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2.3.2 Amphetamine and Ecstasy

Amphetamine and methamphetamine are powerful stimulants used for over
100 years. Some of their methylenedioxy analogs like methylene-
dioxymethamphetamine (MDMA), methylenedioxyethylamphetamine
(MDEA) or methylenedioxyamphetamine (MDA) were already synthesized
in 1914 and tested in treatment of psychiatric disorders. In contrast to
amphetamine, MDMA did not become widely abused until the late 1970s.
This drug is known under the names “Ecstasy,” “XTC,” and “Adam.” Para-
doxically, the widespread abuse of psychoactive phenethylamines was prop-
agated by eminent pharmacologist Alexander Shulgin who, in his book
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Pihkal, A Chemical Love Story, published procedures for synthesizing 179
various drugs of this group. Also, the information concerning recommended
dosages and expected symptoms was given. The book is freely available and
certainly helped to proliferate psychoactive phenethylamines in the society.
Amphetamine derivatives are usually manufactured as tablets and distributed
illegally in discotheques. These drugs, besides stimulating action, may alter
thermoregulation, and they caused a growing number of death cases, mainly
due to heat stroke at rave parties. 67–69 It must be stressed that the recreational
use of Ecstasy is very often associated with consumption of other psychotro-
pic drugs or alcohol. A review of 81 Ecstasy-related death cases in England,
as well as examination of urine samples taken from 64 attendees of rave
parties, revealed that in the majority of cases, MDMA was present in com-
bination with amphetamine, methamphetamine, other designer amphet-
amines, or opiates. 69,70 This suggests that the majority of the ravers are multi-
drug users. A similar observation was also made by Bogusz. 7

2.3.2.1 Analysis of Biological Fluids
Bogusz et al. compared the sensitivity of UV/DAD and APCI/MS detection
for amphetamines. Amphetamine, methamphetamine, MDMA, MDA, and
MDEA, as well as eight other phenethylamines, were extracted with ether
from serum and urine, derivatized with phenylisothiocyanate and subjected
to HPLC with APCI/MS or UV/DAD detection. LC/APCI/MS assured about
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10 times higher detection than UV with LODs ranged from 1 to 5 mg/l. In
72
the next study of the same group, the derivatization, as well as diode array
detection, was abandoned. Fourteen amphetamines and related compounds
were isolated from biofluids with SPE cartridges and subjected to
LC/APCI/MS examination in SIM mode. Again, the limit of detection
ranged from 1 to 5 mg/l. This method was applied in routine casework. 47
Kataoka et al. applied SPME for isolation of amphetamine, methamphet-
73
amine, MDMA, MDEA, and MDA from urine. The drugs were desorbed by
mobile-phase flow and detected with ESI/MS (SIM), with a LOD below
1 mg/l urine.

© 2004 by CRC Press LLC