''para''-Chloromethamphetamine (also known as 4-chloromethamphetamine and 4-CMA; code name Ro 4-6861) is a

stimulant Stimulants (also known as central nervous system stimulants, or psychostimulants, or colloquially as uppers) are a class of drugs that increase alertness. They are used for various purposes, such as enhancing attention, motivation, cognition, ...

that is the ''N''-methyl

derivative In mathematics, the derivative is a fundamental tool that quantifies the sensitivity to change of a function's output with respect to its input. The derivative of a function of a single variable at a chosen input value, when it exists, is t ...

and

prodrug A prodrug is a pharmacologically inactive medication or compound that, after intake, is metabolized (i.e., converted within the body) into a pharmacologically active drug. Instead of administering a drug directly, a corresponding prodrug can be ...

of the neurotoxic drug ''para''-chloroamphetamine (4-CA). It has been found to decrease

serotonin Serotonin (), also known as 5-hydroxytryptamine (5-HT), is a monoamine neurotransmitter with a wide range of functions in both the central nervous system (CNS) and also peripheral tissues. It is involved in mood, cognition, reward, learning, ...

in rats. Further investigation into the long-term effects of chloroamphetamines discovered that administration of 4-CMA caused a prolonged reduction in the levels of

and the activity of

tryptophan hydroxylase Tryptophan hydroxylase (TPH) is an enzyme () involved in the synthesis of the monoamine neurotransmitter serotonin. Tyrosine hydroxylase, phenylalanine hydroxylase, and tryptophan hydroxylase together constitute the family of biopterin-depen ...

in the brain one month after injection of a single dose of the drug. Another study on rats found that 4-chloromethamphetamine was more potent at inducing conditioned taste aversion than

methamphetamine Methamphetamine (contracted from ) is a potent central nervous system (CNS) stimulant that is mainly used as a recreational drug use, recreational or Performance-enhancing substance, performance-enhancing drug and less commonly as a secon ...

. 4-Chloromethamphetamine was further investigated in the 1960s along with 4-CA and it was noted that they differed from their parent

amphetamine Amphetamine (contracted from Alpha and beta carbon, alpha-methylphenethylamine, methylphenethylamine) is a central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, an ...

and methamphetamine substances by exhibiting only a slight central stimulant effect in both animals and humans and that they acted like

antidepressant Antidepressants are a class of medications used to treat major depressive disorder, anxiety disorders, chronic pain, and addiction. Common side effects of antidepressants include Xerostomia, dry mouth, weight gain, dizziness, headaches, akathi ...

s rather than stimulants. Tablet containing 4-chloromethamphetamine

Studies in the 1970s found that a single dose of 10 mg/1 kg 4-CMA resulted in a decreased level of 5-hydroxytryptamine in the brain for several weeks. 4-Chloromethamphetamine was identified outside of the laboratory for the first time at the Tomorrowland festival edition 2015, where a tablet was found in possession of a drug dealer (see picture). In the following year, tablets with 4–CMA were also found in

Romania Romania is a country located at the crossroads of Central Europe, Central, Eastern Europe, Eastern and Southeast Europe. It borders Ukraine to the north and east, Hungary to the west, Serbia to the southwest, Bulgaria to the south, Moldova to ...

Austria Austria, formally the Republic of Austria, is a landlocked country in Central Europe, lying in the Eastern Alps. It is a federation of nine Federal states of Austria, states, of which the capital Vienna is the List of largest cities in Aust ...

and

Croatia Croatia, officially the Republic of Croatia, is a country in Central Europe, Central and Southeast Europe, on the coast of the Adriatic Sea. It borders Slovenia to the northwest, Hungary to the northeast, Serbia to the east, Bosnia and Herze ...

. Fortuitously, and for unknown reasons, 4-CMA disappeared briefly from the European

rave scene A rave (from the verb: '' to rave'') is a dance party at a warehouse, club, or other public or private venue, typically featuring performances by DJs playing electronic dance music. The style is most associated with the early 1990s dance mus ...

after the Spring of 2016. However, a 2019 study of participants of a dance music festival in

Belgium Belgium, officially the Kingdom of Belgium, is a country in Northwestern Europe. Situated in a coastal lowland region known as the Low Countries, it is bordered by the Netherlands to the north, Germany to the east, Luxembourg to the southeas ...

reported detection of 4-CMA in pills (out of 178 analyzed samples only one was mostly 4-CMA, while in one other 4-CMA was a minor ingredient).Lessons to be learned from toxicological analyses in intoxicated patients and seized materials at an electronic music dance festival. 2019. Forensic Sci Int. 299/174-9. P. Calle, K. Maudens, S. Lemoyne, S. Geerts, D. Van Sassenbroeck, P. Jensen, et al. doi: 10.1016/j.forsciint.2019.03.047.

References

{{DEFAULTSORT:Chloromethamphetamine, para- 4-Chlorophenyl compounds Designer drugs Methamphetamines Monoaminergic neurotoxins Serotonin-norepinephrine-dopamine releasing agents Stimulants

See also

References