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| Other names | AP-237 |
| Drug class | Opioid |
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| Chemical and physical data | |
| Formula | C17H24N2O |
| Molar mass | 272.392 g·mol−1 |
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Bucinnazine (AP-237,1-butyryl-4-cinnamylpiperazine) is annon-opioid analgesic drug that was widely used in China to treatpain incancer patients as of 1986.[1] It is one of the most potent compounds among a series of piperazine-amides first synthesized and reported in Japan in the 1970s.[2][3][4] Bucinnazine hasanalgesic potency comparable to that ofmorphine, but with a relatively highertherapeutic 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 selectiveagonists ofμ-opioid receptor (MOR) with relatively low affinity for theδ-opioid receptor and theκ-opioid receptor.[5] In accordance with these studies, results from theintravenous self-administration experiments in rats showed that bucinnazine has a marked reinforcing effect withtolerance anddependence quickly developing.[1] In addition, the opioid receptor antagonistnaloxone reverses the effect of bucinnazine and precipitateswithdrawal symptoms in bucinnazine treated rats further indicating a mechanism of analgesia mediated via selective agonist activity at μ-opioid receptors.
2-Methyl-AP-237 has been sold on the grey market as adesigner opioid, first identified by a police forensic laboratory in Slovenia in March 2019.[6][7][8] In 2023, theUnited States Department of Justice took criminal action against two individuals for selling 2-Methyl-AP-237 under the false pretenses that such product was intended for'research purposes' only. One of the pair was sentenced to five years infederal prison.[9]
TheWHO and theMinistry of Social Affairs, Health, Care and Consumer Protection have published reports on 2-Methyl-AP-237. According to their analysis, it is a little bit less potent thanfentanyl and can be reversed usingnaltrexone. There haven't been any studies on its systemic toxicity but there have been overdose deaths linked to it, most incombination with other drugs. It is primarily consumed orally or through snorting. While the methyl substitution creates astereocenter, the drug is sold as theracemat.[10][11]
