Analytical profiles of Methcathinone Related Compounds
The compounds
O 2-amino-1-phenylpropan-1-one CH3 A Cathinone Molecular Formula = C9H11NO Formula Weight = 149.18974 NH2
O 2-(methylamino)-1-phenylpropan-1-one CH3 B Methcathinone Molecular Formula = C10H13NO Formula Weight = 163.21632 HN CH3
O 2-(dimethylamino)-1-phenylpropan-1-one CH3 C Dimethylcathinone Molecular Formula = C11H15NO Formula Weight = 177.2429 N H3C CH3
O 2-(ethylamino)-1-phenylpropan-1-one CH3 D Ethcathinone* Molecular Formula = C11H15NO Formula Weight = 177.2429 HN CH3
O 2-(methylamino)-1-(4-methylphenyl)propan-1- 4-Methyl- one CH3 E methcathinone* Molecular Formula = C H NO (Mephedrone) 11 15 HN Formula Weight = 177.2429 CH H3C 3
F O 1-(2-fluorophenyl)-2-(methylamino)propan-1- one 2- Fluoro- CH3 F methcathinone Molecular Formula = C H FNO 10 12 HN Formula Weight = 181.2067832 CH3
Page 1 of 11 O 1-(3-fluorophenyl)-2-(methylamino)propan-1- 3- Fluoro- one F CH3 G methcathinone* Molecular Formula = C10H12FNO Formula Weight = 181.2067832 HN CH3
3- Fluoro-iso- CH3 methcathinone* 1-(3-fluorophenyl)-1-(methylamino)propan-2- HN (by-product of one H FO synthesis of 3- Molecular Formula = C10H12FNO fluoro- Formula Weight = 181.2067832 CH3 methcathinone)
O 1-(4-fluorophenyl)-2-(methylamino)propan-1- one 4- Fluoro- CH3 I methcathinone Molecular Formula = C H FNO 10 12 HN Formula Weight = 181.2067832 F CH3
1-(4-methoxyphenyl)-2-(methylamino)butan-1- O one 4-methoxy- CH J methylaminobutyrone 3 Molecular Formula = C12H17NO2 H3C HN Formula Weight = 207.26888 O CH3
O 1-(4-methoxyphenyl)-2-(methylamino)propan- 4-Methoxy- CH3 methcathinone 1-one K (Methedrone, bk- Molecular Formula = C11H15NO2 H3C HN PMMA) Formula Weight = 193.2423 O CH3
* Compounds seen in UK products Background and products
Cathinone is a pharmacologically active (stimulant) alkaloid extracted from the leaves of the Khat plant (Catha edulis). Khat leaves are chewed recreationally in parts of East Africa to produce a mild high much like caffeine from tea and coffee. Human metabolism of cathinone produces cathine and norpseudoephedrine, that are structurally similar to amfetamine and adrenaline. Cathine is one of the optical isomers of phenylpropanolamine, an appetite suppressant and nasal decongestant.
Cathinone and methcathinone are controlled under the UK Misuse of Drugs Act 1971; cathinone is Class C listed in Part III of schedule 2; methcathinone is Class B listed in Part II of Schedule 2.
Page 2 of 11 Derivatives such as ethcathinone, 4-methylmethcathinone and the fluoromethcathinones, which are not controlled under current law, have been produced and marketed to satisfy the growing dance-scene drug culture. They are promoted as safe alternatives to ecstasy presumably to individuals who want to stay within the law. However, the safety of these compounds has not been evaluated and they are often sold in products where the contents are not accurately declared. Seven products were originally purchased from the BioRepublik website, sold as ‘legal alternatives to ecstasy’. They were described as ‘Neorganics’ and described two generations of products. The first being ‘Neo-Dove 1’– “a well known, best seller, unique supplement designed especially to be the ultimate influence”. ‘Neo-Dove 2’ is the next generation – “a superior supplement that will make you feel vital and happy”. The other products purchased are listed below. The price of all Neorganics on the BioRepublik site was €28 for pack of four capsules or a multiple pack of up to 36 capsules could be purchased for €183. We took advantage of a special offer and purchased two capsules of each for €99.
14 capsules were received; Ten (two of each colour) in a large pot labelled ‘Multi Vitamin’ and four white capsules in a smaller pot, with same outer label. It is unknown which capsule is which.
Sub Coca
Further products obtained from the Future Legals website; High Spirit, S.C.D and Lift Neorganics were also analysed.
A product called ‘Charge’ was purchased from the popular legal high website Everyonedoesit.com. It was a powder and was described as ‘novelty bath salts’
Page 3 of 11
Product Contents
Product TICTAC No. Source Contents
BioRepublik.com Ethcathinone + 24198 (Large pot) 4-Methylmethcathinone BioRepublik.com Ethcathinone + 24199 (Large pot) 4-Methylmethcathinone
BioRepublik.com 24200 3-Fluoromethcathinone (Large pot)
BioRepublik.com 24201 3-Fluoromethcathinone (Large pot)
BioRepublik.com Ethcathinone + 24202 (Small pot) 4-Methylmethcathinone BioRepublik.com 24203 3-Fluoromethcathinone (Large pot) BioRepublik.com Ethcathinone + 24388 (Small pot) 4-Methylmethcathinone BioRepublik.com Ethcathinone + 24180 (Small pot) 4-Methylmethcathinone
BioRepublik.com Ethcathinone + 24192 (Small pot) 4-Methylmethcathinone
Everyonedoesit 24197 3-Fluoromethcathinone .com 24095 Future Legals 3-Fluoromethcathinone
24096 Future Legals 3-Fluoromethcathinone
24093 Future Legals 3-Fluoromethcathinone
Page 4 of 11 GC/MS
Samples were analysed on a Shimadzu QP2010 gas chromatograph mass spectrometer with an HP5MS column (30m x 0.25mm, 0.50µm).
Injection temperature 225°C Injection mode Splitless Carrier gas Helium Flow rate 1.0 ml/min Pressure 9.5 psi Ion source temperature 200°C Interface temperature 250°C
Column oven temperature programme: Rate Final temperature Time - 140°C Hold 6.1 minutes 20.00°C/min 200°C Until 9.1 minutes 40.00°C/min 280°C Until 12.2 minutes
Page 5 of 11 Chromatogram:-
(x1,000,000) 1.0 Scan:TIC (1.00) IS-2
0.9 D 11.844 K 0.8 7.442
0.7 9.966 E 0.6 C IS-1
0.5 8.304 7.150 4.565 0.4 H I B G J
0.3 5.971 6.388 5.293 5.848
0.2 10.406
0.1
0.0 5.0 6.0 7.0 8.0 9.0 10.0 11.0 12.0
Retention time ID Compound Name Abbreviations (mins.) IS-1 Quinoline IS-1 4.565 Methcathinone B MC 6.388 (Ephedrone) C Dimethyl-methcathinone DMMC 7.150 Ethcathinone D EC 7.442 (Ethylpropion) 4-MethylMethcathinone E 4-MMC 8.304 (Mephedrone) Separate F 2-Fluoromethcathinone 2-FMC chromatogram (see below) G 3-Fluoromethcathinone 3-FMC 5.848 H 3-Fluoroisomethcathinone 3-FisoMC 5.293 I 4-Fluoromethcathinone 4-FMC 5.971
J 4-methoxy-methylaminobutyrone 4-MAB 10.406 K 4-methoxy-methcathinone BK-PMMA 9.966 (Methedrone) IS-2 Pyribenzamine IS-2 11.844
Page 6 of 11
(B) METHCATHINONE %
100.0 58
75.0
50.0
25.0
56 77 42 105 0.0 79 91 115132 148 161 179 197207 223 234 245 50 100 150 200 250
(C) DIMETHYLCATHINONE %
100.0 72
75.0
50.0
25.0
44 105 0.0 134 177223256 331 355 382 100 200 300 400
(D) ETHCATHINONE %
100.0 72
75.0
50.0 44
25.0
51 91 105 132 161 0.0 6379 117 146 176197 208 229239 249 50 100 150 200 250
Page 7 of 11 (E) 4-METHYLMETHCATHINONE %
100.0 58
75.0
50.0
25.0
56 42 91 119 0.0 78105 147158 177 193205 219 250 50 100 150 200 250
(F) 2-FLUOROMETHCATHINONE (Chromatogram and Mass Spectra)
(x1,000,000) Scan:TIC Separate chromatogram 1.25 SIM:TIC (1.00)
SIM:58.00 (1.00) 5.716 to show breakdown in SIM:72.00 (18.69) GC: 1.00 IS-1 4.598
0.75 8.646 2-FMC peak 1 5.716 2-FMC peak 2 8.646 IS-2………………9.660 0.50
9.660 4.598 0.25
0.00 5.0 6.0 7.0 8.0 9.0 10.0
2-FMC peak 1: %
100.0 58
75.0
50.0
25.0
42 59 75 95 123 0.0 94109 132 150 161 181191 207218 235 246 50 100 150 200 250
2-FMC peak 2: Page 8 of 11 %
100.0 161
91 75.0 132
50.0
77 42 118 25.0 51 146 65 105 89 144 0.0 183195209 226 236 50 100 150 200 250
(G) 3-FLUOROMETHCATHINONE %
100.0 58
75.0
50.0
25.0
42 75 95 59 91 123 161 0.0 146 181 195 216 230 50 100 150 200 250
(H) 3-FLUOROISOMETHCATHINONE BY-PRODUCT OF SYNTHESIS OF 3-FMC %
100.0 138
75.0 42
50.0
25.0
95 75 83 109 122 0.0 5057 149165 185197 207 239 249 50 100 150 200 250
Page 9 of 11 (I) 4-FLUOROMETHCATHINONE %
100.0 58
75.0
50.0
25.0
42 75 95 123 0.0 166186 221 246 279314 332 372 397 50 100 150 200 250 300 350 400
(J) 4-METHOXY-METHYLAMINOBUTYRONE %
100.0 72
75.0
50.0
25.0
42 57 92 135 0.0 79 107 121 147 163178 191 207 223 238 50.0 75.0 100.0 125.0 150.0 175.0 200.0 225.0 250.0 (K) 4-METHOXY-METHCATHINONE (METHEDRONE) %
100.0 58
75.0
50.0
25.0
77 42 59 92 107 135 0.0 121 147162178 193 207222 234 250 50 100 150 200 250 Page 10 of 11 Susannah Davies John Ramsey Roland Archer Nov 2009
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