6659-30-9

Usage

Functionality

Insecticide and Pesticide
Inhibits the activity of cholinesterase enzymes in insects' nervous systems, leading to paralysis and death.

Effectiveness

Broad-spectrum
Controls various pests, including aphids, scale insects, and mites.

Toxicity

Harmful to humans and other organisms
Poses significant health risks if not handled and used properly.

Environmental and Health Impact

Subject to regulatory scrutiny and concern
Potential negative effects on the environment and human health due to its mode of action and toxicity.

Upstream product

• 3554-74-3 3-Hydroxy-1-methylpiperidine 
• 79-44-7 N,N-Dimethylcarbamoyl chloride 
• 101-26-8 pyridostigmine bromide 
• 109-00-2 3-HYDROXYPYRIDINE 
• 51581-32-9 3-(N,N-Dimethylcarbamoyl)-oxipyridin 

Relevant academic research and scientific papers

Analogues of carbacholine: Synthesis and relationship between structure and affinity for muscarinic and nicotinic acetylcholine receptors

A series of acyclic and heterocyclic analogues of carbacholine (1) was synthesized using N-methylcarbacholine (MCC, 2), N,N-dimethylcarbacholine (DMCC, 3), and the corresponding tertiary amine (4) as leads. Whereas nicotinic acetylcholine receptor affinity was determined using [3H]nicotine as the radioactive ligand, [3H]oxotremorine-M ([3H]Oxo-M) and [3H]quinuclidinyl benzilate ([3H]QNB), in some cases supplemented with [3H]pirenzepine ([3H]PZ), were used as radioligands for muscarinic acetylcholine receptors on rat brain membranes. On the basis of receptor binding data, nicotinic/muscarinic (N/M) selectivity factors were determined, and muscarinic receptor efficacy (M agonist index) and M1 selectivity (M2/M1 index) estimated. In most cases, quaternized analogues showed higher affinity than the corresponding tertiary amines for muscarinic and, in particular, nicotinic receptor sites. Among the new compounds, N,N-diethylcarbacholine (9e) (IC50 = 0.046 μM), (S)-1-methyl-2-(N,N-dimethylaminocarbonyloxymethyl)pyrrolidine (17k) (IC50 = 0.068 μM), and the corresponding quaternized analogue, 18k (IC50 = 0.018 μM) showed the highest nicotinic receptor affinity. The tertiary amine, 17k showed much higher nicotinic receptor affinity than the acyclic analogue, 4 (IC50 = 5.7 μM), and the N/M selectivity factor determined for 17k (150) is an order of magnitude lower than that of nicotine (1400). The N/M selectivity factors for MCC (2) and DMCC (3), previously reported to be highly selective nicotinic receptor ligands, were shown to be 6.5 and 60, respectively, the latter value being comparable with that of 18k (89).

Determination of the Structure of Products of the Reduction of Pyridostigmine with NaBH4

The chemical structure of 5 different products of pyridostigmine obtained by reduction with NaBH4 was determined by GC - MS and subsequently confirmed by means of 1H and 13C NMR spectroscopy.Reaction conditions leading almost exclusively to the main product: 3--1-methyl-1,2,5,6-tetrahydropyridine (4) have been determined. - Key words: Pyridostigmine, 3--1-methylpyridiniumbromide, Reduction Products, 1H NMR Spectra, 13C NMR Spectra