ContaminantDB: Deltamethrin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (26)XML

Record Information

Version

1.0

Creation Date

2009-06-18 17:03:35 UTC

Update Date

2026-05-14 19:35:06 UTC

Accession Number

CHEM000893

Identification

Common Name

Deltamethrin

Class

Small Molecule

Description

Deltamethrin is a pyrethroid (type 2) ester insecticide. This material is a member of one of the safest classes of pesticides: synthetic pyrethroids. While mammalian exposure to deltamethrin is classified as safe, this pesticide is highly toxic to aquatic life, particularly fish, and therefore must be used with extreme caution around water. A pyrethroid is a synthetic chemical compound similar to the natural chemical pyrethrins produced by the flowers of pyrethrums (Chrysanthemum cinerariaefolium and C. coccineum). Pyrethroids are common in commercial products such as household insecticides and insect repellents. In the concentrations used in such products, they are generally harmless to human beings but can harm sensitive individuals. They are usually broken apart by sunlight and the atmosphere in one or two days, and do not significantly affect groundwater quality except for being toxic to fish. Since deltamethrin is a neurotoxin, it temporarily attacks (in medical terms, insults) the nervous system of any animal with which it comes into contact. Skin contact can lead to tingling or reddening of the skin local to the application. If taken in through the eyes or mouth, a common symptom is facial paraesthesia, which can feel like many different abnormal sensations, including burning, partial numbness, pins and needles, skin crawling, etc.

Contaminant Sources

IARC Carcinogens Group 3
My Exposome Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Bromide Compound
Ester
Ether
Household Toxin
Human Neurotoxin
Insecticide
Metabolite
Nitrile
Organic Compound
Organobromide
Pesticide
Pyrethroid
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(S)-alpha-Cyano-3-phenoxybenzyl (1R)-cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate	ChEBI
(S)-alpha-Cyano-3-phenoxybenzyl (1R,3R)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate	ChEBI
(S)-Cyano(3-phenoxyphenyl)methyl (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate	ChEBI
Ballistic	ChEBI
Cropro D-sect	ChEBI
Decamethrin	ChEBI
Decamethrine	ChEBI
Decis	ChEBI
Decis options	ChEBI
DeltaGard	ChEBI
Deltashield	ChEBI
Scalibor	ChEBI
(S)-a-Cyano-3-phenoxybenzyl (1R)-cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate	Generator
(S)-a-Cyano-3-phenoxybenzyl (1R)-cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylic acid	Generator
(S)-alpha-Cyano-3-phenoxybenzyl (1R)-cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylic acid	Generator
(S)-Α-cyano-3-phenoxybenzyl (1R)-cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate	Generator
(S)-Α-cyano-3-phenoxybenzyl (1R)-cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylic acid	Generator
(S)-a-Cyano-3-phenoxybenzyl (1R,3R)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate	Generator
(S)-a-Cyano-3-phenoxybenzyl (1R,3R)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylic acid	Generator
(S)-alpha-Cyano-3-phenoxybenzyl (1R,3R)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylic acid	Generator
(S)-Α-cyano-3-phenoxybenzyl (1R,3R)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate	Generator
(S)-Α-cyano-3-phenoxybenzyl (1R,3R)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylic acid	Generator
(S)-Cyano(3-phenoxyphenyl)methyl (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylic acid	Generator
(S)-Cyano(3-phenoxyphenyl)methyl (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylate	HMDB
Butox	HMDB
Cislin	HMDB
Crackdown	HMDB
Decis 0.5ulv	HMDB
Decis 1.5ulv	HMDB
Decis 2.5ulv	HMDB
Dekametrin	HMDB
Deltagran	HMDB
Deltamethrine	HMDB
Esbecythrin	HMDB
Glossinex 200	HMDB
K-Obiol	HMDB
K-Othrin	HMDB
K-Othrine	HMDB
New musigie	HMDB
Phagase 1	HMDB
Suspend	HMDB
Zorcis	HMDB
Decamethrin, (1S-(1alpha(s*),3alpha))-isomer	HMDB
alpha-Cyano-3-phenoxybenzyl (1R,3R)-cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate	HMDB
Decamethrin, (1R-(1alpha(r*),3beta))-isomer	HMDB
Difexon	HMDB
Decamethrin, (1R-(1alpha(r*),3alpha))-isomer	HMDB
Decamethrin, (1R-(1alpha(s*),3beta))-isomer	HMDB
Decamethrin, (1S-(1alpha(r*),3alpha))-isomer	HMDB
NRDC 161	HMDB

Chemical Formula

C₂₂H₁₉Br₂NO₃

Average Molecular Mass

505.199 g/mol

Monoisotopic Mass

502.973 g/mol

CAS Registry Number

52918-63-5

IUPAC Name

(S)-cyano(3-phenoxyphenyl)methyl (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate

Traditional Name

stricker

SMILES

[H][C@@](OC(=O)[C@]1([H])[C@]([H])(C=C(Br)Br)C1(C)C)(C#N)C1=CC(OC2=CC=CC=C2)=CC=C1

InChI Identifier

InChI=1S/C22H19Br2NO3/c1-22(2)17(12-19(23)24)20(22)21(26)28-18(13-25)14-7-6-10-16(11-14)27-15-8-4-3-5-9-15/h3-12,17-18,20H,1-2H3/t17-,18+,20-/m0/s1

InChI Key

OWZREIFADZCYQD-NSHGMRRFSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as pyrethroids. These are organic compounds similar to the pyrethrins. Some pyrethroids containing a chrysanthemic acid esterified with a cyclopentenone (pyrethrins), or with a phenoxybenzyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Pyrethroids

Alternative Parents

Substituents

Pyrethroid skeleton
Diphenylether
Diaryl ether
Benzyloxycarbonyl
Phenoxy compound
Phenol ether
Monocyclic benzene moiety
Cyclopropanecarboxylic acid or derivatives
Benzenoid
Carboxylic acid ester
Ketene acetal or derivatives
Carboxylic acid derivative
Ether
Bromoalkene
Monocarboxylic acid or derivatives
Carbonitrile
Nitrile
Haloalkene
Vinyl halide
Vinyl bromide
Carbonyl group
Organic oxygen compound
Organopnictogen compound
Organohalogen compound
Organobromide
Organonitrogen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

organobromine compound (CHEBI:4388 )
aromatic ether (CHEBI:4388 )
carboxylic ester (CHEBI:4388 )
nitrile (CHEBI:4388 )
Pyrethroid insecticides (C10985 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor

Physical Properties

State

Solid

Appearance

Colourless crystalline powder (12).

Experimental Properties

Property	Value
Melting Point	100°C
Boiling Point	Not Available
Solubility	2e-06 mg/mL at 25°C

Predicted Properties

Property	Value	Source
Water Solubility	0.0012 g/L	ALOGPS
logP	6.13	ALOGPS
logP	5.74	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	10.62	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	59.32 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	124.29 m³·mol⁻¹	ChemAxon
Polarizability	42.76 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zfr-3290000000-fc2670ebdafd72059d49	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0060190000-d06e22076d1773eb0a44	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fb9-0190220000-42d1b03d814ec594ac38	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004s-2390000000-81cbf54d9ff1579aaee8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0010190000-74170f71f0cac166e6c6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0uk9-3151590000-565197ea502710a2b39e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9430000000-f63f1a3abdb315fa7b1a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0zfr-0050290000-ae219751f7022f5de5c3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0zi1-3291140000-49559be6170bc80632d4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a59-2980000000-38996b5e6c79b7a6a39a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0050290000-dabcbd6a2915829d16b4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udj-3290150000-1ee946d210b195df7f8c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9010100000-1b3ae98f2c93d34b79a9	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0ff3-7940000000-0aa3b4a622f8410e5b43	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Inhalation (9) ; oral (9) ; dermal (9) ; eye contact (9).

Mechanism of Toxicity

Both type I and type II pyrethroids exert their effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. They appear to bind to the membrane lipid phase in the immediate vicinity of the sodium channel, thus modifying the channel kinetics. This blocks the closing of the sodium gates in the nerves, and thus prolongs the return of the membrane potential to its resting state. The repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential produces effects quite similar to those produced by DDT, leading to hyperactivity of the nervous system which can result in paralysis and/or death. Other mechanisms of action of pyrethroids include antagonism of gamma-aminobutyric acid (GABA)-mediated inhibition, modulation of nicotinic cholinergic transmission, enhancement of noradrenaline release, and actions on calcium ions. They also inhibit calium channels and Ca2+, Mg2+-ATPase. (13, 14, 9)

Metabolism

Deltamethrin is readily absorbed by the oral route, but less so dermally; absorbed deltamethrin is readily metabolized and excreted. The major degradation pathway of cypermethrin is hydrolysis of the ester linkage to (yield ultimately) 3-phenoxybenzoic acid and 3-(2,2-dichlorovinyl)-2,2- dimethylcyclopropanecarboxylic acid. (From the cis-isomer both cis- and trans- cyclopropanecarboxylic acids are found.) A minor degradative route is ring hydroxylation to give an alpha-cyano-3-(4-hydroxyphenyl)benzyl ester followed by hydrolysis to produce the corresponding hydroxycarboxylic acid (3).

Toxicity Values

LD50: 4123 mg/kg (Oral, Rat) (4) LD50: >2460 mg/kg (Dermal, Rabbit) (4)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

3, not classifiable as to its carcinogenicity to humans. (5)

Uses/Sources

Pyrethroids are used as insecticides. (9)

Minimum Risk Level

Not Available

Health Effects

At high doses, signs of poisoning attributable to deltamethrin include profuse salivation and pulmonary edema, clonic seizures, opisthotonos (i.e., the spine is bent forward such that a supine body rests on its head and heels), coma, and death. At lower doses, commonly observed effects include paresthesia and erythema (10).

Symptoms

Following dermal exposure to deltamethrin, feelings of numbness, itching, burning, stinging, tingling, or warmth may occur, that could last for a few hours. Ddizziness, headache, nausea, muscle twitching, reduced energy, and changes in awareness can reult from inhalation or ingestion of large amounts of deltamethrin. Paralysis can occur after exposure (9).

Treatment

Following oral exposure, the treatment is symptomatic and supportive and includes monitoring for the development of hypersensitivity reactions with respiratory distress. Provide adequate airway management when needed. Gastric decontamination is usually not required unless the pyrethrin product is combined with a hydrocarbon. Following inhalation exposure, move patient to fresh air. monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. In case of eye exposure, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. If irritation, pain, swelling, lacrimation, or photophobia persist, the patient should be seen in a health care facility. If the contamination occurs through dermal exposure, Remove contaminated clothing and wash exposed area thoroughly with soap and water. A physician may need to examine the area if irritation or pain persists. Vitamin E topical application is highly effective in relieving parenthesis. (6)

Concentrations

Not Available

External Links

DrugBank ID

DB13600

HMDB ID

HMDB0041866

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID