Rhynchophylline

Rhynchophylline
Names
	IUPAC name Methyl (7R,16E)-17-methoxy-2-oxo-16,17-didehydro-20α-corynoxan-16-carboxylate
	Systematic IUPAC name Methyl (2E)-2-[(1′R,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	76-66-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:70069;
ChEMBL	ChEMBL519266;
ChemSpider	4444758;
ECHA InfoCard	100.208.612
KEGG	C09236;
PubChem CID	3033948;
UNII	46BQ79VJ8D;
CompTox Dashboard (EPA)	DTXSID70878612 ;
	InChI 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;
	SMILES 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). verify (what is ?) Infobox references

Rhynchophylline is an alkaloid found in certain Uncaria species (Rubiaceae), notably Uncaria rhynchophylla and Uncaria tomentosa. It also occurs in the leaves of Mitragyna speciosa (kratom) and Mitragyna tubulosa, 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.

Uncaria species have had a variety of uses in traditional herbal medicine, such as for lightheadedness, convulsions, numbness, and hypertension. 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.