Convolutindole A

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Convolutindole A
Convolutindole A.svg
Ball-and-stick model of convolutindole A
Names
IUPAC name
2,4,6-Tribromo-1,7-dimethoxy-N,N-dimethyltryptamine
Identifiers
443356-86-3 YesY
ChemSpider 4481610 N
Jmol 3D model Interactive image
PubChem 5324072
  • 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
  • CN(C)CCc2c1c(c(OC)c(Br)cc1Br)n(OC)c2Br
Properties
C14H17Br3N2O2
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).
N verify (what is YesYN ?)
Infobox references

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.

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 - A similar molecule that also occurs in many 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 such as Lespedamine also occur in Legumes and the Brassicaceae, the plant family that cabbage and mustard belong to.[clarification needed]

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.
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