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Convolutindole A

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 corals.

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 plants of the bean and mustard families.

Biological activity

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

References

References

  1. (2010). "Bryozoans". Ecology and Classification of North American Freshwater Invertebrates.
  2. (October 2023). "Synthetic studies toward the marine alkaloid convolutindole A, a structurally remarkable derivative of the hallucinogen N,N-Dimethyltryptamine (DMT)". Tetrahedron Letters.
  3. (May 2002). "Convolutindole A and Convolutamine H, New Nematocidal Brominated Alkaloids from the Marine Bryozoan Amathia convoluta". Journal of Natural Products.
  4. Narkowicz, C. K.; Blackman, A. J., (June 2001). ''Abstracts of Papers''; 10th International Symposium on Marine Natural Products: Nago, Okinawa, Abstract OR1.
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bromoarenes n,n-dialkyltryptamines halogen-containing-alkaloids hydroxylamines indole-ethers-at-the-benzene-ring tryptamine-alkaloids
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