Rhynchophylline

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

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 Y
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). N verify (what is YN ?) Infobox references

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

• Ibotenic acid
• Mitragynine pseudoindoxyl
• Proboscidea parviflora