Dezocine Free Base | CAS# 53648-55-8 | µ/κ-opioid receptor agonist

MedKoo Cat#: 413454 | Name: Dezocine Free Base

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Description:

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

Dezocine is a partial agonist of the µ- and κ-opioid receptors. It is selective for µ- and κ-opioid receptors (Kis = 1.46 and 22.01 nM, respectively) over the δ-opioid receptor (Ki = 398.6 nM). Dezocine inhibits the norepinephrine transporter (NET) and serotonin transporter (SERT) with Ki values of 0.001 and 109 nM, respectively. It stimulates [35S]GTPγS binding to CHO membranes expressing the human µ- and κ-opioid receptors with Emax values of 45.8 and 33.6% compared to the µ- and κ-agonists DAMGO and U50,488 H, respectively, when used at a concentration of 10 µM. It has antinociceptive effects in mice in the acetic acid abdominal constriction test (ED50 = 0.02 mg/kg) and the formalin test (ED50s = 0.4 mg/kg for both phases). Dezocine (10 mg/kg) increases the latency to tail withdrawal in the tail-flick test in rats. It also decreases the number of lung metastases in a 4T1 murine mammary cancer model when administered at doses ranging from 0.75 to 2 mg/kg. Formulations containing dezocine have been used in the treatment of post-operative pain.

Chemical Structure

Dezocine Free Base

CAS#53648-55-8 (free base)

Theoretical Analysis

MedKoo Cat#: 413454

Name: Dezocine Free Base

CAS#: 53648-55-8 (free base)

Chemical Formula: C16H23NO

Exact Mass: 245.1780

Molecular Weight: 245.37

Elemental Analysis: C, 78.32; H, 9.45; N, 5.71; O, 6.52

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 750.00	2 Weeks

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Related CAS #

53648-55-8 (free base) 57236-36-9 (HBr)

Synonym

Dezocine Free Base; (-)-Dezocine; Dalgan; Dezocina; Dezocinum; Docozine; Dozocine; WY16225; WY-16225; WY 16225;

IUPAC/Chemical Name

(5R,11S,13S)-13-amino-5-methyl-5,6,7,8,9,10,11,12-octahydro-5,11-methanobenzo[10]annulen-3-ol

InChi Key

VTMVHDZWSFQSQP-VBNZEHGJSA-N

InChi Code

InChI=1S/C16H23NO/c1-16-8-4-2-3-5-12(15(16)17)9-11-6-7-13(18)10-14(11)16/h6-7,10,12,15,18H,2-5,8-9,17H2,1H3/t12-,15-,16+/m0/s1

SMILES Code

C[C@]12C3=CC(O)=CC=C3C[C@@H]([C@@H]2N)CCCCC1

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

to be determined

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

Instruction

View handling instruction

	Solvent	mg/mL	mM
Solubility
	To be determined	0.0	100.00

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 245.37 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: Ye RR, Jiang S, Xu X, Lu Y, Wang YJ, Liu JG. Dezocine as a potent analgesic: overview of its pharmacological characterization. Acta Pharmacol Sin. 2022 Jul;43(7):1646-1657. doi: 10.1038/s41401-021-00790-6. Epub 2021 Nov 4. PMID: 34737418; PMCID: PMC9253008. 2: O'Brien JJ, Benfield P. Dezocine. A preliminary review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy. Drugs. 1989 Aug;38(2):226-48. doi: 10.2165/00003495-198938020-00005. PMID: 2670517. 3: Zhou C, Yang Y, Zhu Y, Ruan L. Effects of dezocine on prevention of propofol injection pain: a meta-analysis. J Pain Res. 2017 Jun 1;10:1369-1375. doi: 10.2147/JPR.S128889. PMID: 28615968; PMCID: PMC5460620. 4: Wang H, Chiang C, Xue C, Zhou L, Li S, Zhou Y, Zhang Z, Xie M, Xiao T, Hu H, Zhu L, Long C, Zou Y, Wang T, Zheng D. Dezocine induces apoptosis in human cervical carcinoma Hela cells via the endoplasmic reticulum stress pathway. Toxicol Res (Camb). 2022 May 30;11(3):498-510. doi: 10.1093/toxres/tfac026. Erratum in: Toxicol Res (Camb). 2022 Dec 01;12(1):143. PMID: 35782639; PMCID: PMC9244724. 5: Zhang C, Pan R, Ma S, Xu S, Wang B. Dezocine inhibits cell proliferation, migration, and invasion by targeting CRABP2 in ovarian cancer. Open Med (Wars). 2022 Dec 14;17(1):2052-2061. doi: 10.1515/med-2022-0541. PMID: 36568517; PMCID: PMC9755696. 6: Wu FX, Babazada H, Gao H, Huang XP, Xi CH, Chen CH, Xi J, Yu WF, Liu R. Dezocine Alleviates Morphine-Induced Dependence in Rats. Anesth Analg. 2019 Jun;128(6):1328-1335. doi: 10.1213/ANE.0000000000003365. PMID: 31094808; PMCID: PMC6173660. 7: Grothusen J, Lin W, Xi J, Zanni G, Barr GA, Liu R. Dezocine is a Biased Ligand without Significant Beta-Arrestin Activation of the mu Opioid Receptor. Transl Perioper Pain Med. 2022;9(1):424-429. Epub 2022 Mar 1. PMID: 35572183; PMCID: PMC9097853. 8: Gong WY, Xu B, Liu L, Li ST. Dezocine relieves the postoperative hyperalgesia in rats through suppressing the hyper-action of Akt1/GSK-3β pathway. Exp Brain Res. 2022 May;240(5):1435-1444. doi: 10.1007/s00221-022-06341-7. Epub 2022 Mar 25. PMID: 35333956. 9: Childers WE, Abou-Gharbia MA. "I'll Be Back": The Resurrection of Dezocine. ACS Med Chem Lett. 2021 May 19;12(6):961-968. doi: 10.1021/acsmedchemlett.1c00233. PMID: 34141081; PMCID: PMC8201756. 10: Han S, Zhang C, Chen Z, Sha X, Hasi W. Rapid Detection of Dezocine in Biological Fluids Based on SERS Technology. Anal Sci. 2021 Feb 10;37(2):315-320. doi: 10.2116/analsci.20P259. Epub 2020 Sep 4. PMID: 32893251. 11: Shang L, Duan C, Chang S, Chang N, Jia S. Antidepressant-like effects of dezocine in mice: involvement of 5-HT1A and κ opioid receptors. Behav Pharmacol. 2021 Sep 1;32(6):472-478. doi: 10.1097/FBP.0000000000000641. PMID: 34101632. 12: Xue C, Chen W, Yuan A, Chen C, Li S, Chen K, Zhao Y, Xiao T, Shao G, Zou Y, Zheng D. Dezocine, An Opioid Analgesic, Exerts Antitumor Effects in Triple- Negative Breast Cancer by Targeting Nicotinamide Phosphoribosyltransferase. Front Pharmacol. 2021 Apr 12;12:600296. doi: 10.3389/fphar.2021.600296. PMID: 33912035; PMCID: PMC8072669. 13: Zhou J, Qi F, Hu Z, Zhang L, Li Z, Wang ZJ, Tang H, Chen Z. Dezocine attenuates the remifentanil-induced postoperative hyperalgesia by inhibition of phosphorylation of CaMKⅡα. Eur J Pharmacol. 2020 Feb 15;869:172882. doi: 10.1016/j.ejphar.2019.172882. Epub 2019 Dec 19. Erratum in: Eur J Pharmacol. 2021 Oct 5;908:174359. PMID: 31863769. 14: Ahsan MZ, Zhao MJ, Shoaib RM, Zhang Y, Wang YX. Comparative study of dezocine, pentazocine and tapentadol on antinociception and physical dependence. Life Sci. 2021 Nov 15;285:119996. doi: 10.1016/j.lfs.2021.119996. Epub 2021 Sep 28. PMID: 34597607. 15: Fu B, Jiang J, Huang Y. The analgesic effects of dezocine in rats with chronic constriction injuries. Exp Anim. 2023 Jun 19. doi: 10.1538/expanim.23-0036. Epub ahead of print. PMID: 37331802. 16: Zhong ZW, Zhou WC, Sun XF, Wu QC, Chen WK, Miao CH. Dezocine regulates the malignant potential and aerobic glycolysis of liver cancer targeting Akt1/GSK-3β pathway. Ann Transl Med. 2020 Apr;8(7):480. doi: 10.21037/atm.2020.03.28. PMID: 32395524; PMCID: PMC7210161. 17: Xiong Z, Yi P, Song J, Tan M. Dezocine prevents sufentanil-induced cough during general anesthesia induction: a meta-analysis of randomised controlled trials. BMC Anesthesiol. 2020 Jun 22;20(1):154. doi: 10.1186/s12871-020-01076-w. PMID: 32571219; PMCID: PMC7310133. 18: Song Q, Liu G, Liu D, Feng C. Dezocine promotes T lymphocyte activation and inhibits tumor metastasis after surgery in a mouse model. Invest New Drugs. 2020 Oct;38(5):1342-1349. doi: 10.1007/s10637-020-00921-6. Epub 2020 Mar 13. PMID: 32170576. 19: Wang L, Liu X, Wang J, Sun Y, Zhang G, Liang L. Comparison of the efficacy and safety between dezocine injection and morphine injection for persistence of pain in Chinese cancer patients: a meta-analysis. Biosci Rep. 2017 Jun 8;37(3):BSR20170243. doi: 10.1042/BSR20170243. PMID: 28533424; PMCID: PMC5463259. 20: Dezocine. Med Lett Drugs Ther. 1990 Oct 19;32(829):95-6. PMID: 1978230.