Deoxy ephedrine

Fig. 6.5 Molecular complex formed between (a) cocaine, AA and IA (b) deoxy-ephedrine, IA and HEM (c) methadone, IA and HEM (d) morphine, MAA and HEM, as predicted from molecular modeling.81 Reproduced with permission...

Almost all analogs of ephedrine and epinephrine have been synthesized and subjected to pharmacological evaluation. Some of them are used in medicine. The list includes amphetamine or benzedrine (XX), deoxy-ephedrine (XXI), vonedrine (XXII), propadrine (XXIII), paredrine (XXIV), veritol (XXV), suprifen (XXVI), and neosynephrine (XXVII). They are advocated as vasoconstrictors in otolaryngology. The marketed form of neosynephrine is the Z-isomer. Amphetamine and deoxyephedrine are now better known for their stimulating action on the central nervous system (78, 79) and are used by persons whose duties call for long periods of alertness. The d-forms of both amines are more effective than the Z-forms in this respect. The commercial names of cZ-deoxyephedrine and cZ-amphetamine are pervitin and dexedrine, respectively. Two catechol derivatives have been recommended as substitutes for epinephrine. They are epinine (XXVIII) and corbasil (XXIX). 

The most successful modifier is cinchonidine and its enantiomer cinchonine, but some work in expanding the repertoire of substrate/modifier/catalyst combinations has been reported (S)-(-)-l-(l-naphthyl)ethylamine or (//)-1 -(I -naphth T)eth Tamine for Pt/alumina [108,231], derivatives of cinchona alkaloid such as 10,11-dihydrocinchonidine [36,71], 2-phenyl-9-deoxy-10, 11-dihydrocinchonidine [55], and O-methyl-cinchonidine for Pt/alumina [133], ephedrine for Pd/alumina [107], (-)-dihydroapovincaminic acid ethyl ester (-)-DHVIN for Pd/TiOz [122], (-)-dihydrovinpocetine for Pt/alumina [42], chiral amines such as 1 -(1 -naphtln I)-2-(I -pyrro 1 idiny 1) ethanol, l-(9-anthracenyl)-2-(l-pyrrolidinyl)ethanol, l-(9-triptycenyl)-2-(l-pyrrol idi nyl)cthanol, (Z )-2-(l-pyrrolidinyl)-l-(l-naphthyl)ethanol for Pt/alumina [37,116], D- and L-histidine and methyl esters of d- and L-tryptophan for Pt/alumina [35], morphine alkaloids [113],... 

CDs Chiral recognition is based on inclusion of the bulky hydrophobic group of the analyte into the hydrophobic cavity of the CD and on lateral interactions of the hydroxyl groups, such as hydrogen bonds and dipole-dipole interactions, with the analyte. Carboxymethylated P-CD, heptakis- 0-methyl- P-CD, hy dr oxy ethyl- P- CD, mono(6-P-aminoethylamino-6-deoxy)-P-CD, and mono(6-amino-6-deoxy)-P-CD. Acebutolol, acenocoumarol, carnitine, cathinone, ephedrine, epinephrine, glutethimide, ketotifen, thioridazine, etc. 

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