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M168

Sigma-Aldrich

Methyllycaconitine citrate salt

from Delphinium brownii seeds, ≥96% (HPLC)

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Synonym(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
Empirical Formula (Hill Notation):
C37H50N2O10 · xC6H8O7
CAS Number:
Molecular Weight:
682.80 (salt-free basis)
MDL number:
PubChem Substance ID:
NACRES:
NA.77

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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