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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.[1] Bryozoans are aquatic invertebrates that grow in colonies and may resemble corals.[2]

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.[1] Convolutamine A is chemically related to 5-bromo-DMT which also occurs in many marine invertebrates.[3]

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.[3][4]

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.[3]

References

  1. ^ a b Ichikawa K, Neville JC, Yu Y, Sperry J (October 2023). “Synthetic studies toward the marine alkaloid convolutindole A, a structurally remarkable derivative of the hallucinogen N,N-Dimethyltryptamine (DMT)”. Tetrahedron Letters. 129 154756. doi:10.1016/j.tetlet.2023.154756. ISSN 0040-4039.
  2. ^ Wood TS (2010). “Bryozoans”. Ecology and Classification of North American Freshwater Invertebrates: 437–454. doi:10.1016/B978-0-12-374855-3.00013-3.
  3. ^ a b c Narkowicz CK, Blackman AJ, Lacey E, Gill JH, Heiland K (May 2002). “Convolutindole A and Convolutamine H, New Nematocidal Brominated Alkaloids from the Marine Bryozoan Amathia convoluta”. Journal of Natural Products. 65 (6): 938–941. doi:10.1021/np010574x. ISSN 0163-3864. PMID 12088445.
  4. ^ Narkowicz, C. K.; Blackman, A. J., (June 2001). Abstracts of Papers; 10th International Symposium on Marine Natural Products: Nago, Okinawa, Abstract OR1.