Malouetine

Malouetine is an aminosteroid neuromuscular blocking agent and antinicotinic alkaloid isolated from Malouetia spp.[1]

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
3D model (JSmol)
ChemSpider
  • 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
  • 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
C27H52I2N2
Molar mass 658.536 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

The structure of malouetine inspired the development of modern aminosteroid muscle relaxants such as pancuronium bromide and vecuronium bromide by workers at Organon.[2][3][4]

References
  1. 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.
  2. 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.
  3. 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.
  4. McKenzie, A.G. (June 2000). "Prelude to pancuronium and vecuronium". Anaesthesia. 55 (6): 551–556. doi:10.1046/j.1365-2044.2000.01423.x.
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