ContaminantDB: (E)-Monocrotophos

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (4)XML

Record Information

Version

1.0

Creation Date

2013-04-25 07:56:53 UTC

Update Date

2026-03-25 19:18:11 UTC

Accession Number

CHEM002849

Identification

Common Name

(E)-Monocrotophos

Class

Small Molecule

Description

Monocrotophos is an organophosphorus insecticide and acaricide which works systemically and on contact. It is extremely toxic to birds and is used as a bird poison. It is also very poisonous to mammals. It is used to control a variety of sucking, chewing and boring insects and spider mites on cotton, sugarcane, peanuts, ornamentals, and tobacco. The EPA classifies monocrotophos as a class I toxicity - highly toxic. Use of monocrotophos on potatoes and tomatoes was withdrawn in 1985. All applications of monocrotophos were discontinued in the United States in 1988.

Contaminant Sources

Clean Air Act Chemicals
FooDB Chemicals
HPV EPA Chemicals
My Exposome Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amide
Amine
Ester
Food Toxin
Insecticide
Metabolite
Organic Compound
Organophosphate
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Azodrin	ChEBI
Dimethyl (e)-1-methyl-2-(methylcarbamoyl)vinyl phosphate	ChEBI
Dimethyl (e)-3-hydroxy-N-methylcrotonamide	ChEBI
Phosphoric acid, dimethyl (e)-1-methyl-3-(methylamino)-3-oxo-1-propenyl ester	ChEBI
Dimethyl (e)-1-methyl-2-(methylcarbamoyl)vinyl phosphoric acid	Generator
Phosphate, dimethyl (e)-1-methyl-3-(methylamino)-3-oxo-1-propenyl ester	Generator
3-(Dimethoxyphosphinyloxy)N-methyl-cis-crotonamide	HMDB
3-Dimethoxyphosphinoyloxy-N-methylisocrotonamide	HMDB
3-Hydroxy-N-methyl-cis-crotonamide dimethyl phosphate	HMDB
3-Hydroxy-N-methyl-cis-crotonamide dimethyl phosphate ester	HMDB
3-Hydroxy-N-methyl-dimethylphosphate(e)-crotonamide	HMDB
3-Hydroxy-N-methyl-dimethylphosphatecis-crotonamide	HMDB
Aimocron	HMDB
Apadrin	HMDB
Azadrin	HMDB
Azodrin 202R	HMDB
Azodrin insecticide	HMDB
Azodrin-71	HMDB
Biloborn	HMDB
Bilobran	HMDB
cis-1-Methyl-2-methyl carbamoyl vinyl phosphate	HMDB
Corophos	HMDB
Crisodin	HMDB
Crisodrin	HMDB
Croton 36	HMDB
Crotos	HMDB
Des-N-methyl dicrotophos	HMDB
Dimethyl 1-methyl-2-(methylcarbamoyl)vinyl phosphate, cis	HMDB
Dimethyl phosphate OF 3-hydroxy-N-methyl-cis-crotonamide	HMDB
e-Monocrotophos	HMDB
Glore phos 36	HMDB
Hazodrin	HMDB
Monocil	HMDB
Monocil 40	HMDB
Monocron	HMDB
Monocrotophos 40 ec	HMDB
Monodrin	HMDB
Monokrotofosz	HMDB
Monostar	HMDB
N-Desmethyl bidrin	HMDB
Nuvacron	HMDB
Nuvacron 20	HMDB
Nuvacron-20	HMDB
O,O-Dimethyl cis-1-methyl-2-methylcarbamoylvinylphosphate	HMDB
O,O-Dimethyl-O-(2-N-methylcarbamoyl-1-methyl-vinyl)-fosfaat	HMDB
O,O-Dimetil-O-(2-N-metilcarbamoil-1-metil-vinil)-fosfato	HMDB
Pandar	HMDB
Parryfos	HMDB
Pillardrin	HMDB
Plantdrin	HMDB
Rapid X	HMDB
Shell SD 9129	HMDB
Susvin	HMDB
Ulvair	HMDB
(e)-Monocrotophos	ChEBI

Chemical Formula

C₇H₁₄NO₅P

Average Molecular Mass

223.164 g/mol

Monoisotopic Mass

223.061 g/mol

CAS Registry Number

6923-22-4

IUPAC Name

(2E)-3-[(dimethoxyphosphoryl)oxy]-N-methylbut-2-enamide

Traditional Name

monocrotophos

SMILES

CNC(=O)\C=C(/C)OP(=O)(OC)OC

InChI Identifier

InChI=1S/C7H14NO5P/c1-6(5-7(9)8-2)13-14(10,11-3)12-4/h5H,1-4H3,(H,8,9)/b6-5+

InChI Key

KRTSDMXIXPKRQR-AATRIKPKSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as dialkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly two alkyl chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphoric acids and derivatives

Sub Class

Phosphate esters

Direct Parent

Dialkyl phosphates

Alternative Parents

Substituents

Dialkyl phosphate
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:38728 )
dialkyl phosphate (CHEBI:38728 )
organophosphate insecticide (CHEBI:38728 )
alkenyl phosphate (CHEBI:38728 )
Organophosphorus insecticides (C18663 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	54 - 55°C
Boiling Point	Not Available
Solubility	1000 mg/mL at 20°C

Predicted Properties

Property	Value	Source
Water Solubility	8.7 g/L	ALOGPS
logP	-0.26	ALOGPS
logP	-0.47	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	15.73	ChemAxon
pKa (Strongest Basic)	-0.75	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	73.86 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	51.64 m³·mol⁻¹	ChemAxon
Polarizability	20.26 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-4900000000-e97ee38f28a0c37d737a	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-4900000000-e97ee38f28a0c37d737a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0adi-1910000000-d0a2fd9e1d3db52548cf	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-002f-0900000000-bc93c9f49b96b126240c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-004i-0900000000-5bef9f97534886d7bbc1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-004i-0900000000-62b02093267f5b04a4c6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-004i-0900000000-c0b68f0a70caf30dde61	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-004i-0900000000-45b4da314919775f4d8b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-002f-0900000000-117fc8ca973d0f3a2269	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-004i-0900000000-31c044afec62150ed234	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-004i-0900000000-6f006f7dd8fb4313bb4d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-004i-0900000000-9ab358a8bea057c26f2a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-004i-0900000000-45b4da314919775f4d8b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0900000000-b733d425aecee271615f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0900000000-6d8b96a01aee3a46f311	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-004i-0900000000-c0b68f0a70caf30dde61	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-004i-0900000000-372d6bf8c22bd7aeb50a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-002f-0900000000-fef4343d64994e5383dc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0900000000-3da25e2416a223eb8529	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fft-7930000000-7407d8205c3ca4de8df8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-054k-9510000000-55fdc29c7e5ebc6c1393	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00or-9500000000-fab7d8fe424250861d0b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00dl-1960000000-1dc3d4bd92c27f7b5848	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002f-2910000000-9db8c31b2df0f599540d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000x-9200000000-1386bb26d28d0f9dfa6e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00ba-7950000000-683d6727b83458b9961f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9300000000-21f6ab78dfd677e72a53	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-4900000000-61a6cd864c33f5fb06b8	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-004i-8900000000-0426bb5e86a7ce455ca3	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

(E)-Monocrotophos 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.

Metabolism

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.

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.

Minimum Risk Level

Not Available

Health Effects

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.

Symptoms

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.

Treatment

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.

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0031805

FooDB ID

FDB006215

Phenol Explorer ID

Not Available

KNApSAcK ID