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T3D0235 - Naled

Record Information
Version 1.0
Creation Date 2009-03-06 18:58:20 UTC
Update Date 2013-04-25 08:33:24 UTC
Accession Number T3D0235
Identification
Common Name Naled
Description Naled is an organophosphate insecticide registered since 1959 for use in the United States. Naled is used primarily to control adult mosquitoes but also is used on food and feed crops and in greenhouses. The mode of action of naled is as a nonsystemic contact and stomach poison. State and local authorities apply naled by truck-mounted or aircraft-mounted sprayers. Because of the very small quantities of pesticide applied, naled does not pose a moderate or serious health risk if applied according to the guidelines for use. One of the degradation products of naled is dichlorvos, another registered organophosphate. (S689)
Compound Type
  • Organic Compound
  • Organochloride
  • Pesticide
  • Organophosphate
  • Organobromide
Chemical Structure
Thumb
MOL SDF SMILES InChI
Synonyms
  1. 1,2-Dibromo-2,2-Dichloroethyl dimethyl phosphate
  2. 1,2-Dibromo-2,2-dichloroethyl dimethyl phosphatic Acid
  3. Alvora
  4. Arthodibrom
  5. Bromchlophos
  6. Bromex
  7. Bromex (insecticide)
  8. Bromex 50
  9. BRP
  10. Dibrom
  11. Dibromfos
  12. Dimethyl 1,2-dibromo-2,2-dichloroethyl phosphate
  13. dimethyl-1,2-dibromo-2,2-dichloroethyl phosphate
  14. Flibol ex
  15. Fosbrom
  16. Hibrom
  17. Naled
  18. Naled dibromo-
  19. Naledu [polish]
  20. Nikabrom
  21. O,O-dimethyl O-2,2-dichloro-1,2-dibromoethyl phosphate
  22. O,O-Dimethyl-O-(1,2-dibromo-2,2-dichloroethyl)phosphate
  23. o-Dibrom 8E
  24. Ortho Dibrom 8E
  25. Ortho-dibrom
  26. Orthodibromo
Chemical Formula C4H7Br2Cl2O4P
Average Molecular Weight 380.784
Monoisotopic Molecular Weight 377.782575932
Chemical IUPAC Name
naled
CAS Registry Number 300-76-5
SMILES
COP(=O)(OC)OC(Br)C(Cl)(Cl)Br
InChI Identifier
InChI=1S/C4H7Br2Cl2O4P/c1-10-13(9,11-2)12-3(5)4(6,7)8/h3H,1-2H3
InChI Key InChIKey=BUYMVQAILCEWRR-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Organophosphorus Compounds
Class Organic Phosphoric Acids and Derivatives
Sub Class Organophosphate Esters
Direct Parent Organophosphate Esters
Alternative Parents
  • Organic Phosphoric Acids
  • Organochlorides
  • Alkyl Bromides
Molecular Framework Aliphatic Acyclic Compounds
Substituents
  • organic halide
  • organochloride
  • organobromide
  • alkyl bromide
External Descriptors
  • Organophosphorus insecticides(KEGG)
  • dialkyl phosphate(ChEBI)
  • organophosphate insecticide(ChEBI)
  • organochlorine compound(ChEBI)
  • organobromine compound(ChEBI)
DrugBank ID Not Available
PubChem Compound ID 4420 Link_out
KEGG ID Not Available
UniProt ID Not Available
OMIM ID Not Available
ChEBI ID 38729 Link_out
BioCyc ID 5-TERT-BUTYLAMINOL-2-HYDROXYPRO-1234-TET Link_out
CTD ID D009267 Link_out
Stitch ID Naled Link_out
PDB ID Not Available
ACToR ID 6490
Wikipedia Link Not Available
Physical Properties
Appearance Colorless solid or straw-colored liquid with a slightly pungent odor. (S689)
Melting Point 27 C
Solubility 0.0015 mg/mL [USDA PESTICIDE PROP DATABASE]
Predicted LogP 2.6517798329999995
Toxicity Profile
Route of Exposure Oral (S689) ; inhalation (S689) ; dermal (S689)
Mechanism of Action Naled is a cholinesterase inhibitor. (S689)
Metabolism Naled can be absorbed into the body by inhalation, dermal contact, and ingestion. It does not accumulate in body tissues, but repeated exposure may have a cumulative effect on cholinesterase levels. Naled is hydrolysed rapidly in the body to produce a number of metabolites, including dichlorvos, dichlorobromoacetaldehyde, dimethyl phosphate, and an amino acid conjugate of degraded naled. (S689)
Toxicity Values Not Available
Lethal Dose Not Available
Carcinogenicity (IARC Classification) Not Available
Uses/Sources Major routes of exposure are by application from fog and mist sprayers. The use of application by aircraft increases the potential for exposure of humans and nontarget organisms to naled. Human exposure to naled during mixing, handling, application, and reentry operations can be minimized by use of approved respirators and other protective clothing. (S689)
Minimum Risk Level Not Available
Health Effects Naled primarily affects the nervous system through cholinesterase inhibition, by which there is a deactivation of cholinesterase, an enzyme required for proper nerve functioning. Lab studies have shown liver damage in rats. (S691)
Symptoms If inhaled, effects on the respiratory system and the eyes are the first to appear. (S689)
Treatment Not Available
References
General References
  • S689 — ATSDR - Agency for Toxic Substances and Disease Registry (2005). Toxicologic information about insecticides used for eradicating mosquitoes (West e Virus Control): Naled. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  • S691 — Extension Toxicology Network (1993). Pesticide Information Profile for Naled. A Pesticide Information Project of Cooperative Extension Offices of Cornell University, Michigan State University, Oregon State University, and University of California at Davis. [Link]

Targets

1. Cholinesterase

Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.

UniProt ID: P06276 Link_out
Gene: BCHE Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • W971 — Effect of acute and chronic cholinesterase inhibition on biogenic amines in rat brain [1711162 Link_out]

2. Acetylcholinesterase

Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.

UniProt ID: P22303 Link_out
Gene: ACHE Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • W970 — Protective efficacy of mitochondrial targeted antioxidant MitoQ against dichlorvos induced oxidative stress and cell death in rat brain [21784090 Link_out]