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Pellotine

From Wikipedia, the free encyclopedia
Not to be confused withpeyotine.
This articleneeds morereliable medical references forverification or relies too heavily onprimary sources. Please review the contents of the article andadd the appropriate references if you can. Unsourced or poorly sourced material may be challenged andremoved.Find sources: "Pellotine" – news ·newspapers ·books ·scholar ·JSTOR(April 2019)
Pellotine
Names
Systematic IUPAC name
6,7-Dimethoxy-1,2-dimethyl-3,4-dihydro-1H-isoquinolin-8-ol
Other names
Peyotline;N-Methylanhalonidine; 8-Hydroxy-6,7-dimethoxy-1,2-dimethyl-1,2,3,4-tetrahydroisoquinoline
Identifiers
3D model (JSmol)
ChemSpider
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 mass237.299 g·mol−1
Melting point110 to 113
Hazards
Lethal dose or concentration (LD, LC):
10 mg/kg (intravenous, dog)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Pellotine, also known aspeyotline orN-methylanhalonidine, is atetrahydroisoquinolinealkaloid found inLophophora species, in particularL. diffusa.[1][2][3] It is the second most common alkaloid found inLophophora williamsii (peyote).[1] Pellotine is slightlysedative, and has been used by Native Americans as a constituent of peyote for sacramental purposes.[1][4] It was reportedly once marketed for use as asedative.[1]

Pharmacology and effects

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Doses of 8 to 10 mg of isolated pellotine are known to causeconvulsions in frogs.[5] Wheninjected subcutaneously to humans, participants have reporteddrowsiness and a desire not to exert any physical or mental effort, with one study reporting it to havehypnotic effects.[4][1][6] It is also reported tolower blood pressure andheart rate.[4] Pellotine produced nohallucinogenic effects in humans at doses of up to 250 mg.[6][7] However, it has been reported to have acalming orsedative effect instead.[6][7]

Pellotine has been identified as aselective andpotentserotonin5-HT6 receptor weakpartial agonist, serotonin5-HT7 receptorinverse agonist, and serotonin5-HT1D receptorligand.[8][9] In rodents, pellotinedose-dependently produceshypolocomotion, inhibitsREM sleep, and promotessleep fragmentation.[8] The hypnotic effects of pellotine may be mediated by interactions withserotonin receptors.[8]

Side effects of pellotine includedizziness,nausea,vertigo, andvomiting.[1]

Ancient use

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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) containingmescaline, pellotine, and other related alkaloids. While it is known that thecytisine-containing "mescal beans" were at least ornamental, it is unclear whether "mescal buttons" were ornamental or used for their psychoactive effects.[10]

See also

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References

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  1. ^abcdefDoesburg-van Kleffens M, Zimmermann-Klemd AM, Gründemann C (December 2023)."An Overview on the Hallucinogenic Peyote and Its Alkaloid Mescaline: The Importance of Context, Ceremony and Culture".Molecules.28 (24): 7942.doi:10.3390/molecules28247942.PMC 10746114.PMID 38138432.
  2. ^Gabermann, V (1978). "Estimation of mescaline and pellotine inLophophora coulter plants (Cactaceae) by means of the oscillographic polarography".Biokhimiia (Moscow, Russia).43 (2):246–51.PMID 647075.
  3. ^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.Bibcode:2021JNAtP..84.2398C.doi:10.1021/acs.jnatprod.1c00381.PMID 34264089.S2CID 235907705.
  4. ^abcJones, 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.
  5. ^Heffter, Arthur (1894)."Ueber Pellote".Archiv für Experimentelle Pathologie und Pharmakologie.34 (1–2):65–86.doi:10.1007/bf01864855.S2CID 28789116.
  6. ^abcShulgin AT (March 1973)."Mescaline: the chemistry and pharmacology of its analogs".Lloydia.36 (1):46–58.PMID 4576313.The pharmacological action of peyotline in human subjects is one of calming or sedation, rather than that of a hallucinogen. Jolly (14) has reported the production of an uneventful sleep in patients with a dosage of SO mg. At levels of as much as 240 mg (total dosage) there are no indications of sensory distortions (5). There is a dizziness and a generalized tiredness that undergoes a gentle transition into sleep. This latter quantity of drug is greater than that which would be encountered in a single dosage unit of peyote. It is certainly possible that peyotline could contribute to the pharmacological picture associated with peyote as this sedative action is noted at levels that might well be encountered in the total cactus. At low levels in man (15-30 mg) there has been described a calming effect, without overt hypnosis (14).
  7. ^abMangner TJ (1978).Potential Psychotomimetic Antagonists. N,n -diethyl-1-methyl-3-aryl-1, 2, 5, 6-tetrahydropyridine-5-carboxamides (Ph.D. thesis). University of Michigan.doi:10.7302/11268. Archived fromthe original on 30 March 2025.In addition to compounds strictly related to mescaline just described, L. williamsii also contains at least 23 variously substituted tetrahydroisoquinolines,95 of which four have been clinically tested. The two phenolic tetrahydroisoquinolines peyotline (63a) and anhalonidine (63b) were found to produce no sensory distortions, characteristic of the effects of mescaline, at doses of up to 250 mg.98 These compounds appear to induce a calming or sedative effect rather than a psychotomimetic one. Two methylenedioxy tetrahydroisoquinolines, lophophorine (64a) and anhalonine (64b), were also found to lack any psychotomimetic-type effects.98
  8. ^abcPoulie CB, Chan CB, Parka A, Lettorp M, Vos J, Raaschou A, Pottie E, Bundgaard MS, Sørensen LM, Cecchi CR, Märcher-Rørsted E, Bach A, Herth MM, Decker A, Jensen AA, Elfving B, Kretschmann AC, Stove CP, Kohlmeier KA, Cornett C, Janfelt C, Kornum BR, Kristensen JL (October 2023)."In Vitro and In Vivo Evaluation of Pellotine: A Hypnotic Lophophora Alkaloid".ACS Pharmacol Transl Sci.6 (10):1492–1507.doi:10.1021/acsptsci.3c00142.PMC 10580395.PMID 37854625.
  9. ^Chan CB, Pottie E, Simon IA, Rossebø AG, Herth MM, Harpsøe K, Kristensen JL, Stove CP, Poulie CB (February 2025). "Synthesis, Pharmacological Characterization, and Binding Mode Analysis of 8-Hydroxy-Tetrahydroisoquinolines as 5-HT7 Receptor Inverse Agonists".ACS Chem Neurosci.16 (3):439–451.doi:10.1021/acschemneuro.4c00667.PMID 39836645.
  10. ^El-Seedi, Hesham R.;De Smet, Peter A. G. M.; Beck, Olof; Possnert, Göran; Bruhn, Jan G. (2005-10-03). "Prehistoric peyote use: Alkaloid analysis and radiocarbon dating of archaeological specimens ofLophophora from Texas".Journal of Ethnopharmacology.101 (1):238–242.doi:10.1016/j.jep.2005.04.022.ISSN 0378-8741.PMID 15990261.

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