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(+)-Himbacine

Muscarinic acetylcholine receptor antagonist



ALX-550-061-M001	1 mg	85.00 USD

ALX-550-061-M005	5 mg	362.00 USD
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Replaces Prod. #: BML-C116

Potent muscarinic antagonist that displays selectivity for the M2 or M4 receptors.

Product Details

Alternative Name:	(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

Formula:	C₂₂H₃₅NO₂

MW:	345.5

Source:	Isolated from the Australian pine Galbulimima baccata.

CAS:	6879-74-9

RTECS:	QL0843500

Purity:	≥98%

Appearance:	White to off-white powder.

Solubility:	Soluble in methanol, 100% ethanol or methylene chloride; insoluble in water.

Shipping:	Ambient

Long Term Storage:	Ambient

Handling:	Hygroscopic.

Regulatory Status:	RUO - Research Use Only

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Product Literature References

Himbacine analogs as muscarinic receptor antagonists--effects of tether and heterocyclic variations: S. Chackalamannil, et al.; Bioorg. Med. Chem. Lett. 14, 3967 (2004), Abstract;

Design, synthesis, and structure-activity relationship studies of himbacine derived muscarinic receptor antagonists: D. Doller, et al.; Bioorg. Med. Chem. Lett. 9, 901 (1999), Abstract;

Characterization of muscarinic receptors mediating contractions of circular and longitudinal muscle of human isolated colon: P.M. Kerr, et al.; Br. J. Pharmacol. 115, 1518 (1995), Abstract;

Chemical modification of ring C of himbacine: discovery of a pharmacophoric element for M2-selectivity: M.J. Malaska, et al.; Bioorg. Med. Chem. Lett. 5, 61 (1995),

Total Syntheses of (+)-Himbacine and (+)-Himbeline: D.J. Hart, et al.; JACS 117, 9369 (1995),

Simplified analogs of himbacine displaying potent binding affinity for muscarinic receptors: M.J. Malaska, et al.; Bioorg. Med. Chem. Lett. 3, 1247 (1993),

Binding and functional selectivity of himbacine for cloned and neuronal muscarinic receptors: J.H. Miller, et al.; Pharmacol. Exp. Ther. 263, 663 (1992), Abstract;

Structural basis of the subtype selectivity of muscarinic antagonists: a study with chimeric m2/m5 muscarinic receptors: J. Wess, et al.; Mol. Pharmacol. 41, 369 (1992), Abstract;