Convolutindole A
Convolutindole A | |
---|---|
File:Convolutindole A.svg | |
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
This article's citation style may be unclear. The references used may be made clearer with a different or consistent style of citation, footnoting, or external linking. (September 2007) |
- 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.
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- Natural tryptamine alkaloids
- Halogen-containing alkaloids
- Organobromides
- Phenol ethers