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Merck

M168

Methyllycaconitine citrate salt

From Delphinium brownii seeds, ≥96% (HPLC), α7 nicotinic acetylcholine receptor (α7 nAChR) antagonist

Synonyme(s) :

MLA, [1α,4(S),6β,14α,16β]-20-Ethyl-1,6,14,16-tetramethoxy-4-[[[2-(3-methyl-2,5-dioxo-1-pyrrolidinyl)benzoyl]oxy]methyl]aconitane-7,8-diol citrate salt

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A propos de cet article

Formule empirique (notation de Hill) :
C37H50N2O10 · xC6H8O7
Numéro CAS:
Poids moléculaire :
682.80 (salt-free basis)
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Assay:
≥96% (HPLC)
Quality level:
Service technique
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Nom du produit

Methyllycaconitine citrate salt, from Delphinium brownii seeds, ≥96% (HPLC)

biological source

Delphinium brownii seeds

Quality Level

assay

≥96% (HPLC)

color

white

solubility

H2O: 42 mg/mL

storage temp.

−20°C

SMILES string

O=C(OC[C@]12[C@@]([C@]3([C@H](CC1)OC)[C@@H]4N(C2)CC)([H])[C@@H]([C@]4(O)[C@]5(O)[C@]6([H])[C@@]3([H])C[C@@]([C@H](C5)OC)([H])[C@@H]6OC)OC)C7=CC=CC=C7N8C([C@@H](C)CC8=O)=O.OC(CC(CC(O)=O)(C(O)=O)O)=O

InChI

1S/C37H50N2O10.C6H8O7/c1-7-38-17-34(18-49-32(42)20-10-8-9-11-23(20)39-26(40)14-19(2)31(39)41)13-12-25(46-4)36-22-15-21-24(45-3)16-35(43,27(22)28(21)47-5)37(44,33(36)38)30(48-6)29(34)36;7-3(8)1-6(13,5(11)12)2-4(9)10/h8-11,19,21-22,24-25,27-30,33,43-44H,7,12-18H2,1-6H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/t19-,21+,22+,24-,25-,27+,28-,29+,30-,33?,34-,35+,36-,37+;/m0./s1

InChI key

INBLZNJHDLEWPS-DDIMIZGISA-N

Application

Methyllycaconitine citrate salt has been used as an α7 nicotinic acetylcholine receptor (α7 nAChR) antagonist:
  • to study its effects on inflammatory response in rats post nicotine treatment
  • to block the activity of galantamine
  • to study its effects on the hepatic branch of the vagus nerve (hVNS) in rats

Biochem/physiol Actions

Methyllycaconitine (MLA) is an α7 nicotinic acetylcholine receptor (α7 nAChR) antagonist. It is a norditerpenoid alkaloid synthesized by several species of Delphinium. MLA binds to the binding site of neuronal α-bungarotoxin. Low doses of MLA are associated with improvement of cognition in animals.

Features and Benefits

This compound is featured on the Acetylcholine Receptors (Nicotinic) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.


Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)



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Consulter la Bibliothèque de documents



Francesca Prestori et al.
PloS one, 8(5), e64828-e64828 (2013-06-07)
The brain needs mechanisms able to correlate plastic changes with local circuit activity and internal functional states. At the cerebellum input stage, uncontrolled induction of long-term potentiation or depression (LTP or LTD) between mossy fibres and granule cells can saturate
Maria A Schlöffel et al.
Plant physiology, 183(1), 371-384 (2020-03-11)
Plants have evolved effective strategies to defend themselves against pathogen invasion. Starting from the plasma membrane with the recognition of microbe-associated molecular patterns (MAMPs) via pattern recognition receptors, internal cellular signaling pathways are induced to ultimately fend off the attack.
Cecília Cerqueira Café-Mendes et al.
Neuroscience letters, 636, 218-224 (2016-12-17)
The hippocampus is a brain region that is rich in nicotinic acetylcholine receptors (nAChRs), especially the α7 subtype. The hippocampus is severely affected in disorders that have a neuroinflammatory component, such as Alzheimer's disease, Parkinson's disease, and schizophrenia. Previous studies