Bucinnazine

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Bucinnazine
Clinical data
Other namesAP-237
Legal status
Legal status
Identifiers
  • 1-[4-[(E)-3-Phenylprop-2-enyl]piperazin-1-yl]butan-1-one
JSmol)
  • CCCC(=O)N1CCN(CC1)C/C=C/C2=CC=CC=C2
  • InChI=1S/C17H24N2O/c1-2-7-17(20)19-14-12-18(13-15-19)11-6-10-16-8-4-3-5-9-16/h3-6,8-10H,2,7,11-15H2,1H3/b10-6+
  • Key:ZQBMUHABRSEAIK-UXBLZVDNSA-N

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

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]

2-Methyl-AP-237; CAS# 98608-59-4; PubChem 6447698

See also

References

  1. ^ "2-Methyl-AP-237" (PDF). Office of Diversion Control. U.S Drug Enforcement Administration.
  2. ^ a b Qing T, Zhi-Ji C, Wei-Ping W (1986). "Experimental Study on the Dependence-Producing Properties of Qiang Tong Ding (AP-237)". Chin. J. Clin. Pharmacol. (2).
  3. PMID 4916908
    .
  4. PMID 1156018
    .
  5. PMID 1156016
    .
  6. S2CID 23360530
    .
  7. ^ "Analytical Report 2-Methyl-AP-237" (PDF). Ljubljana, Slovenia: National Forensic Laboratory. 19 March 2019.
  8. S2CID 247383361
    .
  9. PMID 35918775
    .
  10. ^ Affairs Oo (2023-10-30). "New Braunfels Man Sentenced to Five Years in Prison for Selling Misbranded Drugs". DOJ.
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