Bucinnazine Explained

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.[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 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.[5] 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.[1] In addition, the opioid receptor 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.[6] [7] [8] 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.[9]

See also

Notes and References

  1. Qing T, Zhi-Ji C, Wei-Ping W . Experimental Study on the Dependence-Producing Properties of Qiang Tong Ding (AP-237) . Chin. J. Clin. Pharmacol. . 1986 . 2 .
  2. Nishimura N, Kiuchi M, Kanetake Y, Takahashi T . [Clinical exaluation of a new analgesic agent Ap-237] . Masui. The Japanese Journal of Anesthesiology . 19 . 6 . 653–656 . June 1970 . 4916908 .
  3. Carrano RA, Kimura KK, McCurdy DH . Analgesic and tolerance studies with AP-237, a new analgesic . Archives Internationales de Pharmacodynamie et de Therapie . 213 . 1 . 41–57 . January 1975 . 1156018 .
  4. Carrano RA, Kimura KK, Landes RC, McCurdy DH . General pharmacology of a new analgesic-AP-237 . Archives Internationales de Pharmacodynamie et de Therapie . 213 . 1 . 28–40 . January 1975 . 1156016 .
  5. Barlocco D, Cignarella G, Greco G, Novellino E . 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 . 8294946 . 10.1007/bf00124362 . 23360530 . 1993JCAMD...7..557B .
  6. Web site: Analytical Report 2-Methyl-AP-237 . 19 March 2019 . Ljubljana, Slovenia . National Forensic Laboratory .
  7. Fogarty MF, Vandeputte MM, Krotulski AJ, Papsun D, Walton SE, Stove CP, Logan BK . 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 . 35275255 . 10.1007/s00204-022-03257-7 . 247383361 .
  8. Giorgetti A, Brunetti P, Pelotti S, Auwärter V . 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 . 35918775 . 9804899 . 10.1002/dta.3351 . free .
  9. Affairs . Office of Regulatory . 2023-10-30 . New Braunfels Man Sentenced to Five Years in Prison for Selling Misbranded Drugs . DOJ . en.

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