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Issue 9, 2002
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Effective complexation of psychotropic phenethylammonium salts from a disodium dipyrazolate salt of macrocyclic structure

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Abstract

The equilibrium stability constants (Ks) of ammonium pyrazolate complexes [L2−]2RN(R′)H2+ (3, R′ = H and 4, R′ = Me) formed from a macrocyclic disodium dipyrazolate salt 2[L2−] 2Na+ and ammonium salts (RNH3+X or RN(Me)H2+X) of psychotropic drugs and neurotransmitter catecholamines have been evaluated by electrochemical methods in DMSO solution. The resulting Ks values demonstrate that, except for (±)-amphetamine, the complexes formed by lipophilic primary [mescaline, (+)-amphetamine, (±)-p-methoxyamphetamine (PMA), (±)-3,4-methylenedioxyamphetamine (MDA)] and secondary [(±)-methamphetamine, (+)-methamphetamine and (±)-3,4-methylenedioxymethamphetamine (MDMA ‘ecstasy’)] phenethylamines are more stable than those formed from hydrophilic ones (dopamine and norepinephrine). A 1H and 13C NMR study on the formation of complexes of structure 3 and 4 formed from primary [mescaline, (+)-amphetamine] and secondary [(+)-methamphetamine] ammonium salts is given.

Graphical abstract: Effective complexation of psychotropic phenethylammonium salts from a disodium dipyrazolate salt of macrocyclic structure

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Publication details

The article was received on 21 Jan 2002, accepted on 18 Jun 2002 and first published on 11 Jul 2002


Article type: Paper
DOI: 10.1039/B200607C
Citation: J. Chem. Soc., Perkin Trans. 2, 2002,0, 1634-1638
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    Effective complexation of psychotropic phenethylammonium salts from a disodium dipyrazolate salt of macrocyclic structure

    F. Reviriego, P. Navarro, A. Domènech and E. García-España, J. Chem. Soc., Perkin Trans. 2, 2002, 0, 1634
    DOI: 10.1039/B200607C

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