Basic Info

Common NameAminocarb(F03956)
2D Structure
Description

Aminocarb 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 IDF03956
CAS Number2032-59-9
PubChem CID16247
FormulaC11H16N2O2
IUPAC Name

[4-(dimethylamino)-3-methylphenyl] N-methylcarbamate

InChI Key

IMIDOCRTMDIQIJ-UHFFFAOYSA-N

InChI

InChI=1S/C11H16N2O2/c1-8-7-9(15-11(14)12-2)5-6-10(8)13(3)4/h5-7H,1-4H3,(H,12,14)

Canonical SMILES

CC1=C(C=CC(=C1)OC(=O)NC)N(C)C

Isomeric SMILES

CC1=C(C=CC(=C1)OC(=O)NC)N(C)C

Synonyms
        
            AMINOCARB
        
            2032-59-9
        
            4-(Dimethylamino)-m-tolyl methylcarbamate
        
            Matacil
        
            Mitacil
        
            Aminocarbe
        
            Matacil 180D
        
            Bayer 5080
        
            Bayer 44646
        
            Aminocarbe [French]
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassPhenoxy compounds
Intermediate Tree NodesNot available
Direct ParentPhenoxy compounds
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsTertiary aliphatic/aromatic amine - Phenoxy compound - Dialkylarylamine - Aminotoluene - Aniline or substituted anilines - Toluene - Tertiary amine - Carboximidic acid derivative - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Organooxygen compound - Organonitrogen compound - Imine - Amine - Hydrocarbon derivative - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as phenoxy compounds. These are aromatic compounds contaning a phenoxy group.

Properties

Property NameProperty Value
Molecular Weight208.261
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Complexity219
Monoisotopic Mass208.121
Exact Mass208.121
XLogP1.9
Formal Charge0
Heavy Atom Count15
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

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
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