Analytical profiles of the beta keto amphetamines (bkMDMA, bkMDEA, and bkMBDB)

The compounds

2-methylamino-1-(3,4- A methylenedioxyphenyl)propan-1-one bkMDMA ‘Methylone’ C11H13NO3 fw 207.2

2-ethylamino-1-(3,4- B methylenedioxyphenyl)propan-1-one bkMDEA ‘Ethylone’ C12H15NO3 fw 221.3

2-methylamino-1-(3,4- C methylenedioxyphenyl)butan-1-one bkMBDB ‘Butylone’ C12H15NO3 fw 221.3

Methylone is a beta-keto analogue of MDMA (Ecstasy). It is also known as bk-MDMA, M1, or MDMCat. Methylone is more properly known as 3,4- methylenedioxymethcathinone and is related to methcathinone as MDMA is related to methamphetamine and MDA is to amphetamine. In spite of some substantial pharmacokinetic differences (its dopaminergic activity is far more pronounced relative to its serotonergic activity), methylone is an empathogen-like drug and a mild stimulant, producing effects similar to, yet less intense than MDMA.

Methylone in powder formulation has recently (2008) been found in an amnesty bin from a UK dance venue.

Ethylone is the cathinone analogue of MDEA. It is reported to be less potent than methylone and has only a short history of human use. bk-MBDB is also known as "butylone": however Butylone is a trademarked name for pentobarbitone. Bk-MBDB shares the same relationship to MBDB as methylone does to MDMA. The dosage range is not fully understood but seems to be lower than for MBDB. No formal research has been published on this substance, and nothing is known of its pharmacological profile or toxicology, although anecdotal reports indicate it is subjectively similar to but milder than methylone. Bk-MBDB has been found in tablets sold by UK based legal-high internet sites supplied by ‘London Underground’.

“Legal high” tablets such as those shown above are known to be inconsistent in their contents. It is possible that the same tablets bought at different times from the same site may differ in their contents.

GC/MS

Samples were analysed on a Shimadzu QP2010 gas chromatograph mass spectrometer with an HP5MS column (30m x 0.25mm, 0.50µm).

Column oven temperature 80°C 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 Hold time - 80°C 4 minutes 40.00°C/min 280°C 8 minutes 40.00°C/min 290°C 11.5 minutes

Chromatogram:-

(x1,000,000) 3.25 TIC IS-2 3.00 A 13.743 2.75 B 12.145 12.456 2.50 2.25 IS-1 2.00 C 12.546

1.75 8.819

1.50

1.25

1.00

0.75

0.50

0.25

0.00 8.0 9.0 10.0 11.0 12.0 13.0 14.0 15.0

Retention time ID Compound Name Abbreviations (mins.) IS-1 Quinoline IS-1 8.819 2-methylamino-1-(3,4- A methylenedioxyphenyl)propan-1-one bkMDMA 12.145 ‘Methylone’ 2-ethylamino-1-(3,4- B methylenedioxyphenyl)propan-1-one bkMDEA 12.456 ‘Ethylone’ 2-methylamino-1-(3,4- C methylenedioxyphenyl)butan-1-one bkMBDB 12.546 ‘Butylone’ IS-2 Pyribenzamine (tripelenamine) IS-2 13.743

(A) 2-methylamino-1-(3,4-methylenedioxyphenyl)propan-1-one ‘Methylone’ (bkMDMA) 12.145 mins %

% 58 100.0 58 12.5

10.0 75.0 30 7.5

50.0 5.0

121 2.5 149 91 25.0 119 0.0 176 50 100 150 20 30 91 121 149 0.0 176207222 250 281 301344 387 407 453 481495 50 100 150 200 250 300 350 400 450 500

(B) 2-ethylamino-1-(3,4-methylenedioxyphenyl)propan-1-one ‘Ethylone’ (bkMDEA) 12.456 mins % 72 % 100.0 72 35.0

30.0 75.0 44 25.0

20.0

50.0 15.0

10.0 42

44 5.0 25.0 121 149 0.0 103 178 50 100 150 20 42 121 149 0.0 93 178 219 254 283338360 377 405 442 479 494 50 100 150 200 250 300 350 400 450 500

(C) 2-methylamino-1-(3,4-methylenedioxyphenyl)butan-1-one ‘Butylone’ (bkMBDB) 12.546 mins % 72 % 100.0 72 15.0

12.5 75.0 10.0

7.5 42 57 50.0 5.0

121 149 2.5 25.0 96 192 0.0 50 100 150 20 42 57 121 149 0.0 96 192 219262281 308 341355 377 412 441 479 497 50 100 150 200 250 300 350 400 450 500

Susannah Davies John Ramsey 7th August 2008