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cis-Mevinphos

HCID 5355863
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
298-01-1
Standard SMILES
COC(=O)/C=C(\C)OP(=O)(OC)OC
InChIKey
GEPDYQSQVLXLEU-AATRIKPKSA-N
Molecular formula
C7H13O6P
Average molar mass
224.15 g/mol
Monoisotopic mass
224.04497513

Overview

Mevinphos is a dialkyl phosphate and an organophosphate insecticide. It has a role as an acaricide, an agrochemical, an avicide and an EC 3.1.1.7 (acetylcholinesterase) inhibitor. It is functionally related to a methyl 3-hydroxybut-2-enoate.

Names & identifiers

Preferred name
cis-Mevinphos
IUPAC
methyl (E)-3-dimethoxyphosphoryloxybut-2-enoate
English name
CIS-MEVINPHOS PESTANAL 50 MG
Molecular formula
C7H13O6P
Molecular weight
224.15

Names & synonyms

cis-Mevinphos(E)-Mevinphoscis-Phosdrin298-01-126718-65-0E-MevinphosPD 5methyl (E)-3-dimethoxyphosphoryloxybut-2-enoatePhosdrin, .alpha.(E)-Mevinphos (cis-butenoic acid)Dimethyl phosphate of methyl 3-hydroxy-cis-crotonateQ6VSZ656WV
Show more names
CIS-MEVINPHOSPESTANAL(E)-Mevinphos Standardcis-Mevinphos solutionCIS-MEVINPHOS PESTANAL 50 MGcis-Mevinphos, 100 μg /μL in acetonitrileC15221000 (E)-Mevinphos (cis-butenoiCacid)3-hydroxy-,methylester,dimethylphosphate,(e)-crotonicaci3-((dimethoxyphosphinyl)oxy)-,methylester,(e)-2-butenoicaci(e)-3-(dimethoxyphosphinyloxy)-2-butenoic acid methyl ester
methyl (2E)-3-[(dimethoxyphosphoryl)oxy]but-2-enoatealpha-MevinphosCrotonic acid, 3-hydroxy-, methyl ester, dimethyl phosphate, (E)-Mevinfos [Dutch]Caswell No. 160BMevinphos [BSI:ISO]2-Butenoic acid, 3-((dimethoxyphosphinyl)oxy)-, methyl ester, (2E)-2-Butenoic acid, 3-((dimethoxyphosphinyl)oxy)-, methyl ester, (E)-

Properties

Computed structural properties

XLogP
1.2
Topological polar surface area
71.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
6
Rotatable bonds
6
Heavy atoms
14
Formal charge
0
Complexity
263

Experimental & physicochemical properties

Collision Cross Section146.02 Ų [M+Na]+

Physicochemical properties

Melting point
21 °C · 21 °C
Boiling point
101 °C · 101 °C
Density
1.216 · 1.216±0.06 g/cm3(Predicted)
storage temp.
2 · 2-8°C
FDA UNII
6 VSZ656WV · Q6VSZ656WV
EPA Substance Registry System
cis-Mevinphos (298-01-1)
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302-H312-H319-H332
Precautionary statements
280 · P280-P305+P351+P338
Hazard Codes
T+,N,Xn,F
Risk Statements
27 · 27/28-50/53-36-20/21/22-11

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]

P262, P264, P270, P273, P280, P301+P316, P302+P352, P316, P321, P330, P361+P364, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Other Safety InformationIMAP assessments - 2-Butenoic acid, 3-[(dimethoxyphosphinyl)oxy]-, methyl ester, (E)-: Human health tier I assessment
Hazard Classes and CategoriesAcute Tox. 2 (100%)

Toxicology

Treatment · 1 item

If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.

Health Effects · 1 item

Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides.

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

Metabolism of organophosphates occurs principally by oxidation, by hydrolysis via esterases and by reaction with glutathione. Demethylation and glucuronidation may also occur. Oxidation of organophosphorus pesticides may result in moderately toxic products. In general, phosphorothioates are not directly toxic but require oxidative metabolism to the proximal toxin. The glutathione transferase reactions produce products that are, in most cases, of low toxicity. Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of organophosphate exposure.

Uses & manufacturing

UsesThis is a man-made compound that is used as a pesticide.

Suppliers7 total

杭州摩库生物医药科技有限公司+86-057181025280; +8617767106207 · [email protected]
安耐吉化学&3A(安徽泽升科技有限公司)021-58432009 400-005-6266 · [email protected]
梯希爱(上海)化工贸易有限公司021-61109150 · [email protected]
天津阿尔塔科技有限公司022-65378550-8551 · [email protected]
陕西缔都医药化工有限公司029-029-81120477 17792793610 · [email protected]

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes

Database identifiers

CAS
298-01-1、7786-34-7
PubChem CID
5355863
DTXSID
DTXSID0058358
ChEMBL
CHEMBL1903674
ChEBI
CHEBI:38725
UNII
Q6VSZ656WV
EC Number
206-051-7
Nikkaji
J124.959B、J2.270E
Safety Statements
23 · 23-28-36/37-45-60-61-16
RIDADR
2810 · UN 2810 6.1/PG 1
WGK Germany
2 · 2
RTECS
5251000 · GQ5251000
Toxicity Summary · 1 item

Mevinphos is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.

Signs and Symptoms · 1 item

Symptoms of low dose exposure include excessive salivation and eye-watering. Acute dose symptoms include severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Hypertension, hypoglycemia, anxiety, headache, tremor and ataxia may also result.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Safety data

wgk
2
rtecs
GQ5251000
ridadr
UN 2810 6.1/PG 1
risk_code
27/28-50/53-36-20/21/22-11
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
T+,N,Xn,F
safety_code
23-28-36/37-45-60-61-16
Hazard statements
H302-H312-H319-H332
Precautionary statements
P280-P305+P351+P338
上海一飞生物科技有限公司
021-65675885 18964387627 · [email protected]
上海安谱实验科技股份有限公司18502138905 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Mevinphos is a dialkyl phosphate and an organophosphate insecticide. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor, an acaricide, an agrochemical and an avicide. It is functionally related to a methyl 3-hydroxybut-2-enoate.