Kinetics of racemization of (+)- and (-)-diethylpropion: studies in aqueous solution, with and without the addition of cyclodextrins, in organic solvents and in human plasma. Tolerance pattern of the anorexigenic action of amphetamines, fenfluramine, phenmetrazine and diethylpropion in rats. Use of amphetamine-like appetite suppressants: a cross-sectional survey in Southern Brazil. Tenuate online references

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Chirality. 1998;10(4):307-15.
Kinetics of racemization of (+)- and (-)-diethylpropion: studies in aqueous solution, with and without the addition of cyclodextrins, in organic solvents and in human plasma.

Mey B, Paulus H, Lamparter E, Blaschke G.

Central Institute, Federal Armed Forces Medical Service, Munich, Germany.

The configurational stability of (+)- and (-)-diethylpropion [(+)- and (-)-2-(diethyl)-1-phenyl-1-propanone or (+)- and (-)-DEP] was investigated systematically from chemical, pharmaceutical, and pharmacological aspects. The enantiomeric ratio was monitored directly with a recently developed stability-indicating enantioselective HPLC method. In aqueous solutions, the rate of racemization increased non-linearly with increasing pH and with increasing phosphate buffer concentration. The racemization rate showed a positive slope with increasing temperature and decreasing ionic strength. The racemization rates of (+)- and (-)-DEP in the presence of cyclodextrins (CDs) did not differ significantly. CDs that were added to (+)- and (-)-DEP in a molar ratio 5:1 showed the following effects after dissolution in 10 mM phosphate buffer (final pH 6.7): sulfobutyl ether-beta-CD (SBE-beta-CD) and methylated-beta-CD (Me-beta-CD) retarded racemization; whereas hydroxypropyl-beta-CD (HP-beta-CD), acetyl-gamma-CD (Ac-gamma-CD), acetyl-beta-CD (Ac-beta-CD), gamma-CD, and beta-CD showed a weak destabilising effect. In contrast to the described CDs, alpha-CD distinctly accelerated the rate of racemization. The configurational stability of (+)- and (-)-DEP was also studied under physiological conditions. The half-life of racemization in heparinised human plasma was for both enantiomers determined to be approximately 23-25 min. In phosphate buffer (10 mM, pH 7.4), rac-DEP showed a high, but unselective affinity towards human alpha 1-acid glycoprotein (orosomucoid) immobilised on silica (Chiral AGP). The rate of racemization of the free base of (-)-DEP dissolved in organic solutions generally increases with the polarity of the solvating agent.

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Br J Pharmacol. 1976 Aug;57(4):479-85.
Tolerance pattern of the anorexigenic action of amphetamines, fenfluramine, phenmetrazine and diethylpropion in rats.

Ghosh MN, Parvathy S.

The tolerance pattern to anorectic drugs was studied in starved rats by measuring two consecutive 2 h food intakes. 2 There was a reduction in the first 2 h food intake with development of complete tolerance after fenfluramine and phenmetrazine, and of partial tolerance after amphetamine, (+)-amphetamine and diethylpropion. 3 During the second 2 h intake, the anorectic effect was transient after fenfluramine and diethylpropion; while there was an absolute increase in the intake after amphetamine and (+)-amphetamine. 4 A pair-feeding experiment revealed that the increase in the second 2 h food intake was not a direct effect of the drug but a consequence of the deficit in food intake during the preceding 2 hours. 5 There was an overall correlation between the food and water intake. 6 A significant loss in body weight was observed after amphetamine, fenfluramine and phenmetrazine but not after (+)-amphetamine or diethylpropion. 7 The results indicate that so-called tolerance to the anorexigenic effect of drugs is apparent rather than real and that the duration of food access is a determining factor. The body weight changes may be brought about by the metabolic effects of these drugs rather than their effect on food and water intake.

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Subst Use Misuse. 1998 Jun;33(8):1711-9.
Use of amphetamine-like appetite suppressants: a cross-sectional survey in Southern Brazil.

de Lima MS, Beria JU, Tomasi E, Mari JJ.

Departamento de Saude Mental, Universidade Federal de Pelotas, RS, Brazil.

In 1994 a cross-sectional survey was undertaken in Pelotas, Southern Brazil, to assess the prevalence of amphetamine-like appetite suppressant use. 1,277 adults were interviewed, and the prevalence of anorectic drug use was 1.3% (95% CI = 0.7-1.9): 15 women and one man, mainly from higher socioeconomic groups. Most of the users (81%) had a medical prescription. Forty-one different drugs had been prescribed. Mean length of use was 8.7 months. These findings are discussed in terms of the overreliance on anorectics as aids to dieting, the dangers of polypharmacy, and the risks of long-term use.

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