Names | |
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Preferred IUPAC name (1S)-1-[(4-Hydroxyphenyl)methyl]-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol | |
Identifiers | |
3D model (JSmol) | |
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PubChem CID | |
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CompTox Dashboard (EPA) | |
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Properties | |
C17H19NO3 | |
Molar mass | 285.343 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Coclaurine is a nicotinic acetylcholine receptor antagonist [1] which has been isolated from a variety of plant sources including Nelumbo nucifera , Sarcopetalum harveyanum , [2] Ocotea duckei , [3] and others. It belongs to the class of tetrahydroisoquinoline alkaloids. Dimerization of coclaurine leads to the biscoclaurine alkaloids such as cepharanthine.
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 or sulfur. Rarer still, they may contain elements such as phosphorus, chlorine, and bromine.
Medicinal plants, also called medicinal herbs, have been discovered and used in traditional medicine practices since prehistoric times. Plants synthesize hundreds of chemical compounds for various functions, including defense and protection against insects, fungi, diseases, and herbivorous mammals.
Phytochemistry is the study of phytochemicals, which are chemicals derived from plants. Phytochemists strive to describe the structures of the large number of secondary metabolites found in plants, the functions of these compounds in human and plant biology, and the biosynthesis of these compounds. Plants synthesize phytochemicals for many reasons, including to protect themselves against insect attacks and plant diseases. The compounds found in plants are of many kinds, but most can be grouped into four major biosynthetic classes: alkaloids, phenylpropanoids, polyketides, and terpenoids.
Ocotea is a genus of flowering plants belonging to the family Lauraceae. Many are evergreen trees with lauroid leaves.
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 known 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).
The name Catuaba is used for the infusions of the bark of a number of trees native to Brazil. The most widely used barks are derived from the trees Trichilia catigua and Erythroxylum vaccinifolium. Other catuaba preparations use the bark of trees from the following genera or families: Anemopaegma, Ilex, Micropholis, Phyllanthus, Secondatia, Tetragastris and species from the Myrtaceae. Local synonyms are Chuchuhuasha, Tatuaba, Pau de Reposta, Piratancara and Caramuru.
Erythrina mulungu (Mulungu) is a Brazilian ornamental tree and medicinal plant native to the cerrado and caatinga ecoregions in Brazil, South America.
Mesembryanthemum tortuosum is a succulent plant in the family Aizoaceae native to the Cape Provinces of South Africa. It is known as the Namaqua skeletonfig, kanna, channa, kougoed —which literally means, 'chew(able) things' or 'something to chew'.
Mesembrine is an alkaloid present in Sceletium tortuosum (kanna). It has been shown to act as a serotonin reuptake inhibitor (Ki = 1.4 nM), and has also been found to behave as a weak inhibitor of the enzyme phosphodiesterase 4 (PDE4) (Ki = 7,800 nM). In an in vitro study published in 2015, researchers concluded that "a high-mesembrine Sceletium extract" may exert anti-depressant effects by acting as a monoamine releasing agent." As such, mesembrine likely plays a dominant role in the antidepressant effects of kanna. The levorotatory isomer, (−)-mesembrine, is the natural form.
Ocotea foetens, commonly called til or stinkwood is a species of tree in the family Lauraceae. It is evergreen and grows up to 40 m tall. It is a common constituent of the laurisilva forests of Madeira and the Canary Islands. Leaf fossils of this species are known from the Mio-Pleistocene of Madeira Island.
Erythravine is a tetrahydroisoquinoline alkaloid found in the plant Erythrina mulungu and other species of the genus Erythrina.
Sarcopetalum harveyanum, known as the pearl vine, is a common plant found mostly in coastal areas of eastern Australia. It can be found in or around rainforests, and is also seen in eucalyptus forests.
Reticuline is a chemical compound found in a variety of plants including Lindera aggregata, Annona squamosa, and Ocotea fasciculata.
Echinopsidine (Adepren) is an antidepressant that was under development in Bulgaria for the treatment of depression. It increases serotonin, norepinephrine, and dopamine levels in the brain and is believed to act as a monoamine oxidase inhibitor (MAOI). Echinopsidine is found naturally in Echinops echinatus along with the related alkaloids echinopsine and echinozolinone.
Erythrina velutina is a species of leguminous tree. It is indigenous to Brazil, Peru, Ecuador, Colombia, Venezuela, and Hispaniola and has been introduced to much of the Caribbean, Uganda, and Sri Lanka. It also occurs on the Galápagos Islands, but whether it is indigenous or introduced there is unclear. In Brazil, it occurs on plains and near rivers in the arid parts of the northeast of the country and is commonly known as "mulungu". Erythrina velutina grows as a large tree to around 10 m (30 ft) high and has short spines on the stem. It is perennial.
Zanthoxylum rhoifolium is a species of tree in the family Rutaceae known by the common names mamica de cadela, tambataru, and prickly ash. It is native to South America. It is a common tree on the Cerrado.
Mesembrenone is an alkaloid constituent of Sceletium tortuosum (Kanna) and minor constituent of Lampranthus aureus and Lampranthus spectabilis.
Furoquinoline alkaloids are a group of alkaloids with simple structure. Distribution of this group of alkaloids is essentially limited to plant family Rutaceae. The simplest member of this group is dictamnine and most widespread member is skimmianine.
Affinisine is a monoterpenoid indole alkaloid which can be isolated from plants of the genus Tabernaemontana. Structurally, it can be considered a member of the sarpagine alkaloid family and may be synthesized from tryptophan via a Pictet-Spengler reaction.
Tabernaemontanine is a naturally occurring monoterpene indole alkaloid found in several species in the genus Tabernaemontana including Tabernaemontana divaricata.