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Malouetine

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Malouetine
Names

IUPAC name [(3S,5S,8R,9S,10S,13S,14S)-10,13-Dimethyl-17-[(1S)-1-(trimethylazaniumyl)ethyl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]-trimethylazanium diiodide
Identifiers
CAS Number	10308-44-8^N
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../s1 Key: ZKPCQHGEQUQGJK-DMZQXVSVSA-L
SMILES C[C@@H]([C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(CC[C@@H](C4)[N+](C)(C)C)C)C)[N+](C)(C)C.[I-].[I-]
Properties
Chemical formula	C₂₇H₅₂I₂N₂
Molar mass	658.536 g·mol⁻¹
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

Malouetine is anaminosteroid neuromuscular blocking agent andantinicotinic alkaloid isolated fromMalouetia spp.^[1]

The structure of malouetine inspired the development of modern aminosteroid muscle relaxants such aspancuronium bromide andvecuronium bromide by workers atOrganon.^[2]^[3]^[4]

^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.