Lophophorine

Last updated
Lophophorine
Lophophorine.svg
Names
IUPAC name
4-Methoxy-8,9-dimethyl-7,9-dihydro-6H-[1,3]dioxolo[4,5-h]isoquinoline
Other names
N-Methylanhalonine
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C13H17NO3/c1-8-11-9(4-5-14(8)2)6-10(15-3)12-13(11)17-7-16-12/h6,8H,4-5,7H2,1-3H3
    Key: PNFBXEKHLUDPIM-UHFFFAOYSA-N
  • CC1C2=C3C(=C(C=C2CCN1C)OC)OCO3
Properties
C13H17NO3
Molar mass 235.283 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Lophophorine is a bio-active alkaloid made by various cacti in the Lophophora family. [1]

Related Research Articles

Alkaloid Class of naturally occurring chemical compounds

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.

Mescaline Chemical compound

Mescaline (3,4,5-trimethoxyphenethylamine) is a naturally occurring psychedelic protoalkaloid of the substituted phenethylamine class, known for its hallucinogenic effects comparable to those of LSD and psilocybin. It occurs naturally in the San Pedro cactus, the Peruvian torch, the Bolivian torch cactus , the peyote cactus, and other species of cacti. It is also found in small amounts in certain members of the bean family, Fabaceae, including Acacia berlandieri. However those claims concerning Acacia species have been challenged and have been unsupported in any additional analysis.

Hecuba is a fairly large and bright main-belt asteroid. It was discovered by Karl Theodor Robert Luther on 2 April 1869, and named after Hecuba, wife of King Priam in the legends of the Trojan War in Greek Mythology. This object is orbiting the Sun with a period of 5.83 years and an eccentricity of 0.06. It became the first asteroid discovered to orbit near a 2:1 mean-motion resonance with the planet Jupiter, and is the namesake of the Hecuba group of asteroids.

Batrachotoxin Chemical compound

Batrachotoxin (BTX) is an extremely potent cardio- and neurotoxic steroidal alkaloid found in certain species of beetles, birds, and frogs. The name is from the Greek word βάτραχος, bátrachos, 'frog'. Structurally-related chemical compounds are often referred to collectively as batrachotoxins. It is an extremely poisonous alkaloid. In certain frogs, this alkaloid is present mostly on the skin. Such frogs are among those used for poisoning darts. Batrachotoxin binds to, and irreversibly opens, the sodium channels of nerve cells and prevents them from closing, resulting in paralysis and death. No antidote is known.

David Burton Wake was an American herpetologist. He was professor of integrative biology and Director and curator of herpetology of the Museum of Vertebrate Zoology at the University of California, Berkeley. Wake is known for his work on the biology and evolution of salamanders as well as general issues of vertebrate evolutionary biology. He has served as president of the Society for the Study of Evolution, the American Society of Naturalists, and American Society of Zoologists. He was a member of the American Association for the Advancement of Science, the Linnean Society of London, the American Academy of Arts and Sciences, the American Philosophical Society, and in 1998 was elected into the National Academy of Sciences. He was awarded the 2006 Leidy Award from the Academy of Natural Sciences of Philadelphia.

<i>Lophophora diffusa</i> Species of cactus

Lophophora diffusa, commonly known as false peyote, is a species of plant in the family Cactaceae and one of the only two species in the Lophophora genus. It is endemic to Mexico in the outskirts of Querétaro. This species contains zero to trace amounts of mescaline; pellotine, whose psychoactive effects are comparatively minimal, is the principal alkaloid. The species name diffusa refers to the flat tubercles that are outspread without the plant having prominent ribs.

Deoxyepinephrine Chemical compound

Deoxyepinephrine, also known by the common names N-methyldopamine and epinine, is an organic compound and natural product that is structurally related to the important neurotransmitters dopamine and epinephrine. All three of these compounds also belong to the catecholamine family. The pharmacology of epinine largely resembles that of its "parent", dopamine. Epinine has been found in plants, insects and animals. It is also of significance as the active metabolic breakdown product of the prodrug ibopamine, which has been used to treat congestive heart failure.

Peyote Species of plant

The peyote is a small, spineless cactus which contains psychoactive alkaloids, particularly mescaline. Peyote is a Spanish word derived from the Nahuatl peyōtl, meaning "caterpillar cocoon", from a root peyōni, "to glisten". Peyote is native to Mexico and southwestern Texas. It is found primarily in the Sierra Madre Occidental, the Chihuahuan Desert and in the states of Nayarit, Coahuila, Nuevo León, Tamaulipas, and San Luis Potosí among scrub. It flowers from March to May, and sometimes as late as September. The flowers are pink, with thigmotactic anthers.

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.

Akuammicine Alkaloid

Akuammicine is a monoterpene indole alkaloid of the Vinca sub-group. It is found in the Apocynaceae family of plants including Picralima nitida, Vinca minor and the Aspidosperma.

Lobivine Chemical compound

Lobivine is a phenethylamine alkaloid found in Lophophora williamsii.

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.

Anhalonidine Chemical compound

Anhalonidine a naturally occurring alkaloid which can be isolated from certain members of the cactus family, such as Lophophora. It is structurally related to mescaline.

Anhalamine Chemical compound

Anhalamine is a naturally occurring alkaloid which can be isolated from Lophophora williamsii. It is structurally related to mescaline.

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.

Vasicine Chemical compound

Vasicine (peganine) is a quinazoline alkaloid. It is found in Justicia adhatoda, after which it is named. It is additionally found in Peganum harmala.

Vasicinone Chemical compound

Vasicinone is a quinazoline alkaloid. It shows bronchodilatory activity in vitro but bronchoconstrictory activity in vivo. Vasicinone was shown to have an antianaphylactic action. It has been found within Peganum harmala.

Peyonine Chemical compound

Peyonine is a beta-phenethylpyrrole made by Lophophora.

Vinervine Vinca alkaloid

Vinervine is a monoterpene indole alkaloid of the Vinca sub-group. It is a derivative of akuammicine, with one additional hydroxy (OH) group in the indole portion, hence it is also known as 12-hydroxyakuammicine.

References

  1. Bruhn, J. G.; Lindgren, J.-E.; Holmstedt, B.; Adovasio, J. M. (1978). "Peyote alkaloids: identification in a prehistoric specimen of Lophophora from coahuila, Mexico". Science. 199 (4336): 1437–1438. Bibcode:1978Sci...199.1437B. doi:10.1126/science.199.4336.1437. PMID   17796678. S2CID   19355963.