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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

[H][C@]12C[C@@]3([H])CCCC[C@]3([H])[C@@H](\C=C\[C@H]4CCC[C@H](C)N4C)[C@@]1([H])[C@H](C)OC2=O

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
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

Description

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

CNS Active
3913
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

Brown, R.F.C. et al.
1
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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
 4.0 nM [Kd]
Antagonist
2778
 7.0 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Antagonist binding profiles of five cloned human muscarinic receptor subtypes.
1991 Feb
Binding and functional selectivity of himbacine for cloned and neuronal muscarinic receptors.
1992 Nov
A toxin from the green mamba Dendroaspis angusticeps: amino acid sequence and selectivity for muscarinic m4 receptors.
1994 Sep 19
Pharmacological comparison of the cloned human and rat M2 muscarinic receptor genes expressed in the murine fibroblast (B82) cell line.
1998 Feb
Patents

Patents

JP2009029820A
1
JP2011052026A
1
JP2013224334A
1

Sample Use Guides

In Vivo Use Guide
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
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 Fri Dec 15 18:05:00 UTC 2023
Edited
by admin
on Fri Dec 15 18:05:00 UTC 2023
Record UNII
M17C7V122D
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
NSC-23969
Code 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 Fri Dec 15 18:05:00 UTC 2023 , Edited by admin on Fri Dec 15 18:05:00 UTC 2023
PRIMARY
NSC
23969
Created by admin on Fri Dec 15 18:05:00 UTC 2023 , Edited by admin on Fri Dec 15 18:05:00 UTC 2023
PRIMARY
CHEBI
5720
Created by admin on Fri Dec 15 18:05:00 UTC 2023 , Edited by admin on Fri Dec 15 18:05:00 UTC 2023
PRIMARY
EPA CompTox
DTXSID401027483
Created by admin on Fri Dec 15 18:05:00 UTC 2023 , Edited by admin on Fri Dec 15 18:05:00 UTC 2023
PRIMARY
MERCK INDEX
m6022
Created by admin on Fri Dec 15 18:05:00 UTC 2023 , Edited by admin on Fri Dec 15 18:05:00 UTC 2023
PRIMARY Merck Index
WIKIPEDIA
HIMBACINE
Created by admin on Fri Dec 15 18:05:00 UTC 2023 , Edited by admin on Fri Dec 15 18:05:00 UTC 2023
PRIMARY
CAS
6879-74-9
Created by admin on Fri Dec 15 18:05:00 UTC 2023 , Edited by admin on Fri Dec 15 18:05:00 UTC 2023
PRIMARY
FDA UNII
M17C7V122D
Created by admin on Fri Dec 15 18:05:00 UTC 2023 , Edited by admin on Fri Dec 15 18:05:00 UTC 2023
PRIMARY
NIH
NCATS
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