Mitraphylline

Mitraphylline
	Mitraphylline
Names
	IUPAC name Methyl 19α-methyl-2-oxoformosanan-16-carboxylate
	Systematic IUPAC name Methyl (1′S,3R,4′aS,5′aS,10′aR)-1′-methyl-2-oxo-1,2,4′a,5′,5′a,7′,8′,10′a-octahydro-1′H,10′H-spiro[indole-3,6′-pyrano[3,4-f]indolizine]-4′-carboxylate
Identifiers
CAS Number	509-80-8 ;
3D model (JSmol)	Interactive image ;
ChEMBL	ChEMBL2135897 ;
ChemSpider	84977 ;
ECHA InfoCard	100.007.370
EC Number	208-106-0;
KEGG	C09227 ;
PubChem CID	94160 ;
UNII	1H9SRL2456 ;
CompTox Dashboard (EPA)	DTXSID50198926 ;
	InChI InChI=1S/C21H24N2O4/c1-12-14-10-23-8-7-21(16-5-3-4-6-17(16)22-20(21)25)18(23)9-13(14)15(11-27-12)19(24)26-2/h3-6,11-14,18H,7-10H2,1-2H3,(H,22,25)/t12-,13-,14+,18-,21+/m0/s1 Key: JMIAZDVHNCCPDM-DAFCLMLCSA-N ;
	SMILES C[C@H]1[C@H]2CN3CC[C@]4([C@@H]3C[C@@H]2C(=CO1)C(=O)OC)C5=CC=CC=C5NC4=O;
Properties
Chemical formula	C21H24N2O4
Molar mass	368.1736 g/mol
	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

Last updated December 29, 2025

Mitraphylline, an oxindole derivative, is an active alkaloid in the leaves of the tree Mitragyna speciosa , commonly known as kratom.^[1] As a non-narcotic constituent, it also occurs in the bark of Uncaria tomentosa (cat's claw) along with isomeric alkaloids.^[2]

References

↑ Manda, Vamshi; Avula, Bharathi; Ali, Zulfiqar; Khan, Ikhlas; Walker, Larry; Khan, Shabana (May 2014). "Evaluation of In Vitro Absorption, Distribution, Metabolism, and Excretion (ADME) Properties of Mitragynine, 7-Hydroxymitragynine, and Mitraphylline". Planta Medica. 80 (7): 568–576. Bibcode:2014PlMed..80..568M. doi:10.1055/s-0034-1368444. ISSN 0032-0943. PMID 24841968.
↑ Stuppner, H.; Sturm, S.; Konwalinka, G. (December 1992). "HPLC analysis of the main oxindole alkaloids from Uncaria tomentosa". Chromatographia. 34 (11–12): 597–600. doi:10.1007/BF02269869. ISSN 0009-5893. S2CID 95048480.

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[1] Manda, Vamshi; Avula, Bharathi; Ali, Zulfiqar; Khan, Ikhlas; Walker, Larry; Khan, Shabana (May 2014). "Evaluation of In Vitro Absorption, Distribution, Metabolism, and Excretion (ADME) Properties of Mitragynine, 7-Hydroxymitragynine, and Mitraphylline". Planta Medica. 80 (7): 568–576. Bibcode:2014PlMed..80..568M. doi:10.1055/s-0034-1368444. ISSN 0032-0943. PMID 24841968.

[2] Stuppner, H.; Sturm, S.; Konwalinka, G. (December 1992). "HPLC analysis of the main oxindole alkaloids from Uncaria tomentosa". Chromatographia. 34 (11–12): 597–600. doi:10.1007/BF02269869. ISSN 0009-5893. S2CID 95048480.

[1]

[2]

Names
Mitraphylline
IUPAC name Methyl 19α-methyl-2-oxoformosanan-16-carboxylate
Systematic IUPAC name Methyl (1′S,3R,4′aS,5′aS,10′aR)-1′-methyl-2-oxo-1,2,4′a,5′,5′a,7′,8′,10′a-octahydro-1′H,10′H-spiro[indole-3,6′-pyrano[3,4-f]indolizine]-4′-carboxylate
Identifiers
CAS Number	509-80-8 ^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL2135897 ^N
ChemSpider	84977 ^N
ECHA InfoCard	100.007.370
EC Number	208-106-0
KEGG	C09227 ^N
PubChem CID	94160
UNII	1H9SRL2456 ^N
CompTox Dashboard (EPA)	DTXSID50198926
InChI InChI=1S/C21H24N2O4/c1-12-14-10-23-8-7-21(16-5-3-4-6-17(16)22-20(21)25)18(23)9-13(14)15(11-27-12)19(24)26-2/h3-6,11-14,18H,7-10H2,1-2H3,(H,22,25)/t12-,13-,14+,18-,21+/m0/s1^N Key: JMIAZDVHNCCPDM-DAFCLMLCSA-N^N
SMILES C[C@H]1[C@H]2CN3CC[C@]4([C@@H]3C[C@@H]2C(=CO1)C(=O)OC)C5=CC=CC=C5NC4=O
Properties
Chemical formula	C₂₁H₂₄N₂O₄
Molar mass	368.1736 g/mol
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