Convolutindole A

Convolutindole A
File:Convolutindole A.svg
IUPAC name 2,4,6-tribromo-1,7-dimethoxy-N,N-dimethyltryptamine
style="background: #F8EABA; text-align: center;" colspan="2" | Properties
Molecular formula	C14H17Br3N2O2
Melting point	61.5-62.5 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Convolutindole A (2,4,6-tribromo-1,7-dimethoxy-N,N-dimethyltryptamine) is a brominated indole alkaloid that was first identified in 2001 in Amathia convoluta, a marine bryozoan. Bryozoans are aquatic invertebrates that grow in colonies and superficially resemble corals.

Chemistry

Convolutamine A is the 2,4,6-tribromo-1,7-dimethoxy analog of DMT, a hallucinogen that occurs naturally in many plants and animals. Other brominated derivatives of DMT include 5-bromo-DMT and 5,6-dibromo-DMT, both of which also occur in marine invertebrates.

The researchers who discovered the chemical drew specific attention to the methoxy group at the indole 1-position (attached to the nitrogen atom in the pentagonal ring) as being an unknown occurrence in the marine world until recently. 1-methoxyindoles also occur in the Brassicaceae, the plant family that cabbage and mustard belong to.

Biological activity

The chemical was tested for its ability to kill nematodes, a type of parasitic worm. It was found to be more effective in this regard than levamisole, a commercial drug used to kill parasitic worms (and in the treatment of colon cancer).

References

• 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. et al., (2002). Convolutindole A and Convolutamine H, New Nematocidal Brominated Alkaloids from the Marine Bryozoan Amathia convoluta. Journal of Natural Products 65(6) pp 938–941.