Methyllycaconitine

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C37H50N2O10
Molecular Weight	682.8003
Optical Activity	UNSPECIFIED
Defined Stereocenters	14 / 14
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12C[C@H]3[C@H](OC)[C@]1([H])[C@](O)(C[C@@H]3OC)[C@@]4(O)[C@@H](OC)[C@@]5([H])[C@]26[C@H](CC[C@@]5(COC(=O)C7=C(C=CC=C7)N8C(=O)C[C@H](C)C8=O)CN(CC)[C@]46[H])OC

InChI

InChIKey=XLTANAWLDBYGFU-HTWFBASDSA-N

InChI=1S/C37H50N2O10/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/h8-11,19,21-22,24-25,27-30,33,43-44H,7,12-18H2,1-6H3/t19-,21+,22+,24-,25-,27+,28-,29+,30-,33-,34-,35+,36+,37+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C37H50N2O10
Molecular Weight	682.8003
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	14 / 14
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://pubs.acs.org/doi/abs/10.1021/ja00411a062
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/7589218 http://www.provizor-online.ru/2013/05/melliktin_Mellictinum

Methyllycaconitine is a diterpenoid alkaloid found in many species of Delphinium (larkspurs). Methyllycaconitine is a potent antagonist for α7-containing neuronal nicotinic receptors. Methyllycaconitine (as mellictin) is used in some countries as a myorelaxant for treatment of pyramidal and extrapyramidal motoric disorders, such as pyramidal insufficiency, Parkinson disease, meningocephalitis and other disorders.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Neuronal acetylcholine receptor subunit alpha-7 14 Target ID: P36544 Gene ID: 1139\|\|\|89832 Gene Symbol: CHRNA7 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/7589218	Antagonist 2778		10.3 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pyramidal and extrapyramidal motoric disorders 1 Sources: http://www.provizor-online.ru/2013/05/melliktin_Mellictinum	Palliative		Approved 8429	Mellictin Approved Use Methyllycaconitine (as mellictin) is used in some countries as a myorelaxant for treatment of pyramidal and extrapyramidal motoric disorders, such as pyramidal insufficiency, Parkinson disease, meningocephalitis and other disorders.

PubMed

Title	Date	PubMed
Stable expression and pharmacological properties of the human alpha 7 nicotinic acetylcholine receptor.	1995 Aug 15	7589218

Sample Use Guides

In Vivo Use Guide

Methyllycaconitine is administered daily, as oral tablets, 0.02 g/day once daily. The dose is increased up to 5 times a day.

Route of Administration: Oral

In Vitro Use Guide

Binding to α7-containing neuronal nicotinic receptors was meaused using K28 cells, stably transfected with human α7 nicotinic receptor. [125I]α-bungarotoxin was used as a radioligand. Methyllycaconitine binds to α7 nicotinic receptor with Ki of 10.3 nM.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:29:48 GMT 2023` Edited by `admin` on `Sat Dec 16 08:29:48 GMT 2023`
Record UNII	8H7EX9Z9QE
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Methyllycaconitine

Common Name

English

Delsemidine

Common Name

English

Aconitane-7,8-diol, 20-ethyl-1,6,14,16-tetramethoxy-4-[[[2-(3-methyl-2,5-dioxo-1-pyrrolidinyl)benzoyl]oxy]methyl]-, [1α,4(S),6β,14α,16β]-

Systematic Name

English

Aconitane-7,8-diol, 20-ethyl-1,6,14,16-tetramethoxy-4-[[[2-[(3S)-3-methyl-2,5-dioxo-1-pyrrolidinyl]benzoyl]oxy]methyl]-, (1α,6β,14α,16β)-

Systematic Name

English

(1α,6β,14α,16β)-20-Ethyl-1,6,14,16-tetramethoxy-4-[[[2-[(3S)-3-methyl-2,5-dioxo-1-pyrrolidinyl]benzoyl]oxy]methyl]aconitane-7,8-diol

Systematic Name

English

Delartine

Common Name

English

Code System Code Type Description

CAS

21019-30-7