Convolutindole A (2,4,6-tribromo-1,7-dimethoxy-''N'',''N''-dimethyltryptamine) is a

brominated Bromine is a chemical element with the symbol Br and atomic number 35. It is the third-lightest element in group 17 of the periodic table (halogens) and is a volatile red-brown liquid at room temperature that evaporates readily to form a simila ...

tryptamine Tryptamine is an indolamine metabolite of the essential amino acid, tryptophan. The chemical structure is defined by an indole ─ a fused benzene and pyrrole ring, and a 2-aminoethyl group at the second carbon (third aromatic atom, with the f ...

alkaloid Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar ...

that was first identified in 2001 in '' Amathia convoluta'', a marine bryozoan. Bryozoans are aquatic

invertebrate Invertebrates are a paraphyletic group of animals that neither possess nor develop a vertebral column (commonly known as a ''backbone'' or ''spine''), derived from the notochord. This is a grouping including all animals apart from the chordate ...

s that grow in colonies and may resemble

coral Corals are marine invertebrates within the class Anthozoa of the phylum Cnidaria. They typically form compact colonies of many identical individual polyps. Coral species include the important reef builders that inhabit tropical oceans and sec ...

Chemistry

Convolutamine A is the 2,4,6-tribromo-1,7-dimethoxy derivative of

DMT ''N'',''N''-Dimethyltryptamine (DMT or ''N'',''N''-DMT, SPL026) is a substituted tryptamine that occurs in many plants and animals, including human beings, and which is both a derivative and a structural analog of tryptamine. It is used as a ...

, a

hallucinogen Hallucinogens are a large, diverse class of psychoactive drugs that can produce altered states of consciousness characterized by major alterations in thought, mood, and perception as well as other changes. Most hallucinogens can be categorized ...

that occurs naturally in many plants and animals. Convolutamine A is chemically related to

5-bromo-DMT 5-Bromo-DMT (5-bromo-''N'',''N''-dimethyltryptamine) is a psychedelic brominated indole alkaloid found in the sponges ''Smenospongia aurea'' and ''Smenospongia echina'', as well as in ''Verongula rigida'' (0.00142% dry weight) alongside 5,6-Dibr ...

which also occurs in many marine

invertebrates Invertebrates are a paraphyletic group of animals that neither possess nor develop a vertebral column (commonly known as a ''backbone'' or ''spine''), derived from the notochord. This is a grouping including all animals apart from the chordate ...

. Until the discovery of convolutindole A, the 1-methoxyindole

moiety Moiety may refer to: Chemistry * Moiety (chemistry), a part or functional group of a molecule ** Moiety conservation, conservation of a subgroup in a chemical species Anthropology * Moiety (kinship), either of two groups into which a society is ...

was unknown in the marine world. 1-Methoxyindoles, such as

lespedamine Lespedamine is an indole alkaloid and substituted tryptamine present in the plant ''Lespedeza bicolor''. The alkaloid bears a close structural resemblance to the psychedelic alkaloid dimethyltryptamine and was speculated to have psychoactivity by ...

, were previously only known to occur in

legume A legume () is a plant in the family Fabaceae (or Leguminosae), or the fruit or seed of such a plant. When used as a dry grain, the seed is also called a pulse. Legumes are grown agriculturally, primarily for human consumption, for livestock f ...

s and the

Brassicaceae Brassicaceae () or (the older) Cruciferae () is a medium-sized and economically important family of flowering plants commonly known as the mustards, the crucifers, or the cabbage family. Most are herbaceous plants, while some are shrubs. The le ...

, the plant family that

cabbage Cabbage, comprising several cultivars of ''Brassica oleracea'', is a leafy green, red (purple), or white (pale green) biennial plant grown as an annual vegetable crop for its dense-leaved heads. It is descended from the wild cabbage ( ''B.&nb ...

and

mustard Mustard may refer to: Food and plants * Mustard (condiment), a paste or sauce made from mustard seeds used as a condiment * Mustard plant, one of several plants, having seeds that are used for the condiment ** Mustard seed, seeds of the mustard p ...

belong to.

Biological activity

This chemical was tested for its ability to kill

parasitic Parasitism is a close relationship between species, where one organism, the parasite, lives on or inside another organism, the host, causing it some harm, and is adapted structurally to this way of life. The entomologist E. O. Wilson has c ...

nematode The nematodes ( or grc-gre, Νηματώδη; la, Nematoda) or roundworms constitute the phylum Nematoda (also called Nemathelminthes), with plant-Parasitism, parasitic nematodes also known as eelworms. They are a diverse animal phylum inhab ...

s. It was found to be more effective than

levamisole Levamisole, sold under the brand name Ergamisol among others, is a medication used to treat parasitic worm infections, specifically ascariasis and hookworm infections. It is taken by mouth. Side effects may include abdominal pain, vomiting, he ...

, a synthetic drug used to kill parasitic worms and to treat

colon cancer Colorectal cancer (CRC), also known as bowel cancer, colon cancer, or rectal cancer, is the development of cancer from the colon or rectum (parts of the large intestine). Signs and symptoms may include blood in the stool, a change in bowel mo ...

References

*Narkowicz, C. K.; Blackman, A. J., (June 2001). ''Abstracts of Papers''; 10th International Symposium on Marine Natural Products: Nago, Okinawa, Abstract OR1. * {{Tryptamines Tryptamine alkaloids Halogen-containing alkaloids Organobromides Indole ethers at the benzene ring Hydroxylamines