Yuremamine

Yuremamine
Names
	Other names Yuremamine
Identifiers
CAS Number	883973-98-6 ;
3D model (JSmol)	Interactive image;
ChemSpider	62702341;
PubChem CID	122386737;
	InChI InChI=1S/C27H28N2O6/c1-29(2)10-9-17-16-5-3-4-6-19(16)28-24(17)23-18-8-7-15(30)13-22(18)35-27(26(23)34)14-11-20(31)25(33)21(32)12-14/h3-8,11-13,23,26-28,30-34H,9-10H2,1-2H3/t23-,26+,27-/m0/s1 Key: KXDXQDYTLNRCHP-RNJDCESWSA-N;
	SMILES CN(C)CCC1=C(NC2=CC=CC=C12)[C@@H]1[C@H](O)[C@H](OC2=C1C=CC(O)=C2)C1=CC=CC=C1;
Properties
Chemical formula	C27H28N2O6
Molar mass	476.529 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

Yuremamine is a phytoindole alkaloid which was isolated from the bark of Mimosa tenuiflora in 2005, and erroneously assigned a pyrrolo[1,2-a]indole structure that was thought to represent a new class of indole alkaloids.^[2] However, in 2015, the bioinspired total synthesis of yuremamine revealed its structure to be a flavonoid derivative.^[3] It was also noted in the original isolation of yuremamine that the alkaloid occurs naturally as a purple solid, but total synthesis revealed that yuremamine as a free base is colorless, and the formation of a trifluoroacetate salt during HPLC purification is what led to the purple appearance.^[3]

Originally proposed chemical structure of yuremamine

References

^ Buckingham, John; Baggaley, Keith H.; Roberts, Andrew D.; Szabo, Laszlo F. (26 January 2010). Dictionary of Alkaloids with CD-ROM. CRC Press. p. 2033. ISBN 978-1-4200-7770-4.
^ Vepsäläinen, J. J.; Auriola, S.; Tukiainen, M.; Ropponen, N. & Callaway, J. (2005). "Isolation and characterization of Yuremamine, a new phytoindole". Planta Medica. 71 (11): 1049–1053. doi:10.1055/s-2005-873131. PMID 16320208. S2CID 260250347.
^ ^a ^b Calvert, Matthew B.; Sperry, Jonathan (2015). "Bioinspired total synthesis and structural revision of yuremamine, an alkaloid from the entheogenic plant Mimosa tenuiflora". Chemical Communications. 51 (28): 6202–6205. doi:10.1039/c5cc00380f. PMID 25756921.

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[1] Buckingham, John; Baggaley, Keith H.; Roberts, Andrew D.; Szabo, Laszlo F. (26 January 2010). Dictionary of Alkaloids with CD-ROM. CRC Press. p. 2033. ISBN 978-1-4200-7770-4.

[PlantaMedica-2] Vepsäläinen, J. J.; Auriola, S.; Tukiainen, M.; Ropponen, N. & Callaway, J. (2005). "Isolation and characterization of Yuremamine, a new phytoindole". Planta Medica. 71 (11): 1049–1053. doi:10.1055/s-2005-873131. PMID 16320208. S2CID 260250347.

[Calvert-3] Calvert, Matthew B.; Sperry, Jonathan (2015). "Bioinspired total synthesis and structural revision of yuremamine, an alkaloid from the entheogenic plant Mimosa tenuiflora". Chemical Communications. 51 (28): 6202–6205. doi:10.1039/c5cc00380f. PMID 25756921.

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