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Pellotine

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Pellotine
Names
Systematic IUPAC name 6,7-Dimethoxy-1,2-dimethyl-3,4-dihydro-1H-isoquinolin-8-ol
Other names Peyotline; N-Methylanhalonidine
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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,5-6H2,1-4H3Key: NKHMWHLJHODBEP-UHFFFAOYSA-N
SMILES
  • CC1C2=C(C(=C(C=C2CCN1C)OC)OC)O
Properties
Chemical formula C13H19NO3
Molar mass 237.299 g·mol
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 , 100 kPa). Infobox references
Chemical compound

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

Psychological and physiological effects

8-10 mg of isolated pellotine is known to cause convulsions in frogs. 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. It is also reported to lower blood pressure and heart rate.

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.

See also

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. ^ 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.
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