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Late 8th Century Burial site in N. Chile includes bag with snuffing paraphernalia and snuff remnants containing DMT, 5-MeO-DMT, and bufotenin. Other sites include seeds of Anadenanthera spp.   
1496 Friar Ramon Pane documented the use of a psychoactive snuff called cohoba/yopo among the Taino who inhabited the island of Hispaniola Haiti/Dominican Republic. It is now agreed that cohoba/yopo was almost certainly made from Anadenanthera peregrina, which has been reported to contain N,N-DMT, 5-MeO-DMT, and bufotenin. 1   [Details]
1560 Indians along the Rio Guaviare in Colombia take yopo along with tobacco.   
16th - 19th Century Cohoba snuff from the yopo tree used by natives of Columbia and surrounding areas.   
1936 5-MeO-DMT is first synthesized [Disputed] 2, 3   [Details]
1959 5-MeO-DMT is identified for the first time as a naturally occurring product, having been detected in the plant Dictyloma incanescens. 4  
1968 5-MeO-DMT is found in the venom of the Bufo alvarius toad.   
1971-1987 Beginning around 1971 and continuing through the late 1980s, 5-MeO-DMT was discretely available as a sacrament to members of the Church of the Tree of Life through the Inner Center. Additional legal psychoactives were also available. After 1987, the Inner Center also began providing their sacraments to members of some other religious groups. 5, 6, 7   [Details]
1970-1990 There is some recreational use of 5-MeO-DMT, though the pure material is rare and difficult to come by. Smoking of Bufo toad venom and limited availability on parsley through the Church of the Tree of Life are probably the most common forms of 5-MeO-DMT ingested in the U.S. during this period.   
c. 1992 5-MeO-DMT becomes available commercially through mail-order.   
Jan 19, 2011 5-MeO-DMT becomes Schedule I in the U.S. 8   [Details] [More Info]

  1.   Ott J. Shamanic Snuffs or Entheogenic Errhines. Entheobotanica, 2001.
  2.   Hoshino T, Shimodaira K. 1936. "Über die Synthese des Bufotenin-Methyl-Äthers (5-Methoxy-N-Dimethyl-Tryptamin) und Bufotenins. Synthesen in der Indol-Gruppe. XV". Bulletin of the Chemical Society of Japan. 11:221-4.
  3.   "Smoking Toad". The New York Times Magazine. Jun 5, 1994;48-9.
  4.   Pachter IJ, et al. "Indole alkaloids of Acer saccharinum, Dictyloma incanescens, Pipdenia colubrina, and Mimosa hostilis". J Organic Chem. 24:1285-1287.
  5.   Comments on DEA 331 PROPOSED RULE: Schedules of Controlled Substances: Placement of 5-Methoxy-N,N-Dimethyltryptamine Into Schedule I of the Controlled Substances Act
  6.   Inner Center. 5-MeO-DMT Order Blank. 1987. Unpublished Erowid copy.
  7.   Inner Center. Sacramental Status report. 1987. Unpublished Erowid copy.
  8.   Federal Register. December 20, 2010. 75(243).