M168

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
• 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

Properties

• biological source: Delphinium brownii seeds
• Quality Level: 100
• 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

Description

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.

Safety Information

• 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