Anhalonidine

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Anhalonidine
Anhalonidin Structural Formula V1.svg
Names
IUPAC name
(1S)-1,2,3,4-Tetrahydro-6,7-dimethoxy-1-methyl-8-isoquinolinol
Identifiers
3D model (JSmol)
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C12H17NO3/c1-7-10-8(4-5-13-7)6-9(15-2)12(16-3)11(10)14/h6-7,13-14H,4-5H2,1-3H3/t7-/m0/s1
    Key: PRNZAMQMBOFSJY-ZETCQYMHSA-N
  • InChI=1/C12H17NO3/c1-7-10-8(4-5-13-7)6-9(15-2)12(16-3)11(10)14/h6-7,13-14H,4-5H2,1-3H3/t7-/m0/s1
    Key: PRNZAMQMBOFSJY-ZETCQYMHBW
  • C[C@H]1c2c(cc(c(c2O)OC)OC)CCN1
Properties
C12H17NO3
Molar mass 223.272 g·mol−1
Melting point 160 °C (320 °F; 433 K) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Anhalonidine a naturally occurring alkaloid which can be isolated from certain members of the cactus family, such as Lophophora . [2] It is structurally related to mescaline.

See also

Related Research Articles

<span class="mw-page-title-main">Alkaloid</span> 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 or sulfur. More rarely still, they may contain elements such as phosphorus, chlorine, and bromine.

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

Macromerine is a phenethylamine derivative. It was first identified from the cactus Coryphantha macromeris. It can also be found in C. runyonii, C. elephantidens, and other related members of the family Cactaceae.

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

Hordenine is an alkaloid of the phenethylamine class that occurs naturally in a variety of plants, taking its name from one of the most common, barley. Chemically, hordenine is the N-methyl derivative of N-methyltyramine, and the N,N-dimethyl derivative of the well-known biogenic amine tyramine, from which it is biosynthetically derived and with which it shares some pharmacological properties. As of September 2012, hordenine is widely sold as an ingredient of nutritional supplements, with the claims that it is a stimulant of the central nervous system, and has the ability to promote weight loss by enhancing metabolism. In experimental animals, given sufficiently large doses parenterally, hordenine does produce an increase in blood pressure, as well as other disturbances of the cardiovascular, respiratory, and nervous systems. These effects are generally not reproduced by oral administration of the drug in test animals, and virtually no scientific reports of the effects of hordenine in human beings have been published.

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

Voacangine is an alkaloid found predominantly in the root bark of the Voacanga africana tree, as well as in other plants such as Tabernanthe iboga, Tabernaemontana africana, Trachelospermum jasminoides, Tabernaemontana divaricata and Ervatamia yunnanensis. It is an iboga alkaloid which commonly serves as a precursor for the semi-synthesis of ibogaine. It has been demonstrated in animals to have similar anti-addictive properties to ibogaine itself. It also potentiates the effects of barbiturates. Under UV-A and UV-B light its crystals fluoresce blue-green, and it is soluble in ethanol.

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

Aporphine is an alkaloid with the chemical formula C17H17N. It is the core chemical substructure of the aporphine alkaloids, a subclass of quinoline alkaloids. It can exist in either of two enantiomeric forms, (R)-aporphine and (S)-aporphine.

<span class="mw-page-title-main">3,4-Dimethoxyphenethylamine</span> Chemical compound

3,4-Dimethoxyphenethylamine (DMPEA) is a chemical compound of the phenethylamine class. It is an analogue of the major human neurotransmitter dopamine where the 3- and 4-position hydroxy groups have been replaced with methoxy groups. It is also closely related to mescaline which is 3,4,5-trimethoxyphenethylamine.

<i>Trichocereus macrogonus</i> Species of cactus

Trichocereus macrogonus, synonym Echinopsis macrogonus, is a species of cactus found in Ecuador, Peru and Bolivia. Two varieties are accepted as of September 2023: var. macrogonus and var. pachanoi. Plants contain varying amounts of the psychoactive alkaloid mescaline. They have been used both ritually and in traditional medicine from pre-Columbian times. Trichocereus macrogonus is one of a number of similar species that may be called San Pedro cactus. Indigenous names include achuma and huachuma, although these too may be applied to similar species.

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

Akuammine (vincamajoridine) is an indole alkaloid. It is the most abundant alkaloid found in the seeds from the tree Picralima nitida, commonly known as akuamma, comprising 0.56% of the dried powder. It has also been isolated from Vinca major. Akuammine is structurally related to yohimbine, mitragynine and more distantly Voacangine, all of which are alkaloid plant products with pharmacological properties.

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

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

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

Pericine is one of a number of indole alkaloids found in the tree Picralima nitida, commonly known as akuamma. As with some other alkaloids from this plant such as akuammine, pericine has been shown to bind to mu opioid receptors in vitro, and has an IC50 of 0.6 μmol, within the range of a weak analgesic. It may also have convulsant effects.

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

Conessine is a steroidal alkaloid found in a number of plant species from the family Apocynaceae, including Holarrhena floribunda, Holarrhena antidysenterica and Funtumia elastica. It acts as a histamine antagonist, selective for the H3 subtype (with an affinity of pKi = 8.27; Ki = ~5 nM). It was also found to have long CNS clearance times, high blood–brain barrier penetration and high affinity for the adrenergic receptors.

<i>Trichocereus macrogonus <span style="font-style:normal;">var.</span> pachanoi</i> Mescaline-containing cactus

Trichocereus macrogonus var. pachanoi is a fast-growing columnar cactus found in the Andes at 2,000–3,000 m (6,600–9,800 ft) in altitude. It is one of a number of kinds of cacti known as San Pedro cactus. It is native to Ecuador, Peru and Colombia, but also found in Argentina, Bolivia,, Chile and Venezuela and cultivated in other parts of the world. Uses for it include traditional medicine and traditional veterinary medicine, and it is widely grown as an ornamental cactus. It has been used for healing and religious divination in the Andes Mountains region for over 3,000 years.

<span class="mw-page-title-main">Peyote</span> 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.

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

Psychotridine is an alkaloid found in some species of the genus Psychotria, namely Psychotria colorata, but also Psychotria forsteriana, Psychotria lyciiflora, Psychotria oleoides, and Psychotria beccarioides. Psychotridine has analgesic effects and dose-dependently inhibits dizocilpine binding to cortical membranes in vitro, suggesting that it acts as a non-competitive NMDA receptor antagonist.

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

Coronaridine, also known as 18-carbomethoxyibogamine, is an alkaloid found in Tabernanthe iboga and related species, including Tabernaemontana divaricata for which it was named.

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 occur in the San Pedro cactus group, 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.

<span class="mw-page-title-main">Akuammicine</span> 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.

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

Apparicine is a monoterpenoid 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 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.

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.

References

  1. Späth, Ernst (August 1923). "Über die Anhaloniumalkaloide". Monatshefte für Chemie (in German). 43 (8): 477–484. doi:10.1007/BF01526801. S2CID   197766778.
  2. Djerassi, Carl; Smith, C. R.; Marfey, S. P.; McDonald, R. N.; Lemin, A. J.; Figdor, S. K.; Estrada, H. (June 1954). "Alkaloid Studies. III.1 Isolation of Pilocereine and Anhalonidine from Four Cactus Species". Journal of the American Chemical Society. 76 (12): 3215–3217. doi:10.1021/ja01641a034.