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Yuremamine
Sign in to saveYuremamine 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. However, in 2015, the bioinspired total synthesis of yuremamine revealed its structure to be a flavonoid derivative. 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 wha
Chemical data
- Formula
- C27H28N2O6
- Molecular weight
- 476.5 g/mol
- IUPAC name
- 5-[(2S,3R,4S)-4-[3-[2-(dimethylamino)ethyl]-1H-indol-2-yl]-3,7-dihydroxy-3,4-dihydro-2H-chromen-2-yl]benzene-1,2,3-triol
- SMILES
- CN(C)CCC1=C(NC2=CC=CC=C21)[C@H]3[C@H]([C@@H](OC4=C3C=CC(=C4)O)C5=CC(=C(C(=C5)O)O)O)O
- InChIKey
- KXDXQDYTLNRCHP-RNJDCESWSA-N
- XLogP
- 3.3
- Polar surface area
- 129 Ų
- H-bond donors
- 6
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- alkaloid
- Mass
- 476.194736616
Show 4 more facts
- chemical formula
- C₂₇H₂₈N₂O₆
- found in taxon
- Mimosa tenuiflora
- isomeric SMILES
- CN(C)CCc1c([C@@H]2c3ccc(O)cc3O[C@@H](c3cc(O)c(O)c(O)c3)[C@@H]2O)[nH]c2ccccc12
- canonical SMILES
- OC1=CC=C2C(OC(C3=CC(O)=C(O)C(O)=C3)C(O)C2C=4NC=5C=CC=CC5C4CCN(C)C)=C1
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Encyclopedic overview
1 sectionsContents
- 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. However, in 2015, the bioinspired total synthesis of yuremamine revealed its structure to be a flavonoid derivative. 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.. The indole group shares the same structure as that of DMT, which is also found in Mimosa tenuiflora and lends it its psychoactive properties. thumb|left|class=skin-invert-image|Originally proposed chemical structure of yuremamine
==References==
Excerpted from Wikipedia’s “Yuremamine” article, available under the CC BY-SA 4.0 licence.