Pellotine

Not to be confused with peyotine.

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]

Pellotine

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
CAS Number	83-14-7 Y
3D model (JSmol)	Interactive image
ChemSpider	59165
PubChem CID	65742
UNII	7RW0YY488A Y
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

Pharmacology and effects

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-HT_1D 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

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

• Substituted tetrahydroisoquinoline
• Anhalamine
• Anhalidine
• Anhalinine
• Anhalonidine
• Gigantine