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3D model (JSmol)
PubChem CID
  • 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
  • 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
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).
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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 Yuremamine.png
Originally proposed chemical structure of yuremamine

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<i>Mimosa tenuiflora</i> Species of plant

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Voacangine Chemical compound

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7-Hydroxymitragynine Chemical compound

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Yuehchukene Chemical compound

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Pericine Chemical compound

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Indole Organic compound with an intense fecal odor

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Substituted tryptamine Class of indoles

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Gelsemine Chemical compound

Gelsemine (C20H22N2O2) is an indole alkaloid isolated from flowering plants of the genus Gelsemium, a plant native to the subtropical and tropical Americas, and southeast Asia, and is a highly toxic compound that acts as a paralytic, exposure to which can result in death. It has generally potent activity as an agonist of the mammalian glycine receptor, the activation of which leads to an inhibitory postsynaptic potential in neurons following chloride ion influx, and systemically, to muscle relaxation of varying intensity and deleterious effect. Despite its danger and toxicity, recent pharmacological research has suggested that the biological activities of this compound may offer opportunities for developing treatments related to xenobiotic or diet-induced oxidative stress, and of anxiety and other conditions, with ongoing research including attempts to identify safer derivatives and analogs to make use of gelsemine's beneficial effects.

Akuammicine Alkaloid

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Affinine Chemical compound

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Affinisine Chemical compound

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Apparicine Chemical compound

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Tabernaemontanine Chemical compound

Tabernaemontanine is a naturally occurring monoterpene indole alkaloid found in several species in the genus Tabernaemontana including Tabernaemontana divaricata.

Dregamine Chemical compound

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Conophylline Chemical compound

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Vobasine Chemical compound

Vobasine is a naturally occurring monoterpene indole alkaloid found in several species in the genus Tabernaemontana including Tabernaemontana divaricata.


  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.
  3. 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 (28): 6202–6205. doi:10.1039/c5cc00380f. PMID   25756921.