Pellotine

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	83-14-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	59165;
PubChem CID	65742;
UNII	7RW0YY488A ;
CompTox Dashboard (EPA)	DTXSID50871560 ;
	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,5-6H2,1-4H3 Key: NKHMWHLJHODBEP-UHFFFAOYSA-N;
	SMILES CC1C2=C(C(=C(C=C2CCN1C)OC)OC)O;
Properties
Chemical formula	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). Infobox references

Pellotine is an alkaloid found in Lophophora species, in particular L. diffusa.^[1]^[2] Pellotine is slightly narcotic, and has been used by Native Americans as a constituent of peyote for sacramental purposes.^[3]

Psychological and physiological effects

8-10 mg of isolated pellotine is known to cause convulsions in frogs.^[4] 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.^[3] It is also reported to lower blood pressure and heart rate.^[3]

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.^[5]

References

^ 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. 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.
^ 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.

[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.

[:0-3] 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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[2]

[3]

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[5]

Psychological and physiological effects

Ancient use

See also

References