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 coral.

Convolutindole A

Names
IUPAC name 2,4,6-Tribromo-1,7-dimethoxy-N,N-dimethyltryptamine
Identifiers
CAS Number	443356-86-3^Y
3D model (JSmol)	Interactive image
ChemSpider	4481610^N
PubChem CID	5324072
CompTox Dashboard (EPA)	DTXSID50415867
InChI InChI=1S/C14H17Br3N2O2/c1-18(2)6-5-8-11-9(15)7-10(16)13(20-3)12(11)19(21-4)14(8)17/h7H,5-6H2,1-4H3^N Key: KPTXBOJWIDAMOS-UHFFFAOYSA-N^N InChI=1/C14H17Br3N2O2/c1-18(2)6-5-8-11-9(15)7-10(16)13(20-3)12(11)19(21-4)14(8)17/h7H,5-6H2,1-4H3 Key: KPTXBOJWIDAMOS-UHFFFAOYAV
SMILES CN(C)CCc2c1c(c(OC)c(Br)cc1Br)n(OC)c2Br
Properties
Chemical formula	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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Infobox references

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 legumes and the Brassicaceae, the plant family that cabbage and mustard belong to.

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

• 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.; Blackman, A. J.; Lacey, E.; Gill, J. H.; Heiland, K. (2002). "Convolutindole a and Convolutamine H, New Nematocidal Brominated Alkaloids from the Marine BryozoanAmathia convoluta". Journal of Natural Products. 65 (6): 938–941. doi:10.1021/np010574x. PMID 12088445.