Structure via PubChem · Public domain (PubChem)
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.
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 Ų
- 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
~2 min read
Encyclopedic overview
1 sectionsContents
- References
{{Drugbox | verifiedrevid = 407836401 | IUPAC_name = (3aR,4R,4aS,8aR,9aS)- 4-{(E)-[(2R,6S)- 1,6-dimethylpiperidin- 2-yl]vinyl}- 3-methyldecahydronaphtho[2,3-c]furan- 1(3H)-one | image = Himbacine.svg | image_class = skin-invert-image
| tradename = | pregnancy_category = | legal_status = | routes_of_administration =
Excerpted from Wikipedia’s “himbacine” article, available under the CC BY-SA 4.0 licence.