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Convolutindole A

From Wikipedia, the free encyclopedia
Convolutindole A
Ball-and-stick model of convolutindole A
Names
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)
ChemSpider
UNII
  • 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
  • CN(C)CCc2c1c(c(OC)c(Br)cc1Br)n(OC)c2Br
Properties
C14H17Br3N2O2
Molar mass485.014 g·mol−1
Melting point61.5 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 theirstandard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound

Convolutindole A (2,4,6-tribromo-1,7-dimethoxy-N,N-dimethyltryptamine) is abrominatedtryptaminealkaloid that was first identified in 2001 inAmathia convoluta, a marinebryozoan.[1] Bryozoans are aquaticinvertebrates that grow in colonies and may resemblecorals.[2]

Chemistry

[edit]

Convolutamine A is the 2,4,6-tribromo-1,7-dimethoxy derivative ofDMT, ahallucinogen that occurs naturally in many plants and animals.[1] Convolutamine A is chemically related to5-bromo-DMT which also occurs in many marineinvertebrates.[3]

Until the discovery of convolutindole A, the 1-methoxyindolemoiety was unknown in the marine world. 1-Methoxyindoles, such aslespedamine, were previously only known to occur in plants of thebean andmustard families.[3][4]

Biological activity

[edit]

This chemical was tested for its ability to killparasiticnematodes. It was found to be more effective thanlevamisole - a synthetic drug used to kill parasitic worms and to treatcolon cancer.[3]

References

[edit]
  1. ^abIchikawa 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.
  2. ^Wood TS (2010). "Bryozoans".Ecology and Classification of North American Freshwater Invertebrates:437–454.doi:10.1016/B978-0-12-374855-3.00013-3.
  3. ^abcNarkowicz 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.
  4. ^Narkowicz, C. K.; Blackman, A. J., (June 2001).Abstracts of Papers; 10th International Symposium on Marine Natural Products: Nago, Okinawa, Abstract OR1.
Tryptamines
4-Hydroxytryptamines
andesters/ethers
5-Hydroxy- and
5-methoxytryptamines
N-Acetyltryptamines
α-Alkyltryptamines
α-Ketotryptamines
Cyclized tryptamines
Isotryptamines
Related compounds
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