Page 106 - Advances in Forensic Applications of Mass Spectrometry - Jehuda Yinon
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                                    2.3.5.2  Other Hallucinogens
                                    Ibogaine, an indole alkaloid occurring in the rain forest shrub Tabernanthe
                                    iboga, has been used for a long time by Western Africans in low doses to
                                    combat fatigue and hunger, and in higher doses as a hallucinogen in religious
                                    rituals. This drug, as well as its analog 18-methoxycoronaridine, promotes
                                    drug abstinence from addictive substances, and was used in experimental
                                    clinical trials. 115,116  Ibogaine has been determined, together with other drugs
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                                    of abuse, by LC/APCI/MS after solid phase extraction by Bogusz et al.  The
                                                                                      117
                                    LOD of 0.2  mg/l in plasma was achieved. Zhang et al.  determined 18-
                                    methoxycoronaridine and its three metabolites with LC/ESI/MS/MS in human
                                    liver microsomes in a study devoted to the metabolic pathway of this drug.
                                       Naturally occurring and synthetic indoleamines such as N,N-dimethyl-
                                    5-hydroxytryptamine (bufotenine),  N,N-dimethyltryptamine (DMT),
                                    5-methoxy-DMT, N-methyltryptamine (NMT), among others, show hallu-
                                    cinogenic properties and are sometimes abused. These drugs were deter-
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                                    mined in urine samples of psychiatric patients with LC/ESI/MS/MS  and
                                    with LC/APCI/MS/MS in rat brain after experimental administration. 119
                                       Mushrooms belonging to the genus Psilocybe, Panaeolus, Conocybe, and
                                    Gymnopilus contain hallucinogenic indole-derivative psilocybine. These
                                    mushrooms were consumed earlier by the Aztecs and are being widely abused
                                    in present times.  Bogusz et al.   analyzed psilocybine and its dephospho-
                                                                 121
                                                  120
                                    rylated active metabolite psilocine in honey mixed with “magic mushrooms.”
                                    The drug was extracted with methanol and subjected to LC/APCI/MS anal-
                                    ysis in SIM mode. Only psilocine was found in honey preparation.

                                    2.3.6  LC/MS of Multiple Drugs of Abuse
                                    The tendency to use multiple drugs is a common feature of drug addicts all
                                    over the world. This was found, in Canadian  and German  sources. There-
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                                                                          122
                                    fore, the analytical toxicologists face the challenge of determining a wide
                                    range of compounds in a very limited amount of sample. For this reason,
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                                    Bogusz et al.  developed a LC/APCI/MS procedure for the determination of
                                    opiates, cocaine and metabolites, LSD, and ibogaine, using a single SPE
                                    isolation procedure and mobile phase consisting of the same components
                                    (acetonitrile and ammonium formate buffer, pH 3.0). This method also was
                                    used later on 14 psychoactive phenethylamines such as amphetamine and
                                    designer amphetamines.  For each compound, a protonated molecular ion
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                                    and one to three fragments were monitored. Practical experience from this
                                    procedure was published by Bogusz. 7
                                       Cailleux et al.  extracted opiate agonists (morphine, 6-MAM, codeine,
                                                    124
                                    norcodeine, pholcodine, and codethyline) as well as nalorphine and cocaine
                                    and its metabolites (benzoylecgonine, ecgonine methyl ester, cocaethylene,
                                    and anhydromethylecgonine) from blood, plasma, or urine with

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