alazocine

Alazocine (SKF-10047), also known as N-allylnormetazocine (NANM), is a synthetic benzomorphan derivative that acts as a prototypical sigma-1 receptor agonist. Originally investigated in the 1960s by Smith Kline & French and Sterling Winthrop as a potential non-addictive opioid analgesic, its clinical development was halted due to severe psychotomimetic side effects, such as dysphoria and hallucinations. Pharmacologically, alazocine exhibits complex stereospecific activity: the (+)-enantiomer is a highly selective agonist of the sigma-1 receptor and an antagonist of the NMDA receptor, whereas the (-)-enantiomer acts as a partial agonist of the kappa-opioid receptor and an antagonist of the mu-opioid receptor. Additionally, alazocine has been shown to directly inhibit voltage-gated sodium channels (Nav1.2, Nav1.4, and Nav1.5) independently of sigma receptor activation. Today, it is widely utilized as a standard research tool to study sigma receptor biology and classification.

Other names

(-)-SKF-10047(-)-alazocine(+)-SKF-10047(+)-alazocine(±)-SKF-10047(±)-alazocineANMCN-allylnormetazocineNANNANMalazocine hydrochloride