Convolutindole A

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
CAS Number	443356-86-3  Y
3D model (JSmol)	Interactive image
ChemSpider	4481610  N
PubChem CID	5324072
UNII	D37997A5KB  Y
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
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). N  verify  (what is  YN ?) 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. ^[1] Bryozoans are aquatic invertebrates that grow in colonies and may resemble corals. ^[2]

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. ^[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

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

1. 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.
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. 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.
4. Narkowicz, C. K.; Blackman, A. J., (June 2001). Abstracts of Papers; 10th International Symposium on Marine Natural Products: Nago, Okinawa, Abstract OR1.