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64023-93-4Relevant academic research and scientific papers
(+)-and (?)-Phenazocine enantiomers: Evaluation of their dual opioid agonist/σ1antagonist properties and antinociceptive effects
Prezzavento,Arena,Sánchez-Fernández,Turnaturi,Parenti,Marrazzo,Catalano,Amata,Pasquinucci,Cobos
, p. 603 - 610 (2016/10/11)
cis-N-Substituted N-normetazocine enantiomers possess peculiar pharmacological profiles. Indeed, dextro enantiomers bind with high affinity σ1receptor while opposite enantiomers bind opioid receptors. In spite of their stereochemistry, cis-N-2-phenylethyl N-normetazocine (phenazocine) enantiomers showed mixed opioid/σ1receptor profiles and a significant in?vivo analgesia. To the best of our knowledge, there is no information available regarding the evaluation of σ1pharmacological profile in the antinociceptive effects of (+)- and (?)-phenazocine. Therefore, the present study was designed to ascertain this component by in?vitro and in?vivo studies. In particular, we tested the σ1affinity of both enantiomers by a predictive binding assay in absence or presence of phenytoin (DPH). Our results showed that DPH (1?mM) did not increase the σ1receptor affinity of (+)-and (?)-phenazocine (Ki?=?3.8?±?0.4?nM, Ki?=?85?±?2.0?nM, respectively) suggesting a σ1antagonist profile of both enantiomers. This σ1antagonistic component of two phenazocine enantiomers was corroborated by in?vivo studies in which the selective σ1receptor agonist PRE-084, was able to unmask their σ1antagonistic component associated with the opioid activity. The σ1antagonistic component of (+)- and (?)-phenazocine may justify their analgesic activity and it suggests that they may constitute useful lead compounds to develop new ligands with this dual activity.