Names | |
---|---|
Preferred IUPAC name (1S)-1-[(4-Hydroxyphenyl)methyl]-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
KEGG | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
| |
| |
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. More rarely 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.
Mimosa tenuiflora, syn. Mimosa hostilis, also known as jurema preta, calumbi (Brazil), tepezcohuite (México), carbonal, cabrera, jurema, black jurema, and binho de jurema, is a perennial tree or shrub native to the northeastern region of Brazil and found as far north as southern Mexico, and the following countries: El Salvador, Honduras, Panama, Colombia and Venezuela. It is most often found in lower altitudes, but it can be found as high as 1,000 m (3,300 ft).
Ocotea is a genus of flowering plants belonging to the family Lauraceae. Many are evergreen trees with lauroid leaves.
Menispermaceae is a family of flowering plants. The alkaloid tubocurarine, a neuromuscular blocker and the active ingredient in the 'tube curare' form of the dart poison curare, is derived from the South American liana Chondrodendron tomentosum. Several other South American genera belonging to the family have been used to prepare the 'pot' and 'calabash' forms of curare. The family contains 68 genera with some 440 species, which are distributed throughout low-lying tropical areas with some species present in temperate and arid regions.
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.
Erythrina mulungu (Mulungu) is a Brazilian ornamental tree and medicinal plant native to the cerrado and caatinga ecoregions in Brazil, South America.
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 more recently, 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.
7-Hydroxymitragynine (7-OH) is a terpenoid indole alkaloid from the plant Mitragyna speciosa, commonly known as kratom. It was first described in 1994 and is a natural product derived from the mitragynine present in the kratom leaf. 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.
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. It is based on the benzylisoquinoline structure.
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.
Substituted tryptamines, or serotonin analogues, are organic compounds which may be thought of as being derived from tryptamine itself. The molecular structures of all tryptamines contain an indole ring, joined to an amino (NH2) group via an ethyl (−CH2–CH2−) sidechain. In substituted tryptamines, the indole ring, sidechain, and/or amino group are modified by substituting another group for one of the hydrogen (H) atoms.
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.