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Aldicarb

Catalog Number: BT-253510

CAS Number: 116-06-3

Molecular Formula: C7H14N2O2S
CH3SC(CH3)2CH=NOCONHCH3

C7H14N2O2S

Molecular Weight: 190.27 g/mol

The product is for non-human research only. Not for therapeutic or veterinary use.

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Product Introduction

Description

Aldicarb is a highly toxic carbamate pesticide that is widely used in agriculture to control pests. It is a potent inhibitor of acetylcholinesterase, an enzyme that is essential for nerve function. Aldicarb is also used in medical research and industrial processes. This paper will discuss the methods of synthesis or extraction, chemical structure and biological activity, biological effects, applications, and future perspectives and challenges of aldicarb.

Properties

CAS Number

116-06-3

Product Name

Aldicarb

IUPAC Name

[(Z)-(2-methyl-2-methylsulfanylpropylidene)amino] N-methylcarbamate

Molecular Formula

C7H14N2O2S
CH3SC(CH3)2CH=NOCONHCH3

C7H14N2O2S

Molecular Weight

190.27 g/mol

InChI

InChI=1S/C7H14N2O2S/c1-7(2,12-4)5-9-11-6(10)8-3/h5H,1-4H3,(H,8,10)/b9-5-

InChI Key

QGLZXHRNAYXIBU-WEVVVXLNSA-N

SMILES

CC(C)(C=NOC(=O)NC)SC

Solubility

0.1 to 1.0 mg/mL at 72° F (NTP, 1992)
0.03 M
Sparingly soluble in certain organic solvents, most soluble in chloroform and acetone
Aldicarb solubilities (expressed as %) at various temperatures.
Table: Percent Solubility [Table#3195]

350 g/kg, acetone; 300 g/kg, dichloromethane; 150 g/kg, benzene; 150 g/kg, xylene; all at 25 °C
In water, 4,930 mg/L at 20 °C
Practically insoluble in hexane
Solubility in water, g/100ml at 25 °C: 0.6

Synonyms

Aldicarb
ENT 27,093
ENT-27,093
ENT27,093
Temik
UC 21,149
UC 21149
UC-21,149
UC-21149
UC21,149
UC21149

Canonical SMILES

CC(C)(C=NOC(=O)NC)SC

Isomeric SMILES

CC(C)(/C=N\OC(=O)NC)SC

Method of Synthesis or Extraction

Aldicarb is synthesized by reacting methyl isocyanate with 2-methyl-2-(methylthio)propanal in the presence of a catalyst. This method has a high yield and efficiency, but it also produces toxic byproducts. Another method involves the reaction of dimethyl sulfate with 2-methyl-2-(methylthio)propanol, followed by reaction with potassium cyanate. This method has a lower yield and efficiency but produces fewer toxic byproducts. Environmental and safety considerations must be taken into account when using aldicarb, as it is highly toxic to humans and animals.

Chemical Structure and Biological Activity

Aldicarb has a molecular formula of C7H14N2O2S and a molecular weight of 190.27 g/mol. It is a white crystalline solid that is soluble in water and organic solvents. Aldicarb is a potent inhibitor of acetylcholinesterase, which leads to the accumulation of acetylcholine in the nervous system and causes symptoms such as muscle weakness, respiratory failure, and death. Aldicarb also has other biological targets, such as voltage-gated sodium channels and nicotinic acetylcholine receptors. It has a high potency, with an LD50 of 0.5-2 mg/kg in humans.

Biological Effects

Aldicarb has a wide range of biological effects on cell function and signal transduction. It can cause oxidative stress, DNA damage, and apoptosis in cells. It also affects neurotransmitter release and synaptic transmission in the nervous system. Aldicarb has potential therapeutic effects in the treatment of Alzheimer's disease and other neurological disorders, but its toxic effects limit its use. Aldicarb is highly toxic to humans and animals, and exposure can cause acute and chronic health effects, such as respiratory failure, neurological damage, and cancer.

Applications

In medical research, aldicarb is used as a tool to study the nervous system and acetylcholinesterase inhibition. It has been used in drug development for the treatment of Alzheimer's disease and other neurological disorders. Clinical trials have shown that aldicarb can improve cognitive function in patients with Alzheimer's disease, but its toxic effects limit its use. In environmental research, aldicarb has been found to have negative effects on ecosystems, such as the decline of bird populations and the contamination of water sources. It is also used in pollution management to control pests in agricultural fields. In industrial research, aldicarb is used in manufacturing processes to improve product quality and efficiency. Health and safety considerations must be taken into account when using aldicarb in industrial processes.

Future Perspectives and Challenges

The use and study of aldicarb face several limitations and challenges. Its high toxicity limits its use in medical research and clinical trials. Its negative effects on ecosystems and the environment raise concerns about its sustainability and environmental impact. Possible solutions and improvements include the development of safer and more effective pesticides, the use of alternative methods for pest control, and the implementation of regulations and policies to reduce the use of toxic pesticides. Future trends and prospects in the application of aldicarb in scientific research include the development of new drugs for the treatment of neurological disorders and the study of its effects on other biological targets.

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