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(+)-Himbacine

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Muscarinic acetylcholine receptor antagonist

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

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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
Appearance	White to off-white powder.
CAS	6879-74-9
Couple Target	Acetylcholine receptor
Couple Type	Inhibitor
Formula	C₂₂H₃₅NO₂
MW	345.5
Purity	≥98%
RTECS	QL0843500
Solubility	Soluble in methanol, 100% ethanol or methylene chloride; insoluble in water.
Source	Isolated from the Australian pine Galbulimima baccata.

Use/Stability	As indicated on product label or CoA when stored as recommended.
Handling	Hygroscopic.
Long Term Storage	Ambient
Shipping	Ambient Temperature

Regulatory Status	RUO – Research Use Only

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
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)
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
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

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