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Names | |
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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 | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
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). |
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.
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 which also occurs in many marine invertebrates.
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 legumes and the Brassicaceae, the plant family that cabbage and mustard belong to.
This chemical was tested for its ability to kill parasitic nematodes. It was found to be more effective than levamisole,[ medical citation needed ] a synthetic drug used to kill parasitic worms and to treat colon cancer.
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 structure may also be termed alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and, more rarely, other elements such as chlorine, bromine, and phosphorus.
Bryozoa are a phylum of simple, aquatic invertebrate animals, nearly all living in sedentary colonies. Typically about 0.5 millimetres long, they have a special feeding structure called a lophophore, a "crown" of tentacles used for filter feeding. Most marine bryozoans live in tropical waters, but a few are found in oceanic trenches and polar waters. The bryozoans are classified as the marine bryozoans (Stenolaemata), freshwater bryozoans (Phylactolaemata), and mostly-marine bryozoans (Gymnolaemata), a few members of which prefer brackish water. 5,869 living species are known. At least two genera are solitary ; the rest are colonial.
N,N-Dimethyltryptamine 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 psychedelic drug and prepared by various cultures for ritual purposes as an entheogen.
Pharmacognosy is the study of medicinal plants and other natural substances as sources of drugs. The American Society of Pharmacognosy defines pharmacognosy as "the study of the physical, chemical, biochemical, and biological properties of drugs, drug substances, or potential drugs or drug substances of natural origin as well as the search for new drugs from natural sources".
Several alkaloids that function as monoamine oxidase inhibitors (MAOIs) are found in the seeds of Peganum harmala, as well as tobacco leaves including harmine, harmaline, and harmalol, which are members of a group of substances with a similar chemical structure collectively known as harmala alkaloids. These alkaloids are of interest for their use in Amazonian shamanism, where they are derived from other plants. The harmala alkaloid harmine, once known as telepathine and banisterine, is a naturally occurring beta-carboline alkaloid that is structurally related to harmaline, and also found in the vine Banisteriopsis caapi. Tetrahydroharmine is also found in B. caapi and P. harmala. Dr. Alexander Shulgin has suggested that harmine may be a breakdown product of harmaline. Harmine and harmaline are both a reversible inhibitor of monoamine oxidase A (RIMAs). They can stimulate the central nervous system by inhibiting the metabolism of monoamine compounds such as serotonin and norepinephrine.
A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical synthesis and have played a central role in the development of the field of organic chemistry by providing challenging synthetic targets. The term natural product has also been extended for commercial purposes to refer to cosmetics, dietary supplements, and foods produced from natural sources without added artificial ingredients.
N-Methyltryptamine (NMT) is a member of the substituted tryptamine chemical class and a natural product which is biosynthesized in the human body from tryptamine by certain N-methyltransferase enzymes, such as indolethylamine N-methyltransferase. It is a common component in human urine. NMT is an alkaloid derived from L-tryptophan that has been found in the bark, shoots and leaves of several plant genera, including Virola, Acacia, Mimosa, and Desmanthus—often together with the related compounds N,N-dimethyltryptamine (DMT) and 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT).
Indole alkaloids are a class of alkaloids containing a structural moiety of indole; many indole alkaloids also include isoprene groups and are thus called terpene indole or secologanin tryptamine alkaloids. Containing more than 4100 known different compounds, it is one of the largest classes of alkaloids. Many of them possess significant physiological activity and some of them are used in medicine. The amino acid tryptophan is the biochemical precursor of indole alkaloids.
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 alongside 5,6-Dibromo-DMT and seven other alkaloids. It is the 5-bromo derivative of DMT, a psychedelic found in many plants and animals.
7-Hydroxymitragynine is a terpenoid indole alkaloid from the plant Mitragyna speciosa, commonly known as Kratom. It is often referred to as ‘7-OH’. It was first described in 1994 and is a natural product derived from the mitragynine present in the Kratom leaf. It is considered an oxidized derivative and active metabolite of mitragynine. 7-OH binds to opioid receptors like mitragynine, but research suggests that 7-OH binds with greater potency and contributes heavily to the analgesic activity of mitragynine as a metabolite.
Tropane alkaloids are a class of bicyclic [3.2.1] alkaloids and secondary metabolites that contain a tropane ring in their chemical structure. Tropane alkaloids occur naturally in many members of the plant family Solanaceae. Certain tropane alkaloids such as cocaine and scopolamine are notorious for their psychoactive effects, related usage and cultural associations. Particular tropane alkaloids such as these have pharmacological properties and can act as anticholinergics or stimulants.
Bromide peroxidase (EC 1.11.1.18, bromoperoxidase, haloperoxidase (ambiguous), eosinophil peroxidase) is a family of enzymes with systematic name bromide:hydrogen-peroxide oxidoreductase. These enzymes catalyses the following chemical reaction:
Suberedamines are bio-active isolates of Suberea, a marine sponge. The compounds are brominated tyrosine dimer derivatives.
Gigactonine is a naturally occurring diterpene alkaloid first isolated from Aconitum gigas. It occurs widely in the Ranunculaceae plant family. The polycyclic ring system of this chemical compound contains nineteen carbon atoms and one nitrogen atom, which is the same as in aconitine and this is reflected in its preferred IUPAC name.
Amathia verticillata, commonly known as the spaghetti bryozoan, is a species of colonial bryozoans with a bush-like structure. It is found in shallow temperate and warm waters in the western Atlantic Ocean and the Caribbean Sea and has spread worldwide as a fouling organism. It is regarded as an invasive species in some countries.
Okenia zoobotryon is a species of sea slug, a dorid nudibranch, a marine gastropod mollusc in the family Goniodorididae. It is normally found on the colonial bryozoan Amathia verticillata on which it lives and feeds.
Tambjamines are a group of natural products that are structurally related to the prodiginines. They are enamine derivatives of 4-methoxy-2,2'-bipyrrole-5-carboxaldehyde (MBC).
Tuticorin Raghavachari Govindachari FNA, FASc (1915–2001), popularly known as TRG, was an Indian natural product chemist, academic, institution builder and the principal of Presidency College, Chennai. He was known for his studies on the synthesis of isoquinolines and phenanthridines and his contributions in elucidating the structure of several plant constituents. He was an elected fellow of the Indian Academy of Sciences and the Indian National Science Academy and was the nominator of Robert Burns Woodward who won the 1965 Nobel Prize in Chemistry. The Council of Scientific and Industrial Research, the apex agency of the Government of India for scientific research, awarded him the Shanti Swarup Bhatnagar Prize for Science and Technology, one of the highest Indian science awards, in 1960, for his contributions to chemical sciences, making him the first recipient of the award in the chemical sciences category.
Pseudoceratina is a genus of sponge within the family Pseudoceratinidae. They are characterized by possession of a dendritic fiber skeleton lacking laminar bark but containing pith. They have been found in a variety of habitats including the Great Barrier reef, the Red Sea, and Jamaica. Sponges of this genus have a microbiome known to produce a variety of chemicals that are used in pharmaceutical and anti-fouling activities. Notably, a species in this genus produces a chemical that is effective in inhibiting the migration of metastatic breast cancer cells.