Skip to Content
Merck
CN

H4904

(+)-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

Sign In to View Organizational & Contract Pricing.

Select a Size

About This Item

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

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

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

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

Gene Information

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

Looking for similar products? Visit Product Comparison Guide

Biochem/physiol Actions

Selective M2/M4 muscarinic acetylcholine receptor antagonist.

Disclaimer

Hygroscopic

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

新产品
This item has

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
091M1779V
120M1691
090M1352
050M1276
029K1502

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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
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
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
Mariappan V Chelliah et al.
Bioorganic & medicinal chemistry letters, 22(7), 2544-2549 (2012-03-13)
Discovery of a novel nor-seco himbacine analog as potent thrombin receptor (PAR-1) antagonist is described. Despite low plasma level, these new analogs showed excellent ex vivo efficacy in the monkey platelet aggregation assay. A potent hydroxy metabolite generated in vivo
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service