|Chemical and physical data|
|Molar mass||272.392 g·mol−1|
|3D model (JSmol)|
Bucinnazine (AP-237, 1-butyryl-4-cinnamylpiperazine) is an opioid analgesic drug that was widely used in China to treat pain in cancer patients as of 1986. It is one of the most potent compounds among a series of analgesic acyl piperazine compounds first synthesized and reported in Japan in the 1970s. Bucinnazine has analgesic potency comparable to that of morphine but with a relatively higher therapeutic index.
The drug was initially claimed to be a non-narcotic analgesic. However, subsequent studies have shown bucinnazine and similar acyl piperazines to be potent and selective agonists of μ-opioid receptor (MOR) with relatively low affinity for the δ-opioid receptor and the κ-opioid receptor. In accordance with these studies, results from the intravenous self-administration experiments in rats showed that bucinnazine has a marked reinforcing effect with tolerance and dependence quickly developing. In addition, the morphine antagonist naloxone reverses the effect of bucinnazine and precipitates withdrawal symptoms in bucinnazine treated rats further indicating a mechanism of analgesia mediated via selective agonist activity at μ-opioid receptors.
The 2-methyl and 2,6-dimethyl derivatives of AP-237 are also known to be active as opioid analgesics, and 2-methyl-AP-237 has been sold as a designer drug, first identified by a police forensic laboratory in Slovenia in March 2019.
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- Analytical Report 2-Methyl-AP-237. 19 March 2019