Phenyl-3-aminobutane

Of special importance among the new stimulants are those which contain 2-phenyl-3-hutane as active principle. 2-Phenyl- methylaminobutane also has proved very effective. 

Such conditions of lassitude are frequently combined with coincident psychical depressions. The new stimulants prove advantageous in all these cases. Since for the most part it will be a matter of a frequently recurring use of the stimulants, it is a great advantage that they show no undesirable secondary affects. For example, the stimulants containing 2-phenyl-3-aminohutane or 2-phenyl-3-methylaminobutane as active principle do not even produce the unpleasant feeling of dryness in the mouth which frequently arises as a consequence of the action of 

1- phenyl-2-aminopropane. Further, no habituation to the new stimulants is developed, so that continually increasing doses are not rendered necessary in addition, no craving for the new stimulants is to be observed. 

As has already heen described, the stimulants according to the invention which are of the greatest importance are those containing 

The new compounds according to the invention are valuable appetite-reducers which have shown themselves to be superior to similarly constituted known compounds. 

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DOM, DOET (structures shown in Fig. 1), LSD, mescaline and (+ )-amphetamine were tested in all 3 test situations and the series of substituted phenyl aminobutanes (structures shown in Fig. 2) were tested in open-field and spontaneous activity tests only. 

AEM a-ETHYLMESC ALIN E 2-AMINO-l-(3,4,5-TRIMETHOXYPHENYL)BUTANE 1 (3,4,5TRIMETHOX Y-PHENYL)-2-AMINOBUTANE... 

It goes yet further. The antidepressant series of Ariadne compounds are 1 -phenyl-2-aminobutanes. Butthe 1 -phenyl is againa 2,4,5-trisubstituted compound. The 2,4,6-isomer will give rise to a pseudo-Ariadne family, and I will bet that they too will be antidepressants. The 1 -phenyl-2-aminobutane analog of t-2C-T-4 is the 2,4,6-analogue and it has been prepared as far as the nitrostyrene. It has not yet been reduced, so it is not yet been evaluated, but it could be a most remarkable psycho-pharmacological probe. 

R)-a-incthylbcnzylairnne (R)-a-( 1 -naphthyl)ethy lamine (R)-a-phenyl-l-propylamine (R)-n orepi n ep h ri n c (R)-2-aminobutane... 

Among these bioactive molecules, SMA derivatives have held an important place ever since Fessenden showed equivalent biological activities of the chlorohydrates of 3-methyl-3-phenyl-2-aminobutane, a sympathomimetic amine, and 1-dimethylphenysilyl-aminoethane, the silicon analog.477 Both the enantiomers of this SMA have been synthesized 478... 

The new compounds show a particularly desirable ratio of appetite-reducing to central nervous system-stimulating activity, particularly through lower toxicity than similarly constituted active appetite-reducing substances. The new compounds may be administered orally and have a long duration of action they may be used in humans at a dose level of about 0.1 to 3.0 mg/kg, preferably from 0.3 to 1.5 mg/kg daily. Particularly useful compounds, from the point of view of their physiological activity include l- p-chlorophenyl)-2-aminobutane, l-(p-chloro-phenyl)-2-methylaminobutane, l-(p-chlorophenyl)-2-aminobutane. 

It goes yet further. The antidepressant series of "Ariadne" compounds are 1-phenyl-2-aminobutanes. But the 1-phenyl is again a... 

Write out a synthesis of 1-phenyl-l-aminobutane from benzyl alcohol. 

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