A vast number of compounds with physiological activity contain nitrogen: from amphetamine to LSD, the chemistry of psychoactive amines
Many simple amines are used as drugs. Ephedrine (also called adrenaline), propylhexedrine, hexamethylenetetramine, and mescaline are a few examples. This is not to mention certain prohibited substances such as the well-known amphetamine, speed, methylenedioxyamphetamine (MDA), and methylenedioxy-N-methylamphetamine (MDMA), referred to in non-academic circles as ecstasy. A common structure in many of these compounds—though not all—is the 2-phenethylamine unit. Although the mechanism of these substances is not yet well established, it appears that this structural particularity is necessary for the compound to bind to its receptor.
These molecules are not only potent central nervous system stimulants, but they also increase cardiovascular activity and body temperature, and cause appetite loss. This last function is one of the reasons for their use in diets and obesity treatment. Unfortunately, they can produce chemical dependence and are potentially dangerous, particularly when taken without medical supervision.
Do not be fooled by claims that there are many types of speed (green, apple, brown, pink…). Real speed is what we include here.
Ecstasy is a variant of speed that was introduced later because, unlike speed, it is not addictive, and this is solely due to the introduction of the methyl group (note the small difference between both structures).
Mescaline is an entheogenic substance extracted from the peyote cactus, which grows in Mexico. A liquor is also made with peyote: mezcal, although its mescaline content is very low. If you see this liquor, you will notice that it contains the worms that inhabit the cactus inside the bottle. It is said that those who ingest the worms get more intoxicated than by simply drinking the liquor, because the worms retain a higher concentration of mescaline. In reality, I do not know the degree of truth to this hypothesis.
It must be taken into account that many of these compounds have different physiological functions depending on their stereoisomerism. Since I assume many of you are not familiar with this topic, I will use the example of amphetamine:
R-Amphetamine is a potent central nervous system stimulant, in addition to being an antidepressant. The thick line means that this bond is in front of the plane of the paper. Its effects are very different from those of S-Amphetamine:
S-Amphetamine is a stimulant of the sympathetic nervous system; the dashed line denotes that the bond is behind the plane of the paper. I only need to mention that R-Amphetamine is the one you are interested in. There are also stereoisomers of this type for speed and ecstasy. If you look closely, they are very similar and will have the same meaning in this case:
R means nitrogen forward (thick line).
S means nitrogen backward (dashed line).
Stereoisomerism is not a property present in all organic molecules; thus, for example, mescaline, which is a potent hallucinogen, does not have R and S isomers. When synthesizing amphetamine, it is normal to obtain a mixture of both isomers. These mixtures are called racemates. Racemates must be separated into their isomers.
Many amines whose nitrogen atom is part of a ring—that is, nitrogen heterocycles—also have significant physiological effects, such as cocaine, nicotine, and lysergic acid diethylamide (LSD):
Cocaine is a stimulant and topical anesthetic found in coca leaves. It generates addiction. Paradoxically, dependence is acquired faster if it is smoked rather than snorted.
Nicotine is found in a concentration of 2–8% in dried tobacco leaves and, despite what many think, it is not what turns smokers’ teeth yellow; tar is responsible for that.
LSD, a legendary substance in the sixties, was discovered by accident by the Swiss chemist Albert Hofmann in the forties and is the most powerful known hallucinogenic substance. In his first self-experiment, he experienced a totalizing mystical experience while riding his bicycle home; hence, some blotter papers sold on the market, impregnated with LSD solutions, show an illustration of a bicycle.
