Pellotine

Overview

Pellotine, also known as peyotline or N-methylanhalonidine, is a tetrahydroisoquinoline alkaloid found in Lophophora species, in particular Lophophora diffusa (false peyote) and to a much lesser extent Lophophora williamsii (peyote). It produces sedative and hypnotic effects and may contribute to the non-hallucinogenic effects of peyote. The drug was once marketed for medical use as a hypnotic in the 1890s, but was abandoned in favor of cheaper barbiturates in the 1900s. Pellotine has also been sold online on chemical trading platforms in modern times.[1–7] WP

Drug class

Serotonin 5-HT6 receptor weak partial agonist Serotonin 5-HT7 receptor inverse agonist Serotonin 5-HT1D receptor ligand Sedative Hypnotic WP

From the Wikipedia article's infobox.

Uses, dosage and effects

Use and effects

Pellotine has been studied in humans and found to produce hypnotic effects in clinical studies. When injected subcutaneously to humans, participants have reported drowsiness and a desire not to exert any physical or mental effort. It is also reported to lower blood pressure and heart rate. Pellotine produced no hallucinogenic effects in humans at doses of up to 240 mg. However, it has been reported to have a calming or sedative effect instead. On the other hand, one single study reported that pellotine produced hallucinations at a dose of 300 mg.[1][2][4][6][8–12] WP

Risks and side effects

Side effects

Side effects of pellotine include dizziness, nausea, vertigo, and vomiting.[4] WP

Pharmacology

Pharmacodynamics

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. It also showed weak affinity for other serotonin receptors, including for the serotonin 5-HT2A receptor (59.9% binding inhibition at 10 μM). In rodents, pellotine dose-dependently produces hypolocomotion, inhibits REM sleep, and promotes sleep fragmentation. The hypnotic effects of pellotine may be mediated by interactions with serotonin receptors. Doses of 8 to 10 mg of isolated pellotine are known to cause convulsions in frogs.[13][14][15] WP

History

History

Native inhabitants of north-eastern Mexico around 810 to 1070 CE (according to carbon dating) are thought to have used a number of "mescal buttons" (cacti of the genus Lophophora) 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.[16] WP

Arthur Heffter isolated pellotine from a Lophophora, most likely Lophophora diffusa, and described it in the scientific literature in 1894. It was the first alkaloid he isolated from Lophophora. Through self-experiments, Heffter found that pellotine produced marked but short-lasting hypnotic effects. In contrast to mescaline, which he discovered later, pellotine produced no hallucinogenic effects even at high doses.[1][2][17] WP

Subsequent to its discovery by Heffter, pellotine was studied as a hypnotic in several hundred patients in Europe and was manufactured and sold as a sleep aid by Boehringer und Soun (Boehringer and Sons) in Germany in the 1890s. However, it was abandoned after the barbiturates were developed and introduced in the 1900s and 1910s. This was related to these synthetic compounds being inexpensive to make, whereas pellotine required costly and tedious isolation from peyote that it made it impractical. In addition, pellotine was said to be not the most reliable or consistent sleep aid, and its effects were quite short-lived.[2][4][18] WP

Legal status

Names

Pellotine and peyotine are sometimes confused.[1] WP

Chemistry

Formula

C13H19NO3 PC

Molar mass (g/mol)

237.29 PC

IUPAC name (computed by PubChem)

6,7-dimethoxy-1,2-dimethyl-3,4-dihydro-1H-isoquinolin-8-ol PC

SMILES

CC1C2=C(C(=C(C=C2CCN1C)OC)OC)O PC

InChIKey

NKHMWHLJHODBEP-UHFFFAOYSA-N PC

PubChem CID

65742

IUPAC name

6,7-dimethoxy-1,2-dimethyl-3,4-dihydro-1H-isoquinolin-8-ol WP

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Journal / agency Bruhn JG, Holmstedt B. Early peyote research an interdisciplinary study. Economic Botany. 1973. doi:10.1007/BF02862854
2. Journal / agency Daniel M. Perrine. Visions of the Night Western Medicine Meets Peyote 1887-1899. The Heffter Review of Psychedelic Research. 2001
3. Journal / agency Chan CB, Poulie CB, Wismann SS, Soelberg J, Kristensen JL. The Alkaloids from Lophophora diffusa and Other "False Peyotes". Journal of Natural Products. August 2021. doi:10.1021/acs.jnatprod.1c00381 · PMID 34264089
4. Journal / agency Doesburg-van Kleffens M, Zimmermann-Klemd AM, Gründemann C. An Overview on the Hallucinogenic Peyote and Its Alkaloid Mescaline: The Importance of Context, Ceremony and Culture. Molecules. December 2023. doi:10.3390/molecules28247942 · PMID 38138432 · PMC10746114
5. Journal / agency Gabermann V. Estimation of mescaline and pellotine in Lophophora coulter plants (Cactaceae) by means of the oscillographic polarography. Biokhimiia. February 1978. PMID 647075
6. Journal / agency Jones P. The American Indian Church and its sacramental use of peyote: A review for professionals in the mental-health arena. Mental Health, Religion & Culture. 2007. doi:10.1080/13674670412331304348
7. Other AIPSIN. Пеллотин (Pellotine)
8. Journal / agency Cassels BK. Alkaloids of the Cactaceae — The Classics. Natural Product Communications. 2019. doi:10.1177/1934578X1901400123
9. Journal / agency Shulgin AT. Mescaline: the chemistry and pharmacology of its analogs. Lloydia. March 1973. PMID 4576313
10. Journal / agency Mangner TJ. Potential Psychotomimetic Antagonists. N,n -diethyl-1-methyl-3-aryl-1, 2, 5, 6-tetrahydropyridine-5-carboxamides. 1978. doi:10.7302/11268
11. Other Keeper Trout & friends. Trout's Notes on The Cactus Alkaloids Nomenclature, Physical properties, Pharmacology & Occurrences (Sacred Cacti Fourth Edition, Part C: Cactus Chemistry: Section 1). 2013
12. Journal / agency Robles C, Gomez Robleda J. Trabajo inicial acerca de la accion fisiologica del clorhidrato de peyotina. Anales del Instituto de Biología, UNAM. 1931
13. Journal / agency 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. In Vitro and In Vivo Evaluation of Pellotine: A Hypnotic Lophophora Alkaloid. ACS Pharmacology & Translational Science. October 2023. doi:10.1021/acsptsci.3c00142 · PMID 37854625 · PMC10580395
14. Journal / agency Chan CB, Pottie E, Simon IA, Rossebø AG, Herth MM, Harpsøe K, Kristensen JL, Stove CP, Poulie CB. Synthesis, Pharmacological Characterization, and Binding Mode Analysis of 8-Hydroxy-Tetrahydroisoquinolines as 5-HT7 Receptor Inverse Agonists. ACS Chemical Neuroscience. February 2025. doi:10.1021/acschemneuro.4c00667 · PMID 39836645
15. Journal / agency Heffter A. Ueber Pellote. Archiv für Experimentelle Pathologie und Pharmakologie. 1894. doi:10.1007/bf01864855
16. Journal / agency El-Seedi HR, De Smet PA, Beck O, Possnert G, Bruhn JG. Prehistoric peyote use: alkaloid analysis and radiocarbon dating of archaeological specimens of Lophophora from Texas. Journal of Ethnopharmacology. October 2005. doi:10.1016/j.jep.2005.04.022 · PMID 15990261
17. Journal / agency Heffter A. Ueber Pellote: Ein Beitrag zur pharmakologischen Kenntniss der Cacteen. Archiv für Experimentelle Pathologie und Pharmakologie. 1894. doi:10.1007/BF01864855
18. Journal / agency Dinis-Oliveira RJ, Pereira CL, da Silva DD. Pharmacokinetic and Pharmacodynamic Aspects of Peyote and Mescaline: Clinical and Forensic Repercussions. Curr Mol Pharmacol. 2019. doi:10.2174/1874467211666181010154139 · PMID 30318013 · PMC6864602

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