Bucinnazine HCl | CAS#17730-82-4 | Analgesic

MedKoo Cat#: 524539 | Name: Bucinnazine HCl

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Bucinnazine is a potent and selective agonist of μ-opioid receptor (MOR) with relatively low affinity for the δ-opioid receptor and the κ-opioid receptor. Bucinnazine 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 piperazine-amides 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.

Chemical Structure

Bucinnazine HCl

CAS#17730-82-4 (HCl)

Theoretical Analysis

MedKoo Cat#: 524539

Name: Bucinnazine HCl

CAS#: 17730-82-4 (HCl)

Chemical Formula: C17H25ClN2O

Exact Mass: 308.1655

Molecular Weight: 308.85

Elemental Analysis: C, 66.11; H, 8.16; Cl, 11.48; N, 9.07; O, 5.18

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 350.00	2 Weeks
5mg	USD 750.00	2 Weeks

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Related CAS #

17719-89-0 (free base) 17730-82-4 (HCl)

Synonym

Bucinnazine Hydrochloride; Bucinnazine HCl; AP 237; AP-237, AP-237 HCl

IUPAC/Chemical Name

(E)-1-(4-cinnamylpiperazin-1-yl)butan-1-one hydrochloride

InChi Key

HPGCBEMVWCCLIT-AAGWESIMSA-N

InChi Code

InChI=1S/C17H24N2O.ClH/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;1H/b10-6+;

SMILES Code

CCCC(N1CCN(C/C=C/C2=CC=CC=C2)CC1)=O.[H]Cl

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Bucinnazine 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. (source: https://en.wikipedia.org/wiki/Bucinnazine)

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 308.85 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Ma T, Yu Y, Cao H, Wang H, Wang M. Effect of Intermittent Thoracic Paravertebral Block on Postoperative Nausea and Vomiting Following Thoracoscopic Radical Resection of the Lung Cancer: A Prospective Randomized Trial. J Pain Res. 2024 Mar 7;17:931-939. doi: 10.2147/JPR.S453615. PMID: 38469556; PMCID: PMC10926915. 2: Gao ZM, Shi JY, Zeng H, Zhang XJ. Rapid Determination of Bucinnazine in Blood by UPLC-MS/MS. Fa Yi Xue Za Zhi. 2023 Aug 25;39(4):388-392. English, Chinese. doi: 10.12116/j.issn.1004-5619.2022.320702. PMID: 37859478. 3: Pelletier R, Bourdais A, Fabresse N, Ferron PJ, Morel I, Gicquel T, Le Daré B. In silico and in vitro metabolism studies of the new synthetic opiate AP-237 (bucinnazine) using bioinformatics tools. Arch Toxicol. 2024 Jan;98(1):165-179. doi: 10.1007/s00204-023-03617-x. Epub 2023 Oct 15. PMID: 37839054. 4: Resnik KN, Babb KN, Bekenstein LW, Moeller FG, Peace MR, Alves EA. Case report: Identification of AP-238 and 2-fluorodeschloroketamine in internet available powder samples sold as bucinnazine. Forensic Sci Int. 2023 Jul;348:111732. doi: 10.1016/j.forsciint.2023.111732. Epub 2023 May 18. PMID: 37216788. 5: Resnik K, Brandão P, Alves EA. DARK Classics in Chemical Neuroscience: Bucinnazine. ACS Chem Neurosci. 2021 Oct 6;12(19):3527-3534. doi: 10.1021/acschemneuro.1c00522. Epub 2021 Sep 16. PMID: 34528782. 6: Zhu R, Zhang Y, Wang T, Wei H, Zhang C, Li D, Zhan S, Sun B. Deep Brain Stimulation of Nucleus Accumbens with Anterior Capsulotomy for Drug Addiction: A Case Report. Stereotact Funct Neurosurg. 2020;98(5):345-349. doi: 10.1159/000509313. Epub 2020 Aug 26. PMID: 32846423. 7: Gao X, Zhang SN. [Clinical observation of filiform fire needling on moderate and severe pain in advanced cancer]. Zhongguo Zhen Jiu. 2020 Jun 12;40(6):601-4. Chinese. doi: 10.13703/j.0255-2930.20190531-k0001. PMID: 32538009. 8: Ping Y, Jing C, Qing J. Comparison of the use of different analgesics in the course of anesthesia care based on pharmacoeconomics. Pak J Pharm Sci. 2018 Sep;31(5(Special)):2241-2247. PMID: 30463819. 9: Zhang C, Han SQ, Zhao H, Lin S, Hasi WL. Detection and Quantification of Bucinnazine Hydrochloride Injection Based on SERS Technology. Anal Sci. 2018 Nov 10;34(11):1249-1255. doi: 10.2116/analsci.18P158. Epub 2018 Jul 6. PMID: 29984780. 10: Yu ZQ, Zhang CL, Xu YJ, Chang MJ, Jin JJ, Luo L, Li XP, Liu D. Chronopharmacology of analgesic effect and tolerance induced by six narcotic analgesics in mice. Drug Res (Stuttg). 2015 Mar;65(3):141-6. doi: 10.1055/s-0034-1374617. Epub 2014 Apr 29. PMID: 24782288. 11: Xu YH, Wang QY, Yu ZB, He YW. [Clinical observation on acupuncture for treatment of abdominal postoperative pain]. Zhongguo Zhen Jiu. 2010 Nov;30(11):904-6. Chinese. PMID: 21246845. 12: Tong PJ, Wang HD, Ma ZC. [Application and effect of auricular acupoint pressing for analgesia in perioperative period of total knee joint replacement]. Zhongguo Zhong Xi Yi Jie He Za Zhi. 2010 Sep;30(9):931-4. Chinese. PMID: 21179731. 13: Lin Q, Hu YL, Han CW, Li Y. [Eye acupuncture for treatment of renal and ureteral colic]. Zhongguo Zhen Jiu. 2007 Sep;27(9):663-4. Chinese. PMID: 17926618.