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Narcotic Analgesics And Antagonists
Published in S.J. Mulé, Henry Brill, Chemical and Biological Aspects of Drug Dependence, 2019
Three clinically useful compounds have been obtained by variation of the substituent of the nitrogen atom. The most popular of these is anileridine (1 (p-aminophenethyl)-4-carbethoxy-4-phenylpiperidine, Formula 17). An N-p-amino-phenethyl group was added to norpethidine as a substitute for the N-methyl group. The compound showed good activity, a surprise to medicinal chemists, anileridine being the first non-N-methyl pethidine to show such activity.37 Anileridine is two to three times as active as pethidine orally or parenterally, and produces less circulatory depression. Although it is satisfactory for the mother in obstetric analgesia (in conjunction with scopolamine) it caused depression in 25% of the infants.38 Piminodine (l-(3-phenylaminopropyl)-4-carbethoxy-4-phenylpiperidine, Formula 18), the N-3-phenylaminopropyl derivative of norpethidine, and phenoperidine (l-(3-phenylpropan-3-ol)-4-carbethoxy-4-phenylpiperidine, Formula 19), containing a 3-phenylpropan-3-ol moiety on the nitrogen atom, the latter available in Britain, are much less frequently prescribed. In terms of their overall spectrum of activity as opposed to their side effects, none show any great advantage over pethidine.38 Piminodine is morphine-like in activity and perhaps causes less drowsiness; phenoperidine is very potent and short acting.
Advances with the discovery and development of novel sigma 1 receptor antagonists for the management of pain
Published in Expert Opinion on Drug Discovery, 2023
Mallory Burns, Nicholas Guadagnoli, Christopher R. McCurdy
Figure 2 highlights the structures of several well-known S1R antagonists that come from distinct chemical classes. Haloperidol (dopamine antagonist) and its derivative (+)-MR200 contain 4-phenylpiperidine moieties that satisfy the pharmacophoric requirements of an ionizable amine and the closer secondary hydrophobic region. The structural modifications to haloperidol to produce (+)-MR200 helped to improve the selectivity, as it shows high affinity and selectivity for the sigma receptors.