ContaminantDB: Pirimicarb

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (8)XML

Record Information

Version

1.0

Creation Date

2009-06-17 23:53:05 UTC

Update Date

2026-03-26 18:29:06 UTC

Accession Number

CHEM000855

Identification

Common Name

Pirimicarb

Class

Small Molecule

Description

Pirimicarb 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

Carbamate
Ester
Insecticide
Organic Compound
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Dimethylcarbamic acid 2-(dimethylamino)-5,6-dimethyl-4-pyrimidinyl ester	ChEBI
Dimethylcarbamate 2-(dimethylamino)-5,6-dimethyl-4-pyrimidinyl ester	Generator
2-dimethylamino-5,6-Dimethylpyrimidin-4-yldimethylcarbamate	MeSH
5,6-Dimethyl-2-dimethylamino-4-dimethylcarbamoyloxypyrimidine	MeSH
Pirimor	MeSH
Pyrimor	MeSH
ZZ-Aphox	MeSH

Chemical Formula

C₁₁H₁₈N₄O₂

Average Molecular Mass

238.286 g/mol

Monoisotopic Mass

238.143 g/mol

CAS Registry Number

23103-98-2

IUPAC Name

2-(dimethylamino)-5,6-dimethylpyrimidin-4-yl N,N-dimethylcarbamate

Traditional Name

pirimicarb

SMILES

CN(C)C(=O)OC1=NC(=NC(C)=C1C)N(C)C

InChI Identifier

InChI=1S/C11H18N4O2/c1-7-8(2)12-10(14(3)4)13-9(7)17-11(16)15(5)6/h1-6H3

InChI Key

YFGYUFNIOHWBOB-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as dialkylarylamines. These are aliphatic aromatic amines in which the amino group is linked to two aliphatic chains and one aromatic group.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Dialkylarylamines

Alternative Parents

Substituents

Dialkylarylamine
Aminopyrimidine
Pyrimidine
Heteroaromatic compound
Carbamic acid ester
Carbonic acid derivative
Azacycle
Organoheterocyclic compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

carbamate ester (CHEBI:8248 )
tertiary amino compound (CHEBI:8248 )
aminopyrimidine (CHEBI:8248 )
Carbamate insecticides (C11079 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

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	90.5°C
Boiling Point	Not Available
Solubility	2.7 mg/mL at 25°C [YALKOWSKY,SH & DANNENFELSER,RM (1992)]

Predicted Properties

Property	Value	Source
Water Solubility	0.78 g/L	ALOGPS
logP	1.45	ALOGPS
logP	1.8	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Basic)	4.99	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	58.56 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	66.65 m³·mol⁻¹	ChemAxon
Polarizability	25.92 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
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-ITFT 16V, positive	splash10-001i-0900000000-e5740c854eb7e7ad3c4f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 7V, positive	splash10-000i-0090000000-119ebb68ddf4e440b683	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 14V, positive	splash10-0080-4790000000-4700bd197df64bf01172	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 21V, positive	splash10-00e9-8900000000-b7381858fe3ce0299f5d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 28V, positive	splash10-00di-9500000000-b8cf29b1203436d01225	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 35V, positive	splash10-00di-9200000000-aa0be7983aec57fbab1a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 42V, positive	splash10-00di-9100000000-6179a70cba6a22566220	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 10V, positive	splash10-000i-0190000000-94b7560c0f9c519d58e9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 20V, positive	splash10-0fer-4960000000-51ffb682b0be3d517b36	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 30V, positive	splash10-00di-9600000000-48515d1eeed29a5ccca4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 40V, positive	splash10-00di-9400000000-b32e71dc3f93b26df492	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 50V, positive	splash10-00di-9300000000-407204c4c3da85d12b49	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT 0V, positive	splash10-001i-2900000000-d950836835aaf04daeb7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 26V, positive	splash10-00e9-9800000000-5ce80c8c19f69148d8ba	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 38V, positive	splash10-00di-9300000000-b85802019265ab8ef32c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 16V, positive	splash10-001i-0910000000-40accc9af95caf9e2357	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT 16V, positive	splash10-00ei-9550000000-15b94f25ca195031ceb0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - NA , positive	splash10-00di-9420000000-005b33570a1d36c2f1f8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - NA , positive	splash10-03di-0090000000-c23356a41acab4bfe7ca	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0190000000-df3ac4872d3bfbb37ef8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udu-4940000000-48e9e2ce7263ae73cdac	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9800000000-a5055c18aa1449e07430	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0190000000-07314debcdcbd5a16f98	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000l-6980000000-74a27d368386f745e7b9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00y0-9200000000-5fc58ffeb356a62f4146	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-01b9-9710000000-313bbf6b18b18b212ba3	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Inhalation (2) ; oral (2); dermal (2)

Mechanism of Toxicity

Pirimicarb 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.

Metabolism

The carbamates are hydrolyzed enzymatically by the liver; degradation products are excreted by the kidneys and the liver. (2)

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

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

Uses/Sources

Pirimicarb is widely used as an insecticide or pesticide in homes, gardens and agricultural applications. It is a synthetic compound.

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. Chronically high (>10 years) exposure leads to neuropsychological consequences including disturbances in perception and visuo-motor processing (1).

Symptoms

As 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)

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

HMDB0256598

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID