Himbacine

Himbacine
Clinical data

ATC code	none
Identifiers
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
CAS Number	6879-74-9^Y
PubChem CID	6436265
IUPHAR/BPS	324
ChemSpider	4940913^Y
ChEBI	CHEBI:5720^Y
ChEMBL	CHEMBL277642^Y
Chemical and physical data
Formula	C₂₂H₃₅NO₂
Molar mass	345.27 g/mol
3D model (Jmol)	Interactive image
SMILES O=C3O[C@H]([C@@H]4[C@H](/C=C/[C@@H]1N(C)[C@@H](C)CCC1)[C@@H]2[C@H](CCCC2)C[C@H]34)C
InChI InChI=1S/C22H35NO2/c1-14-7-6-9-17(23(14)3)11-12-19-18-10-5-4-8-16(18)13-20-21(19)15(2)25-22(20)24/h11-12,14-21H,4-10,13H2,1-3H3/b12-11+/t14-,15-,16+,17+,18-,19+,20-,21+/m0/s1^Y Key:FMPNFDSPHNUFOS-LPJDIUFZSA-N^Y

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.