Convolutindole A

Convolutindole A
Names
	IUPAC name 2,4,6-Tribromo-1,7-dimethoxy-N,N-dimethyltryptamine
Identifiers
CAS Number	443356-86-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	4481610;
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 Key: KPTXBOJWIDAMOS-UHFFFAOYSA-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
Melting point	61.5-62.5 °C
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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.
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