Toxicokinetics of amphetamines: Metabolism and toxicokinetic data of designer drugs, amphetamine, methamphetamine, and their N-alkyl derivatives

Therapeutic Drug Monitoring

Volumn 24, Issue 2, 2002, Pages 277-289

  Kraemer, Thomas ^a   Maurer, Hans H ^a  

^a SAARLAND UNIVERSITY   (Germany)

Author keywords

Amphetamine; Cytochrome P450; Designer drugs; Metabolism; Methamphetamine; Toxicokinetics

Indexed keywords

1 (1',3' BENZODIOXOL 5' YL) 2 BUTANAMINE; 1 (3',4' METHYLENEDIOXYPHENYL) 2 BUTANAMINE; 1 (3',4' METHYLENEDIOXYPHENYL) 2 PROPANAMINE; 3,4 METHYLENEDIOXYAMPHETAMINE; 3,4 METHYLENEDIOXYETHYLAMPHETAMINE; 3,4 METHYLENEDIOXYMETHAMPHETAMINE; AMPHETAMINE; AMPHETAMINE DERIVATIVE; AMPHETAMINIL; BENZODIOXOLYLBUTANAMINE; BENZPHETAMINE; CLOBENZOREX; CYTOCHROME P450; DIMETAMFETAMINE; FENETYLLINE; FENPROPOREX; FURFENOREX; MEFENOREX; METHAMPHETAMINE; N ETHYLAMPHETAMINE; N METHYL BENZODIOXOLYLBUTANAMINE; PRENYLAMINE; SELEGILINE; SYDNOCARB; UNCLASSIFIED DRUG;

DRUG IDENTIFICATION; DRUG METABOLISM; HUMAN; METABOLITE; NONHUMAN; PRIORITY JOURNAL; REVIEW; TOXICITY TESTING; TOXICOKINETICS;

AMPHETAMINES; DESIGNER DRUGS; FORENSIC MEDICINE; HUMANS; METHAMPHETAMINE;

EID: 0036129441     PISSN: 01634356     EISSN: None     Source Type: Journal    
DOI: 10.1097/00007691-200204000-00009     Document Type: Review

References (72)

1. 3,4-Methylenedioxy analogues of amphetamine: Defining the risks to humans
2. Differences between the mechanism of action of MDMA, MBDB, and the classic hallucinogens. Identification of a new therapeutic class: Entactogens
3. Fatal multi-organ failure after suicidal overdose with MDMA, "Ecstasy": Case report and review of the literature
4. Ecstasy and related substances - Serum levels in impaired drivers
5. Toxicological detection of the designer drug 3,4-methylenedioxyethylamphetamine (MDE, "Eve") and its metabolites in urine by gas chromatography-mass spectrometry and fluorescence polarization immunoassay
6. Determination of amphetamine, methamphetamine and amphetamine-derived designer drugs or medicaments in blood and urine
7. Review article: Mechanisms and management of hepatotoxicity in ecstasy (MDMA) and amphetamine intoxications
8. Toxicodynamics and long-term toxicity of the recreational drug, 3, 4-methylenedioxymethamphetamine (MDMA, "Ecstasy")
9. Metabolism of methylenedioxymethamphetamine: Formation of dihydroxymethamphetamine and a quinone identified as its glutathione adduct
10. d-amphetamine interaction with glutathione in freshly isolated rat hepatocytes
11. In vivo and in vitro metabolism of 3,4-(methylenedioxy)methamphetamine in the rat: Identification of metabolites using an ion trap detector
12. In vivo formation of aromatic hydroxylated metabolites of 3,4-(methylenedioxy)methamphetamine in the rat: Identification by ion trap tandem mass spectrometric (MS/MS and MS/MS/MS) techniques
13. On the metabolism of designer drugs, part 1: Studies on methylenedioxyetilamfetamine (MDE) in rats
14. Metabolism of racemic 3,4-methylenedioxyethylamphetamine in humans. Isolation, identification, quantification, and synthesis of urinary metabolites
15. On the metabolism and the toxicological analysis of methylenedioxyphenylalkylamine designer drugs by gas chromatography-mass spectrometry
16. Toxicokinetics and analytical toxicology of amphetamine-derived designer drugs ("Ecstasy")
17. Ion trap tandem mass spectrometric evidence for the metabolism of 3,4-(methylenedioxy)methamphetamine to the potent neurotoxins 2,4,5-trihydroxymethamphetamine and 2,4,5-trihydroxyamphetamine
18. Effects of salicylate on 3,4-methylenedioxymethamphetamine (MDMA)-induced neurotoxicity in rats
19. Basic profiles of organic acids in urine
20. The demethylenation of methylenedioxymethamphetamine ("Ecstasy") by debrisoquine hydroxylase (CYP2D6)
21. Disposition of methylenedioxymethamphetamine and three metabolites in the brains of different rat strains and their possible roles in acute serotonin depletion
22. Oxidation of methamphetamine and methylenedioxymethamphetamine by CYP2D6
23. Interactions of amphetamine analogs with human liver CYP2D6
24. The hyperthermic and neurotoxic effects of Ecstasy (MDMA) and 3,4 methylenedioxyamphetamine (MDA) in the Dark Agouti (DA) rat, a model of the CYP2D6 poor metabolizer phenotype
25. Identification of the human cytochromes P450 involved in the oxidative metabolism of "Ecstasy"-related designer drugs
26. An association between the allele coding for a low activity variant of catechol-O-methyltransferase and the risk for breast cancer
27. Non-linear pharmacokinetics of MDMA ("Ecstasy") in humans
28. Analysis of 3,4-methylenedioxymethamphetamine (MDMA) and its metabolites in plasma and urine by HPLC-DAD and GC-MS
29. Pharmacokinetics of ecstasy (MDMA) in healthy subjects
30. Quantitation of N-ethyl-3,4-methylenedioxyamphetamine and its major metabolites in human plasma by high-performance liquid chromatography and fluorescence detection
31. Excretion of MBDB and BDB in urine, saliva, and sweat following single oral administration
32. MDA-MDMA concentrations in urine specimens
33. Fatal MDMA intoxication
34. Determination of drugs of abuse in blood
35. Determination of "Ecstasy" components in alternative biologic specimens
36. Illegal or legitimate use? Precursor compounds to amphetamine and methamphetamine
37. Studies on the metabolism and toxicological detection of the amphetamine-like anorectic fenproporex in human urine by gas chromatography-mass spectrometry and fluorescence polarization immunoassay (FPIA)
38. Involvement of CYP2D6 in the in vitro metabolism of amphetamine, two N- alkylamphetamines and their 4-methoxylated derivatives
39. Metabolic transformation of deprenyl enantiomers in rats
40. Stereoselective metabolism of famprofazone in humans: N-dealkylation and beta- and p-hydroxylation
41. Metabolism of selegiline in humans. Identification, excretion, and stereochemistry of urine metabolites
42. Studies on the metabolism and toxicological detection of the amphetamine-like anorectic mefenorex in human urine by gas chromatography-mass spectrometry and fluorescence polarization immunoassay
43. Amphetamine concentrations in human urine following single-dose administration of the calcium antagonist prenylamine
44. Metabolic production of amphetamine following multidose administration of clobenzorex
45. Metabolic production of amphetamine following administration of clobenzorex
46. Detection of amphetamine and methamphetamine following administration of benzphetamine
47. Identification of famprofazone ingestion
48. Detection of amphetamine following administration of fenproporex
49. Amphetamine and fenproporex levels following multidose administration of fenproporex
50. Gas chromatography-mass spectrometry (GC-MS) and liquid chromatography-mass spectrometry (LC-MS) in toxicological analysis. Studies on the detection of clobenzorex and its metabolites within a systematic toxicological analysis procedure by GC-MS and by immunoassay and studies on the detection of alpha- and beta-amanitin in urine by atmospheric pressure ionization electrospray LC-MS
51. A gas chromatography-mass spectrometry method for the quantitation of clobenzorex
52. Differentiation of clobenzorex use from amphetamine abuse using the metabolite 4-hydroxyclobenzorex
53. Toxicological detection of selegiline and its metabolites in urine using fluorescence polarization immunoassay (FPIA) and gas chromatography-mass spectrometry (GC-MS) and differentiation by enantioselective GC-MS of the intake of selegiline from abuse of methamphetamine or amphetamine
54. Stereoselective analyses of selegiline metabolites: Possible urinary markers for selegiline therapy
55. Stereochemical determination of selegiline metabolites in postmortem biologic specimens
56. Stereoselective metabolic study of famprofazone
57. Enantiomeric composition of amphetamine and methamphetamine derived from the precursor compound famprofazone
58. Enantiomer profile for amphetamine derived from the precursor compound fenproporex
59. Metabolism of N,N-dialkylated amphetamines, including deprenyl, by CYP2D6 expressed in a human cell line
60. Cytochrome P4502D isozymes catalyze the 4-hydroxylation of methamphetamine enantiomers
61. CYP2D6 polymorphism is not crucial for the disposition of selegiline
62. Major role of the CYP2C isozymes in deamination of amphetamine and benzphetamine: Evidence for the quinidine-specific inhibition of the reactions catalyzed by rabbit enzyme
63. Cytochrome P450-dependent N-dealkylation of L-deprenyl in C57BL mouse liver microsomes: Effects of in vivo pretreatment with ethanol, phenobarbital, betanaphthoflavone and L-deprenyl
64. Inactivation of cytochrome P4502B1 by the monoamine oxidase inhibitors R-(-)-deprenyl and clorgyline
65. Investigation of stereoselective metabolism of amphetamine in rat liver microsomes by microdialysis and liquid chromatography with precolumn chiral derivatization
66. Selective involvement of cytochrome P450 2D subfamily in vivo 4-hydroxylation of amphetamine in rat
67. Deamination of amphetamines by cytochromes P450: Studies on substrate specificity and regioselectivity with microsomes and purified CYP2C subfamily isozymes
68. Quinidine inhibits in vivo metabolism of amphetamine in rats: Impact upon correlation between GC/MS and immunoassay findings in rat urine
69. Atypical metabolism of deprenyl and its enantiomer, (S)-(+)-N,alpha-dimethyl-N-propynylphenethylamine, by cytochrome P450 2D6
70. Clinical pharmacokinetics and pharmacodynamics of selegiline. An update
71. Pharmacokinetics and relative bioavailability of selegiline in healthy volunteers
72. Urinary excretion of damphetamine following oral doses in humans: Implications for urine drug testing