Pellotine
Chemical compound
From Wikipedia, the free encyclopedia
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][5] Pellotine has been sold online.[5]
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| 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) |
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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) |
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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Pharmacology and effects
Doses of 8 to 10 mg of isolated pellotine are known to cause convulsions in frogs.[6] 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][7] 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.[7][8] However, it has been reported to have a calming or sedative effect instead.[7][8]
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.[9][10] In rodents, pellotine dose-dependently produces hypolocomotion, inhibits REM sleep, and promotes sleep fragmentation.[9] The hypnotic effects of pellotine may be mediated by interactions with serotonin receptors.[9]
Side effects of pellotine include dizziness, nausea, vertigo, and vomiting.[1]
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.[11]