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Merck
CN

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

Key Documents

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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.

Disclaimer

Hygroscopic

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

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

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F Dörje et al.
The Journal of pharmacology and experimental therapeutics, 256(2), 727-733 (1991-02-01)
A variety of muscarinic antagonists are currently used as tools to pharmacologically subclassify muscarinic receptors into M1, M2 and M3 subtypes. In the present study, we have determined the affinity profiles of several of these antagonists at five cloned human
A Sagrada et al.
Life sciences, 54(17), PL305-PL310 (1994-01-01)
This study describes the antagonistic properties of himbacine, in comparison with those of pirenzepine, at muscarinic receptors mediating the depolarization of rat superior cervical ganglion, the inhibition of electrically-induced twitch contractions of rabbit vas deferens and the contraction of dog
Yan Xia et al.
Bioorganic & medicinal chemistry letters, 16(18), 4969-4972 (2006-07-11)
The structure-activity relationship (SAR) of the lactone ring of himbacine derived thrombin receptor (PAR-1) antagonists (e.g., 2-5) is described. The effect of the lactone carbonyl group on binding to PAR-1 is dependent on the substitution pattern of the pyridine ring.
Satin Salehi et al.
Journal of natural medicines, 63(1), 1-8 (2008-08-13)
Hawthorn (Crataegus spp.) plant extract is used as a herbal alternative medicine for the prevention and treatment of various cardiovascular diseases. Recently, it was shown that hawthorn extract preparations caused negative chronotropic effects in a cultured neonatal murine cardiomyocyte assay
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
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