Some new urinary metabolites of famprofazone and morazone in man

Neugebauer, Michael

doi:10.1016/0731-7085(84)80089-8

Cited by 19 publications

(4 citation statements)

References 11 publications

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“…Previous studies (2,3,16,17) have shown famprofazone is stereoselectively metabolized. The data presented in the present study support this conclusion.…”

Section: 20mentioning

confidence: 96%

Metabolic Profile of Famprofazone Following Multidose Administration

Rodriguez¹,

Valtier²,

Cody³

2004

Journal of Analytical Toxicology

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One of the 14 different drugs known to be metabolized to methamphetamine and/or amphetamine is famprofazone, a component in the multi-ingredient formulation Gewodin. Because of its conversion to methamphetamine and amphetamine, which can result in positive drug-testing results, the excretion pattern of these metabolites is critical for proper interpretation of drug-testing results. Multiple doses of famprofazone were administered to healthy volunteers with no previous history of methamphetamine, amphetamine, or famprofazone use. Following administration, urine samples were collected ad lib for nine days, and pH, specific gravity, and creatinine values were determined. To determine the methamphetamine and amphetamine excretion profile, samples were extracted, derivatized, and analyzed by gas chromatography-mass spectrometry (GC-MS). Peak concentrations of methamphetamine ranged from 5327 to 14,155 ng/mL and from 833 to 3555 ng/mL for amphetamine and were reached between 12:22 and 48:45 h post initial dose. There were 15-19 samples per subject that were positive under HHS testing guidelines, with the earliest at 03:37 h post initial dose and as late as 70:30 h post last dose. Methamphetamine and amphetamine were last detected (LOD > or = 5 ng/mL) up to 159 h and 153 h post last dose for methamphetamine and amphetamine, respectively. GC-MS was also used to determine the enantiomeric composition of methamphetamine and amphetamine. This analysis revealed both enantiomers were present in a predictable pattern.

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“…Previous studies (2,3,16,17) have shown famprofazone is stereoselectively metabolized. The data presented in the present study support this conclusion.…”

Section: 20mentioning

confidence: 96%

Metabolic Profile of Famprofazone Following Multidose Administration

Rodriguez¹,

Valtier²,

Cody³

2004

Journal of Analytical Toxicology

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“…There have been several reports of studies of famprofazone metabolism. [5][6][7][8][9][10] Famprofazone has a chiral center on the ␣-carbon atom of the phenylethylamine moiety and thus exists in both (+)-and (−)-enantiomers. There has been no study on stereochemical metabolism of famprofazone in the literature.…”

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confidence: 99%

Stereoselective metabolism of famprofazone in humans: N-dealkylation and ?-and p-hydroxylation

Shin¹

1997

Chirality

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Following administration of famprofazone to humans, the stereoselective metabolism from the drug to its known metabolites (+,−)‐ephedrine, (+,−)‐pseudoephedrine, (+,−)‐norephedrine, (+,−)‐norpseudoephedrine, (+,−)‐p‐hydroxy‐amphetamine, (+,−)‐p‐hydroxymethamphetamine, and (+,−)‐p‐hydroxynorephedrine was studied. The enantiomers of the metabolites were derivatized with α‐methoxy‐α‐(trifluoromethyl)‐phenylacetyl chloride (MTPA.Cl) as the chiral derivatizing agent for amino groups and N‐methyl‐N‐trimethylsilyl trifluoroacetamide (MSTFA) or N‐methyl‐N‐triethylsilyl trifluoroacetamide (MTESTFA) as protecting agents of the hydroxyl groups. The diastereomeric derivatives were well separated by capillary gas‐liquid chromatography and determined by mass spectrometry with selected‐ion monitoring (SIM). (−)‐Methamphetamine, (−)‐amphetamine, (−)‐p‐hydroxyamphetamine, and‐(−)‐hydroxymethamphetamine were excreted in greater amounts than their enantiomers after administration of racemic famprofazone; and (−)‐ephedrine, (−)‐pseudoephedrine, (−)‐norephedrine, and (−)‐norpseudoephedrine were found in higher concentration than their enantiomers. Famprofazone was metabolized by product and substrate stereoselective N‐dealkylation, β‐hydroxylation, and p‐hydroxylation, metabolites of which may be predominantly responsible for the side effects of famprofazone. Chirality 9:52–58, 1997. © 1997 Wiley‐Liss, Inc.

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“…Following oral administration of famprofazone, methamphetamine and the conjugate of 3-hydroxymethylpyrazolone have been detected in the urine of mice [6] and man [7]. 3-Formylpyrazolone, unchanged famprofazone, hydroxylated famprofazone, and 3-carboxylpyrazolone were not detected.…”

Section: Discussionmentioning

confidence: 99%

Identification of famprofazone ingestion

Mußhoff¹,

Kræmer²

1998

International Journal of Legal Medicine

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After a traffic accident a 32-year-old man was suspected of having previously taken an illegal drug. An immunochemical screening procedure revealed positive results for amphetamines in both urine and blood samples. The preliminary test was confirmed by GC/MS and both amphetamine and methamphetamine were found in both body fluids. However, the man denied any use of drugs but claimed to have taken four tablets of Gewodin. One of the ingredients, famprofazone, undergoes metabolic conversion to amphetamine and methamphetamine. Using GC/ MS the ingestion of famprofazone was verified by identification of the unchanged parent compound in the urine sample.

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Some new urinary metabolites of famprofazone and morazone in man

Cited by 19 publications

References 11 publications

Metabolic Profile of Famprofazone Following Multidose Administration

Metabolic Profile of Famprofazone Following Multidose Administration

Stereoselective metabolism of famprofazone in humans: N-dealkylation and ?-and p-hydroxylation

Identification of famprofazone ingestion

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