Mexacarbate

Basic Info

Common NameMexacarbate(F04012)
2D Structure
Description

Mexacarbate 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. (L795)

FRCD IDF04012
CAS Number315-18-4
PubChem CID9414
FormulaC12H18N2O2
IUPAC Name

[4-(dimethylamino)-3,5-dimethylphenyl] N-methylcarbamate

InChI Key

YNEVBPNZHBAYOA-UHFFFAOYSA-N

InChI

InChI=1S/C12H18N2O2/c1-8-6-10(16-12(15)13-3)7-9(2)11(8)14(4)5/h6-7H,1-5H3,(H,13,15)

Canonical SMILES

CC1=CC(=CC(=C1N(C)C)C)OC(=O)NC

Isomeric SMILES

CC1=CC(=CC(=C1N(C)C)C)OC(=O)NC

Synonyms
        
            4-Dimethylamino-3,5-xylyl methylcarbamate
        
            Mexacarbate
        
            ZECTRAN
        
            Zactran
        
            Zectane
        
            Zextran
        
            315-18-4
        
            Mexicarbate
        
            Zectrane
        
            Dowco 139
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassPhenyl methylcarbamates
Intermediate Tree NodesNot available
Direct ParentPhenyl methylcarbamates
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsPhenyl methylcarbamate - Phenoxy compound - Tertiary aliphatic/aromatic amine - M-xylene - Xylene - Dialkylarylamine - Aniline or substituted anilines - Carbamic acid ester - Carbonic acid derivative - Tertiary amine - Amine - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Carbonyl group - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as phenyl methylcarbamates. These are aromatic compounds containing a methylcarbamic acid esterified with a phenyl group.

Properties

Property NameProperty Value
Molecular Weight222.288
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Complexity231
Monoisotopic Mass222.137
Exact Mass222.137
XLogP2.5
Formal Charge0
Heavy Atom Count16
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9659
Human Intestinal AbsorptionHIA+0.9923
Caco-2 PermeabilityCaco2+0.7075
P-glycoprotein SubstrateNon-substrate0.7925
P-glycoprotein InhibitorNon-inhibitor0.8782
Non-inhibitor0.8889
Renal Organic Cation TransporterNon-inhibitor0.9123
Distribution
Subcellular localizationMitochondria0.7074
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7357
CYP450 2D6 SubstrateSubstrate0.5176
CYP450 3A4 SubstrateSubstrate0.6348
CYP450 1A2 InhibitorNon-inhibitor0.5251
CYP450 2C9 InhibitorNon-inhibitor0.9128
CYP450 2D6 InhibitorNon-inhibitor0.9233
CYP450 2C19 InhibitorNon-inhibitor0.7256
CYP450 3A4 InhibitorNon-inhibitor0.8555
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.6135
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9251
Non-inhibitor0.8736
AMES ToxicityAMES toxic0.7236
CarcinogensNon-carcinogens0.6937
Fish ToxicityHigh FHMT0.9088
Tetrahymena Pyriformis ToxicityHigh TPT0.5676
Honey Bee ToxicityHigh HBT0.5306
BiodegradationNot ready biodegradable0.9634
Acute Oral ToxicityI0.7776
Carcinogenicity (Three-class)Non-required0.6933
Model Value Unit
Absorption
Aqueous solubility-2.4228LogS
Caco-2 Permeability1.5118LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.8441LD50, mol/kg
Fish Toxicity0.4148pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.2814pIGC50, ug/L

Targets

Target Details

Acetylcholinesterase

General Function:
Serine hydrolase activity
Specific Function:
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name:
ACHE
Uniprot ID:
P22303
Molecular Weight:
67795.525 Da
References
  1. Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension.: http://edis.ifas.ufl.edu/PI088
Target Details

Cholinesterase

General Function:
Identical protein binding
Specific Function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular Weight:
68417.575 Da
Mechanism of Action:
Like the organophosphates, their mode of action is inhibition of cholinesterase enzymes, affecting nerve impulse transmission.
References
  1. Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension.: http://edis.ifas.ufl.edu/PI088