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1 See also  





2 References  














Rhynchophylline






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From Wikipedia, the free encyclopedia
 


Rhynchophylline
Chemical structure of rhynchophylline
Names
IUPAC name

Methyl (7R,16E)-17-methoxy-2-oxo-16,17-didehydro-20α-corynoxan-16-carboxylate

Systematic IUPAC name

Methyl (2E)-2-[(1R,6′R,7′S,8a′S)-6′-ethyl-2-oxo-1,2,2′,3′,6′,7′,8′,8a′-octahydro-5′H-spiro[indole-3,1′-indolizin]-7′-yl]-3-methoxyprop-2-enoate

Other names
  • Rhyncophylline
  • Mitrinermin
  • Mitrinermine
  • Rhynchophyllin
  • Rhynocophylline
  • Identifiers

    CAS Number

    3D model (JSmol)

    ChEBI
    ChEMBL
    ChemSpider
    ECHA InfoCard 100.208.612 Edit this at Wikidata
    KEGG

    PubChem CID

    UNII

    CompTox Dashboard (EPA)

    • InChI=1S/C22H28N2O4/c1-4-14-12-24-10-9-22(17-7-5-6-8-18(17)23-21(22)26)19(24)11-15(14)16(13-27-2)20(25)28-3/h5-8,13-15,19H,4,9-12H2,1-3H3,(H,23,26)/b16-13+/t14-,15-,19-,22+/m0/s1

      Key: DAXYUDFNWXHGBE-KAXDATADSA-N

    • InChI=1/C22H28N2O4/c1-4-14-12-24-10-9-22(17-7-5-6-8-18(17)23-21(22)26)19(24)11-15(14)16(13-27-2)20(25)28-3/h5-8,13-15,19H,4,9-12H2,1-3H3,(H,23,26)/b16-13+/t14-,15-,19-,22+/m0/s1

      Key: DAXYUDFNWXHGBE-KAXDATADBC

    • CC[C@H]1CN2CC[C@]3([C@@H]2C[C@@H]1/C(=C\OC)/C(=O)OC)C4=CC=CC=C4NC3=O

    Properties

    Chemical formula

    C22H28N2O4
    Molar mass 384.476 g·mol−1

    Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

    ☒N verify (what is checkY☒N ?)

    Infobox references

    Rhynchophylline is an alkaloid found in certain Uncaria species (Rubiaceae), notably Uncaria rhynchophylla[1] and Uncaria tomentosa.[2] It also occurs in the leaves of Mitragyna speciosa (kratom) and Mitragyna tubulosa,[3] a tree native to Thailand. Chemically, it is related to the alkaloid mitragynine.

    Rhynchophylline is a non-competitive NMDA antagonist (IC50 = 43.2 μM) and a calcium channel blocker.[4][5]

    Uncaria species have had a variety of uses in traditional herbal medicine, such as for lightheadedness, convulsions, numbness, and hypertension.[6] These uses have been associated with the presence of rhynchophylline and have encouraged its investigation as a drug candidate for several cardiovascular and central nervous system diseases; however, few clinically relevant studies have been conducted.[6]

    See also[edit]

    References[edit]

    1. ^ Shi JS, Yu JX, Chen XP, Xu RX (2003). "Pharmacological Actions of Uncaria Alkaloids, Rhynchophylline and Isorhynchophylline" (PDF). Acta Pharmacologica Sinica. 24 (2): 97–101. PMID 12546715.
  • ^ Mohamed AF, Matsumoto K, Tabata K, Takayama H, Kitajima M, Watanabe H (2000). "Effects of Uncaria tomentosa Total Alkaloid and its Components on Experimental Amnesia in Mice: Elucidation Using the Passive Avoidance Test". Journal of Pharmacy and Pharmacology. 52 (12): 1553–1561. doi:10.1211/0022357001777612. PMID 11197086. S2CID 40280160.
  • ^ "Mitragyna Speciosa (Kratom) - World Roots".
  • ^ Kang TH, Murakami Y, Matsumoto K, Takayama H, Kitajima M, Aimi N, Watanabe H (2002). "Rhynchophylline and Isorhynchophylline Inhibit NMDA Receptors Expressed in Xenopus Oocytes". European Journal of Pharmacology. 455 (1): 27–34. doi:10.1016/S0014-2999(02)02581-5. PMID 12433591.
  • ^ Kang TH, Murakami Y, Takayama H, Kitajima M, Aimi N, Watanabe H, Matsumoto K (2004). "Protective Effect of Rhynchophylline and Isorhynchophylline on in vitro Ischemia-Induced Neuronal Damage in the Hippocampus: Putative Neurotransmitter Receptors Involved in their Action". Life Sciences. 76 (3): 331–343. doi:10.1016/j.lfs.2004.08.012. PMID 15531384.
  • ^ a b Zhou J, Zhou S (2010). "Antihypertensive and neuroprotective activities of rhynchophylline: the role of rhynchophylline in neurotransmission and ion channel activity". Journal of Ethnopharmacology. 132 (1): 15–27. doi:10.1016/j.jep.2010.08.041. PMID 20736055.

  • Retrieved from "https://en.wikipedia.org/w/index.php?title=Rhynchophylline&oldid=1223592242"

    Categories: 
    Alkaloids
    Calcium channel blockers
    NMDA receptor antagonists
    Spiro compounds
    Methyl esters
    Ethers
    Oxindoles
    Hidden categories: 
    ECHA InfoCard ID from Wikidata
    Articles containing unverified chemical infoboxes
    Chembox image size set
    Articles with short description
    Short description matches Wikidata
     



    This page was last edited on 13 May 2024, at 04:15 (UTC).

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