Convolutindole A
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| Names | |
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| Preferred IUPAC name
N,N-Dimethyl-2-(2,4,6-tribromo-1,7-dimethoxy-1H-indol-3-yl)ethan-1-amine | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| 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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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
[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.[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
[edit]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
[edit]- 1 2 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.
- ↑ Wood TS (2010). "Bryozoans". Ecology and Classification of North American Freshwater Invertebrates: 437–454. doi:10.1016/B978-0-12-374855-3.00013-3.
- 1 2 3 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.
- ↑ Narkowicz, C. K.; Blackman, A. J., (June 2001). Abstracts of Papers; 10th International Symposium on Marine Natural Products: Nago, Okinawa, Abstract OR1.