Pellotine

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Pellotine
Pellotin Structural Formula V1.svg
Names
Systematic IUPAC name
6,7-Dimethoxy-1,2-dimethyl-3,4-dihydro-1H-isoquinolin-8-ol
Other names
Peyotline; N-Methylanhalonidine
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C13H19NO3/c1-8-11-9(5-6-14(8)2)7-10(16-3)13(17-4)12(11)15/h7-8,15H,5-6H2,1-4H3
    Key: NKHMWHLJHODBEP-UHFFFAOYSA-N
  • CC1C2=C(C(=C(C=C2CCN1C)OC)OC)O
Properties
C13H19NO3
Molar mass 237.299 g·mol−1
Melting point 110 to 113
Hazards
Lethal dose or concentration (LD, LC):
10 mg/kg (intravenous, dog)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Pellotine is an alkaloid found in Lophophora species, in particular L. diffusa. [1] [2] Pellotine is slightly narcotic, and has been used by Native Americans as a constituent of peyote for sacramental purposes. [3]

Contents

Psychological and physiological effects

8-10 mg of isolated pellotine is known to cause convulsions in frogs. [4] When injected subcutaneously to humans, participants have reported drowsiness and a desire not to exert any physical or mental effort with one study reporting it to have hypnotic effects. [3] It is also reported to lower blood pressure and heart rate. [3]

Ancient use

Native inhabitants of north-eastern Mexico around 810–1070 CE (according to carbon dating) are thought to have used a number of "mescal buttons" (peyote plant material) containing mescaline, pellotine, and other related alkaloids. While it is known that the cytisine-containing "mescal beans" were at least ornamental, it is unclear whether "mescal buttons" were ornamental or used for their psychoactive effects. [5]

See also

Related Research Articles

<span class="mw-page-title-main">Mescaline</span> Naturally occurring psychedelic compound


Mescaline or mescalin or mezcalin (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 is an agonist that binds to a seratonin receptor in the brain, activating hallucinogenic effects.

<span class="mw-page-title-main">Psychedelic drug</span> Hallucinogenic class of psychoactive drug

Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary mental states and a perceived "expansion of consciousness". Also referred to as classic hallucinogens or serotonergic hallucinogens, the term psychedelic is sometimes used more broadly to include various types of hallucinogens, such as those which are atypical or adjacent to psychedelia like salvia and MDMA, respectively.

<span class="mw-page-title-main">Entheogen</span> Psychoactive substances that induce spiritual experiences

Entheogens are psychoactive substances, including psychedelic drugs, used in sacred contexts in religion for inducing spiritual development throughout history.

<span class="mw-page-title-main">Psilocybin mushroom</span> Mushrooms containing psychoactive indole alkaloids

Psilocybin mushrooms, commonly known as magic mushrooms,shrooms, or broadly as hallucinogenic mushrooms, are a polyphyletic informal group of fungi that contain psilocybin, which turns into psilocin upon ingestion. The most potent species are members of genus Psilocybe, such as P. azurescens, P. semilanceata, and P. cyanescens, but psilocybin has also been isolated from approximately a dozen other genera, including Panaeolus, Inocybe, Pluteus, Gymnopilus, and Pholiotina.

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

<i>Dermatophyllum secundiflorum</i> Species of plant

Dermatophyllum secundiflorum is a species of flowering shrub or small tree in the family Fabaceae that is native to the Southwestern United States and Mexico. Its common names include Texas mountain laurel, Texas mescalbean, frijolito, and frijolillo.

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

Cytisine, also known as baptitoxine, cytisinicline, or sophorine, is an alkaloid that occurs naturally in several plant genera, such as Laburnum and Cytisus of the family Fabaceae. It has been used medically to help with smoking cessation. It has been found effective in several randomized clinical trials, including in the United States and New Zealand, and is being investigated in additional trials in the United States and a non-inferiority trial in Australia in which it is being compared head-to-head with the smoking cessation aid varenicline. It has also been used entheogenically via mescalbeans by some Native American groups, historically in the Rio Grande Valley predating even peyote.

<span class="mw-page-title-main">Drug</span> Substance having effect(s) on the body of an individual

A drug is any chemical substance other than a nutrient or an essential dietary ingredient, which, when administered to a living organism, produces a biological effect. Consumption of drugs can be via inhalation, injection, smoking, ingestion, absorption via a patch on the skin, suppository, or dissolution under the tongue.

<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 species in the Lophophora genus. It is endemic to Mexico in the outskirts of Querétaro. This species contains zero to trace amounts of mescaline. Instead, pellotine is the principal alkaloid - the psychoactive effects of which are comparatively minimal. The species name diffusa refers to the flat tubercles that are outspread without the plant having prominent ribs.

<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.

<i>Boerhavia diffusa</i> Species of flowering plant

Boerhavia diffusa is a species of flowering plant in the four o'clock family which is commonly known as punarnava, red spiderling, spreading hogweed, or tarvine. It is taken in herbal medicine for pain relief and other uses. The leaves of Boerhavia diffusa are often used as a green vegetable in many parts of India.

<span class="mw-page-title-main">Psychoactive cactus</span> Cactus containing psychoactive chemicals

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">Anhalamine</span> Chemical compound

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

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

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

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

<span class="mw-page-title-main">Mitragynine</span> Opioid analgesic compound

Mitragynine is an indole-based alkaloid and the most abundant active alkaloid in the Southeast Asian plant Mitragyna speciosa, commonly known as kratom. The total alkaloid concentration in dried leaves ranges from 0.5 to 1.5%. In Thai varieties, mitragynine is the most abundant component, while 7-hydroxymitragynine is a minor constituent. In Malaysian kratom varieties, mitragynine is present at lower concentration. Such preparations are orally consumed and typically involve dried kratom leaves which are brewed into tea or ground and placed into capsules. Mitragynine consumption for medicinal and recreational purposes dates back centuries, although early use was primarily limited to Southeast Asian countries such as Indonesia and Thailand, where the plant grows indigenously. Recently, mitragynine use has spread throughout Europe and the Americas as both a recreational and medicinal drug. While research into the effects of kratom have begun to emerge, investigations on the active compound mitragynine are less common.

<span class="mw-page-title-main">Peter A. G. M. De Smet</span> Ethnopharmacologist

Peter A.G.M. De Smet is a retired drug information pharmacist and clinical pharmacologist, emeritus professor of pharmaceutical patient care, and lyricist. He is still active as an ethnopharmacological and ethnomedical researcher.

Cactus alkaloids are alkaloids that occur in cactus. Structurally, they are tetrahydroisoquinolines and phenylethylamines.

References

  1. Gabermann, V (1978). "Estimation of mescaline and pellotine in Lophophora coulter plants (Cactaceae) by means of the oscillographic polarography". Biokhimiia (Moscow, Russia). 43 (2): 246–51. PMID   647075.
  2. Chan, Camilla B.; Poulie, Christian B. M.; Wismann, Simon S.; Soelberg, Jens; Kristensen, Jesper L. (27 August 2021). "The Alkaloids from Lophophora diffusa and Other "False Peyotes"". Journal of Natural Products. 84 (8): 2398–2407. doi:10.1021/acs.jnatprod.1c00381. PMID   34264089. S2CID   235907705.
  3. 1 2 3 Jones, Peter (2007). "The American Indian Church and its sacramental use of peyote: A review for professionals in the mental-health arena". Mental Health, Religion & Culture. 8 (4): 277–290. doi:10.1080/13674670412331304348. S2CID   144932041.
  4. Heffter, Arthur (1894). "Ueber Pellote". Archiv für Experimentelle Pathologie und Pharmakologie. 34 (1–2): 65–86. doi:10.1007/bf01864855. S2CID   28789116.
  5. El-Seedi, Hesham R.; Smet, Peter A. G. M. De; Beck, Olof; Possnert, Göran; Bruhn, Jan G. (2005-10-03). "Prehistoric peyote use: Alkaloid analysis and radiocarbon dating of archaeological specimens of Lophophora from Texas". Journal of Ethnopharmacology. 101 (1): 238–242. doi:10.1016/j.jep.2005.04.022. ISSN   0378-8741. PMID   15990261.