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H4904

Sigma-Aldrich

(+)-Himbacine

~98% (GC), powder, muscarinic receptor antagonist

Synonym(s):

(3S,3aR,4R,4aS,8aR,9aS)-4-[(1E)-2-[(2R,6S)-1,6-dimethyl-2-piperdinyl]ethenyl]decahydro-3-methyl-naphtho[2,3-c]furan-1(3H)-one

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About This Item

Empirical Formula (Hill Notation):
C22H35NO2
CAS Number:
6879-74-9
Molecular Weight:
345.52
MDL number:
MFCD00274559
UNSPSC Code:
12352200
PubChem Substance ID:
24895661

assay

~98% (GC)

form

powder

optical activity

[α]/D +51.4°, c = 1.01 in chloroform(lit.)

color

off-white

solubility

ethanol: 50 mg/mL
H2O: insoluble

SMILES string

[H][C@]12CCCC[C@]1([H])[C@@H](\C=C\[C@@H]3CCC[C@@H](C)N3C)[C@@]4([H])[C@H](C)OC(=O)[C@@]4([H])C2

Gene Information

rat ... Chrm1(25229) , Chrm2(81645)

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Biochem/physiol Actions

Selective M2/M4 muscarinic acetylcholine receptor antagonist.

Caution

Hygroscopic

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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J H Miller et al.
The Journal of pharmacology and experimental therapeutics, 263(2), 663-667 (1992-11-01)
The binding potencies for the putative M2-selective antagonist himbacine were determined in radioligand binding and in functional response assays in neuronal tissue and Chinese hamster ovary cells containing transfected muscarinic receptors. Himbacine was shown to bind to all five cloned
Mariappan V Chelliah et al.
Journal of medicinal chemistry, 50(21), 5147-5160 (2007-09-15)
Pursuing our earlier efforts in the himbacine-based thrombin receptor antagonist area, we have synthesized a series of compounds that incorporate heteroatoms in the C-ring of the tricyclic motif. This effort has resulted in the identification of several potent heterocyclic analogs
Samuel Chackalamannil et al.
Journal of medicinal chemistry, 48(19), 5884-5887 (2005-09-16)
Structurally novel thrombin receptor (protease activated receptor 1, PAR-1) antagonists based on the natural product himbacine are described. The prototypical PAR-1 antagonist 55 showed a Ki of 2.7 nM in the binding assay, making it the most potent PAR-1 antagonist
Michaela Bitzer et al.
Experimental eye research, 82(3), 379-388 (2005-09-07)
Muscarinic antagonists, particularly atropine, can inhibit myopia development in several animal models and also in children. However, the biochemical basis of the inhibition of axial eye growth remains obscure, and there are doubts whether muscarinic receptors are involved at all.
Yoshito Takahashi et al.
Brain research, 1339, 26-40 (2010-04-14)
Cholinergic modulation of spontaneous GABAergic currents (mIPSC) was studied using whole-cell patch methods in mouse accessory olfactory bulb slices. Carbachol (above 100 microM) administration produced an increase in the mIPSC frequency in mitral cells, but did not affect the responses
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