Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

M168

Sigma-Aldrich

Methyllycaconitine citrate salt

from Delphinium brownii seeds, ≥96% (HPLC)

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C37H50N2O10 · xC6H8O7
CAS Number:
112825-05-5
Molecular Weight:
682.80 (salt-free basis)
MDL number:
MFCD00153837
UNSPSC Code:
12352200
PubChem Substance ID:
24896681
NACRES:
NA.77

biological source

Delphinium brownii seeds

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Natalia Pinilla-Echeverri et al.
Circulation. Cardiovascular interventions, 13(7), e008768-e008768 (2020-07-11)
Complete revascularization with routine percutaneous coronary intervention of nonculprit lesions after primary percutaneous coronary intervention improves outcomes in ST-segment-elevation myocardial infarction. Whether this benefit is associated with nonculprit lesion vulnerability is unknown. In a prospective substudy of the COMPLETEs trial
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
Elizabeth Glenn Guy et al.
Psychopharmacology, 225(2), 429-440 (2012-08-14)
Stimuli associated with nicotine can become motivationally significant and may play a role in tobacco dependence. Previous work indicates that nicotine enhances responding for a conditioned reinforcer (CR). These studies examined the effects of prior exposure to nicotine on responding
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.
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service