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Query: CAS:5119-88-0 (
2-methylpiperidine
)
40
document(s) hit in 31,850,051 MEDLINE articles (0.00 seconds)
The interactions of eight piperidine derivatives with nicotinic receptor complexes from Torpedo californica electric organ were studied using [125I] alpha-bungarotoxin [( 125I]BGT) as a probe for the acetylcholine binding site and [3H]perhydrohistrionicotoxin [( 3H]H12-HTX) as a probe for a site associated with the receptor-gated ion channel. Cis- and trans-2-methyl-6-n-undecanyl piperidines (MUP), major constituents of fire ant venom, had a high-affinity for [3H]H12-HTX binding sites (Ki = 0.08-0.24 microM), but had no affect on receptor binding. MUP affinity for [3H]H12-HTX binding sites was approximately doubled in the presence of 1 microM carbamylcholine. Introduction of a 2'-hydroxyl group to the undecanyl side channel had little effect on activity of the alkaloid. The analog 2,6- (but not 3,5-) dimethylpiperidine was a moderately active inhibitor of [3H]H12-HTX binding (Ki = 8.8 microM). 2-Methylpiperidine was considerably less active (Ki = 600 microM), although it was more potent than either 3- or 4-methylpiperidine. The affinities of
2,6-dimethylpiperidine
and
2-methylpiperidine
for [3H]H12-HTX binding sites were decreased in the presence of 1 microM carbamylcholine. Carbamylcholine affinity for the receptor was increased by up to 7 fold in the presence of 10 and 32 microM MUP, but was decreased in the presence of
2,6-dimethylpiperidine
and
2-methylpiperidine
. The cis- and trans-isomers of MUP were equipotent in producing each of its effects. In these actions, MUP resembles a variety of other compounds derived from 2,6-disubstituted piperidines, including histrionicotoxins, gephyrotoxins and pumiliotoxins.(ABSTRACT TRUNCATED AT 250 WORDS)
...
PMID:Interactions of piperidine derivatives with the nicotinic cholinergic receptor complex from Torpedo electric organ. 245 57
The mechanism of hydrodenitrogenation (HDN) of
2-methylpiperidine
was studied over a silica-supported nickel phosphide catalyst (Ni2P/SiO2, Ni/P = 1/2) and a commercial Ni-Mo-S/Al2O3 catalyst in a three-phase trickle-bed reactor operated at 3.1 MPa and 450-600 K. Analysis of the product distribution as a function of contact time indicated that the reaction proceeded in both cases predominantly by a substitution mechanism, with a smaller contribution of an elimination mechanism. Fourier transform infrared spectroscopy (FTIR) of the
2-methylpiperidine
indicated that at reaction conditions a piperidinium ion intermediate was formed on both the sulfide and the phosphide. It is concluded that the mechanism of HDN on nickel phosphide is very similar to that on sulfides. The mechanism on the nickel phosphide was also probed by comparing the reactivity of piperidine and several of its derivatives in the presence of 3000 ppm S. The relative elimination rates depended on the structure of the molecules, and followed the sequence: 4-methylpiperidine approximately piperidine > 3-methylpiperidine >
2,6-dimethylpiperidine
>
2-methylpiperidine
. [Chemical structure: see text] This order of reactivity was not dependent on the number of alpha-H or beta-H atoms in the molecules, ruling out their reaction through a single, simple mechanism. It is likely that the unhindered piperidine molecules reacted by an S(N)2 substitution process and the more hindered
2,6-dimethylpiperidine
reacted by an E2 elimination process.
...
PMID:Mechanism of hydrodenitrogenation on phosphides and sulfides. 1685 Dec 2
