Peyotine

Peyotine
Names
IUPAC name
8-Hydroxy-6,7-dimethoxy-1,2,2-trimethyl-1,2,3,4-tetrahydroisoquinolin-2-ium
Other names
8-Hydroxy-6,7-dimethoxy-1,2,2-trimethyl-1,2,3,4-tetrahydroisoquinoline; 8-Hydroxy-6,7-dimethoxy-1,2,2-trimethyl-THIQ
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • InChI=1S/C14H21NO3/c1-9-12-10(6-7-15(9,2)3)8-11(17-4)14(18-5)13(12)16/h8-9H,6-7H2,1-5H3/p+1/t9-/m0/s1
    Key: ZARLYMQBOSEMJI-VIFPVBQESA-O
  • RS: InChI=1S/C14H21NO3/c1-9-12-10(6-7-15(9,2)3)8-11(17-4)14(18-5)13(12)16/h8-9H,6-7H2,1-5H3/p+1
    Key: ZARLYMQBOSEMJI-UHFFFAOYSA-O
  • OC1=C2C(=CC(OC)=C1OC)CC[N+](C)(C)[C@H]2C
  • RS: COc1c(OC)cc2c(c1O)C(C)[N+](CC2)(C)C
Properties
C14H21NO3+
Molar mass 251.325 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Peyotine is a trace tetrahydroisoquinoline and quaternary alkaloid found in peyote (Lophophora williamsii). It is often confused with pellotine, its N-demethylated analogue, which has often been known by the same name as peyotine or by similar names like peyotina or peyotline. Peyotine was first described in the scientific literature by G. J. Kapadia and colleagues in 1968.

See also

References

  1. ↑ Menachery, Mary D.; Lavanier, Gregory L.; Wetherly, Mark L.; Guinaudeau, Hélène; Shamma, Maurice (1986). "Simple Isoquinoline Alkaloids". Journal of Natural Products. 49 (5): 745–778. Bibcode:1986JNAtP..49..745M. doi:10.1021/np50047a001. ISSN 0163-3864. Retrieved 20 May 2025.
  2. 1 2 https://bitnest.netfirms.com/external/TCA/198
  3. 1 2 Kapadia GJ, Shah NJ, Zalucky TB (February 1968). "Peyote alkaloids. II. Anhalotine, lophotine, and peyotine, the quaternary alkaloids of Lophophora williamsii". J Pharm Sci. 57 (2): 254–262. PMID 5641668.
  4. 1 2 Bruhn JG, Holmstedt B (1973). "Early peyote research an interdisciplinary study". Economic Botany. 28 (4): 353–390. doi:10.1007/BF02862854. ISSN 0013-0001. Pellotine 16 constitutes more than 90% of the alkaloid fraction of Lophophora diffusa. [...] 16 The name pellotine was given by Heffter (1894a) to the first alkaloid isolated by him from Anhalonium williamsii "pellote". But in Mexico "pellote" and "peyote" are pronounced in the same way. Both forms derive from the ancient Aztec word "peyotl", and Lewin (1894a) thus considered "peyotlin" to be a more correct name for the alkaloid. The name pellotine has, however, entered the literature and is now well established, although some authors have used the variant spelling "peyotine" (e.g. Anonymous, 1959) and, in Spanish, "peyotina" (e.g. Robles and Gómez Robleda, 1931). Notwithstanding, Kapadia et al. (1968) have given the name "peyotine" to the quaternary methyl derivative of pellotine, thus creating more confusion. Shulgin's reintroduction of Lewin's name "peyotline" for pellotine is also most unfortunate (Shulgin, 1973). Isopellotine was recently found in L. williamsii by Lundström (1972).