relevant to deployment scenarios.[2][12] Its liquid density is approximately 1.10 g/mL at 20 °C, slightly denser than water, which influences its behavior in environmental releases or mixtures.[2] Sarin demonstrates high solubility in water (miscible, though subject to hydrolysis) as well as in organic solvents, alcohols, fats, oils, and gasoline, enhancing its penetration in diverse media.[4][12]| Property | Value | Conditions |
|---|---|---|
| Boiling Point | 147 °C | 1 atm |
| Melting Point | -57 °C | Standard pressure |
| Liquid Density | 1.10 g/mL | 20 °C |
| Vapor Pressure | 2.9 mm Hg | 25 °C |