Gas-chromatographic resolution of optical isomers in microgram samples of amphetamine

Gordis, Enoch

doi:10.1016/0006-2952(66)90245-0

Cited by 39 publications

(7 citation statements)

References 4 publications

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“…On the other hand, gas chromatography (GC) and radioimmunoassay (RIA) have reportedly been applied [13][14][15]. For GC, however, an optically active liquid phase, which is highly heat stable, and diastereomers must be produced, and for RIA a specific antiserum against the optically different compounds is required.…”

Section: Discussionmentioning

confidence: 99%

Forensic toxicologic analysis of methamphetamine and amphetamine optical isomers by high performance liquid chromatography

Nagai

Kamiyama

1988

Z Rechtsmed

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Optical isomers (d and l) and racemic compounds (dl) of methamphetamine (MAMP) and amphetamine (AMP), and biologic materials including those substances, could be analyzed by high performance liquid chromatography. Examining the temperature for the analysis, 40 degrees C was the optimal condition in the reproducibility of separated MAMP-isomers. The reproducibility at the temperature did not vary significantly. The measured values of optical isomers were 0.116 +/- 0.012, 1.082 +/- 0.070 and 8.984 +/- 0.136 for the mixing ratios (l/d) of 0.111, 1.000, and 9.000, respectively. The detection limit for both d- and l-isomers was 25 ng. The analytic result of hair specimens from two stimulant abusers by the present method indicates that they contained only d-MAMP and d-AMP, which is believed to have the strongest pharmacologic effect among the optical isomers of MAMP. The coefficient of variation in the analysis of five replicate standards, prepared by adding 1,000 ng each of racemate MAMP and AMP to hair, was less than 4%. The measured value against l/d = 1.000 was 1.040 +/- 0.040 in MAMP and 0.980 +/- 0.030 in AMP. The detection limit for both racemate MAMP and AMP accumulated in hair was 250 ng. The analysis of the optical isomers by our method would contribute to identifying the smuggling routes or the illicit method.

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Section: Discussionmentioning

confidence: 99%

Forensic toxicologic analysis of methamphetamine and amphetamine optical isomers by high performance liquid chromatography

Nagai

Kamiyama

1988

Z Rechtsmed

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“…The isomeric purity of the (+)-and (-)-isomers of Amphet and AMPT administered to rats was determined by reacting each compound with trifluoroacetyl-(-)-prolyl chloride (Gordis, 1966). The resulting diasterioisomers were separated and estimated by methane c.i.g.c.m.s.…”

Section: Stereochemical Impuritiesmentioning

confidence: 99%

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

Dougan

Duffield

et al. 1986

British J Pharmacology

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1 The stereoselective accumulation of x-methyl-p-tyramine (AMPT) and x-methyl-p-octopamine (AMPO) in rat striatum and hypothalamus after acute and chronic administration ofthe (+ )-and (-)-isomers of amphetamine (Amphet) and the acute administration of (+ )-and (-)-AMPT has been investigated by chemical ionization gas chromatography mass spectrometry (c.i.g.c.m.s.). 2 Two h after the administration of (+ )-or (-)-AMPT (5 mg kg-' i.p.), the concentrations of the isomers in striatal tissue were approximately equal; 18 h later, the concentration of the (+ )-isomer was 10 times that of the (-)-isomer. 3 The concentrations of AMPO in the striatum and hypothalamus 20 h after administration of (+ )-AMPT were 68 ng g-' and 484 ng g-' respectively. After the administration of the (-)-isomer of AMPT, small quantities of AMPO were detected in both brain areas. 4 Twenty h after the last of 7 daily injections of (+ )-Amphet (5 mg kg-', i.p.), the concentration of AMPO in the hypothalamus was 5.4 times the concentration at 20 h after one injection. In the striatum, the corresponding ratio for AMPO was 3.5 and for AMPT was 2.5. 5 These data indicate that, although both isomers of AMPT formed from Amphet administered systemically, cross the blood brain barrier, the (+)-isomers AMPT and AMPO are preferentially stored in striatal and hypothalamic aminergic nerve terminals. 6 The accumulations of AMPT and AMPO in rat striatum and hypothalamus after chronic administration of Amphet demonstrates that these metabolites persist in neuronal storage in these brain areas for days after administration. The half-lives of (+)-AMPT and (+)-AMPO in striatal neuronal storage, calculated from this data, were 1.5 days and 2.5 days, respectively. The corresponding half-life for hypothalamic (+)-AMPO was 7 days. 7 These findings suggest the involvement of accumulated AMPT and AMPO in the development of behavioural augmentation to repeated injections of Amphet (Randrup & Munkvad, 1970).

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“…In addition to the earlier mentioned ready availability and stability of V, this reagent was superior to 1-111 in providing better GLC resolution in cases where comparison could be made. For example, VI (5,6), VII (13), and XI11 (14) were derivatized with reagent I; VI, VIII, and XIV were resolved with I1 (2) and I11 (3). In these cases, V tended to give better resolution and/or shorter retention times.…”

Section: XIVmentioning

confidence: 99%

“…The tube was then shaken for I0 min and centrifuged for 10 min, followed by GLC analysis of the lower organic layer as described. 6 Life Sciences gas chromatograph 2100, Varian Associates, Palo Alto, Calif. Gas International bottle shaker, International Equipment Co., Boston, Mass. Derivatization of Pure Compounds-The amine or amine salt (0.1-0.2 mg) in a conical screw-capped tube was treated with XV (50fil), V reagent solution (50 pl), and pyridine (20 pl).…”

mentioning

confidence: 99%

“…In vitro and in vivo test procedures were derived to evaluate the microcapsules as a timed-release parenteral dosage form and as a radiopharmaceutical imaging agent. EXPERIMENTAL Basic Procedure-Coacervation was selected as the microencapsulation method after a review of other methods (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16). The following general procedure (Table I) was used in preparing all microcapsules.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Stereochemistry of Metabolism of Amphetamines: Use of (–)-α-Methoxy-α-(trifluoromethyl)phenylacetyl Chloride for GLC Resolution of Chiral Amines

Gál

1977

Journal of Pharmaceutical Sciences

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Gas-chromatographic resolution of optical isomers in microgram samples of amphetamine

Cited by 39 publications

References 4 publications

Forensic toxicologic analysis of methamphetamine and amphetamine optical isomers by high performance liquid chromatography

Forensic toxicologic analysis of methamphetamine and amphetamine optical isomers by high performance liquid chromatography

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

Stereochemistry of Metabolism of Amphetamines: Use of (–)-α-Methoxy-α-(trifluoromethyl)phenylacetyl Chloride for GLC Resolution of Chiral Amines

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