Compounds Related to Pethidine--II. Mannich Bases Derived from Various Esters of 4-Carboxy-4-phenylpiperidine and Acetophenones

Pa, Janssen; Ah, Jageneau; Pj, Demoen; C, Van De Westeringh; Jh, De Canniere; Ah, Raeymaekers; Ms, Wouters; Sanczuk, S; Bk, Hermans

doi:10.1021/jm50005a002

Cited by 12 publications

(4 citation statements)

References 1 publication

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“…Among the most widely used of the synthetic opiates are the 4-anilidopiperidines, originally developed by Janssen et al (1959). This class includes fentanyl (Fig.…”

Section: Othermentioning

confidence: 99%

Mu Opioids and Their Receptors: Evolution of a Concept

Pasternak

Pan

2013

Pharmacological Reviews

494

526

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“…Among the most widely used of the synthetic opiates are the 4-anilidopiperidines, originally developed by Janssen et al (1959). This class includes fentanyl (Fig.…”

Section: Othermentioning

confidence: 99%

Mu Opioids and Their Receptors: Evolution of a Concept

Pasternak

Pan

2013

Pharmacological Reviews

494

526

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“…The double bond in the imine ( 2 ) is reduced with lithium aluminum hydride, and the resulting 1-benzyl-4-anilinopiperidine ( 3 ) is acylated using propionic anhydride. Debenzylation of 1-benzyl-4- N -propinoyl-anilinopiperidine ( 4 ) using standard H 2 –Pd/C conditions produces norfentanyl ( 5 ), which is N -alkylated by 2-phenylethyl chloride (or tosylate) to give the final desired compound, fentanyl ( 6 ). ,,− …”

Section: Properties and Chemical Synthesismentioning

confidence: 99%

DARK Classics in Chemical Neuroscience: Fentanyl

Burns

Cunningham

Mercer

2018

ACS Chem. Neurosci.

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Fentanyl rose to prominence as an alternative analgesic to morphine nearly 50 years ago; today, fentanyl has re-emerged as a dangerous recreational substance. The increased potency and analgesic effect of fentanyl are advantageous in the treatment of pain but are also responsible for the rise in unintentional opioid overdose deaths. In response to this crisis, fentanyl, its analogues, and even precursors are under heightened regulatory scrutiny. Despite this controversial history, derivatization of fentanyl has resulted in numerous synthetic analogues that provide valuable insights into opioid receptor binding and signaling events. In this review, the impact of fentanyl on chemical neuroscience is shown through its synthesis and properties, manufacturing, metabolism, pharmacology, approved and off-label indications, adverse effects, and the responsibility it has in the opioid epidemic.

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“…The dramatic increase of opioid‐related overdose deaths during the last few years, especially in North America and Europe, appears to be particularly linked to fentanyl and its analogues 1,2 . Fentanyl was synthesised in 1959 3 and is considered as an μ‐receptor‐selective agonist about 100‐fold more potent than morphine 4 . Fentanyl abuse is linked with high risk of central respiratory depression, fatal overdose, and addiction.…”

Section: Introductionmentioning

confidence: 99%

Ghrelin receptor antagonism of fentanyl‐induced conditioned place preference, intravenous self‐administration, and dopamine release in the nucleus accumbens in rats

et al. 2019

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The extended occurrence of fentanils abuse associated with the dramatic increase in opioid fatal overdoses and dependence strongly emphasizes insufficiencies in opioid addiction treatment. Recently, the growth hormone secretagogue receptor (GHS-R1A) antagonism was proposed as a promising mechanism for drug addiction therapy. However, the role of GHS-R1A and its endogenous ligand ghrelin in opioid abuse is still unclear. Therefore, the aim of our study was to clarify whether the GHS-R1A antagonist JMV2959 could reduce the fentanyl-induced conditioned place preference (CPP), the fentanyl intravenous self-administration (IVSA), and the tendency to relapse, but also whether JMV2959 could significantly influence the fentanylinduced dopamine efflux in the nucleus accumbens (NAC) in rats, that importantly participates in opioids' reinforcing effects. Following an ongoing fentanyl selfadministration, JMV2959 3 mg/kg was administered intraperitoneally 20 minutes before three consequent daily 360-minute IVSA sessions under a fixed ratio FR1, which significantly reduced the number of active lever-pressing, the number of infusions, and the fentanyl intake. Pretreatment with JMV2959 also reduced the fentanyl-seeking/relapse-like behaviour tested in rats on the 12 th day of the forced abstinence period. Pretreatment with JMV2959 significantly and dose-dependently reduced the manifestation of fentanyl-CPP. The fentanyl-CPP development was reduced after the simultaneous administration of JMV2959 with fentanyl during conditioning. The JMV2959 significantly reduced the accumbens dopamine release induced by subcutaneous and intravenous fentanyl. Simultaneously, it affected the concentration of byproducts associated with dopamine metabolism in the NAC. Our findings suggest that GHS-R1A importantly participates in the rewarding/reinforcing effects of fentanyl.

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Compounds Related to Pethidine--II. Mannich Bases Derived from Various Esters of 4-Carboxy-4-phenylpiperidine and Acetophenones

Cited by 12 publications

References 1 publication

Mu Opioids and Their Receptors: Evolution of a Concept

Mu Opioids and Their Receptors: Evolution of a Concept

DARK Classics in Chemical Neuroscience: Fentanyl

Ghrelin receptor antagonism of fentanyl‐induced conditioned place preference, intravenous self‐administration, and dopamine release in the nucleus accumbens in rats

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