Malouetine - Misplaced Pages

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Malouetine
Names

IUPAC name -2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopentaphenanthren-3-yl]-trimethylazanium diiodide
Identifiers
CAS Number	10308-44-8
3D model (JSmol)	Interactive image
ChemSpider	166177198
PubChem CID	166177198
InChI InChI=1S/C27H52N2.2HI/c1-19(28(4,5)6)23-12-13-24-22-11-10-20-18-21(29(7,8)9)14-16-26(20,2)25(22)15-17-27(23,24)3;;/h19-25H,10-18H2,1-9H3;2*1H/q+2;;/p-2/t19-,20-,21-,22-,23+,24-,25-,26-,27+;;/m0../s1Key: ZKPCQHGEQUQGJK-DMZQXVSVSA-L
SMILES C(1CC21(CC32CC43(CC(C4)(C)(C)C)C)C)(C)(C)C..
Properties
Chemical formula	C₂₇H₅₂I₂N₂
Molar mass	658.536 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Chemical compound

Malouetine is an aminosteroid neuromuscular blocking agent and antinicotinic alkaloid isolated from Malouetia spp.

The structure of malouetine inspired the development of modern aminosteroid muscle relaxants such as pancuronium bromide and vecuronium bromide by workers at Organon.

References

Janot MM; Laine F; Goutarel R (1960). "Steroid alkaloids. V. Alkaloids of Malouetia bequaertiana e. Woodson (Apocynaceae): Funtuphyllamine B and malouetine. Preliminary communication". Annales Pharmaceutiques Françaises. 18: 673–677. PMID 13789457.
Alauddin, M.; Caddy, B.; Lewis, J.J.; Martin-Smith, M.; Sugrue, M.F. (January 1965). "Non-depolarising neuromuscular blockade by 3α,17α-bis(quaternary ammonium) 5α-androstanes". Journal of Pharmacy and Pharmacology. 17 (1): 55–59. doi:10.1111/j.2042-7158.1965.tb07569.x. PMID 14285698. S2CID 71497007.
Buckett, W.R.; Hewett, C.L.; Savage, D.S. (October 1973). "Pancuronium bromide and other steroidal neuromuscular blocking agents containing acetylcholine fragments". Journal of Medicinal Chemistry. 16 (10): 1116–24. doi:10.1021/jm00268a011. PMID 4356139.
McKenzie, A.G. (June 2000). "Prelude to pancuronium and vecuronium". Anaesthesia. 55 (6): 551–556. doi:10.1046/j.1365-2044.2000.01423.x. PMID 10866718. S2CID 22476701.

nAChRsTooltip Nicotinic acetylcholine receptors

Agonists
(and PAMsTooltip positive allosteric modulators)

Antagonists
(and NAMsTooltip negative allosteric modulators)

See also: Receptor/signaling modulators; Muscarinic acetylcholine receptor modulators; Acetylcholine metabolism/transport modulators

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