Chemistry:Bucinnazine
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| Other names | AP-237 |
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| Formula | C17H24N2O |
| Molar mass | 272.392 g·mol−1 |
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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.[2] It is one of the most potent compounds among a series of piperazine-amides first synthesized and reported in Japan in the 1970s.[3][4][5] 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.[6] 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.[2] 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.
Derivatives
2-methyl-AP-237 has been sold on the grey market as a designer opioid, first identified by a police forensic laboratory in Slovenia in March 2019.[7][8][9] In 2023, the United 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 in federal prison.[10]
See also
References
- ↑ "2-Methyl-AP-237". U.S Drug Enforcement Administration. https://deadiversion.usdoj.gov/drug_chem_info/2-Methyl-AP-237.pdf.
- ↑ 2.0 2.1 "Experimental Study on the Dependence-Producing Properties of Qiang Tong Ding (AP-237)". Chin. J. Clin. Pharmacol. (2). 1986. http://en.cnki.com.cn/Article_en/CJFDTotal-GLYZ198602003.htm.
- ↑ "[Clinical exaluation of a new analgesic agent Ap-237]". Masui. The Japanese Journal of Anesthesiology 19 (6): 653–656. June 1970. PMID 4916908.
- ↑ "Analgesic and tolerance studies with AP-237, a new analgesic". Archives Internationales de Pharmacodynamie et de Therapie 213 (1): 41–57. January 1975. PMID 1156018.
- ↑ "General pharmacology of a new analgesic-AP-237". Archives Internationales de Pharmacodynamie et de Therapie 213 (1): 28–40. January 1975. PMID 1156016.
- ↑ "Computer-aided structure-affinity relationships in a set of piperazine and 3,8-diazabicyclo[3.2.1]octane derivatives binding to the mu-opioid receptor". Journal of Computer-Aided Molecular Design 7 (5): 557–571. October 1993. doi:10.1007/bf00124362. PMID 8294946. Bibcode: 1993JCAMD...7..557B.
- ↑ "Analytical Report 2-Methyl-AP-237". Ljubljana, Slovenia: National Forensic Laboratory. 19 March 2019. https://www.policija.si/apps/nfl_response_web/0_Analytical_Reports_final/2-Methyl-AP-237-ID-2053-19_report.pdf.
- ↑ "Toxicological and pharmacological characterization of novel cinnamylpiperazine synthetic opioids in humans and in vitro including 2-methyl AP-237 and AP-238". Archives of Toxicology 96 (6): 1701–1710. June 2022. doi:10.1007/s00204-022-03257-7. PMID 35275255.
- ↑ "Detection of AP-237 and synthetic cannabinoids on an infused letter sent to a German prisoner". Drug Testing and Analysis 14 (10): 1779–1784. October 2022. doi:10.1002/dta.3351. PMID 35918775.
- ↑ Affairs, Office of Regulatory (2023-10-30). "New Braunfels Man Sentenced to Five Years in Prison for Selling Misbranded Drugs" (in en). DOJ. https://www.fda.gov/inspections-compliance-enforcement-and-criminal-investigations/press-releases/new-braunfels-man-sentenced-five-years-prison-selling-misbranded-drugs.
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