Gigantine

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Gigantine
Gigantine.svg
Names
Preferred IUPAC name
(1S)-6,7-Dimethoxy-1,2-dimethyl-1,2,3,4-tetrahydroisoquinolin-5-ol
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C13H19NO3/c1-8-10-7-11(16-3)13(17-4)12(15)9(10)5-6-14(8)2/h7-8,15H,5-6H2,1-4H3/t8-/m0/s1 X mark.svgN
    Key: HRJQUAXWKYISJC-QMMMGPOBSA-N X mark.svgN
  • InChI=1/C13H19NO3/c1-8-10-7-11(16-3)13(17-4)12(15)9(10)5-6-14(8)2/h7-8,15H,5-6H2,1-4H3/t8-/m0/s1
    Key: HRJQUAXWKYISJC-QMMMGPOBBT
  • O(c1cc2c(c(O)c1OC)CCN(C)[C@H]2C)C
Properties
C13H19NO3
Molar mass 237.299 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Gigantine is an tetrahydroisoquinoline alkaloid found in Carnegiea gigantea and other related cacti. [1] Gigantine was first discovered along with macromerine in 1967. [2] It is found in significant quantities in many mescaline-containing cactus species, but it is unclear whether gigantine contributes in any way to their psychoactive effects. [3]

Related Research Articles

Cactus Family of mostly succulent plants, adapted to dry environments

A cactus is a member of the plant family Cactaceae, a family comprising about 127 genera with some 1750 known species of the order Caryophyllales. The word cactus derives, through Latin, from the Ancient Greek word κάκτος (káktos), a name originally used by Theophrastus for a spiny plant whose identity is now not certain. Cacti occur in a wide range of shapes and sizes. Although some species live in quite humid environments, most cacti live in habitats subject to at least some drought. Many live in extremely dry environments, even being found in the Atacama Desert, one of the driest places on Earth. Because of this, cacti show many adaptations to conserve water. For example, almost all cacti are succulents, meaning they have thickened, fleshy parts adapted to store water. Unlike many other succulents, the stem is the only part of most cacti where this vital process takes place. Most species of cacti have lost true leaves, retaining only spines, which are highly modified leaves. As well as defending against herbivores, spines help prevent water loss by reducing air flow close to the cactus and providing some shade. In the absence of true leaves, cacti's enlarged stems carry out photosynthesis. Cacti are native to the Americas, ranging from Patagonia in the south to parts of western Canada in the north—except for Rhipsalis baccifera, which also grows in Africa and Sri Lanka.

Isoquinoline Chemical compound

Isoquinoline is a heterocyclic aromatic organic compound. It is a structural isomer of quinoline. Isoquinoline and quinoline are benzopyridines, which are composed of a benzene ring fused to a pyridine ring. In a broader sense, the term isoquinoline is used to make reference to isoquinoline derivatives. 1-Benzylisoquinoline is the structural backbone in naturally occurring alkaloids including papaverine. The isoquinoline ring in these natural compound derives from the aromatic amino acid tyrosine.

<i>Cylindropuntia bigelovii</i> Species of cactus

Cylindropuntia bigelovii, the teddy-bear cholla(choy-ya), is a cholla cactus species native to Northwestern Mexico, and to the United States in California, Arizona, and Nevada.

The Pictet–Spengler reaction is a chemical reaction in which a β-arylethylamine undergoes condensation with an aldehyde or ketone followed by ring closure. The reaction was first discovered in 1911 by Amé Pictet and Theodor Spengler. Traditionally an acidic catalyst in protic solvent was employed with heating, however the reaction has been shown to work in aprotic media in superior yields and sometimes without acid catalysis. The Pictet–Spengler reaction can be considered a special case of the Mannich reaction, which follows a similar reaction pathway. The driving force for this reaction is the electrophilicity of the iminium ion generated from the condensation of the aldehyde and amine under acid conditions. This explains the need for an acid catalyst in most cases, as the imine is not electrophilic enough for ring closure but the iminium ion is capable of undergoing the reaction.

Lophophine Chemical compound

Lophophine is a putative psychedelic and entactogen drug of the methylenedioxyphenethylamine class. It is the α-demethylated homologue of MMDA, and is also closely related to mescaline.

Erythravine Chemical compound

Erythravine is a tetrahydroisoquinoline alkaloid found in the plant Erythrina mulungu and other species of the genus Erythrina.

Saguaro Species of cactus in the Sonoran Desert

The saguaro is a tree-like cactus species in the monotypic genus Carnegiea that can grow to be over 12 meters tall. It is native to the Sonoran Desert in Arizona, the Mexican state of Sonora, and the Whipple Mountains and Imperial County areas of California. The saguaro blossom is the state wildflower of Arizona. Its scientific name is given in honor of Andrew Carnegie. In 1994, Saguaro National Park, near Tucson, Arizona, was designated to help protect this species and its habitat.

C. gigantea may refer to:

Acanthochronology

Acanthochronology is the study of cactus spines or Euphorbia thorns grown in time ordered sequence. Physical, morphological or chemical characteristics and information about the relative order or absolute age of the spines or thorns is used to study past climate or plant physiology.

Many cacti are known to be psychoactive, containing phenethylamine alkaloids such as mescaline. However, the two main ritualistic (folkloric) genera are Echinopsis, of which the most psychoactive species is the San Pedro cactus, and Lophophora, with peyote being the most psychoactive species. Several other species pertaining to other genera are also psychoactive, though not always used with a ritualistic intent.

<i>Lycium berlandieri</i> Species of flowering plant

Lycium berlandieri is a species of flowering plant in the nightshade family known by the common name Berlandier's wolfberry. It is native to Mexico and the south-western United States from Arizona to Texas.

Pellotine Chemical compound

Pellotine is an alkaloid found in Lophophora species. Pellotine is slightly narcotic, and has been used by Native Americans as a constituent of peyote for sacramental purposes.

Anhalidine Chemical compound

Anhalidine is a naturally occurring tetrahydroisoquinoline based alkaloid which can be isolated from Lophophora williamsii; it has also been detected other cactii and several species of Acacia. It is part of a family of compounds that are structurally related to mescaline.

Coclaurine Chemical compound

Coclaurine is a nicotinic acetylcholine receptor antagonist which has been isolated from a variety of plant sources including Nelumbo nucifera, Sarcopetalum harveyanum, Ocotea duckei, and others. It belongs to the class of tetrahydroisoquinoline alkaloids. Dimerization of coclaurine leads to the biscoclaurine alkaloids such as cepharanthine.

Flora of the Sonoran Desert includes six subdivisions based on vegetation types. Two are north of the boundary between the United States and Mexico, and four are south of the boundary. The flora of the Colorado Desert are influenced by the environment of the very dry and hot lower areas of the Colorado River valley, which may be barren, treeless, and generally have no large cacti. Flora of the Arizona Upland are comparatively lush, with trees and large columnar cacti that can withstand winter frosts. South of the border subdivisions are characterized by plants that cannot withstand frost.

Drosophila nigrospiracula is a fly species indigenous to the Sonoran Desert, spanning Arizona, California, and part of Sonora, Mexico. D. nigrospiracula share the Sonoran Desert with three other species of Drosophila: D. pachea, D. mettleri, and D. mojavensis. This fly breeds on the decomposing tissues of two species of cacti that are also endemic to the region: cardón (Pachycereus pringlei) and saguaro (Carnegiea gigantea).

The Bobbitt reaction is a name reaction in organic chemistry. It is named after the American chemist James M. Bobbitt. The reaction allows the synthesis of 1-, 4-, and N-substituted 1,2,3,4-tetrahydroisoquinolines and also 1-, and 4-substituted isoquinolines.

Drosophila metlerri, commonly known as the Sonoran Desert fly, is a fly in the genus Drosophila. The species is found in North America and is most concentrated along the southern coast of California and in Mexico. D. mettleri are dependent on plant hosts, namely, the saguaro and cardon cacti. Thus, they are most prevalent in arid, desert conditions. It is able to detoxify chemicals found in the rotting liquid of cacti hosts, which allows it to use otherwise lethal soil as a nesting site.

Echinocereeae Tribe of cacti

The Echinocereeae are a tribe of cacti in the subfamily Cactoideae. Since 2006, the tribe has included the former tribe Pachycereeae in many treatments of cactus classification. The exact circumscription of the tribe has been subject to considerable change, particularly since molecular phylogenetic approaches have been used in determining classifications, and remains uncertain. The tribe includes large treelike species, such as the saguaro, as well as shorter shrubby species. Most members of the tribe are found in desert regions, particularly in Mexico and the southwestern United States.

Kate Lajtha is an ecologist known for her use of stable isotopes to examine biogeochemical cycling in soils.

References

  1. Bruhn JG, Lundström J (1976). "Alkaloids of Carnegiea gigantea. Arizonine, a new tetrahydroisoquinoline alkaloid". Lloydia. 39 (4): 197–203. PMID   957908.
  2. "Two New Alkaloids in Cacti" [macromerine and gigantine] J E Hodgkins, Tetrahedron Lett., 14, 1321 (1967)
  3. Shulgin AT, Perry WE. The Simple Plant Isoquinolines. Transform Press, 2002. ISBN   978-0-9630096-2-3