{"Absorption, Distribution and Excretion":"The fate of sarin in the blood is a major determinant of how much sarin reaches the central nervous system and other sites of systemic toxicity. In the blood, sarin first interacts with several esterases... Some of the esterases, such as paraoxonase, hydrolyze sarin to inactive metabolites. Two other blood esterases - AChE and butyrylcholinesterase (BuChE) - irreversibly bind to sarin. AChE found on the surface of red blood cells (RBCs), although chemically indistinguishable from AChE in the nervous system, has unknown physiological functions. These esterases in the blood are often described as \"false targets\" - by binding irreversibly to sarin, AChE and BuChE sequester sarin in the blood, thereby preventing some or all from reaching the CNS. However, esterases in the blood can be overwhelmed by high doses of sarin. The acute cholinergic syndrome occurs when RBC AChE is inhibited by 75 to 80 percent","Adverse Effects":"Other Poison - Organophosphate","Aliases":["Sarin","IMPF","Sarin II","Trilone 46","O-Isopropyl methylphosphonofluoridate","Isopropyl methylphosphonofluoridate","Isopropyl methylfluorophosphate","Gas, Sarin","Isopropyl methanefluorophosphonate","Isopropoxymethylphosphoryl fluoride","Isopropyl-methyl-phosphoryl fluoride","Methylphosphonofluoridic acid isopropyl ester","EA 1208","TL 1618","Isopropoxymethylphoshoryl fluoride","Phosphine oxide, fluoroisopropoxymethyl-","Phosphonofluoridic acid, methyl-, isopropyl ester","Phosphonofluoridic acid, methyl-, 1-methylethyl ester","T-144","Phosphoric acid, methylfluoro-, isopropyl ester","T-2106","Dtxsid0042371","Methlyfluorophosphonic acid isopropyl ester","Isopropylester kyseliny methylfluorfosfonove","Methylphosphonofluoride acid, isopropyl ester","1-Methylethyl (+-)-methylphosphonofluoridate","Methylfluorphosphorsaeureisopropylester","Phosphonofluoridic acid, P-methyl-, 1-methylethyl ester","Chebi:75701","Chebi:75873","2-(fluoro(methyl)phosphoryl)oxypropane","o-Isopropylmethyl Phosphonofluoridate","ortho-Isopropylmethyl Phosphonofluoridate","o Isopropylmethyl Phosphonofluoridate","Phosphonofluoridate, o-Isopropylmethyl","ortho Isopropylmethyl Phosphonofluoridate","Phosphonofluoridate, ortho-Isopropylmethyl","G-Series Nerve Agent GB","Dtxcid8022371","T144","Phosphine oxide, fluoroisopropoxymethyl","T2106","Sarin.","GB","propan-2-yl methylphosphonofluoridate","Methylphosphonofluoridic acid 1-methylethyl ester","Isopropyl methylfluorophosphonate","MFI","CCRIS 3416","HSDB 6382","Unii-b4xg72qgfm","Brn 1750114","Zarin","Phosphonofluoridic acid, methyl-, isopropyl ester, (+-)-","(.+/-.)-Sarin","Schembl50256","4-04-00-03507","Chembl509554","O-Isopropyl methylfluorophosphonate","Bdbm50027343","Isopropyl methylphosphonofluoridoate #","1-Methylethyl methylphosphonofluoridate","Akos006273454","Methylfluorphosphorsaeureisopropyl ester","Methylfluorophosphoric acid isopropyl ester","NS00075366","NS00075518"],"Associated Disorders and Diseases":"Organophosphates \u0026 carbamates, acute poisoning [Category: Acute Poisoning]","Biological Half-Life":"... rats /were injected/ sc with a single dose of 75 ug/kg of sarin ... . Urinary elimination was found to be quite rapid; the terminal elimination half-life of sarin metabolites in urine was 3.7 +/- 0.1 hours. Nearly all of the administered dose of sarin was retrieved from the urine in metabolite form after 2 days.","Boiling Point":"297 °","CAS":"107-44-8","Chemical Classes":"Toxic Gases \u0026 Vapors -\u003e Chemical Weapons","ChemicalClasses":[],"Chirality":"racemic","Classes":["Nerve agent"],"Color/Form":"Liquid","Decomposition":"Decomposes thermally to form a variety of phosphorus containing products as well as propylene. The rate of decomposition increases with increase in temperature, and in the presence of acids. At the boiling point of GB, under atmospheric conditions, decomposition is fairly rapid.","Density":"1.1 at 68 °F (EPA, 1998) - Denser than water; will sink g/cm\u003csup\u003e3\u003c/sup\u003e","Esters":[],"Flash Point":"Non-flammable (EPA, 1998)","Formating":[],"HMDB ID":"HMDB0257497","HeavyAtomCount":8,"Human Toxicity Values":"LD50 Man percutaneous 28 mg/kg /From table/","IUPACName":"2-[fluoro(methyl)phosphoryl]oxypropane","InChI":"InChI=1S/C4H10FO2P/c1-4(2)7-8(3,5)6/h4H,1-3H3","InChIKey":"DYAHQFWOVKZOOW-UHFFFAOYSA-N","Interactions":"A time-course study was carried out to measure the acetylcholinesterase (AChE) gene expression in the brain of female rats exposed to different doses of sarin and physostigmine. Short-term effects were studied with an acute single subcutaneous dose (s.c.) of 80 ug kg(-1) (0.5 x LD50) sarin. Cortex and cerebellum showed a significant decline in AChE mRNA expression at 2.5, 24 and 72 hr. Biochemical studies showed that plasma butrylcholinesterase (BChE) and brain AChE activities were significantly decreased at 2.5 hr, which came back to near control values by 24 hr in both cases. For long-term chronic studies, three groups of female rats received daily doses of physostigmine (0.1 mg kg(-1) day(-1)) intramuscularly (i.m.), sarin (15 ug kg(-1) day(-1)) s.c. independently and a combined dose of physostigmine (i.m.) (0.1 mg kg(-1) day(-1)) followed by sarin (s.c.) (15 ug kg(-1) day(-1)) continuously for 30 days. Differential AChE mRNA levels in cortex and cerebellum of rat brain were observed after 30 days and after a lag period of another 30 days with no further administration. Plasma (BChE) and brain (AChE) showed irregular inhibition profile in biochemical studies at 30 days and returned to control levels after 60 days. The acute single subcutaneous administration of sarin for short-term as well as chronic long-term studies showed that AChE inhibition alone does not lead to observed changes in mRNA expression of AChE gene. These observations further suggest that route of administration as well as dose exposure regimen also contributes to the regulation of AChE mRNA expression.","MeSH Headers":[{"Id":"M0019449","Link":"https://id.nlm.nih.gov/mesh/M0019449.html","Name":"Sarin","Ref":40},{"Id":"DescTree","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":"MeSH Tree","Ref":42},{"Id":"M0004009","Link":"https://id.nlm.nih.gov/mesh/M0004009.html","Name":"Chemical Warfare Agents","Ref":57},{"Id":"M0004295","Link":"https://id.nlm.nih.gov/mesh/M0004295.html","Name":"Cholinesterase Inhibitors","Ref":58}],"MeSH Pharmacological Classification":[{"Id":"M0004009","Link":"https://id.nlm.nih.gov/mesh/M0004009.html","Name":"Chemical Warfare Agent","Ref":57},{"Id":"M0004295","Link":"https://id.nlm.nih.gov/mesh/M0004295.html","Name":"Cholinesterase Inhibitor","Ref":58}],"Mechanism of Action":"The principal mechanism of acute toxicity of sarin and cyclosarin, as of other OP compounds, is inhibition of AChE. AChE is responsible for the hydrolysis of acetylcholine (ACh) at the synapse, and inhibition of AChE leads to a rise in ACh and overstimulation at cholinergic synapses. At those synapses, the ACh binds and activates muscarinic and nicotinic receptors, the two major subtypes of ACh receptors. Sarin inhibits AChE by phosphorylating a serine hydroxyl on the ester portion of the active site of the enzyme. The phosphorylated enzyme is hydrolyzed very slowly, with a half-life of reactivation of hours to days. The phosphorylated enzyme can undergo a second process, called aging, by loss of an alkyl group (dealkylation). Aging occurs within about 5 hr of sarin exposure. After aging has occurred, the phosphorylated enzyme is resistant to cleavage or hydrolysis and can be considered irreversibly inhibited. Recovery of AChE function occurs only with synthesis of new enzyme. Most of the effects of sarin, including the acute cholinergic syndrome, are thought to be mediated by the excess ACh at the synapse.","Melting Point":"-71 °F (EPA, 1998)","Metabolism/Metabolites":"More than 20,000 passengers of Tokyo underground trains were intoxicated with warfare toxic chemicals. Most of the patients examined had marked miosis and decreased serum cholinesterase activity. Transient increase of serum CPK activity after 3 days of the exposure was the another sign. /The authors/  intensively analyzed the metabolites in the urine of 4 patients. The following analytic results indicated the exposure to sarin as well as contaminated compounds such as diisopropyl methylphosphonate (DIMP), ethyl methylphosphonate fluoridate (EMPF, or ethylsarin), diethyl methylphosphonate (DEMP), and ethyl isopropyl methylphosphonate (EIMP). (1) Isopropanol (IPA) and ethanol (EtOH) were detected of large quantities in the urine samples, and were thought to be derived from sarin and the sarin counterpart, ethyl methylphosphonate fluoridate, diisopropyl methylphosphonate, diethyl methylphosphonate and ethyl isopropyl methylphosphonate. (2) Monoalkyl methylphosphonic acids (isopropyl methylphosphonic acid (IMPA) and ethyl methylphosphonic acid (EMPA) also were excreted in large amounts with taking the similar excretion pattern of isopropanol and EtOH. (3) The metabolite only derived from sarin and ethylsarin is F anions whose integral output in the urine was less than the equimolar level of the excreted (isopropyl methylphosphonic acid + ethyl methylphosphonic acid + isopropanol + ethanol). (4) Other corroborative findings were low lethality: of more than 5,510 patients treated, 11 were acutely dead. (5) Nine exposed males had higher sister chromatid exchange (SCE) rate (5.00 + or - 1.48/cell) than the control (3.81 + or - 0.697/cell), because dialkyl methylphosphonates seemed to have alkylating activity and producing DNA adducts. The sister chromatid exchange rate also increased after the in vitro exposure of lymphocytes to dialkyl methylphosphonates.","MolecularFormula":"C\u003csub\u003e4\u003c/sub\u003eH\u003csub\u003e10\u003c/sub\u003eFO\u003csub\u003e2\u003c/sub\u003eP","MolecularWeight":"140.09 g/mol","Non-Human Toxicity Values":"LD50 Rat oral 550 ug/kg","Odor":"Almost odorless in pure state","Opticalactivity":"( + / - )","Physical Description":"Sarin appears as a chemical warfare nerve agent. A colorless, odorless liquid. Almost no odor in pure state.","PubChemId":7871,"Records":{"UNII":{"Impurities":[]}},"RefChem":"6212","RefCount":3,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Sarin","Name":"Sarin","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q187695","Name":"Sarin","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/7871","Name":"Sarin","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=107-44-8","Name":"Sarin","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0257497","Name":"Sarin","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/C11764","Name":"Sarin","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/B4XG72QGFM","Name":"Sarin","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID0042371","Name":"Sarin","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 7871, Sarin. Accessed April 8, 2026. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/7871\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/7871\u003c/a\u003e","U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. Sarin. UNII: B4XG72QGFM. Global Substance Registration System. Accessed April 8, 2026. \u003ca href=https://gsrs.ncats.nih.gov/ginas/app/beta/substances/B4XG72QGFM\u003ehttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/B4XG72QGFM\u003c/a\u003e"],"Reported Fatal Dose":"The lethal dose for man is estimated to be 0.01 mg/kg.","SMILES":"CC(C)OP(=O)(C)F","SaltData":[],"Salts":[],"Solubility":"Miscible with water /1X10+6 mg/L at 25 °C /","Stability/Shelf Life":"Unstable in the presence of water.","StereoisomerData":[{"ChemicalClasses":[],"SMILES":"CC(C)O[P@@](C)(=O)F","Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 56.65 32.358\"\u003e\u003crect width=\"100%\" height=\"100%\" fill=\"#fff\"/\u003e\u003cdesc\u003eGenerated by the Chemistry Development Kit (http://github.com/cdk)\u003c/desc\u003e\u003cg fill=\"#ff0d0d\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".7\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 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0-1.262-.315-.506-.316-.756-.887Q.56 9.277.56 8.515q0-.75.244-1.31.25-.565.756-.881.506-.315 1.274-.315.732 0 1.232.315.5.31.756.876.256.565.256 1.327m-3.863 0q0 .923.387 1.459.393.529 1.22.529.84 0 1.221-.529.387-.536.387-1.459 0-.929-.387-1.452-.381-.524-1.209-.524-.833 0-1.226.524-.393.523-.393 1.452\" class=\"atom\"/\u003e\u003cpath fill=\"#90e050\" stroke=\"none\" d=\"M7.644 31.798h-.613v-4.899h2.733v.541h-2.12v1.739h1.995v.541H7.644z\" class=\"atom\"/\u003e\u003cpath stroke=\"#ff0d0d\" d=\"m32.494 21.877 4.96-2.863\" class=\"hi\"/\u003e\u003cpath stroke=\"#ff8000\" d=\"m17.891 12.905 2.873-4.977\" class=\"hi\"/\u003e\u003c/g\u003e\u003c/g\u003e\u003c/svg\u003e","Title":"(S)-Sarin"}],"StereoisomerType":"enantiomer","Stereoisomers":["(R)-Sarin","(S)-Sarin"],"Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 56.65 32.358\"\u003e\u003crect width=\"100%\" height=\"100%\" 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1.327m-3.863 0q0 .923.387 1.459.393.529 1.22.529.84 0 1.221-.529.387-.536.387-1.459 0-.929-.387-1.452-.381-.524-1.209-.524-.833 0-1.226.524-.393.523-.393 1.452\" class=\"atom\"/\u003e\u003cpath fill=\"#90e050\" stroke=\"none\" d=\"M7.644 31.798h-.613v-4.899h2.733v.541h-2.12v1.739h1.995v.541H7.644z\" class=\"atom\"/\u003e\u003cpath stroke=\"#ff0d0d\" d=\"m32.494 21.877 4.96-2.863M25.932 21.874l-3.927-2.267\" class=\"hi\"/\u003e\u003cpath stroke=\"#ff8000\" d=\"m18.078 17.34 3.927 2.267M17.891 12.905l2.873-4.977M13.903 19.812l-1.719 2.979\" class=\"hi\"/\u003e\u003cpath stroke=\"#90e050\" d=\"m10.464 25.769 1.72-2.978\" class=\"hi\"/\u003e\u003c/g\u003e\u003c/g\u003e\u003c/svg\u003e","Subjective Effects":null,"Taste":"Tasteless in its pure form","Title":"Sarin","Toxicity Data":"LC50 (rat) = 150 mg/m3/10min","UNII":"B4XG72QGFM","Wikidata":"Q187695","Wikipedia":"Sarin","XLogP":0.8}