Propamocarb (CHEM000860)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (2)XML
Record Information
Version1.0
Creation Date2009-06-17 23:53:05 UTC
Update Date2026-03-26 18:31:53 UTC
Accession NumberCHEM000860
Identification
Common NamePropamocarb
ClassSmall Molecule
DescriptionPropamocarb is a carbamate pesticide. Carbamate pesticides are derived from carbamic acid and kill insects in a similar fashion as organophosphate insecticides. They are widely used in homes, gardens and agriculture. The first carbamate, carbaryl, was introduced in 1956 and more of it has been used throughout the world than all other carbamates combined. Because of carbaryl's relatively low mammalian oral and dermal toxicity and broad control spectrum, it has had wide use in lawn and garden settings. Most of the carbamates are extremely toxic to Hymenoptera, and precautions must be taken to avoid exposure to foraging bees or parasitic wasps. Some of the carbamates are translocated within plants, making them an effective systemic treatment. (3)
Contaminant Sources
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Carbamate
  • Ester
  • Ether
  • Organic Compound
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
PropamocarbeChEBI
Propyl (3-(dimethylamino)propyl)carbamateChEBI
Propyl 3-(dimethylamino)propylcarbamateChEBI
Propyl N-[3-(dimethylamino)propyl]carbamateChEBI
Propyl (3-(dimethylamino)propyl)carbamic acidGenerator
Propyl 3-(dimethylamino)propylcarbamic acidGenerator
Propyl N-[3-(dimethylamino)propyl]carbamic acidGenerator
PrevicurMeSH
Propamocarb monohydrochlorideMeSH
Propyl(3-(dimethylamino)propyl)carbamate monohydrochlorideMeSH
Chemical FormulaC9H20N2O2
Average Molecular Mass188.267 g/mol
Monoisotopic Mass188.152 g/mol
CAS Registry Number24579-73-5
IUPAC Namepropyl N-[3-(dimethylamino)propyl]carbamate
Traditional Namepropamocarb
SMILESCCCOC(=O)NCCCN(C)C
InChI IdentifierInChI=1S/C9H20N2O2/c1-4-8-13-9(12)10-6-5-7-11(2)3/h4-8H2,1-3H3,(H,10,12)
InChI KeyWZZLDXDUQPOXNW-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as carbamate esters. Carbamate esters are compounds containing an ester of carbamic acid with the general structure R2NC(=O)OR' (R' not H). They are esters of carbamic acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentCarbamate esters
Alternative Parents
Substituents
  • Carbamic acid ester
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carbonic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
Solubility900 mg/mL at 20°C [TOMLIN,C (1997); pH 7.0]
Predicted Properties
PropertyValueSource
Water Solubility80.7 g/LALOGPS
logP1ALOGPS
logP0.77ChemAxon
logS-0.37ALOGPS
pKa (Strongest Acidic)16.18ChemAxon
pKa (Strongest Basic)9.3ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.57 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity53.14 m³·mol⁻¹ChemAxon
Polarizability22.44 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 13V, positivesplash10-0f6x-0900000000-873a325a84c6dbc6bee2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 5V, positivesplash10-000i-0900000000-92087a38838b583b4a7dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 11V, positivesplash10-000i-0900000000-3c477777fce241a50544Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 16V, positivesplash10-0udi-0900000000-789848dcf9622f7b1158Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 22V, positivesplash10-0udi-1900000000-d562e26ee5bbd46c19b5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 28V, positivesplash10-0udi-2900000000-0365de5ebdc7b565ff81Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 33V, positivesplash10-0udi-4900000000-8b70973112cba329d2afSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-000i-0900000000-6da3f000dfd6b416dec9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-000l-0900000000-8c87479fb8c6a80f8c30Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 30V, positivesplash10-004l-0900000000-d2e333be530cd31b6cb8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 22V, positivesplash10-0udi-2900000000-d09d67c40a2fc1ba5eabSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f7c-6900000000-5a1c9dda4f6020c59370Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udl-9600000000-39088f2ead1f86a0a3ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-059f-9000000000-d597f8f385668d0b3fc8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-3900000000-cdbf9f495fa84c1e5e38Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-9600000000-e947524fbc96af70ce87Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0536-9200000000-80f2ea9b18dd78d81934Spectrum
Toxicity Profile
Route of ExposureInhalation (2) ; oral (2); dermal (2)
Mechanism of ToxicityPropamocarb is a cholinesterase or acetylcholinesterase (AChE) inhibitor. Carbamates form unstable complexes with chlolinesterases by carbamoylation of the active sites of the enzymes. This inhibition is reversible. A cholinesterase inhibitor suppresses the action of acetylcholine esterase. Because of its essential function, chemicals that interfere with the action of acetylcholine esterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. 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.
MetabolismThe carbamates are hydrolyzed enzymatically by the liver; degradation products are excreted by the kidneys and the liver. (2)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesPropamocarb is widely used as an insecticide or pesticide in homes, gardens and agricultural applications. It is a synthetic compound.
Minimum Risk LevelNot Available
Health EffectsAcute 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. Chronically high (>10 years) exposure leads to neuropsychological consequences including disturbances in perception and visuo-motor processing (1).
SymptomsAs with organophosphates, the signs and symptoms are based on excessive cholinergic stimulation. Unlike organophosphate poisoning, carbamate poisonings tend to be of shorter duration because the inhibition of nervous tissue acetylcholinesterase is reversible, and carbamates are more rapidly metabolized. Muscle weakness, dizziness, sweating and slight body discomfort are commonly reported early symptoms. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Contraction of the pupils with blurred vision, incoordination, muscle twitching and slurred speech have been reported. (3)
TreatmentIf 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
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPropamocarb
Chemspider IDNot Available
ChEBI ID82033
PubChem Compound ID32490
Kegg Compound IDC18885
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=14985943
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15204535
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22699710
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24791956