Boldine

Last updated
Boldine
Boldine.svg
Names
IUPAC name
1,10-Dimethoxyaporphine-2,9-diol
Systematic IUPAC name
(6aS)-1,10-Dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,9-diol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.006.828 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C19H21NO4/c1-20-5-4-10-7-15(22)19(24-3)18-12-9-16(23-2)14(21)8-11(12)6-13(20)17(10)18/h7-9,13,21-22H,4-6H2,1-3H3/t13-/m0/s1 Yes check.svgY
    Key: LZJRNLRASBVRRX-ZDUSSCGKSA-N Yes check.svgY
  • InChI=1/C19H21NO4/c1-20-5-4-10-7-15(22)19(24-3)18-12-9-16(23-2)14(21)8-11(12)6-13(20)17(10)18/h7-9,13,21-22H,4-6H2,1-3H3/t13-/m0/s1
    Key: LZJRNLRASBVRRX-ZDUSSCGKBM
  • CN1CCC2=CC(=C(C3=C2[C@@H]1CC4=CC(=C(C=C43)OC)O)OC)O
Properties
C19H21NO4
Molar mass 327.380 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Boldine is an alkaloid of the aporphine class that is characteristic of the boldo tree Peumus boldus Molina. It is the most abundant alkaloid found in boldo bark, [1] although it is not present in the leaves. [2] Boldine is also found in Lindera aggregata . [3]

Related Research Articles

<i>N</i>,<i>N</i>-Dimethyltryptamine Chemical compound

N,N-Dimethyltryptamine is a substituted tryptamine that occurs in many plants and animals, including humans, and which is both a derivative and a structural analog of tryptamine. DMT is used as a psychedelic drug and prepared by various cultures for ritual purposes as an entheogen.

<span class="mw-page-title-main">Noscapine</span> Chemical compound

Noscapine, also known as narcotine, nectodon, nospen, anarcotine and (archaic) opiane, is a benzylisoquinoline alkaloid of the phthalideisoquinoline structural subgroup, which has been isolated from numerous species of the family Papaveraceae. It lacks effects associated with opioids such as sedation, euphoria, or analgesia (pain-relief) and lacks addictive potential. Noscapine is primarily used for its antitussive (cough-suppressing) effects.

<span class="mw-page-title-main">Ibogaine</span> Psychoactive substance found in plants in the family Apocynaceae

Ibogaine is a psychoactive indole alkaloid obtained either by extraction from plants in the family Apocynaceae such as Tabernanthe iboga, Voacanga africana, and Tabernaemontana undulata or by semi-synthesis from the precursor compound voacangine, another plant alkaloid. The total synthesis of ibogaine was described in 1956. Structural elucidation by X-ray crystallography was completed in 1960.

<span class="mw-page-title-main">Boldo</span> Species of plant

Peumus boldus, commonly known as boldo, is a species of tree in the family Monimiaceae and the only species in the genus Peumus. It is endemic to the central region of Chile, between 33° and 40° southern latitude. Boldo has also been introduced to Europe and North Africa, though it is not often seen outside botanical gardens.

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.

<span class="mw-page-title-main">Veratridine</span> Steroidal alkaloid found in plants of the lily family

Veratridine is a steroidal alkaloid found in plants of the lily family, specifically the genera Veratrum and Schoenocaulon. Upon absorption through the skin or mucous membranes, it acts as a neurotoxin by binding to and preventing the inactivation of voltage-gated sodium ion channels in heart, nerve, and skeletal muscle cell membranes. Veratridine increases nerve excitability and intracellular Ca2+ concentrations.

<span class="mw-page-title-main">18-Methoxycoronaridine</span> Chemical compound

18-Methoxycoronaridine, also known as zolunicant, is a derivative of ibogaine invented in 1996 by the research team around the pharmacologist Stanley D. Glick from the Albany Medical College and the chemists Upul K. Bandarage and Martin E. Kuehne from the University of Vermont. In animal studies it has proven to be effective at reducing self-administration of morphine, cocaine, methamphetamine, nicotine and sucrose. It has also been shown to produce anorectic effects in obese rats, most likely due to the same actions on the reward system which underlie its anti-addictive effects against drug addiction.

<span class="mw-page-title-main">Anabasine</span> Chemical compound

Anabasine is a pyridine and piperidine alkaloid found in the tree tobacco plant, as well as in tree tobacco's close relative the common tobacco plant. It is a structural isomer of, and chemically similar to, nicotine. Its principal (historical) industrial use is as an insecticide.

<span class="mw-page-title-main">Mesembrine</span> Chemical compound

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.

The Duquenois reagent is used in the Rapid Modified Duquenois–Levine test, which is an established screening test for the presence of cannabis. The test was initially developed in the 1930s by the French medical biochemist Pierre Duquénois (1904–1986) and was adopted in the 1950s by the United Nations as the preferred test for cannabis. The test was originally claimed to be specific to cannabis.

<span class="mw-page-title-main">Glaucine</span> Chemical compound

Glaucine(1,2,9,10-TetraMethoxyAporphine, Bromcholitin, Glauvent, Tusidil, Tussiglaucin) is an aporphine alkaloid found in several different plant species in the family Papaveraceae such as Glaucium flavum, Glaucium oxylobum and Corydalis yanhusuo, and in other plants like Croton lechleri in the family Euphorbiaceae.

<span class="mw-page-title-main">Delphinine</span> Chemical compound

Delphinine is a toxic diterpenoid alkaloid found in plants from the Delphinium (larkspur) and Atragene genera, both in the family Ranunculaceae. Delphinine is the principal alkaloid found in Delphinium staphisagria seeds – at one time, under the name stavesacre, a very well known herbal treatment for body lice. It is related in structure and has similar effects to aconitine, acting as an allosteric modulator of voltage gated sodium channels, and producing low blood pressure, slowed heart rate and abnormal heart rhythms. These effects make it highly poisonous. While it has been used in some alternative medicines, most of the medical community does not recommend using it due to its extreme toxicity.

<i>Lindera aggregata</i> Species of flowering plant

Lindera aggregata is a plant species belonging to the genus Lindera.

<span class="mw-page-title-main">Reticuline</span> Chemical compound

Reticuline is a chemical compound found in a variety of plants including Lindera aggregata, Annona squamosa, and Ocotea fasciculata.

<span class="mw-page-title-main">Ibogamine</span> Anti-convulsant, anti-addictive CNS stimulant alkaloid

Ibogamine is an anti-convulsant, anti-addictive, CNS stimulant alkaloid found in Tabernanthe iboga and Crepe Jasmine. Basic research related to how addiction affects the brain has used this chemical.

<span class="mw-page-title-main">Matrine</span> Chemical compound

Matrine is an alkaloid found in plants from the genus Sophora. It has a variety of pharmacological effects, including anti-cancer effects, as well as κ-opioid and μ-opioid receptor agonism.

<span class="mw-page-title-main">Miquelianin</span> Chemical compound

Miquelianin is a flavonol glucuronide, a type of phenolic compound present in wine, in species of St John's wort, like Hypericum hirsutum, in Nelumbo nucifera or in green beans.

<i>Xanthogaleruca</i> Genus of beetles

Xanthogaleruca is a genus of beetles belonging to the family Chrysomelidae. These elm leaf beetles are pests that feed on ornamental plants until they are stripped of their leaves entirely.

<i>Picralima</i> Genus of flowering plants

Picralima is a plant genus in the family Apocynaceae, first described as a genus in 1896. It contains only one known species, Picralima nitida, native to tropical Africa.

<span class="mw-page-title-main">Apparicine</span> Chemical compound

Apparicine is a monoterpenoid tricyclic indole alkaloid. It is named after Apparicio Duarte, a Brazilian botanist who studied the Aspidosperma species from which apparicine was first isolated. It was the first member of the vallesamine group of indole alkaloids to be isolated and have its structure established, which was first published in 1965. It has also been known by the synonyms gomezine, pericalline, and tabernoschizine.

References

  1. O'Brien, P.; Carrasco-Pozo, C.; Speisky, H. (2006). "Boldine and its Antioxidant or Health-Promoting Properties". Chemico-Biological Interactions. 159 (1): 1–17. doi:10.1016/j.cbi.2005.09.002. PMID   16221469.
  2. Fuentes-Barros, G.; Castro-Saavedra, S.; Liberona, L.; et al. (2018). "Variation of the alkaloid content of Peumus boldus (boldo)". Fitoterapia. 127 (2): 179–185. doi:10.1016/j.fitote.2018.02.020. PMID   29454020.
  3. Han, Z.; Zheng, Y.; Chen, N.; et al. (2008). "Simultaneous Determination of Four Alkaloids in Lindera aggregata by Ultra-High-Pressure Liquid Chromatography–Tandem Mass Spectrometry". Journal of Chromatography A. 1212 (1–2): 76–81. doi:10.1016/j.chroma.2008.10.017. PMID   18951552.