Detection of Δ9-tetrahydrocannabinol in exhaled breath collected from cannabis users.
Exhaled breath has recently been proposed as a new possible matrix for drugs of abuse testing. A key drug is cannabis, and the present study was aimed at investigating the possibility of detecting tetrahydrocannabinol and tetrahydrocannabinol carboxylic acid in exhaled breath after cannabis smoking. Exhaled breath was sampled from 10 regular cannabis users and 8 controls by directing the exhaled breath by suction through an Empore C(18) disk. The disk was extracted with hexane/ethyl acetate, and the resulting extract was evaporated to dryness and redissolved in 100 μL hexane/ethyl acetate. A 3-μL aliquot was injected onto the LC-MS-MS system and analyzed using positive electrospray ionization and selected reaction monitoring. In samples collected 1-12 h after cannabis smoking, tetrahydrocannabinol was detected in all 10 subjects. The rate of excretion was between 9.0 and 77.3 pg/min. Identification of tetrahydrocannabinol was based on correct retention time relative to tetrahydrocannabinol-d(3) and correct product ion ratio. In three samples, peaks were observed for tetrahydrocannabinol carboxylic acid, but these did not fulfill identification criteria. Neither tetrahydrocannabinol or tetrahydrocannabinol carboxylic acid was detected in the controls. These results confirm older reports that tetrahydrocannabinol is present in exhaled breath following cannabis smoking and extend the detection time from minutes to hours. The results further support the idea that exhaled breath is a promising matrix for drugs-of-abuse testing.
Amphetamines detected in exhaled breath from drug addicts: A new possible method for drugs-of-abuse testing.
Testing for drugs of abuse in sample matrices alternative to urine such as blood, sweat, and saliva have received increasing attention and is needed, for example, in traffic medicine. Human breath is known to contain a large number of substances including non-volatile molecules. We explore whether intake of amphetamines could be detected by analytical investigation of exhaled breath from drug addicts. Exhaled breath was collected from 12 drug addict patients after recovering from acute intoxication. Self-reported intake of "amphetamine" was confirmed by analysis of urine and plasma. The compounds were trapped by filtering the air through a modified silica surface and subsequently analyzed by a combined liquid chromatography-tandem mass spectrometry method. As a control, exhaled breath was collected in the same way from eight healthy volunteers. Here we report for the first time that amphetamine and methamphetamine are present in exhaled breath following ingestion of these compounds by drug addicts. Both amphetamine and methamphetamine were indisputably identified by means of the mass spectrometry technique in exhaled breath samples from all 12 patients. Identifications were based on monitoring two product ions in selected reaction monitoring mode and having correct relative ratios (+/- 20%). Excretion rates ranged from 0.2 to 139 pg/min. No amphetamine or methamphetamine was detected in the control subjects. This finding, using a yet non-validated sampling procedure, opens a new possibility for drugs-of-abuse testing. Collection of exhaled breath is likely to be more convenient and safe as compared to matrices presently in use.
Highly enantio- and diastereoselective synthesis of β-methyl-γ-monofluoromethyl-substituted alcohols.
Enanatiopure β-methyl-γ-monofluoromethyl alcohols were prepared from the allylic alkylation between fluorobis(phenylsulfonyl)methane with Morita-Baylis-Hillman carbonates. The reaction was catalyzed by using the Cinchona alkaloid derivative, (DHQD)(2)AQN. The origin of the stereoselectivity was verified by DFT methods. Calculated geometries and relative energies of various transition states strongly support the observed stereoselectivity.