Rhynchophylline

Drugbox
IUPAC_name = methyl (E)-​2-​ [(3R,6'R,7'S,8'aS)-​6'-​ethyl-​2-​oxospiro [1H-​indole-​3,1'-​3,5,6,7,8,8a-​hexahydro-​2H-​indolizine] -​7'-​yl] -​3-​methoxyprop-​2-​enoate

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width= 250
CAS_number= 76-66-4
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PubChem= 3033948
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C=22 | H=28 | N=2 | O=4
molecular_weight = 384.46872 g/mol
smiles = CC [C@H] 1CN2CC [C@] 3( [C@@H] 2C [C@@H] 1/C(=COC)/C(=O)OC)C4=CC=CC=C4NC3=O
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Rhynchophylline is an alkaloid found in certain "Uncaria" species, notably "Uncaria rhynchophylla" [Shi JS, Yu JX, Chen XP, Xu RX. Pharmacological actions of Uncaria alkaloids, rhynchophylline and isorhynchophylline. "Acta Pharmacologica Sinica". 2003 Feb;24(2):97-101. PMID 12546715] and "Uncaria tomentosa". [Mohamed AF, Matsumoto K, Tabata K, Takayama H, Kitajima M, Watanabe H. 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". 2000 Dec;52(12):1553-61. PMID 11197086] It is a non-competitive NMDA antagonist and calcium channel blocker [ Kang TH, Murakami Y, Matsumoto K, Takayama H, Kitajima M, Aimi N, Watanabe H.Rhynchophylline and isorhynchophylline inhibit NMDA receptors expressed in Xenopus oocytes. "Eur J Pharmacol". 2002 Nov 22;455(1):27-34.] [Kang TH, Murakami Y, Takayama H, Kitajima M, Aimi N, Watanabe H, Matsumoto K. Protective effect of rhynchophylline and isorhynchophylline on in vitro ischemia-induced neuronal damage in the hippocampus: putative neurotransmitter receptors involved in their action. "Life Sci". 2004 Dec 3;76(3):331-43.]

References