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Convolutindole A
Convolutindole A.svg
Ball-and-stick model of convolutindole A
Names
Preferred IUPAC name
N,N-Dimethyl-2-(2,4,6-tribromo-1,7-dimethoxy-1H-indol-3-yl)ethan-1-amine
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C14H17Br3N2O2/c1-18(2)6-5-8-11-9(15)7-10(16)13(20-3)12(11)19(21-4)14(8)17/h7H,5-6H2,1-4H3 ☒N
    Key: KPTXBOJWIDAMOS-UHFFFAOYSA-N ☒N
  • CN(C)CCc2c1c(c(OC)c(Br)cc1Br)n(OC)c2Br
Properties
C14H17Br3N2O2
Molar mass 485.014 g·mol−1
Melting point 61.5 to 62.5 °C (142.7 to 144.5 °F; 334.6 to 335.6 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Convolutindole A (2,4,6-tribromo-1,7-dimethoxy-N,N-dimethyltryptamine) is a brominated tryptamine alkaloid that was first identified in 2001 in Amathia convoluta, a marine bryozoan. Bryozoans are aquatic invertebrates that grow in colonies and may resemble coral.

Chemistry

Convolutamine A is the 2,4,6-tribromo-1,7-dimethoxy derivative of DMT, a hallucinogen that occurs naturally in many plants and animals. Convolutamine A is chemically related to 5-bromo-DMT which also occurs in many marine invertebrates.

Until the discovery of convolutindole A, the 1-methoxyindole moiety was unknown in the marine world. 1-Methoxyindoles, such as lespedamine, were previously only known to occur in legumes and the Brassicaceae, the plant family that cabbage and mustard belong to.

Biological activity

This chemical was tested for its ability to kill parasitic nematodes. It was found to be more effective than levamisole,[medical citation needed] a synthetic drug used to kill parasitic worms and to treat colon cancer.

References