Pellotine
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| Names | |
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| 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
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C13H19NO3 | |
| Molar mass | 237.299 g·mol−1 |
| Melting point | 110 to 113 |
| Hazards | |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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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).
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Pellotine, also known as peyotline or N-methylanhalonidine, is a tetrahydroisoquinoline alkaloid found in Lophophora species, in particular L. diffusa.[1][2][3] It is the second most common alkaloid found in Lophophora williamsii (peyote).[1] Pellotine is slightly sedative, 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 a sedative.[1]
Pharmacology and effects
[edit]Doses of 8 to 10 mg of isolated pellotine are known to cause convulsions in frogs.[5] 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.[4][1][6] It is also reported to lower blood pressure and heart rate.[4] Pellotine produced no hallucinogenic effects in humans at doses of up to 250 mg.[6][7] However, it has been reported to have a calming or sedative effect instead.[6][7]
Pellotine has been identified as a selective and potent serotonin 5-HT6 receptor weak partial agonist, serotonin 5-HT7 receptor inverse agonist, and serotonin 5-HT1D receptor ligand.[8][9] In rodents, pellotine dose-dependently produces hypolocomotion, inhibits REM sleep, and promotes sleep fragmentation.[8] The hypnotic effects of pellotine may be mediated by interactions with serotonin receptors.[8]
Side effects of pellotine include dizziness, nausea, vertigo, and vomiting.[1]
Ancient use
[edit]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.[10]
See also
[edit]References
[edit]- ^ a b c d e f Doesburg-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.
- ^ 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.
- ^ 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.
- ^ a b c 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.
- ^ Heffter, Arthur (1894). "Ueber Pellote". Archiv für Experimentelle Pathologie und Pharmakologie. 34 (1–2): 65–86. doi:10.1007/bf01864855. S2CID 28789116.
- ^ a b c Shulgin 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).
- ^ a b Mangner 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 from the 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
- ^ a b c Poulie 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.
- ^ 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.
- ^ 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.