The enantiomers of a series of methoxy-and alkyl-substituted phenylisopropylamines were prepared by low-pressure reduction of imines formed by reaction of the appropriate phenylacetones with either (+)or (-)-a-methylbenzylamine, followed by hydrogenolysis of the hydrochlorides of the resulting-/V-(a-phenethyl)phenylisopropylamines. Values of [a]D are reported and enantiomeric purities were, in the range 96-99%. Overall yields ranged from 30 to 60%. Glc or fluorine nmr analysis of enantiomeric purity was accomplished using a-methoxy-a-trifluoromethylphenylacetamides. Glc analysis of the jV-trifluoroacetyl-S-prolylarnides was used to confirm R-(-) and S-{+) absolute configurations of all compounds. (+)or (-)-2,5-dimethoxyamphetamine was brominated to give the (+)or (-)-4-bromo compound. The enantiomers of 1,2,3,4-tetrahydro-2-naphthylamine could not be prepared by this method.Generally, optical isomers of a drug molecule possess differing degrees of biological activity. In the case of amphetamine, norepinephrine uptake into synaptosomes from noradrenergic regions of the brain is inhibited to a greater degree by the 5-(+) than by the R-(-) enantiomer.2'3 In addition, the two isomers of amphetamine are not equally good substrates for side-chain metabolizing enzymes in certain animal species.4 Since Gordis5 has found that no racemization of either isomer occurs when amphetamine is administered to man, it is possible that the complex effects of psychotomimetic amphetamines could be partially due to the fact that racemic mixtures have been used for testing.In the report by Barfknecht and Nichols® on the effects of (i?)-(-)-and (S)-(+)-3,4-dimethoxyamphetamine (3, in the rat, it was suggested that LSD could be considered as a phenethylamine derivative. Natural lysergic acid 1 possesses the 5R,8R absolute configuration7'8 and it was predicted that the psychotomimetic effects of the amphetamines might reside in the R enantiomers, based on their stereochemical relationship to lysergic acid. This prediction is consistent with stereochemical correlations between LSD, phenethylamines, and tryptamines proposed by Kang and Green.9 Indeed, it was found that the R-(-) isomer of 3,4-DMA seemed to be responsible for the psychotomimetic effects in the rat.6

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The incidence and quantities of dimethyltryptamine and O-methylbufotenine were studied in the cerebrospinal fluid of patients suffering acute schizophrenic illnesses and in surgical and neurological control groups. Some schizophrenic patients have higher levels of both amines than do controls, though the differences in distribution did not reach statistical significance in the sample studied. The gas-chromatographic technique used is sensitive at the low picogram level.

The interiors of two large Kentucky caves — Mammoth Cave and nearby Salts Cave, both within Mammoth Cave National Park — were much visited and utilized by prehistoric Indians. Large quantities of artifacts and numerous other evidences of human activity are still present in both caves, especially in undisturbed portions of Salts Cave. Most of the remains comprise perishable materials of vegetable fiber and wood, and plants or plant parts carried into the caves by the aboriginal inhabitants of the region. Several collections of artifacts gathered 40 or 50 years ago from the surface in the Mammoth Cave area have recently been examined by D. W. Schwartz of the University of Kentucky. One such collection hints at a village site of the late Archaic-Early Woodland time range somewhere near the entrance to Salts Cave. In 1961, specimens of the black-brown ceiling and wall deposits which are quite extensive in parts of both Salts and Mammoth caves were collected and analyzed. The deposits were found to be soot, presumably from aboriginal torches and hearths whose remains occur plentifully in some areas of the caves. A sample of soot from Salts Cave was submitted for radiocarbon determination; the resulting date is 3075 ± 140 B.P. Two dates had been previously obtained by the National Park Service from artifacts in Mammoth Cave: 2230 ± 40 B.P. and 2370 ± 60 B.P. These three dates support the suggestion of a late Archaic-Early Woodland placement for the prehistoric activity in Salts and Mammoth caves.

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