anethole.peracid.neo.. - mdma

136 D. Waumans et al. / Forensic Science International 143 (2004) 133–139
preparations have been confiscated by Belgian Law
Enforcement in 2001/2002 and have been transferred to
our laboratory for investigation. Previous findings
have meanwhile entered the published scientific literature
(a)
(b)
(c)
(d)
1
1
1
1
m/z 268
5.00 10.00 15.00 20.00 25.00 30.00
min
[10]. The screened preparations include two brownish
powders (seized from different sources), a capsule containing
a similarly appearing brownish powder, and a
beige tablet bearing an ‘xTc’-logo. The latter has been
20.00 21.00 22.00 23.00 24.00 25.00
Fig. 2. Chromatograms: [a] performic acid oxidation in acetone [b] performic acid oxidation in DCM [c] peracetic acid oxidation in acetone
[d] peracetic acid oxidation in DCM [e] extracted ion chromatogram (m/z 268) for retention time interval 20.00–25.00 from [a]. Mass
spectrum: The diastereomers have identical mass spectra. The four theoretically possible diastereomers are shown. Reaction scheme: Anethole
is epoxidized (A), after which the obtained anethole epoxide is converted to a stable carbocation (5) (B). Formation of neolignan (1) follows
from the interaction between (5) and anethole (C), which results in the formation of an unstable intermediary product prone to intramolecular
rearrangements (E).
O
(e)
O
O
(1)
O
O
B
E
O
OH
O
A
+
(5)
+
min
OH
O
O
C
D
OH
O
+
O