Nuciferine | CAS#475-83-2 | CNS depressant

MedKoo Cat#: 596549 | Name: Nuciferine

Featured

Description:

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

Nuciferine is a CNS depressant; glutamic acid antagonist. Nuciferin is an drug candidate for the treatment of obesity-related diseases. It is not well studied and its pharmacokinetics in vivo have not been fully investigated.

Chemical Structure

Nuciferine

CAS#475-83-2

Theoretical Analysis

MedKoo Cat#: 596549

Name: Nuciferine

CAS#: 475-83-2

Chemical Formula: C19H21NO2

Exact Mass: 295.1572

Molecular Weight: 295.38

Elemental Analysis: C, 77.26; H, 7.17; N, 4.74; O, 10.83

Price and Availability

Size	Price	Availability	Quantity
25mg	USD 400.00	2 Weeks
50mg	USD 750.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

Nuciferine; l-Nuciferine; Sanjoinine E;

IUPAC/Chemical Name

(R)-1,2-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline

InChi Key

ORJVQPIHKOARKV-OAHLLOKOSA-N

InChi Code

InChI=1S/C19H21NO2/c1-20-9-8-13-11-16(21-2)19(22-3)18-14-7-5-4-6-12(14)10-15(20)17(13)18/h4-7,11,15H,8-10H2,1-3H3/t15-/m1/s1

SMILES Code

CN1CCC2=CC(OC)=C(OC)C3=C2[C@@]1([H])CC4=CC=CC=C34

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:

Nuciferine is an antagonist at 5-HT2A (IC50=478 nM), 5-HT2C (IC50=131 nM), and 5-HT2B (IC50=1 μM), an inverse agonist at 5-HT7 (IC50=150 nM), a partial agonist at D2 (EC50=64 nM), D5 (EC50=2.6 μM) and 5-HT6 (EC50=700 nM), an agonist at 5-HT1A (EC50=3.2 μM) and D4 (EC50=2 μM) receptor.

In vitro activity:

In RAW 264.7 cells, NCF (nuciferine) pretreatment significantly decreased the expression of inducible nitric oxide synthase (iNOS), the expression and release of pro-inflammatory cytokines including interleukin (IL)-1β, IL-18, and tumor necrosis factor-α (TNF-α) and interfered with the activation of mitogen-activated protein kinase (MAPK), nuclear factor-κB (NF-κB), and NOD-like family pyrin domain containing 3 (NLRP3) signaling pathways. Reference: Int Immunopharmacol. 2023 Feb;115:109613. https://pubmed.ncbi.nlm.nih.gov/36577154/

In vivo activity:

This study found that nuciferine could reduce the myocardial infarct size in a mouse myocardial ischemia-reperfusion model and improve cardiac function. Furthermore, nuciferine could effectively inhibit hypoxia and reoxygenation (H/R) stimulated apoptosis of primary mouse cardiomyocytes. In addition, nuciferine significantly reduced the level of oxidative stress. Reference: Heliyon. 2023 Feb 11;9(2):e13630. https://pubmed.ncbi.nlm.nih.gov/36865453/

	Solvent	mg/mL	mM
Solubility
	DMF	1.0	3.39
	DMSO	3.5	11.85
	Ethanol	1.0	3.39
	Ethanol:PBS (pH 7.2) (1:3)	0.3	0.85

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 295.38 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. Kulhari U, Kundu S, Mugale MN, Sahu BD. Nuciferine alleviates intestinal inflammation by inhibiting MAPK/NF-κB and NLRP3/Caspase 1 pathways in vivo and in vitro. Int Immunopharmacol. 2023 Feb;115:109613. doi: 10.1016/j.intimp.2022.109613. Epub 2022 Dec 26. PMID: 36577154. 2. Charoensin S, Weera W. Preventive Effect of Nuciferine on H2O2-Induced Fibroblast Senescence and Pro-Inflammatory Cytokine Gene Expression. Molecules. 2022 Nov 23;27(23):8148. doi: 10.3390/molecules27238148. PMID: 36500241; PMCID: PMC9741010. 3. Li R, Qin X, Yue L, Liu W, Gao Y, Zhu F, Wang D, Zhou Q. Nuciferine improves cardiac function in mice subjected to myocardial ischemia/reperfusion injury by upregulating PPAR-γ. Heliyon. 2023 Feb 11;9(2):e13630. doi: 10.1016/j.heliyon.2023.e13630. PMID: 36865453; PMCID: PMC9970911. 4. Xiao M, Xian C, Wang Y, Qi X, Zhang R, Liu Z, Cheng Y. Nuciferine attenuates atherosclerosis by regulating the proliferation and migration of VSMCs through the Calm4/MMP12/AKT pathway in ApoE(-/-) mice fed with High-Fat-Diet. Phytomedicine. 2023 Jan;108:154536. doi: 10.1016/j.phymed.2022.154536. Epub 2022 Nov 9. PMID: 36395561.

In vitro protocol:

In vivo protocol:

1. Li R, Qin X, Yue L, Liu W, Gao Y, Zhu F, Wang D, Zhou Q. Nuciferine improves cardiac function in mice subjected to myocardial ischemia/reperfusion injury by upregulating PPAR-γ. Heliyon. 2023 Feb 11;9(2):e13630. doi: 10.1016/j.heliyon.2023.e13630. PMID: 36865453; PMCID: PMC9970911. 2. Xiao M, Xian C, Wang Y, Qi X, Zhang R, Liu Z, Cheng Y. Nuciferine attenuates atherosclerosis by regulating the proliferation and migration of VSMCs through the Calm4/MMP12/AKT pathway in ApoE(-/-) mice fed with High-Fat-Diet. Phytomedicine. 2023 Jan;108:154536. doi: 10.1016/j.phymed.2022.154536. Epub 2022 Nov 9. PMID: 36395561.

1: Geng P, Luo J, Weng Z, Fan Z, Zhang B, Ma J, Wang X, Zhang M. Determination of armepavine in mouse blood by UPLC-MS/MS and its application to pharmacokinetic study. Biomed Chromatogr. 2018 May 3:e4273. doi: 10.1002/bmc.4273. [Epub ahead of print] PubMed PMID: 29726027. 2: Li Z, Liu J, Li Y, Du X, Li Y, Wang R, Lv C, He X, Wang B, Huang Y, Zhang D. Identify super quality markers from prototype-based pharmacokinetic markers of Tangzhiqing tablet (TZQ) based on in vitro dissolution/ permeation and in vivo absorption correlations. Phytomedicine. 2018 Apr 4. pii: S0944-7113(18)30101-6. doi: 10.1016/j.phymed.2018.04.001. [Epub ahead of print] PubMed PMID: 29685365. 3: Cai T, Cocci A, Cito G, Giammusso B, Zucchi A, Chiancone F, Carrino M, Mastroeni F, Comerci F, Franco G, Palmieri A. The role of diallyl thiosulfinate associated with nuciferine and diosgenin in the treatment of premature ejaculation: A pilot study. Arch Ital Urol Androl. 2018 Mar 31;90(1):59-64. doi: 10.4081/aiua.2018.1.59. PubMed PMID: 29633800. 4: Zhao JR, Ren XL, Wang M. [Biopharmaceuticals classification system(BCS) of nuciferin in Nelumbinis Folium]. Zhongguo Zhong Yao Za Zhi. 2018 Feb;43(3):511-519. doi: 10.19540/j.cnki.cjcmm.20171023.001. Chinese. PubMed PMID: 29600615. 5: Li Z, Liu J, Zhang D, Du X, Han L, Lv C, Li Y, Wang R, Wang B, Huang Y. Nuciferine and paeoniflorin can be quality markers of Tangzhiqing tablet, a Chinese traditional patent medicine, based on the qualitative, quantitative and dose-exposure-response analysis. Phytomedicine. 2018 Feb 21. pii: S0944-7113(18)30032-1. doi: 10.1016/j.phymed.2018.02.006. [Epub ahead of print] PubMed PMID: 29519686. 6: Kang EJ, Lee SK, Park KK, Son SH, Kim KR, Chung WY. Liensinine and Nuciferine, Bioactive Components of Nelumbo nucifera, Inhibit the Growth of Breast Cancer Cells and Breast Cancer-Associated Bone Loss. Evid Based Complement Alternat Med. 2017;2017:1583185. doi: 10.1155/2017/1583185. Epub 2017 Dec 3. PubMed PMID: 29333179; PubMed Central PMCID: PMC5733186. 7: Wu H, Yang Y, Guo S, Yang J, Jiang K, Zhao G, Qiu C, Deng G. Nuciferine Ameliorates Inflammatory Responses by Inhibiting the TLR4-Mediated Pathway in Lipopolysaccharide-Induced Acute Lung Injury. Front Pharmacol. 2017 Dec 21;8:939. doi: 10.3389/fphar.2017.00939. eCollection 2017. PubMed PMID: 29311940; PubMed Central PMCID: PMC5742629. 8: Wu N, Xie H, Fang Y, Liu Y, Xi X, Chu Q, Dong G, Lan T, Wei Y. Isolation and purification of alkaloids from lotus leaves by ionic-liquid-modified high-speed countercurrent chromatography. J Sep Sci. 2018 Jan;41(2):571-577. doi: 10.1002/jssc.201700851. Epub 2017 Dec 5. PubMed PMID: 29087605. 9: Yin XW, Hou CB, Chen JP, Pan M, Li XL, Wang ZY, Dong L. [Overall intestinal permeability of multiple components in lotus leaf by in situ single pass intestinal perfusion models]. Zhongguo Zhong Yao Za Zhi. 2017 Apr;42(8):1525-1531. doi: 10.19540/j.cnki.cjcmm.20170223.006. Chinese. PubMed PMID: 29071857. 10: Yang X, Yu MF, Lei J, Peng YB, Zhao P, Xue L, Chen W, Ma LQ, Liu QH, Shen J. Nuciferine Relaxes Tracheal Rings via the Blockade of VDLCC and NSCC Channels. Planta Med. 2018 Jan;84(2):83-90. doi: 10.1055/s-0043-118178. Epub 2017 Aug 17. PubMed PMID: 28817840. 11: Fang Y, Li Q, Shao Q, Wang B, Wei Y. A general ionic liquid pH-zone-refining countercurrent chromatography method for separation of alkaloids from Nelumbo nucifera Gaertn. J Chromatogr A. 2017 Jul 21;1507:63-71. doi: 10.1016/j.chroma.2017.05.048. Epub 2017 May 24. PubMed PMID: 28571916. 12: Wu XL, Wu MJ, Chen XZ, Ma HL, Ding LQ, Qiu F, Pan Q, Zhang DQ. Metabolic profiling of nuciferine in rat urine, plasma, bile and feces after oral administration using ultra-high performance liquid chromatography-diode array detection-quadrupole time-of-flight mass spectrometry. J Pharm Biomed Anal. 2017 Jun 5;140:71-80. doi: 10.1016/j.jpba.2017.03.022. Epub 2017 Mar 18. PubMed PMID: 28342305. 13: Poklis JL, Mulder HA, Halquist MS, Wolf CE, Poklis A, Peace MR. The Blue Lotus Flower (Nymphea caerulea) Resin Used in a New Type of Electronic Cigarette, the Re-Buildable Dripping Atomizer. J Psychoactive Drugs. 2017 Jul-Aug;49(3):175-181. doi: 10.1080/02791072.2017.1290304. Epub 2017 Mar 7. PubMed PMID: 28266899; PubMed Central PMCID: PMC5638439. 14: Liu Y, Wu X, Mi Y, Zhang B, Gu S, Liu G, Li X. PLGA nanoparticles for the oral delivery of nuciferine: preparation, physicochemical characterization and in vitro/in vivo studies. Drug Deliv. 2017 Nov;24(1):443-451. doi: 10.1080/10717544.2016.1261381. PubMed PMID: 28165858. 15: Wang MX, Zhao XJ, Chen TY, Liu YL, Jiao RQ, Zhang JH, Ma C, Liu JH, Pan Y, Kong LD. Nuciferine Alleviates Renal Injury by Inhibiting Inflammatory Responses in Fructose-Fed Rats. J Agric Food Chem. 2016 Oct 10. [Epub ahead of print] PubMed PMID: 27718563. 16: Sharma BR, Gautam LN, Adhikari D, Karki R. A Comprehensive Review on Chemical Profiling of Nelumbo Nucifera: Potential for Drug Development. Phytother Res. 2017 Jan;31(1):3-26. doi: 10.1002/ptr.5732. Epub 2016 Sep 26. Review. PubMed PMID: 27667670. 17: Morikawa T, Kitagawa N, Tanabe G, Ninomiya K, Okugawa S, Motai C, Kamei I, Yoshikawa M, Lee IJ, Muraoka O. Quantitative Determination of Alkaloids in Lotus Flower (Flower Buds of Nelumbo nucifera) and Their Melanogenesis Inhibitory Activity. Molecules. 2016 Jul 19;21(7). pii: E930. doi: 10.3390/molecules21070930. PubMed PMID: 27447599. 18: Chan JD, Acharya S, Day TA, Marchant JS. Pharmacological profiling an abundantly expressed schistosome serotonergic GPCR identifies nuciferine as a potent antagonist. Int J Parasitol Drugs Drug Resist. 2016 Dec;6(3):364-370. doi: 10.1016/j.ijpddr.2016.06.001. Epub 2016 Jun 23. PubMed PMID: 27397763; PubMed Central PMCID: PMC5196489. 19: Qi Q, Li R, Li HY, Cao YB, Bai M, Fan XJ, Wang SY, Zhang B, Li S. Identification of the anti-tumor activity and mechanisms of nuciferine through a network pharmacology approach. Acta Pharmacol Sin. 2016 Jul;37(7):963-72. doi: 10.1038/aps.2016.53. Epub 2016 May 16. PubMed PMID: 27180984; PubMed Central PMCID: PMC4933762. 20: Guo Y, Chen X, Qi J, Yu B. Simultaneous qualitative and quantitative analysis of flavonoids and alkaloids from the leaves of Nelumbo nucifera Gaertn. using high-performance liquid chromatography with quadrupole time-of-flight mass spectrometry. J Sep Sci. 2016 Jul;39(13):2499-507. doi: 10.1002/jssc.201501315. Epub 2016 Jun 7. PubMed PMID: 27161554.