himbacine
Sign in to saveAlso 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.
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 sectionsContents
- 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.