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156-34-3Relevant articles and documents
Quantitative structure-activity relationships in drug metabolism and disposition: Pharmacokinetics of N-substituted amphetamines in humans
Testa,Salvesen
, p. 497 - 501 (1980)
Pharmacokinetic data of 15 N-alkyl-substituted amphetamines in humans have been the object of a retrospective quantitative structure-activity relationship study. The urinary excretion of amphetamines was shown to decrease with increasing lipophilicity; the correlation equations revealed that, for identical lipophilicities, tertiary amines are excreted faster than secondary amines, which are secreted faster than primary amines. The apparent n-heptane-pH 7.4 buffer partition coefficient correlates better with urinary excretion than does the true n-octanol-water partition coefficient, probably because it includes a pKa term that accounts for the fraction of the drug present in the tubules as nonionic species. The N-dealkylation rate increases with increasing lipophilicity of the substrates (enhanced enzyme affinity) but decreases with increasing bulk of the N-substituent that is split off (steric hindrance of initial C(α)-hydroxylation.
δ13C and δ13H isotope ratios in amphetamine synthesized from benzaldehyde and nitroethane
Collins, Michael,Salouros, Helen,Cawley, Adam T.,Robertson, James,Heagney, Aaron C.,Arenas-Queralt, Andrea
, p. 1653 - 1658 (2010)
Previous work in these laboratories and by Butzenlechner et al. and Culp et al. has demonstrated that the δ2H isotope value of industrial benzaldehyde produced by the catalytic oxidation of toluene is profoundly positive, usually in the range +300% to +500%. Synthetic routes leading to amphetamine, methylamphetamine or their precursors and commencing with such benzaldehyde may be expected to exhibit unusually positive δ2H values. Results are presented for δ13C and δ2H isotope values of 1-phenyl-2-nitropropene synthesized from an industrial source of benzaldehyde, having a positive δ2H isotope value, by a Knoevenagel condensation with nitroethane. Results are also presented for δ13C and δ2H isotope values for amphetamine prepared from the resulting 1-phenyl-2-nitropropene. The values obtained were compared with δ13C and δ2H isotope values obtained for an amphetamine sample prepared using a synthetic route that did not involve benzaldehyde. Finally, results are presented for samples of benzaldehyde, 1-phenyl-2-nitropropene and amphetamine that had been seized at a clandestine amphetamine laboratory.
Reduction of amphetamine hydroxylamine and other aliphatic hydroxylamines by benzamidoxime reductase and human liver microsomes
Clement,Behrens,Moller,Cashman
, p. 1037 - 1045 (2000)
For the reduction of N-hydroxylated derivatives of strongly basic functional groups, such as amidines, guanidines, and aminohydrazones, an oxygen-insensitive liver microsomal system, the benzamidoxime reductase, has been described. To reconstitute the complete activity of the benzamidoxime reductase, the system required cytochrome b5, NADH-cytochrome b5-reductase, and the benzamidoxime reductase, a cytochrome P450 enzyme, which has been purified to homogeneity from pig liver. It was not known if this enzyme system was also capable of reducing aliphatic hydroxylamines. The N-hydroxylation of aliphatic amines is a well-known metabolic process. It was of interest to study the possibility of benzamidoxime reductase reducing N-hydroxylated metabolites of aliphatic amines back to the parent compound. Overall, N-hydroxylation and reduction would constitute a futile metabolic cycle. As examples of medicinally relevant compounds, the hydroxylamines ofmethamphetamine, amphetamine, and N-methylamine as model compounds were investigated. Formation of methamphetamine and amphetamine was analyzed by newly developed HPLC methods. All three hydroxylamines were easily reduced by benzamidoxime reductase to their parent amines with reduction rates of 220.6 nmol min-1 (mg of protein)-1 for methamphetamine, 5.25 nmol min-1 (mg of protein)-1 for amphetamine, and 153 nmol min-1 (mg of protein)-1 for N-methylhydroxylamine. Administration of synthetic hydroxylamines of amphetamine and methamphetamine to primary rat neuronal cultures produced frank cell toxicity. Compared with amphetamine or the oxime of amphetamine, the hydroxylamines were significantly more toxic to primary neuronal cells. The benzamidoxime reductase is therefore involved in the detoxication of these reactive hydroxylamines.
Rapid Synthesis of Primary Amines from Ketones using Choline Chloride/Urea Deep Eutectic as a Reaction Medium
Basso, Ernani A.,Fernandes, Cleverton de S.,Francisco, Camila B.,Gauze, Gisele de F.,Rittner, Roberto
, (2021/12/29)
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Markovnikov Wacker-Tsuji Oxidation of Allyl(hetero)arenes and Application in a One-Pot Photo-Metal-Biocatalytic Approach to Enantioenriched Amines and Alcohols
Albarrán-Velo, Jesús,Gotor-Fernández, Vicente,Lavandera, Iván
supporting information, p. 4096 - 4108 (2021/08/19)
The Wacker-Tsuji aerobic oxidation of various allyl(hetero)arenes under photocatalytic conditions to form the corresponding methyl ketones is presented. By using a palladium complex [PdCl2(MeCN)2] and the photosensitizer [Acr-Mes]ClO4 in aqueous medium and at room temperature, and by simple irradiation with blue led light, the desired carbonyl compounds were synthesized with high conversions (>80%) and excellent selectivities (>90%). The key process was the transient formation of Pd nanoparticles that can activate oxygen, thus recycling the Pd(II) species necessary in the Wacker oxidative reaction. While light irradiation was strictly mandatory, the addition of the photocatalyst improved the reaction selectivity, due to the formation of the starting allyl(hetero)arene from some of the obtained by-products, thus entering back in the Wacker-Tsuji catalytic cycle. Once optimized, the oxidation reaction was combined in a one-pot two-step sequential protocol with an enzymatic transformation. Depending on the biocatalyst employed, i. e. an amine transaminase or an alcohol dehydrogenase, the corresponding (R)- and (S)-1-arylpropan-2-amines or 1-arylpropan-2-ols, respectively, could be synthesized in most cases with high yields (>70%) and in enantiopure form. Finally, an application of this photo-metal-biocatalytic strategy has been demonstrated in order to get access in a straightforward manner to selegiline, an anti-Parkinson drug. (Figure presented.).
Transaminase-mediated synthesis of enantiopure drug-like 1-(3′,4′-disubstituted phenyl)propan-2-amines
Lakó, ágnes,Mendon?a, Ricardo,Molnár, Zsófia,Poppe, László
, p. 40894 - 40903 (2020/11/23)
Transaminases (TAs) offer an environmentally and economically attractive method for the direct synthesis of pharmaceutically relevant disubstituted 1-phenylpropan-2-amine derivatives starting from prochiral ketones. In this work, we report the application of immobilised whole-cell biocatalysts with (R)-transaminase activity for the synthesis of novel disubstituted 1-phenylpropan-2-amines. After optimisation of the asymmetric synthesis, the (R)-enantiomers could be produced with 88-89% conversion and >99% ee, while the (S)-enantiomers could be selectively obtained as the unreacted fraction of the corresponding racemic amines in kinetic resolution with >48% conversion and >95% ee. This journal is