Yuremamine

Yuremamine
Names
	Other names Yuremamine
Identifiers
3D model (JSmol)	Interactive image;
	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	476.53 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	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.^[1] However in 2015, the bioinspired total synthesis of yuremamine revealed its true structure as a flavonoid derivative.^[2] It was also noted in the original isolation of yuremamine that the alkaloid occurs naturally as a purple solid, however though total synthesis it was revealed that yuremamine as a free base is colorless, and the formation of a trifluoroacetate salt during HPLC purification led to the purple color.^[2]

Originally proposed chemical structure of yuremamine

References

↑ 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.
1 2 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: 6202-6205. doi:10.1039/c5cc00380f.

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[PlantaMedica-1] 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.

[Calvert-2] 1 2 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: 6202-6205. doi:10.1039/c5cc00380f.