Convolutindole A

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Convolutindole A
Convolutindole A.svg
Ball-and-stick model of convolutindole A
Names
IUPAC name
2,4,6-Tribromo-1,7-dimethoxy-N,N-dimethyltryptamine
Identifiers
3D model (JSmol)
ChemSpider
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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Infobox references

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[edit]

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[edit]

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[edit]

  • Narkowicz, C. K.; Blackman, A. J., (June 2001). Abstracts of Papers; 10th International Symposium on Marine Natural Products: Nago, Okinawa, Abstract OR1.
  • Narkowicz, C. K.; Blackman, A. J.; Lacey, E.; Gill, J. H.; Heiland, K. (2002). "Convolutindole a and Convolutamine H, New Nematocidal Brominated Alkaloids from the Marine BryozoanAmathia convoluta". Journal of Natural Products. 65 (6): 938–941. doi:10.1021/np010574x. PMID 12088445.