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Anagyrine

$1,440

  • Brand : BIOFRON

  • Catalogue Number : BN-O1753

  • Specification : 98%(HPLC)

  • CAS number : 486-89-5

  • Formula : C15H20N2O

  • Molecular Weight : 244.3

  • PUBCHEM ID : 5351589

  • Volume : 5mg

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Catalogue Number

BN-O1753

Analysis Method

Specification

98%(HPLC)

Storage

-20℃

Molecular Weight

244.3

Appearance

Cryst.

Botanical Source

This product is isolated and purified from the herbs of Cytisus scoparius

Structure Type

Category

SMILES

C1CCN2CC3CC(C2C1)CN4C3=CC=CC4=O

Synonyms

Anagyrin/Monolupine/3,4,5,6-Tetradehydrospartein-2-one/RHOMBININE/Alkaloid III/Rhombinin/Monolupin

IUPAC Name

Applications

Density

1.22 g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

216.3ºC

Boiling Point

455.6ºC at 760 mmHg

Melting Point

InChl

InChl Key

FQEQMASDZFXSJI-JHJVBQTASA-N

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:486-89-5) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

28494312

Abstract

Anagyrine, a teratogenic quinolizidine alkaloid found in Lupinus spp., is proposed to undergo metabolism by pregnant cattle to a piperidine alkaloid which inhibits fetal movement, the putative mechanism behind crooked calf syndrome. The objective of this study was to test the hypothesis that anagyrine but not lupanine or sparteine can directly, without metabolism, desensitize nicotinic acetylcholine receptors (nAChR) in a cell culture model. SH-SY5Y cells expressing autonomic nAChR, and TE-671 cells expressing fetal muscle-type nAChR were exposed to lupine alkaloids or Dimethylphenylpiperazinium (DMPP) in log10 molar increments from 10nM to 100μM and then to a fixed concentration of acetylcholine (ACh) (10μM for SH-SY5Y cells and 1μM for TE-671 cells) and the responses measured with a membrane potential sensing dye to assess nAChR activation and desensitization. The selective ganglionic nAChR agonist DMPP used as a positive control, was a potent activator and desensitizer of nAChR expressed by SH-SY5Y cells. Lupanine was a weak agonist and desensitizer in SH-SY5Y cells and sparteine was without effect. Anagyrine acted as a partial agonist in both cell lines with EC50 values of 4.2 and 231μM in SH-SY5Y and TE-671 cells, respectively. Anagyrine was a desensitizer of nAChR with DC50 values of 6.9 and 139μM in SH-SY5Y and TE-671 cells, respectively. These results confirm the hypothesis that anagyrine is a potent and effective desensitizer of nAChR, and that anagyrine can directly, without metabolism, desensitize nAChR. Moreover, serum anagyrine concentrations may be a potential biomarker for lupine teratogenicity in cattle.

Published by Elsevier Ltd.

KEYWORDS

Anagyrine; Biomarker; DMPP; Lupanine; Sparteine; nAChR

Title

Anagyrine desensitization of peripheral nicotinic acetylcholine receptors. A potential biomarker of quinolizidine alkaloid teratogenesis in cattle.

Author

Green BT1, Lee ST2, Welch KD2, Cook D2.

Publish date

2017 Dec

PMID

3110390

Title

Anagyrine-induced red cell aplasia, vascular anomaly, and skeletal dysplasia.

Author

Ortega JA, Lazerson J.

Publish date

1987 Jul

PMID

3339518

Title

Anagyrine-induced congenital defects.

Author

Finnell RH, Chernoff GF.

Publish date

1988 Feb