Nalorphine
Nalorphine , also known as N-allylnormorphine, is a mixed opioid agonist–antagonist with opioid antagonist and analgesic properties. It was introduced in 1954 and was used as an antidote to reverse opioid overdose and in a challenge test to determine opioid dependence. It acts at two opioid receptors — the μ-opioid receptor where it has antagonistic effects, and at the κ-opioid receptor where it exerts high-efficacy partial agonist/near-full agonist characteristics. Nalorphine was the second opioid antagonist to be introduced, preceded by nalodeine in 1915 and followed by naloxone in 1960 and naltrexone in 1963. Due to potent activation of the KOR, nalorphine produces side effects such as dysphoria, anxiety, confusion, and hallucinations, and for this reason, is no longer used medically. Nalorphine has a number of analogues including niconalorphine, diacetylnalorphine, dihydronalorphine and a number of others and a number of codeine-based ones as well.Chemistry
Synthesis
More recently, it has become much more commonplace to use ethyl chloroformate instead of cyanogen bromide for the Von Braun degradation demethylation step. See for example the list of phenyltropanes or the synthesis of paroxetine for further examples of this.
