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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
  • 10308-44-8 N
3D model (JSmol)
  • Interactive image
ChemSpider
  • 166177198
  • 166177198
  • 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).

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 edit

  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. PMID 14285698. S2CID 71497007.
  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. PMID 10866718. S2CID 22476701.

malouetine, aminosteroid, neuromuscular, blocking, agent, antinicotinic, alkaloid, isolated, from, malouetia, names, iupac, name, dimethyl, trimethylazaniumyl, ethyl, tetradecahydro, cyclopenta, phenanthren, trimethylazanium, diiodide, identifiers, number, 103. 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 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 s1Key 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 C 27H 52I 2N 2 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 edit 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 Francaises 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 3a 17a bis quaternary ammonium 5a 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 nbsp This article about a steroid is a stub You can help Wikipedia by expanding it vte nbsp This drug article relating to the musculoskeletal system is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Malouetine amp oldid 1188988981, wikipedia, wiki, book, books, library,

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