Raising awareness of new psychoactive substances: chemical analysis and in vitro toxicity screening of ‘legal high’ packages containing synthetic cathinones. ArchievesofToxicology. Araújo, A.M.; Valente, M.J.; Carvalho, M.; Dias da Silva, D.; Gaspar, H.; Carvalho, F.; Bastos, M.L. and Guedes de Pinho, P.. Correspondingauthor: Márcia Carvalho, REQUIMTE, Laboratório de Toxicologia, Departamento de Ciências Biológicas, Faculdade de Farmácia, Universidade do Porto, Porto, Portugal, – ElectronicSupplementary Material Table S2

Supplementary Table S2: NMR data of compounds in Methanol-d4: δC(carbon signal in ppm at 100MHz),δH(proton signal in ppm at 400MHz), m (multiplicity, s-singlet, d-doublet, dd-double doublet, t-triplet, q-quartet, m-multiplet, br-broad), J (coupling constant).The isopentedrone, 3-MEC and 4-APB are not included in this table since they are by-products of pentedrone, 4-MEC and 6-APB, respectively, and it has not been possible to obtain complete data through this methodology. These NMR data are similar to the previously reported data for pentedrone and buphedrone (Maheux and Copeland 2011; Westphal et al. 2012) in methanol-d4 and consistent with the data published for other compounds in different NMR solvent (Archer 2009; Brandt et al. 2010; Camilleri et al. 2010; Casale and Hays 2012; Casale and Hays 2011; Elliott et al. 2012; Jankovics et al. 2011; Kavanagh 2012;Locos and Reynolds 2012; McDermott et al. 2011; Rösner et al. 2005).

Pentedrone / Buphedrone / Ethcathinone / 4-MEC / Methedrone / Flephedrone / 4-fluoramphetamine
Position / δC / δH, m,
J (Hz) / δC / δH, m,
J (Hz) / δC / δH, m,
J (Hz) / δC / δH, m,
J (Hz) / δC / δH, m,
J (Hz) / δC, m,
J (Hz) / δH, m,
J (Hz) / δC, m,
J (Hz) / δH, m,
J (Hz)
1 / 196.7 / - / 196.6 / - / 197.1 / - / 196.5 / - / 195.3 / - / 195.7 / - / 40.9 / 2.81dd, 8.4, 13.7
3.00dd, 6.1, 13.7
2 / 64.6 / 5.24t, 5.3 / 65.3 / 5.27t, 5.3 / 59.2 / 5.24q, 7.2 / 59.1 / 5.17q, 7.2 / 60.3 / 5.11q, 7.2 / 60.6 / 5.19q, 7.2 / 18.2 / 1.26d, 6.7
3 / 33.4 / 1.99m / 24.4 / 2.06m/2.17m / 16.6 / 1.60d, 7.2 / 16.7 / 1.59d, 7.2 / 16.6 / 1.59d, 7.2 / 16.2 / 1.61d, 7.2
4 / 18.4 / 1.28m/1.39m / 8.4 / 0.89t, 7.6
5 / 14.1 / 0.89t, 7.3
1´ / 135.1 / - / 135.1 / - / 134.2 / - / 131.7 / - / 126.9 / - / 130.8d, 2.9 / - / 133.5d, 3.2 / -
2´ / 129.9 / 8.08d, 7.6 / 129.9 / 8.09d,7.5 / 130.0 / 8.09d,7.5 / 130.2 / 7.98d, 8.1 / 132.5 / 8.05d, 8.9 / 133.2d, 9.8 / 8.17dd, 5.4, 8.7 / 132.2d, 8.1 / 7.29dd, 5.5,8.7
3´ / 130.4 / 7.61t, 7.6 / 130.3 / 7.60t, 7.5 / 130.3 / 7.60t, 7.5 / 131.0 / 7.41d, 8.1 / 115.5 / 7.09d, 8.9 / 117.4d, 22.5 / 7.34t, 8.7 / 116.6d,21.7 / 7.09t, 8.7
4´ / 136.1 / 7.75t, 7.6 / 136.0 / 7.74t, 7.5 / 136.0 / 7.74t, 7.5 / 147.6 / - / 166.5 / - / 168.0d, 256.0 / - / 163.5d, 244.3 / -
5´ / 130.4 / 7.61t, 7.6 / 130.3 / 7.60t, 7.5 / 130.3 / 7.60t, 7.5 / 131.0 / 7.41d,8.1 / 115.5 / 7.09d, 8.9 / 117.4d, 22.5 / 7.34t, 8.7 / 116.6d,21.7 / 7.09t, 8.7
6´ / 129.9 / 8.08d, 7.6 / 129.9 / 8.09t, 7.5 / 130.0 / 8.09t, 7.5 / 130.2 / 7.98d, 8.1 / 132.5 / 8.05d, 8.9 / 133.2d, 9.8 / 8.17dd, 5.4, 8.7 / 132.2d, 8.1 / 7.29dd, 5.5,8.7
7´ / 21.8 / 2.45s / 56.3 / 3.90s
8´
1´´ / 32.6 / 2.76 / 32.5 / 2,77s / 42.4 / 3.16m / 42.4 / 3.09m/3.18m / 31.8 / 2.77s / 31.8 / 2.81s
2´´ / 11.8 / 1.40t, 7.3 / 11.8 / 1.37t, 7.2
3,4-DMMC / MDPV / Methylone / 6-APB / 6-APDB / Dimethocaine / AMT
Position / δC / δH, m,
J (Hz) / δC / δH, m,
J (Hz) / δC / δH, m,
J (Hz) / δC / δH, m,
J (Hz) / δC / δH, m,
J (Hz) / δC / δH, m,
J (Hz) / δC, m,
J (Hz) / δH, m,
J (Hz)
1 / 196.8 / - / 195.1 / - / 195.2 / - / 41.9 / 2. 92dd, 8.3, 13.6
3.09dd, 6.3, 13.6 / 41.7 / 2.74dd, 8.3, 13.4
2.91dd, 6.1, 13.4 / 168.1 / - / 109.9 / -
2 / 60.5 / 5.13q, 7.2 / 69.9 / 5.33t, 5.5 / 60.4 / 5.05q, 7.2 / 50.4 / 3.50m / 50.3 / 3.47m / 70.2 / 4.10s / 31.7 / 3.00dd, 7.6,14.4
3.09dd, 6.6, 14.4
3 / 16.5 / 1.58d, 7.2 / 33.8 / 2.03m / 16.7 / 1.59d, 7.2 / 18.4 / 1.27d, 6.9 / 18.3 / 1.25d, 6.6 / 36.3 / - / 49.6 / 3.58m
4 / 18.6 / 1,24m / 61.5 / 3.03s / 18.8 / 1.29d, 6.5
5 / 14.2 / 0,89t, 7.3 / 23.3 / 1.15s
6 / 132.1 / - / 23.3 / 1.15s
1´ / 130.8 / 7.83s / 130.3 / - / 128.6 / - / 124.7 / 7.14brd, 7.9 / 122.5 / 6.72d, 7.5 / 117.8 / 128.5 / -
2´ / 139.1 / - / 108.8 / 7.52d, 1.0 / 108.9 / 7.47d, 1.2 / 122.6 / 7.61d, 7.9 / 126.3 / 7.18d, 7.5 / 132.5 / 7.76d, 8.7 / 119.1 / 7.57d, 8.0
3´ / 146.2 / - / 150.4 / - / 150.2 / - / 128.1 / - / 127.8 / - / 114.4 / 6.66d, 8.7 / 120.1 / 7.04brt, 7.4
4´ / 131.4 / 7.35d, 7.9 / 155.3 / - / 154.9 / - / 156.7 / - / 162.1 / - / 155.1 / - / 122.7 / 7.12brt, 7.4
5´ / 127.8 / 7.79d, 7.9 / 109.5 / 7.02d, 8.2 / 109.5 / 7.00d, 8.2 / 113.0 / 7.45brs / 110.9 / 6.65s / 114.4 / 6.66d, 8.7 / 112.5 / 7.38d, 8.0
6´ / 19.74 / 2.36s / 127.6 / 7.78dd, 8.2,1.0 / 127.3 / 7.71dd, 1.2,8.2 / 133.8 / - / 137.3 / - / 132.5 / 7.76d, 8.7 / 138.2 / -
7´ / 20.24 / 2.36s / 104.1 / 6.13s / 104.0 / 6.11s / 107.4 / 6.83brs / 30.2 / 3,18t, 8.7 / 124.9 / 7.18s
8´ / 31.8 / 2.78s / 146.8 / 7.74d, 1.5 / 72.6 / 4.54t, 8.7
1´´ / 196.8 / - / 53.2
56.2 / 3.69m/3.41m
3.62m/3.06m / 31.8 / 2.79s / 51.7 / 3.12q
2´´ / 60.5 / 5.13q, 7.2 / 24.1 / 2.11m / 9.6 / 1.21t, 7.2