Structure via PubChem · Public domain (PubChem)
stepholidine
Sign in to saveAlso known as L-stepholidine, S-stepholidine, (-)-stepholidine
(−)-Stepholidine is a protoberberine alkaloid found in the plant Stephania intermedia.
Chemical data
- Formula
- C19H21NO4
- Molecular weight
- 327.4 g/mol
- IUPAC name
- (13aS)-3,9-dimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline-2,10-diol
- SMILES
- COC1=C(C=C2[C@@H]3CC4=C(CN3CCC2=C1)C(=C(C=C4)O)OC)O
- InChIKey
- JKPISQIIWUONPB-HNNXBMFYSA-N
- XLogP
- 2.6
- Polar surface area
- 62.2 Ų
- H-bond donors
- 2
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
150 papers- (-)-Stepholidine reduces cue-induced reinstatement of cocaine seeking and cocaine self-administration in rats.Drug and alcohol dependence · 2018
- (-)-Stepholidine: a potential novel antipsychotic drug with dual D1 receptor agonist and D2 receptor antagonist actions.Trends in pharmacological sciences · 2002
- (-)-Stepholidine is a potent pan-dopamine receptor antagonist of both G protein- and β-arrestin-mediated signaling.Psychopharmacology · 2015
- (-)-Stepholidine blocks expression, but not development, of cocaine conditioned place preference in rats.Neuroscience letters · 2020
- Recent developments in studies of l-stepholidine and its analogs: chemistry, pharmacology and clinical implications.Current medicinal chemistry · 2007
via PubMed
Wikidata facts
- Mass
- 327.147058
Show 4 more facts
- subject has role
- calcium channel blocker
- chemical formula
- C₁₉H₂₁NO₄
- canonical SMILES
- COC1=C(C=C2C3CC4=C(CN3CCC2=C1)C(=C(C=C4)O)OC)O
- isomeric SMILES
- COC1=C(C=C2[C@@H]3CC4=C(CN3CCC2=C1)C(=C(C=C4)O)OC)O
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
(−)-Stepholidine is a protoberberine alkaloid found in the plant Stephania intermedia.
Stepholidine activity includes dual D2 receptor antagonist and D1 receptor agonist, and has shown antipsychotic activity in animal studies.
Excerpted from Wikipedia’s “stepholidine” article, available under the CC BY-SA 4.0 licence.