Synthesis and pharmacology of hydroxylated metabolites of methyl phenidate

1981 ◽  
Vol 24 (10) ◽  
pp. 1237-1240 ◽  
Author(s):  
Kennerly S. Patrick ◽  
Clinton D. Kilts ◽  
George R. Breese
Keyword(s):  
Hydroxylated Metabolites ◽  
Methyl Phenidate

PHENOLIC METABOLITES OF DL-NORGESTREL: A METHOD FOR THE REMOVAL OF 1-HYDROXYLATED METABOLITES, POTENTIAL SOURCES OF PHENOLIC ARTIFACTS

1974 ◽  
Vol 76 (4) ◽  
pp. 789-800 ◽  
Author(s):  
Samuel F. Sisenwine ◽  
Ann L. Liu ◽  
Hazel B. Kimmel ◽  
Hans W. Ruelius
Keyword(s):  
Urinary Metabolites ◽  
Ion Exchange Resin ◽  
Gas Chromatography Mass Spectrometry ◽  
Phenolic Metabolites ◽  
Hydroxylated Metabolites ◽  
Analytical Work ◽  
Potential Sources ◽  
Alkaline Conditions ◽  
Artifact Formation ◽  
Work Up

ABSTRACT The identification of 1β-hydroxynorgestrel among the urinary metabolites of dl-norgestrel and the facile transformation of this compound under mild alkaline conditions to a potentially oestrogenic phenol provide an experimental basis for the conclusion advanced by others that the oestrogens present in the urine of subjects treated with synthetic progestens are artifacts formed during analytical work-up. A method has been devised which eliminates 1-hydroxylated metabolites as potential sources of phenolic artifacts. This method is based on the reduction by NaBH4 of the 1-hydroxy-4-en-3-one grouping in the A ring thereby excluding the possibility of aromatization during later fractionation on a basic ion exchange resin that separates neutral from phenolic metabolites. In the urines of women treated with 14C-dl-nogestrel, only 0.17–0.27% of the dose is found to have phenolic properties when this method is used. Two of the phenolic metabolites, 18-homoethynyloestradiol and 16β-hydroxy-18-homoethynyloestradiol, are present in amounts smaller than 0.01 % of the dose. Without the reduction steps the percentages are noticeably higher, indicating artifact formation under alkaline conditions. Similar results were obtained with urines from African Green Monkeys (Cercopithecus Aethiops) that had been dosed with 14C-dl-norgestrel. Radiolabelled 18-homoethynyloestradiol and 16β-hydroxy-18-homoethynyloestradiol were isolated from monkey urine and their identity confirmed by gas chromatography-mass spectrometry.

Preparation and structural analysis of (±)-threo-ritalinic acid

2013 ◽  
Vol 69 (11) ◽  
pp. 1225-1228 ◽  
Author(s):  
Sara Wyss ◽  
Irmgard A. Werner ◽  
W. Bernd Schweizer ◽  
Simon M. Ametamey ◽  
Selena Milicevic Sephton
Keyword(s):  
Methyl Ester ◽  
Free Acid ◽  
Nmr Analysis ◽  
Intermolecular Hydrogen Bonds ◽  
X Ray ◽  
X Ray Crystallography ◽  
Ph Values ◽  
Ritalinic Acid ◽  
Methyl Phenidate ◽  
Hydrolysis Of

Hydrolysis of the methyl ester (±)-threo-methyl phenidate afforded the free acid in 40% yield,viz.(±)-threo-ritalinic acid, C13H17NO2. Hydrolysis and subsequent crystallization were accomplished at pH values between 5 and 7 to yield colourless prisms which were analysed by X-ray crystallography. Crystals of (±)-threo-ritalinic acid belong to theP21/nspace group and form intermolecular hydrogen bonds. An antiperiplanar disposition of the H atoms of the (HOOC—)CH—CHpygroup (py is pyridine) was found in both the solid (diffraction analysis) and solution state (NMR analysis). It was also determined that (±)-threo-ritalinic acid conforms to the minimization of negativegauche+–gauche−interactions.

scholarly journals Stereoselective accumulation of hydroxylated metabolites of amphetamine in rat striatum and hypothalamus

1986 ◽  
Vol 88 (1) ◽  
pp. 285-290 ◽  
Author(s):  
D.F.H. Dougan ◽  
A.M. Duffield ◽  
P.H. Duffield ◽  
D.N. Wade
Keyword(s):  
Rat Striatum ◽  
Hydroxylated Metabolites
Sign in / Sign up

Export Citation Format

Share Document