Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C22H35NO2 |
| Molecular Weight | 345.5188 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 8 / 8 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@@H]1OC(=O)[C@H]2C[C@H]3CCCC[C@@H]3[C@@H](\C=C\[C@H]4CCC[C@H](C)N4C)[C@@H]12
InChI
InChIKey=FMPNFDSPHNUFOS-LPJDIUFZSA-N
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
| Molecular Formula | C22H35NO2 |
| Molecular Weight | 345.5188 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 8 / 8 |
| E/Z Centers | 1 |
| Optical Activity | UNSPECIFIED |
Himbacine is a complex piperidine alkaloid isolated from the bark of Galbulimima baccata, a species that belongs to the magnolia family. Himbacine appears to be a potent muscarinic antagonist that displays selectivity for M2 or M4 receptors, as compared to M1 or M3 receptors. Vorapaxar (SCH 530348) is a non-peptide himbacine analogue that has been developed for the reduction of thrombotic cardiovascular events in patients with a history of myocardial infarction or peripheral arterial disease. Vorapaxar is a platelet inhibitor that potently and selectively inhibits thrombin-mediated platelet activation without interfering with thrombin-mediated cleavage of fibrinogen via antagonism of the platelet proteinase-activated receptor PAR1.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1906125
Curator's Comment: Centrally administered himbacine is CNS active in animals, however, its ability to penetrate blood-brain is unclear. No human data available.
Originator
Sources: http://www.publish.csiro.au/CH/CH9560283
Curator's Comment: Himbacine was isolated from the bark of Galbulimima (Himantandra) baccata. reference retrieved from https://www.ncbi.nlm.nih.gov/pubmed/11674285
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Pharmacological comparison of the cloned human and rat M2 muscarinic receptor genes expressed in the murine fibroblast (B82) cell line. | 1998-02 |
|
| A toxin from the green mamba Dendroaspis angusticeps: amino acid sequence and selectivity for muscarinic m4 receptors. | 1994-09-19 |
|
| Binding and functional selectivity of himbacine for cloned and neuronal muscarinic receptors. | 1992-11 |
|
| Antagonist binding profiles of five cloned human muscarinic receptor subtypes. | 1991-02 |
Sample Use Guides
Daily intravitreal injections of himbacine inhibited the inducement of myopia in chick eyes in a dose- dependent manner. Doses < or = 200 ug caused no significant inhibition of induced myopia compared to controls, whilst a dose of 800 ug almost completely inhibited the induced myopia.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23649821
After treatment of primary scleral fibroblasts with varying concentrations of himbacine (0.1, 1, 10 and 100 uM), M2 transcript levels were significantly reduced in a dose-dependent manner in both mouse and human cells. This effect was more significant with himbacine in human cells than with mouse cells.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:02:00 GMT 2025
by
admin
on
Mon Mar 31 19:02:00 GMT 2025
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| Record UNII |
M17C7V122D
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| Record Status |
Validated (UNII)
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| Record Version |
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6436265
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23969
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5720
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DTXSID401027483
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m6022
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HIMBACINE
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6879-74-9
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M17C7V122D
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