Brucine | CAS#357-57-3 | alkaloid

MedKoo Cat#: 596934 | Name: Brucine

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Description:

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

Brucine is a very toxic alkaloid from Nux vomica similar to strychnine; used as reagent in analytical chemistry.

Chemical Structure

Brucine

CAS#357-57-3

Theoretical Analysis

MedKoo Cat#: 596934

Name: Brucine

CAS#: 357-57-3

Chemical Formula: C23H26N2O4

Exact Mass: 394.1893

Molecular Weight: 394.47

Elemental Analysis: C, 70.03; H, 6.64; N, 7.10; O, 16.22

Price and Availability

Size	Price	Availability	Quantity
5g	USD 250.00	2 Weeks
25g	USD 550.00	2 Weeks

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Related CAS #

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Synonym

Brucine; Brucinum; l-Brucine; CCRIS 4754;

IUPAC/Chemical Name

(4aR,4a1R,5aS,8aR,8a1S,15aS)-10,11-dimethoxy-2,4a,4a1,5,5a,7,8,8a1,15,15a-decahydro-14H-4,6-methanoindolo[3,2,1-ij]oxepino[2,3,4-de]pyrrolo[2,3-h]quinolin-14-one

InChi Key

RRKTZKIUPZVBMF-IBTVXLQLSA-N

InChi Code

InChI=1S/C23H26N2O4/c1-27-16-8-14-15(9-17(16)28-2)25-20(26)10-18-21-13-7-19-23(14,22(21)25)4-5-24(19)11-12(13)3-6-29-18/h3,8-9,13,18-19,21-22H,4-7,10-11H2,1-2H3/t13-,18-,19-,21-,22-,23+/m0/s1

SMILES Code

[H][C@@]1([C@@]23[H])C(CN4CC[C@]5([C@@]63[H])[C@@]([H])4C1)=CCO[C@H]2CC(N6C7=C5C=C(OC)C(OC)=C7)=O

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

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

An alkaloid with diverse biological activities.

In vitro activity:

Brucine inhibited the inflammation, cell proliferation and promoted rate of apoptotic cell death ad reduced the mitochondrial potential, which is evidenced by respective (AO/EB, Rh-123, and PI) staining. Reference: Environ Toxicol. 2021 Jun 2. https://pubmed.ncbi.nlm.nih.gov/34076332/

In vivo activity:

Brucine, the main alkaloid bioactive compound from Strychnos nux-vomica seeds, offers unique compatibility advantages in inflammatory diseases associated clinical practices. Thus, the present investigation was projected to explore the activity of brucine towards MI provoked by isoprenaline hydrochloride (ISO) in rats. The cardioprotective properties of brucine were evaluated via detecting the infarct size, serum cardiac marker enzymes (CK, CK-MB, cTnT, and cTnI), endogenous antioxidants (CAT, SOD, GPx), and lipid peroxidation (TBARS and LOOH), inflammatory mediators (NF-κB, TNF-α and IL-6) and histopathological analysis. Brucine's cardioprotective effect might be associated with TNF-α, IL-6 signaling molecules activation, revealing its pharmacological actions. Reference: Exp Gerontol. 2021 Jul 1;149:111332. https://pubmed.ncbi.nlm.nih.gov/33781843/

	Solvent	mg/mL	mM
Solubility
	Acetonitrile	10.0	25.35
	Chloroform	30.0	76.05

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 394.47 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

Formulation protocol:

1. Seshadri VD. Brucine promotes apoptosis in cervical cancer cells (ME-180) via suppression of inflammation and cell proliferation by regulating PI3K/AKT/mTOR signaling pathway. Environ Toxicol. 2021 Jun 2. doi: 10.1002/tox.23304. Epub ahead of print. PMID: 34076332. 2. Liu Q, Wang Q, Lv C, Liu Z, Gao H, Chen Y, Zhao G. Brucine inhibits proliferation of glioblastoma cells by targeting the G-quadruplexes in the c-Myb promoter. J Cancer. 2021 Feb 2;12(7):1990-1999. doi: 10.7150/jca.53689. PMID: 33753997; PMCID: PMC7974541. 3. Liu B, Zhang Y, Wu Q, Wang L, Hu B. Alleviation of isoprenaline hydrochloride induced myocardial ischemia injury by brucine through the inhibition of Na+/K+-ATPase. Exp Gerontol. 2021 Jul 1;149:111332. doi: 10.1016/j.exger.2021.111332. Epub 2021 Mar 27. PMID: 33781843. 4. Ishimwe N, Wei P, Wang M, Zhang H, Wang L, Jing M, Wen L, Zhang Y. Autophagy Impairment through Lysosome Dysfunction by Brucine Induces Immunogenic Cell Death (ICD). Am J Chin Med. 2020;48(8):1915-1940. doi: 10.1142/S0192415X20500962. Epub 2020 Dec 10. PMID: 33308096.

In vitro protocol:

In vivo protocol:

1. Liu B, Zhang Y, Wu Q, Wang L, Hu B. Alleviation of isoprenaline hydrochloride induced myocardial ischemia injury by brucine through the inhibition of Na+/K+-ATPase. Exp Gerontol. 2021 Jul 1;149:111332. doi: 10.1016/j.exger.2021.111332. Epub 2021 Mar 27. PMID: 33781843. 2. Ishimwe N, Wei P, Wang M, Zhang H, Wang L, Jing M, Wen L, Zhang Y. Autophagy Impairment through Lysosome Dysfunction by Brucine Induces Immunogenic Cell Death (ICD). Am J Chin Med. 2020;48(8):1915-1940. doi: 10.1142/S0192415X20500962. Epub 2020 Dec 10. PMID: 33308096.

1: Ren T, Li M, Zheng H, Liu W, Zhang J. Microdialysis combined with RRLC-MS/MS for the pharmacokinetics of two major alkaloids of Bi qi capsule and the potential roles of P-gp and BCRP on their penetration. J Chromatogr B Analyt Technol Biomed Life Sci. 2018 May 31;1092:72-81. doi: 10.1016/j.jchromb.2018.05.048. [Epub ahead of print] PubMed PMID: 29883892. 2: Qin J, Yang L, Sheng X, Sa Z, Huang T, Li Q, Gao K, Chen Q, Ma J, Shen H. Antitumor effects of brucine immuno-nanoparticles on hepatocellular carcinoma in vivo. Oncol Lett. 2018 May;15(5):6137-6146. doi: 10.3892/ol.2018.8168. Epub 2018 Mar 2. PubMed PMID: 29731843; PubMed Central PMCID: PMC5920962. 3: Li S, Chu Y, Zhang R, Sun L, Chen X. Prophylactic Neuroprotection of Total Glucosides of Paeoniae Radix Alba against Semen Strychni-Induced Neurotoxicity in Rats: Suppressing Oxidative Stress and Reducing the Absorption of Toxic Components. Nutrients. 2018 Apr 20;10(4). pii: E514. doi: 10.3390/nu10040514. PubMed PMID: 29677121; PubMed Central PMCID: PMC5946299. 4: Ma JB, Qiu HW, Rui QH, Liao YF, Chen YM, Xu J, Zhang Y, Zhu Y, Zhao YG. Enhanced cleanup efficiency hydroxy functionalized-magnetic graphene oxide and its comparison with magnetic carboxyl-graphene for PRiME pass-through cleanup of strychnine and brucine in human plasma samples. Anal Chim Acta. 2018 Aug 22;1020:41-50. doi: 10.1016/j.aca.2018.03.008. Epub 2018 Mar 19. PubMed PMID: 29655427. 5: Zhang N, Wu Y, Xing R, Xu B, Guoliang D, Wang P. Effect of Ultrasound-Enhanced Transdermal Drug Delivery Efficiency of Nanoparticles and Brucine. Biomed Res Int. 2017;2017:3273816. doi: 10.1155/2017/3273816. Epub 2017 Dec 4. PubMed PMID: 29349071; PubMed Central PMCID: PMC5733966. 6: Guo R, Wang T, Zhou G, Xu M, Yu X, Zhang X, Sui F, Li C, Tang L, Wang Z. Botany, Phytochemistry, Pharmacology and Toxicity of Strychnos nux-vomica L.: A Review. Am J Chin Med. 2018;46(1):1-23. doi: 10.1142/S0192415X18500015. Epub 2018 Jan 3. Review. PubMed PMID: 29298518. 7: Lv M, Zhang M, Cheng Y, Zhang K, Hou C, Chen X. Renoprotective Effects of Total Glucosides from Paeony against Nephrotoxicity Induced by Total Alkaloids from Semen Strychni. Evid Based Complement Alternat Med. 2017;2017:8256278. doi: 10.1155/2017/8256278. Epub 2017 Oct 22. PubMed PMID: 29234433; PubMed Central PMCID: PMC5671718. 8: Liu LL, Guan YM, Lu XP, Liang XL, Chen LH. Mechanisms of P-Glycoprotein Modulation by Semen Strychni Combined with Radix Paeoniae Alba. Evid Based Complement Alternat Med. 2017;2017:1743870. doi: 10.1155/2017/1743870. Epub 2017 Oct 15. PubMed PMID: 29234368; PubMed Central PMCID: PMC5661092. 9: Maddisetty PNP, Doss VA, S M, V S, T M. HPLC and GC-MS: Identification and Quantification of Strychnine and Brucine in Strychnos nux-vomica leaves. Pak J Pharm Sci. 2017 Nov;30(6(Supplementary)):2369-2373. PubMed PMID: 29188771. 10: Wu R, Li Q, Pei X, Hu K. Effects of Brucine on the OPG/RANKL/RANK Signaling Pathway in MDA-MB-231 and MC3T3-E1 Cell Coculture System. Evid Based Complement Alternat Med. 2017;2017:1693643. doi: 10.1155/2017/1693643. Epub 2017 Sep 26. PubMed PMID: 29081815; PubMed Central PMCID: PMC5634620. 11: Zheng H, Wang Z, Liu W, Jin H, Zhang J. Toxicokinetics of strychnine and brucine after the oral administration of Biqi capsule to rats by RRLC-MS/MS. Biomed Chromatogr. 2018 Mar;32(3). doi: 10.1002/bmc.4117. Epub 2017 Nov 3. PubMed PMID: 29027676. 12: Wu Y, Chen J, Fang Y, Dong J. [In vitro transdermal permeation and penetration properties for transfersomes of brucine]. Zhongguo Zhong Yao Za Zhi. 2016 Aug;41(16):3009-3015. doi: 10.4268/cjcmm20161611. Chinese. PubMed PMID: 28920340. 13: Li S, Wang XP. In vitro and in vivo evaluation of novel NGR-modified liposomes containing brucine. Int J Nanomedicine. 2017 Aug 11;12:5797-5804. doi: 10.2147/IJN.S136378. eCollection 2017. PubMed PMID: 28860749; PubMed Central PMCID: PMC5565249. 14: Svobodová J, Kofroňová O, Benada O, Král V, Mikšík I. Separation of oligopeptides, nucleobases, nucleosides and nucleotides using capillary electrophoresis/electrochromatography with sol-gel modified inner capillary wall. J Chromatogr A. 2017 Sep 29;1517:185-194. doi: 10.1016/j.chroma.2017.08.014. Epub 2017 Aug 7. PubMed PMID: 28851524. 15: Lu D, Xie Q, Wu B. N-glucuronidation catalyzed by UGT1A4 and UGT2B10 in human liver microsomes: Assay optimization and substrate identification. J Pharm Biomed Anal. 2017 Oct 25;145:692-703. doi: 10.1016/j.jpba.2017.07.037. Epub 2017 Aug 4. PubMed PMID: 28803208. 16: Li M, Li P, Zhang M, Ma F. Brucine suppresses breast cancer metastasis via inhibiting epithelial mesenchymal transition and matrix metalloproteinases expressions. Chin J Integr Med. 2018 Jan;24(1):40-46. doi: 10.1007/s11655-017-2805-1. Epub 2017 Aug 9. PubMed PMID: 28795388. 17: Savalia R, Chatterjee S. Sensitive detection of brucine an anti-metastatic drug for hepatocellular carcinoma at carbon nanotubes - nafion composite based biosensor. Biosens Bioelectron. 2017 Dec 15;98:371-377. doi: 10.1016/j.bios.2017.07.011. Epub 2017 Jul 6. PubMed PMID: 28709086. 18: Braun DE, Griesser UJ. Why do Hydrates (Solvates) Form in Small Neutral Organic Molecules? Exploring the Crystal Form Landscapes of the Alkaloids Brucine and Strychnine. Cryst Growth Des. 2016 Nov 2;16(11):6405-6418. doi: 10.1021/acs.cgd.6b01078. PubMed PMID: 28670205; PubMed Central PMCID: PMC5486441. 19: Braun DE, Griesser UJ. Stoichiometric and Non-Stoichiometric Hydrates of Brucine. Cryst Growth Des. 2016 Oct 5;16(10):6111-6121. doi: 10.1021/acs.cgd.6b01231. Epub 2016 Aug 26. PubMed PMID: 28670204; PubMed Central PMCID: PMC5486439. 20: Zhang M, Deng Y, Wang C, Cai HL, Wen J, Fang PF, Zhang BK, Li HD, Yan M. An LC-MS/MS method for determination of bioactive components of liquorice and Semen Strychni in rat plasma: Application to a pharmacokinetics study. Drug Test Anal. 2018 Feb;10(2):262-271. doi: 10.1002/dta.2210. Epub 2017 Jul 26. PubMed PMID: 28447397.