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M168

Methyllycaconitine citrate salt

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

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

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About This Item

Empirical Formula (Hill Notation):
C37H50N2O10 · xC6H8O7
CAS Number:
Molecular Weight:
682.80 (salt-free basis)
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Assay:
≥96% (HPLC)
Quality level:
Pricing and availability is not currently available.
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Product Name

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[1]
  • to block the activity of galantamine[2]
  • to study its effects on the hepatic branch of the vagus nerve (hVNS) in rats[3]

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.[4] MLA binds to the binding site of neuronal α-bungarotoxin.[5] Low doses of MLA are associated with improvement of cognition in animals.[4]

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.

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1 of 1

This Item
D204SML2385SML2008
assay

≥96% (HPLC)

assay

≥98% (HPLC)

assay

≥95% (HPLC)

assay

≥98% (HPLC)

Quality Level

100

Quality Level

100

Quality Level

-

Quality Level

-

storage temp.

−20°C

storage temp.

-

storage temp.

−20°C

storage temp.

2-8°C

solubility

H2O: 42 mg/mL

solubility

H2O: 10 mg/mL

solubility

-

solubility

H2O: 2 mg/mL, clear

color

white

color

white

color

white to beige

color

white to beige

biological source

Delphinium brownii seeds

biological source

-

biological source

-

biological source

-


Storage Class

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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Certificates of Analysis (COA)

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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



Global Trade Item Number

SKUGTIN
M168-5MG04061832082899
M168-25MG04061834041030

Questions

  1. The COA states “1.0 mol” of salt content, is that per mole of MLA? I need to know the exact MW of the salt complex in order to make a solution of known molarity. Do I assume there is one citrate molecule for each of MLA?

    1 answer
    1. The molecular weight of methyllycaconitine is 682.80 g/mole. The molecular weight of citric acid is 192.124 g/mole. The overall molecular weight of the salt complex is 874.94 g/mole, which corresponds to 1 mole of methyllycaconitine and 1 mole of citric acid. This calculation does not account for water content or purity. The certificate of analysis provides details on the number of moles of citric acid for each lot, as well as water content and purity, which may vary from lot to lot. The free base consists of one mole of methyllycaconitine.

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