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Supplementary Information for Chemical evidence for the use of multiple psychotropic plants in a 1,000-year-old ritual bundle from South America Melanie J. Miller1,2, Juan Albarracin-Jordan3, Christine Moore4, José M. Capriles5 1Department of Anatomy, University of Otago, 270 Great King Street, Dunedin, 9016, New Zealand 2Archaeological Research Facility, University of California, Berkeley, 2251 College Ave, Berkeley, CA 94720 3Instituto de Investigaciones Antropológicas y Arqueológicas, Universidad Mayor de San Andrés, La Paz, Bolivia 4Immunalysis Corporation, 829 Towne Center Drive, Pomona, CA 91767 5Department of Anthropology, The Pennsylvania State University, 314 Carpenter Building, University Park, PA 16802 Corresponding Authors: Melanie J. Miller Email: [email protected] José M. Capriles Email: [email protected] This PDF file includes: Figs. S1 and S2 Tables S1 and S2 1 ww w .pnas.org/cgi/doi/10.1073/pnas.1902174116 Fig. S1. Horizonal plan of Cueva del Chileno showing the location of the ritual bundle (in brown, unit H) and other features such as the upper plastered floor (in red, across units A, B, F, G, H, J, K), large spherical ground stone (in grey with black outline, unit G), and human hair braids (in yellow, unit C). Fig. S2. Stratigraphic profiles from Unit H of Cueva del Chileno showing the vertical location of the ritual bundle (brown in East profile). 2 Table S1. Psychoactive plants of South America related to this study. Psychoactive Plant species of interest Growing Region(s) Compounds Bufotenine (and reports Anadenanthera colubrina; Brazil, Argentina, Peru, of trace amounts of N,N- Anadenanthera peregrina Bolivia, Paraguay DMT and 5-MeO-DMT) Tropical areas of northern Harmine, harmaline, Banisteriopsis caapi South America tetrahydroharmaline Psychotria viridis Amazonian lowlands N,N-DMT South America (diverse Cocaine, Erythroxylum coca climates, but mostly montane Benzoylecgonine (BZE), forest of the eastern Andes) and other alkaloids Andean highlands (but can Echinopsis pachanoi withstand dry and moist Mescaline environments) Table S2. Multiple reaction monitoring (MRM) transitions and optimized fragmentation voltages for compounds in analytical procedure using LC-MS/MS. Transition (m/z) Fragment Collision Compound (Precursor Ion > voltage (V) Energy (eV) Product Ion) 304 > 182 120 20 Cocaine 304 >82 120 25 D3-cocaine 307>185 120 20 Bufotenine 205 > 160 100 20 5-hydroxydimethytryptamine 205 > 58.4 100 20 5-methoxy- 219 > 174 100 20 dimethyltryptamine 219 > 130 100 20 Dimethyltryptamine (N,N- 189 > 144 120 20 DMT) 189 > 58 120 20 290 > 168 120 15 Benzoylecgonine (BZE) 290 > 105 120 15 D3-benzoylecgonine 293 > 171 120 20 355 > 212 100 20 Yohimbine 355 > 144 100 20 217 > 300 100 20 Tetrahydroharmine 217 > 188 100 20 215 > 200 100 30 Harmaline 215 > 172 100 10 213 > 198 120 20 Harmine 213 > 170 120 20 212 > 195 100 20 Mescaline 212 > 165 100 20 Psilocin 205 > 115 120 20 4-hydroxydimethyltryptamine 3 .

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