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Cytisine

$93

  • Brand : BIOFRON

  • Catalogue Number : BF-C2008

  • Specification : 98%

  • CAS number : 485-35-8

  • Formula : C11H14N2O

  • Molecular Weight : 190.24

  • PUBCHEM ID : 10235

  • Volume : 20mg

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Catalogue Number

BF-C2008

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

190.24

Appearance

White crystalline powder

Botanical Source

Sophora flavescens,Piptanthus nepalensis,Sophora tonkinensis var. polyphylla,Sophora alopecuroides,Thermopsis lanceolata

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

C1C2CNCC1C3=CC=CC(=O)N3C2

Synonyms

CYTISINE/(1R,9S)-7,11-Diazatricyclo[7.3.1.0]trideca-2,4-dien-6-one/Cytitone/(1R)-1,2,3,4,5,6-Hexahydro-1,5-methano-8H-pyrido-[1,2-a][1,5]diazocin-8-one/1,5-Methano-8H-pyrido(1,2-a)(1,5)diazocin-8-one, 1,2,3,4,5,6-hexahydro-, (1R,5S)-/1,5-Methano-8H-pyrido[1,2-a][1,5]diazocin-8-one, 1,2,3,4,5,6-hexahydro-, (1R,5S)-/(1R,5S)-3,4,5,6-Tetrahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocin-8(2H)-one/Sophorin/Sophorin (VAN)/Ulexin/Cytisine (-)/Tabex/Tsitafat;Lupinidine/Baptitoxin/(1R,5S)-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido[1,2-a][1,5]diazocin-8-one/Tsitafat/(-)-Cytisine/Ulexine/5-24-02-00535/Cytiton/Sophorine/Cytisin/Baptitoxine/Laburnin

IUPAC Name

(1R,9S)-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one

Density

1.2±0.1 g/cm3

Solubility

Methanol; Dichloromethane

Flash Point

203.6±25.7 °C

Boiling Point

413.0±34.0 °C at 760 mmHg

Melting Point

154-156ºC

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2939800000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:485-35-8) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31647170

Abstract

A series of camphecene and quinolizidine alkaloid (-)-cytisine conjugates has been obtained for the first time using ‘click’ chemistry methodology. The cytotoxicity and virus-inhibiting activity of compounds were determined against MDCK cells and influenza virus A/Puerto Rico/8/34 (H1N1), correspondingly, in in vitro tests. Based on the results obtained, values of 50 % cytotoxic dose (CC50 ), 50 % inhibition dose (IC50 ) and selectivity index (SI) were determined for each compound. It has been shown that the antiviral activity is affected by the length and nature of linkers between cytisine and camphor units. Conjugate 13 ((1R,5S)-3-(6-{4-[(2-{(E)-[(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene]amino}ethoxy)methyl]-1H-1,2,3-triazol-1-yl}hexyl)-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido[1,2-a][1,5]diazocin-8-one), which contains cytisine fragment separated from triazole ring by -C6 H12 – aliphatic linker, showed the highest activity at relatively low toxicity (CC50 =168 μmol, IC50 =8 μmol, SI=20). Its selectivity index appeared higher than that of reference compound, rimantadine. According to theoretical calculations, the antiviral activity of the lead compound 13 can be explained by its influence on the functioning of neuraminidase.

© 2019 Wiley-VHCA AG, Zurich, Switzerland.

KEYWORDS

(+)-camphor; (−)-cytisine; 1,2,3-triazoles; azides; camphecene; cytotoxicity; heterocyclization; terpenoids; ‘click’ chemistry

Title

Synthesis of Camphecene and Cytisine Conjugates Using Click Chemistry Methodology and Study of Their Antiviral Activity.

Author

Artyushin OI1, Moiseeva AA1, Zarubaev VV2, Slita AV2, Galochkina AV2, Muryleva AA2, Borisevich SS3, Yarovaya OI4,5, Salakhutdinov NF4,5, Brel VK1.

Publish date

2019 Nov

PMID

31315205

Abstract

Background: Identification and quantitative determination of cytisine, especially in biological samples and pharmaceutical formulations, is still a difficult analytical task. Cytisine is an alkaloid with a small and very polar molecule. For this reason, it is very weakly retained on reversed phase (RP) stationary phases, such as commonly used alkyl-bonded phases. The very weak retention of cytisine causes it to be eluted together with the components of biological matrices. Objective: Comparison and evaluation of various chromatographic systems for analysis of cytisine in different matrices-serum, saliva and pharmaceutical formulation-by high performance liquid chromatography (HPLC) with diode array (DAD), fluorescence (FLD) and mass spectrometry (MS) detection. Methods: The analyses were performed using HPLC in reversed phase (RP), hydrophilic interaction liquid chromatography (HILIC) and ion exchange chromatography (IEC) modes. Different sample pre-treatment methods were tested: Protein precipitation (with acetone, methanol (MeOH) or acetonitrile (ACN), and solid phase extraction (SPE) using cartridges with octadecyl (C18), hydrophilic-lipophilic balanced copolymer (HLB) or strong cation exchange sorbents (Strata X-C). Conclusion: Significant differences were observed in retention parameters with a change of the used chromatographic system. The various properties of stationary phases resulted in differences in analyte retention, peaks’ shape and systems’ efficiency. The weakest retention was observed using RP systems; however, the use of the Polar RP phase can be an alternative for application in green chromatography. In the strongest retention was observed using a strong cation exchange (SCX) phase. The most optimal systems were chosen for the analysis of cytisine in the pharmaceutical preparation, serum and saliva after sample pre-treatment with the new SPE procedure. Due to the sensitivity, the use of HPLC-DAD or HPLC-FLD is the most optimal for drug analysis in pharmaceutical preparations, whereas HPLC-MS is suitable for analysis of cytisine in biological samples.

KEYWORDS

HPLC-DAD; HPLC-FLD; HPLC-MS/MS; SPE; cytisine; optimisation of chromatographic systems; pharmaceutical preparation; retention mechanism; saliva; serum

Title

Comparison of Various Chromatographic Systems for Analysis of Cytisine in Human Serum, Saliva and Pharmaceutical Formulation by HPLC with Diode Array, Fluorescence or Mass Spectrometry Detection.

Author

Wroblewski K1,2,3, Petruczynik A4, Tuzimski T5, Przygodzka D6, Buszewicz G6, Kołodziejczyk P7,8, Tutka P7,8,9.

Publish date

2019 Jul 16

PMID

30740869

Abstract

BACKGROUND:
To discover novel natural product-based pesticidal agents for crop protection, a series of N-acyl/sulfonyl derivatives of 5(3,5)-(di)halogenocytisines/cytisine were prepared by structural modifications of cytisine. Their pesticidal activities were evaluated against three typically crop-threatening agricultural pests, Mythimna separata Walker, Tetranychus cinnabarinus Boisduval, and Sitobion avenae Fabricius.

RESULTS:
Compound 5f exhibited the promising pesticidal activities against three tested pests. All N-phenylsulfonylcytisine derivatives showed potent acaricidal activity. Compound 5j exhibited 2.5-fold more potent acaricidal activity than cytisine, and showed good control effects. Intermediates 2, and 3/3′ displayed pronounced aphicidal activity. Some interesting results of structure-activity relationships were also obtained.

CONCLUSION:
These results demonstrate that compounds 5f and 5j could be further modified as pesticidal agents. © 2019 Society of Chemical Industry.

© 2019 Society of Chemical Industry.

KEYWORDS

cytisine; natural product; pesticidal activity; structural modification

Title

Semisynthesis of novel N-acyl/sulfonyl derivatives of 5(3,5)-(di)halogenocytisines/cytisine and their pesticidal activities against Mythimna separata Walker, Tetranychus cinnabarinus Boisduval, and Sitobion avenae Fabricius.

Author

Huang X1, Lv M1, Xu H1,2.

Publish date

2017


Description :

Cytisine is an alkaloid that occurs naturally in several plant genera, such as Laburnum and Cytisus. Cytisine is a partial agonist of α4β2 nAChRs[1], and partial to full agonist at β4 containing receptors and α7 receptors[2]. has been used medically to help with smoking cessation[3].