ContaminantDB: Promecarb

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (2)XML

Record Information

Version

1.0

Creation Date

2009-06-17 23:53:05 UTC

Update Date

2026-03-26 21:38:12 UTC

Accession Number

CHEM000858

Identification

Common Name

Promecarb

Class

Small Molecule

Description

Promecarb 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

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

Contaminant Type

Amine
Carbamate
Ester
Organic Compound
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Methyl-5-isopropylphenyl N-methylcarbamate	MeSH
Carbamult	MeSH
m-Cym-5-yl methylcarbamate	MeSH
3-Cym-5-yl methylcarbamate	MeSH

Chemical Formula

C₁₂H₁₇NO₂

Average Molecular Mass

207.269 g/mol

Monoisotopic Mass

207.126 g/mol

CAS Registry Number

2631-37-0

IUPAC Name

3-methyl-5-(propan-2-yl)phenyl N-methylcarbamate

Traditional Name

3-isopropyl-5-methylphenyl N-methylcarbamate

SMILES

CNC(=O)OC1=CC(C)=CC(=C1)C(C)C

InChI Identifier

InChI=1S/C12H17NO2/c1-8(2)10-5-9(3)6-11(7-10)15-12(14)13-4/h5-8H,1-4H3,(H,13,14)

InChI Key

DTAPQAJKAFRNJB-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phenyl methylcarbamates. These are aromatic compounds containing a methylcarbamic acid esterified with a phenyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenyl methylcarbamates

Direct Parent

Phenyl methylcarbamates

Alternative Parents

Substituents

Phenyl methylcarbamate
Cumene
Phenylpropane
Phenoxy compound
Toluene
Carbamic acid ester
Carbonic acid derivative
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

alkylbenzene (CHEBI:82096 )
Carbamate insecticide (C18956 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	87°C
Boiling Point	Not Available
Solubility	0.092 mg/mL at 25°C [MARTIN,H & WORTHING,CR (1977)]

Predicted Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	2.82	ALOGPS
logP	3.23	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	14.77	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.33 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	60 m³·mol⁻¹	ChemAxon
Polarizability	23.66 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, positive	splash10-0a4i-0190000000-a5f52733f725ac7b6dfc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, positive	splash10-0a4i-0390000000-4370363aad7442d45a6b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-0zfr-0950000000-229b13ceb54fc3e8b98b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-0udi-0910000000-c838b07cfdc8d3aa17f9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-0udi-0900000000-d5187dbbac16ba382475	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-0zfr-0900000000-eae14c41f9c257e91abe	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-0pb9-0900000000-0a4ef7339145dce34505	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, positive	splash10-0a4i-0900000000-84a2a3a3784b05f51732	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, positive	splash10-0a4i-0900000000-9d0c21869311a4ba9ae6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 7V, positive	splash10-0a4i-0900000000-106cf9d7802462a4d09b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 8V, positive	splash10-0a4i-0900000000-afa154b2c7eb691938cf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 9V, positive	splash10-0a4i-0900000000-c26b56b2b12b5c4d1edf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 12V, positive	splash10-0a4i-2900000000-5df5b168211a25443e85	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 15V, positive	splash10-0a4l-6900000000-abb7cf37b117ecebe5aa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 18V, positive	splash10-052f-9300000000-67381698dfd1e84fff0f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 22V, positive	splash10-0006-9100000000-b55283e4527d88867c6d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 27V, positive	splash10-00kf-9000000000-eb3624ddd6d6a3b0282e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 14V, positive	splash10-0udi-0900000000-e9f12672e941d9e39c54	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 14V, positive	splash10-0006-9000000000-032721f0001349351fef	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0pb9-5950000000-0921d07bd7a21397e656	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0zgi-3900000000-d4ffe818f995514ae19c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a59-8900000000-1737f242b2dd2ac0a582	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9550000000-0bc8f7c6c634cd5586d6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4j-7910000000-2612d028c6df8658bc24	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a5a-8900000000-19b6a0e25b404861f209	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0f79-2900000000-9cc92fd2f0dee29c15c5	Spectrum

Toxicity Profile

Route of Exposure

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

Mechanism of Toxicity

Promecarb 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

Promecarb 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

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Promecarb

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

17516

Kegg Compound ID

C18956

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Promecarb (CHEM000858)

Structure for CHEM000858: Promecarb