A homologous series of 4-alkyl-2,5-dimethoxyphenylisopropylamines (alkyl = H through n-C5H11 and t-C4H9) was synthesized and compared with mescaline as serotonin agonists in a sheep umbilical preparation. The three-carbon homolog 6d was found to be the most potent of the straight-chain series in accordance with its observed psychotomimetic effectiveness in man.
In an attempt to relate the hallucinogenic potencies in man of some biologically important amphetamines and phenethylamines, the 1-octanol-water partition coefficients for 11 amphetamines were determined. Using these values and published Hansch pi constants, the log P for 17 additional amines was estimated. It was found that lipophilicity, as measured by the log of the partition coefficient,...
Abstract The crystal and molecular structure of 2,5-dimethoxy-4-ethyl-α-methyl-phenylethylamine (DOET) has been determined by X-ray crystallography and the conformation of the side chain has been examined theoretically by the use of a potential energy calculation. There is no indication in the solid state of any intra or inter-molecular hydrogen bonding. The isopropylamine side chain is...
D-lysergic acid diethylamide (LSD) displays (1) the phenylethylamine pattern present in mescaline, cyclazocine and catecholamines and (2) the 4-substituted tryptamine structure of psilocybin which is a serotonin analog. Hence (a) Naloxone--a blocker of the LSD-like side effects of cyclazocine--should (and does) block effects of LSD, and (b) cross-tolerance may be present between LSD and...
To the Editor.— In a recent issue (229:763, 1974), Shaffer describes a series of cases characterized by anesthesia, analgesia, nystagmus, dizziness, diplopia, visual distortions, and psychosis. These findings were attributed to ketamine, a derivative of phencyclidine. Phencyclidine is a major component of street drug preparations.1In one series, phencyclidine was detected in 184 of 237 street...
An extended battery of neuropsychological tests was administered to three groups of college seniors (lysergic acid diethylamide [LSD]/mescaline users; marihuana/hashish users; and controls) who were matched on predrug usage intellectual and personality dimensions. The study was replicated one year later. In the combined-years' analyses, the three groups showed statistically significant...
Several different molecular conformations of psychedelic drugs have been proposed to explain the very similar effects of drugs with markedly divergent chemical structures, such as mescaline andd-lysergic acid diethylamide (LSD). In some of these models, the α-carbon of methoxyamphetamine psychedelics approximates the asymmetric carbon No. 5 of LSD predicting that the (-) "R" isomer of the...
Abstract 47 undergraduate male volunteers were asked 2 questions relating to their use of marijuana and/or psychedelic drugs (e.g., LSD, mescaline, psilocybin) and were administered the Harvard Group Scale of Hypnotic Susceptibility, Form A (HGSHS:A). The HGSHS:A scores of Ss who had, at some time, taken any of these drugs averaged 2 points higher than scores of Ss who had not. Further research...
Abstract The abuse of nutmeg for narcotic purposes has led to renewed chemical and pharmacological interest in this drug. Several allylbenzene derivatives whose biological transformation products have structures resembling mescaline and amphetamine have been identified as psychotropic constituents. It is suggested that the intensity of the hallucinogenic action of these compounds is due to the...
It is well recognized that LSD (lysergide) can give serious adverse reactions, including suicide and prolonged psychosis; Smart and Bateman (1967) have reviewed the subject thoroughly. However, examples reported refer largely to cases where the LSD was self-administered. Medical case reports usually cover small case numbers, and publication may be determined by high adverse reaction rates....