Methyllycaconitine

• CAT Number: M020005
• CAS Number: 21019-30-7
• Molecular Formula: C37H50N2O10
• Molecular Weight: 682.811
• Purity: ≥95%
• Synonyms: 14,16-tetramethoxy-,(1-alpha,4(s),6-beta,14-alpha,16-beta)-oxy)methyl)-6;aconitane-7,8-diol,20-ethyl-4-(((2-(3-methyl-2,5-dioxo-1-pyrrolidinyl)benzoyl);delartine;delsemidine;methyl-lycaconitin;METHYLLYCACONITINE CITRATE MLA:SYNTHETIC;METHYLLYCACONITI
• Storage: Store at RT
• InChIKey: XLTANAWLDBYGFU-YPHJBQGESA-N
• SMILES: CCN1CC2(CCC(C34C2C(C(C31)(C5(CC(C6CC4C5C6OC)OC)O)O)OC)OC)COC(=O)C7=CC=CC=C7N8C(=O)CC(C8=O)C

Methyllycaconitine (MLA) is a diterpenoid alkaloid found in many species of Delphinium (larkspurs). In common with many other diterpenoid alkaloids, it is toxic to animals, although the acute toxicity varies with species. Early research was focused on identifying, and characterizing the properties of methyllycaconitine as one of the principal toxins in larkspurs responsible for livestock poisoning in the mountain rangelands of North America. Methyllycaconitine has been explored as a possible therapeutic agent for the treatment of spastic paralyses in man, and it has been shown to have insecticidal properties. Most recently, it has become an important molecular probe for studying the pharmacology of the nicotinic acetylcholine receptor.

Reference

1: Andriambeloson E, Huyard B, Poiraud E, Wagner S. Methyllycaconitine- and
scopolamine-induced cognitive dysfunction: differential reversal effect by
cognition-enhancing drugs. Pharmacol Res Perspect. 2014 Aug;2(4):e00048. doi:
10.1002/prp2.48. Epub 2014 Jun 9. PubMed PMID: 25505596; PubMed Central PMCID:
PMC4186438.

2: Zheng X, Xie Z, Zhu Z, Liu Z, Wang Y, Wei L, Yang H, Yang H, Liu Y, Bi J.
Methyllycaconitine alleviates amyloid-β peptides-induced cytotoxicity in SH-SY5Y
cells. PLoS One. 2014 Oct 31;9(10):e111536. doi: 10.1371/journal.pone.0111536.
eCollection 2014. PubMed PMID: 25360664; PubMed Central PMCID: PMC4216102.

3: Absalom NL, Quek G, Lewis TM, Qudah T, von Arenstorff I, Ambrus JI, Harpsøe K,
Karim N, Balle T, McLeod MD, Chebib M. Covalent trapping of methyllycaconitine at
the α4-α4 interface of the α4β2 nicotinic acetylcholine receptor: antagonist
binding site and mode of receptor inhibition revealed. J Biol Chem. 2013 Sep
13;288(37):26521-32. doi: 10.1074/jbc.M113.475053. Epub 2013 Jul 26. PubMed PMID:
23893416; PubMed Central PMCID: PMC3772200.

4: Welch KD, Pfister JA, Gardner DR, Green BT, Panter KE. The role of the α7
subunit of the nicotinic acetylcholine receptor on motor coordination in mice
treated with methyllycaconitine and anabasine. J Appl Toxicol. 2013
Sep;33(9):1017-26. doi: 10.1002/jat.2894. Epub 2013 May 24. PubMed PMID:
23702881.

5: Welch KD, Green BT, Panter KE, Pfister JA, Gardner DR. The role of the α7
subunit of the nicotinic acetylcholine receptor in the acute toxicosis of
methyllycaconitine in mice. J Appl Toxicol. 2013 Sep;33(9):1011-6. doi:
10.1002/jat.2851. Epub 2013 Jan 8. PubMed PMID: 23296980.

6: Thomsen MS, Mikkelsen JD. The α7 nicotinic acetylcholine receptor ligands
methyllycaconitine, NS6740 and GTS-21 reduce lipopolysaccharide-induced TNF-α
release from microglia. J Neuroimmunol. 2012 Oct 15;251(1-2):65-72. doi:
10.1016/j.jneuroim.2012.07.006. Epub 2012 Aug 9. PubMed PMID: 22884467.

7: Nirogi R, Kandikere V, Bhyrapuneni G, Saralaya R, Muddana N, Komarneni P.
Methyllycaconitine: a non-radiolabeled ligand for mapping α7 neuronal nicotinic
acetylcholine receptors – in vivo target localization and biodistribution in rat
brain. J Pharmacol Toxicol Methods. 2012 Jul;66(1):22-8. doi:
10.1016/j.vascn.2012.05.003. Epub 2012 May 16. PubMed PMID: 22609758.