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253300

Sigma-Aldrich

Deltamethrin

Synthetic type II pyrethroid. Potent inhibitor of calcineurin. Causes an increase in neurotransmitter release at synapses, and increases intrasynaptosomal Ca2+ levels.

Synonym(s):

Deltamethrin, (S)-α-Cyano-3-phenoxybenzyl(1R)- cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate, (S)-α-Cyano-3-phenoxybenzyl(1R)-cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate

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About This Item

Empirical Formula (Hill Notation):
C22H19Br2NO3
CAS Number:
52918-63-5
Molecular Weight:
505.20
MDL number:
MFCD00870122
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

assay

≥98% (TLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze

color

white

solubility

ethanol: 1 mg/mL
DMSO: 15 mg/mL

shipped in

ambient

storage temp.

2-8°C

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

General description

Synthetic type II pyrethroid insecticide. Potent inhibitor of calcineurin (protein phosphatase 2B, IC50 = 100 pM). May also have varied effects on ion channels. Causes an increase in neurotransmitter release at synapses and also increases intrasynaptosomal Ca2+ levels.
Synthetic type II pyrethroid. Potent inhibitor of calcineurin (protein phosphatase 2B; IC50 = 100 pM). May also have varied effects on ion channels. Causes an increase in neurotransmitter release at synapses, and increases intrasynaptosomal Ca2+ levels.

Biochem/physiol Actions

Cell permeable: no
Primary Target
protein phosphatase 2B
Product does not compete with ATP.
Reversible: no
Target IC50: 100 pM against calcineurin (protein phosphatase 2B)

Warning

Toxicity: Highly Toxic (H)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C. Avoid acid or alkali conditions.

Other Notes

Due to the nature of the Hazardous Materials in this shipment, additional shipping charges may be applied to your order. Certain sizes may be exempt from the additional hazardous materials shipping charges. Please contact your local sales office for more information regarding these charges.
Richter, A., et al. 1995. Biochem. Pharmacol.49, 367.
Enan, E., and Matsumura, F. 1993. Biochem. Pharmacol. 45, 703.
Enan, E., and Matsumura, F. 1992. Biochem. Pharmacol.43, 1777.
Narahasi, T. 1992. Trends Pharmacol. Sci.13, 236.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

signalword

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1

wgk_germany

WGK 3

flash_point_f

closed cup

flash_point_c

closed cup

Certificates of Analysis (COA)

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T Narahashi
Trends in pharmacological sciences, 13(6), 236-241 (1992-06-01)
The mechanisms of action of neuroactive insecticides on the nervous system has been studied for many years. It is now well established that severe neurological symptoms of poisoning with pyrethroids and DDT in mammals and insects are the result of
A Richter et al.
Biochemical pharmacology, 49(3), 367-373 (1995-01-31)
The ability of the immunosuppressive agent FK506 to affect growth of the epidermal growth factor-receptor (EGF-R) overexpressing cell line, A431, was compared with that of the structurally unrelated immunosuppressive compound, cyclosporin A (CyA). Both were shown to inhibit growth, although
E Enan et al.
Biochemical pharmacology, 45(3), 703-710 (1993-02-09)
We have investigated the effects of a type II pyrethroid insecticide, deltamethrin, on changes in the protein phosphorylation pattern associated with neurotransmitter release in rat brain synaptosomal preparations. Deltamethrin was found to stimulate directly the activity of the protein kinase
E Enan et al.
Biochemical pharmacology, 43(8), 1777-1784 (1992-04-15)
The inhibitory action of synthetic pyrethroids and some chlorinated hydrocarbon insecticides on the neural calcium-calmodulin-dependent protein phosphatase, calcineurin, was studied using one radiotracer and two colorimetric methods. It was found that all insecticidal Type II pyrethroids (cypermethrin, deltamethrin and fenvalerate)

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