leonurine

Also known as Norboldine

Leonurine (also known as SCM-198 in research) is a pseudoalkaloid that has been isolated from Leonotis leonurus, Leonotis nepetifolia, Leonurus japonicus, Leonurus cardiaca (motherwort), Leonurus sibiricus, as well as other plants of family Lamiaceae. Leonurine is easily extracted into water.

Chemical data

Formula: C14H21N3O5
Molecular weight: 311.33 g/mol
IUPAC name: 4-(diaminomethylideneamino)butyl 4-hydroxy-3,5-dimethoxybenzoate
SMILES: COC1=CC(=CC(=C1O)OC)C(=O)OCCCCN=C(N)N
InChIKey: WNGSUWLDMZFYNZ-UHFFFAOYSA-N
XLogP: 0.5
Polar surface area: 129 Å²
H-bond donors: 3
H-bond acceptors: 6
Formal charge: 0

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Wikidata facts

Subclass of: chemical compound
Mass: 311.148121

Show 3 more facts

chemical formula: C₁₄H₂₁N₃O₅
canonical SMILES: COC1=CC(=CC(=C1O)OC)C(=O)OCCCCN=C(N)N
found in taxon: Leonotis leonurus

Sources (2)

via Wikidata · CC0

~2 min read

Encyclopedic overview

5 sections

Contents

Research
Metabolites
Chemical synthesis
References
Further reading

== Research == Leonurine weakly binds to multiple GABA receptor sites including the GABAA receptor. However, it shows much higher affinity as a 5-HT3A receptor antagonist. 5-HT3A antagonists have been shown to help prevent nausea and vomiting as well as the negative effects of serotonin in the gastrointestinal tract.

Excerpted from Wikipedia’s “leonurine” article, available under the CC BY-SA 4.0 licence.