Yuremamine

Yuremamine

Names
Other names Yuremamine
Identifiers
CAS Number	883973-98-6[1]^N
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). N verify (what is ^YN ?) 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]. The indole group shares the same structure as that of DMT, which is also found in Mimosa tenuiflora and lends it its psychoactive properties.

Originally proposed chemical structure of yuremamine

References

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.
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.
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.