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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
Structure of HIMBACINE

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

HIDE SMILES / InChI
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

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

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

PubMed

TitleDatePubMed
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
Patents

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
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.
Name Type Language
NSC-23969
Preferred Name English
HIMBACINE
MI  
Common Name English
(3S,3AR,4R,4AS,8AR,9AS)-4-((1E)-2-((2R,6S)-1,6-DIMETHYL-2-PIPERIDINYL)ETHENYL)DECAHYDRO-3-METHYLNAPHTHO(2,3-C)FURAN-1(3H)-ONE
Systematic Name English
NAPHTHO(2,3-C)FURAN-1(3H)-ONE, 4-((1E)-2-((2R,6S)-1,6-DIMETHYL-2-PIPERIDINYL)ETHENYL)DECAHYDRO-3-METHYL-, (3S,3AR,4R,4AS,8AR,9AS)-
Systematic Name English
HIMBACIN
Common Name English
(+)-HIMBACINE
Common Name English
HIMBACINE [MI]
Common Name English
Code System Code Type Description
PUBCHEM
6436265
Created by admin on Mon Mar 31 19:02:00 GMT 2025 , Edited by admin on Mon Mar 31 19:02:00 GMT 2025
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NSC
23969
Created by admin on Mon Mar 31 19:02:00 GMT 2025 , Edited by admin on Mon Mar 31 19:02:00 GMT 2025
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CHEBI
5720
Created by admin on Mon Mar 31 19:02:00 GMT 2025 , Edited by admin on Mon Mar 31 19:02:00 GMT 2025
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EPA CompTox
DTXSID401027483
Created by admin on Mon Mar 31 19:02:00 GMT 2025 , Edited by admin on Mon Mar 31 19:02:00 GMT 2025
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MERCK INDEX
m6022
Created by admin on Mon Mar 31 19:02:00 GMT 2025 , Edited by admin on Mon Mar 31 19:02:00 GMT 2025
PRIMARY Merck Index
WIKIPEDIA
HIMBACINE
Created by admin on Mon Mar 31 19:02:00 GMT 2025 , Edited by admin on Mon Mar 31 19:02:00 GMT 2025
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CAS
6879-74-9
Created by admin on Mon Mar 31 19:02:00 GMT 2025 , Edited by admin on Mon Mar 31 19:02:00 GMT 2025
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FDA UNII
M17C7V122D
Created by admin on Mon Mar 31 19:02:00 GMT 2025 , Edited by admin on Mon Mar 31 19:02:00 GMT 2025
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