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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

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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

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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)

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

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Certificates of Analysis (COA)

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

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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.
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
Thrombin receptor (protease activated receptor-1) antagonists as potent antithrombotic agents with strong antiplatelet effects.
Samuel Chackalamannil
Journal of medicinal chemistry, 49(18), 5389-5403 (2006-09-01)
D Doller et al.
Bioorganic & medicinal chemistry letters, 9(6), 901-906 (1999-04-17)
A parallel synthesis of racemic himbacine analogs was carried out by N-alkylation of various commercially available cyclic amine derivatives with the alkylating agent 4 which bears the tricyclic unit of himbacine. Several of these analogs have potency comparable to that
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