Ecstasy analogues found in cacti.
Human interest in psychoactive phenethylamines is known from the use of mescaline-containing cacti and designer drugs such as Ecstasy. From the alkaloid composition of cacti we hypothesized that substances resembling Ecstasy might occur naturally. In this article we show that lophophine, homopiperonylamine and lobivine are new minor constituents of two cactus species, Lophophora williamsii (peyote) and Trichocereus pachanoi (San Pedro). This is the first report of putatively psychoactive phenethylamines besides mescaline in these cacti. A search for further biosynthetic analogues may provide new insights into the structure-activity relationships of mescaline. An intriguing question is whether the new natural compounds can be called "designer drugs."
Bruhn
Jan G
JG
Division of Pharmacognosy, Department of Medicinal Chemistry, Uppsala University, Uppsala, Sweden.
El-Seedi
Hesham R
HR
Stephanson
Nikolai
N
Beck
Olof
O
Shulgin
Alexander T
AT
D015104:3,4-Methylenedioxyamphetamine / Q000031:analogs & derivatives* / Q000032:analysis; D029421:Cactaceae / Q000737:chemistry*; D006213:Hallucinogens / Q000032:analysis*; D006801:Humans; D018817:N-Methyl-3,4-methylenedioxyamphetamine / Q000031:analogs & derivatives*; D010627:Phenethylamines / Q000032:analysis*
D006213:Hallucinogens; C533576:N,N-dimethyl-3,4-methylenedioxyphenethylamine; D010627:Phenethylamines; C016575:3,4-methylenedioxyphenethylamine; D015104:3,4-Methylenedioxyamphetamine; D018817:N-Methyl-3,4-methylenedioxyamphetamine