himbacine

Also known as (+)-himbacine

Himbacine is an alkaloid isolated from the bark of Australian magnolias. Himbacine has been synthesized using a Diels-Alder reaction as a key step. Himbacine's activity as a muscarinic receptor antagonist, with specificity for the muscarinic acetylcholine receptor M2, made it a promising starting point in Alzheimer's disease research. The development of a muscarinic antagonist based on himbacine failed, but an analog, vorapaxar, has been approved by the FDA as a thrombin receptor antagonist.

In the Vinony graph

Vinony's link graph records 403 inbound references to himbacine, and connects out to atropine, muscarinic acetylcholine receptor family and muscarinic agonist.

It sits within the topics Chemical pages without DrugBank identifier, Drugs not assigned an ATC code and Drugs with no legal status.

Vinony links it to 5 Wikipedia language editions.

Chemical data

Formula: C22H35NO2
Molecular weight: 345.5 g/mol
IUPAC name: (3S,3aR,4R,4aS,8aR,9aS)-4-[(E)-2-[(2R,6S)-1,6-dimethylpiperidin-2-yl]ethenyl]-3-methyl-3a,4,4a,5,6,7,8,8a,9,9a-decahydro-3H-benzo[f][2]benzofuran-1-one
SMILES: C[C@H]1CCC[C@@H](N1C)/C=C/[C@@H]2[C@H]3CCCC[C@@H]3C[C@H]4[C@@H]2[C@@H](OC4=O)C
InChIKey: FMPNFDSPHNUFOS-LPJDIUFZSA-N
XLogP: 5
Polar surface area: 29.5 Å²
H-bond donors: 0
H-bond acceptors: 3
Formal charge: 0

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Research

170 papers

Himbacine-derived thrombin receptor antagonists: c7-spirocyclic analogues of vorapaxar.ACS medicinal chemistry letters · 2014
Himbacine recognizes a high affinity subtype of M2 muscarinic cholinergic receptors in the rat cerebral cortex.Brain research · 1988
Himbacine derived thrombin receptor antagonists: discovery of a new tricyclic core.Bioorganic & medicinal chemistry letters · 2007
Binding and functional selectivity of himbacine for cloned and neuronal muscarinic receptors.The Journal of pharmacology and experimental therapeutics · 1992
IMDA-radical cyclization approach to (+)-himbacine.Organic letters · 2003

via PubMed

Wikidata facts

Subclass of: chemical compound
Mass: 345.266779

Show 5 more facts

Commons category: Himbacine
chemical formula: C₂₂H₃₅NO₂
isomeric SMILES: C[C@H]1CCC[C@@H](N1C)/C=C/[C@@H]2[C@H]3CCCC[C@@H]3C[C@H]4[C@@H]2[C@@H](OC4=O)C
canonical SMILES: CC1CCCC(N1C)C=CC2C3CCCCC3CC4C2C(OC4=O)C
subject has role: parasympatholytic

Sources (2)

via Wikidata · CC0

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Encyclopedic overview

1 sections

Contents

References

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| tradename = | pregnancy_category = | legal_status = | routes_of_administration =

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