Substituted amphetamine

Racemic amphetamine skeleton
This shows phenethylamine in blue with its substitution points marked. Amphetamine and its substituted derivatives contain a CH3 group at the alpha-position (Rα).
This shows amphetamine with its substitution points marked, excluding the N-position at the NH2 group which is unmarked.
Amphetamine pills

Substituted amphetamines are a class of compounds based upon the amphetamine structure; it includes all derivative compounds which are formed by replacing, or substituting, one or more hydrogen atoms in the amphetamine core structure with substituents.

- Substituted amphetamine

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Empathogens or entactogens are a class of psychoactive drugs that produce experiences of emotional communion, oneness, relatedness, emotional openness—that is, empathy or sympathy—as particularly observed and reported for experiences with 3,4-methylenedioxymethamphetamine (MDMA).

A selection of MDMA pills, which are often nicknamed "Ecstasy" or "E".

This class of drug is distinguished from the classes of hallucinogen or psychedelic, and amphetamine or stimulant.


Psychoactive drug primarily used for recreational purposes.

Addiction experts in psychiatry, chemistry, pharmacology, forensic science, epidemiology, and the police and legal services engaged in delphic analysis regarding 20 popular recreational drugs. Ecstasy was ranked 18th in dependence, physical harm, and social harm.
MDMA induced transporter reversal on human serotonin transporters (SERT), which leads to serotonin release.
In the serotonergic neurons of humans, extracellular MDMA releases serotonin via serotonin transporters (SERT). Intracellular MDMA inhibits VMAT2 and, to a much lesser extent, MAO-A.
Main metabolic pathways of MDMA in humans.
Alexander and Ann Shulgin in December 2011
A 1995 Vibe Tribe rave in Erskineville, New South Wales, Australia being broken up by police. MDMA use spread globally along with rave culture.
UNODC map showing the use of ecstasy by country in 2014 for the global population aged 15–64

This was broadly similar to the percentage of people who use cocaine or amphetamines, but lower than for cannabis or opioids.


Atypical antidepressant primarily used to treat major depressive disorder and to support smoking cessation.

1 : 1 mixture (racemate)
Wellbutrin XL
Principal pathways of bupropion metabolism.
Comparison of steady-state plasma bupropion levels with bupropion IR 100 mg t.i.d. (3x/day), bupropion SR 150 mg b.i.d. (2x/day), and bupropion XL 300 mg q.d. (1x/day).

Chemically, it is an aminoketone that belongs to the class of substituted cathinones and more generally that of substituted amphetamines and substituted phenethylamines.


Central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, and obesity.

It is also the parent compound of its own structural class, the substituted amphetamines, which includes prominent substances such as bupropion, cathinone, MDMA, and methamphetamine.


Medication and stimulant.

Ephedrine Sulphate (1932), Ephedrine Compound (1932), and Swan-Myers Ephedrine Inhalant No. 66 (circa 1940)
Ephedrine tablets
Proposed biosynthetic pathway of ephedrine from L -phenylalanine and pyruvic acid.
The four stereoisomers of ephedrine

As a phenethylamine, ephedrine has a similar chemical structure to amphetamines and is a methamphetamine analogue having the methamphetamine structure with a hydroxyl group at the β position.


About the stimulant drug.

Desoxyn (Methamphetamine Hydrochloride) 100 tablets.
A 2010 study ranking various illegal and legal drugs based on statements by drug-harm experts. Methamphetamine was found to be the fourth most damaging to society.
A suspected case of meth mouth
This diagram depicts the neuroimmune mechanisms that mediate methamphetamine-induced neurodegeneration in the human brain. The NF-κB-mediated neuroimmune response to methamphetamine use which results in the increased permeability of the blood–brain barrier arises through its binding at and activation of sigma receptors, the increased production of reactive oxygen species (ROS), reactive nitrogen species (RNS), and damage-associated molecular pattern molecules (DAMPs), the dysregulation of glutamate transporters (specifically, EAAT1 and EAAT2) and glucose metabolism, and excessive Ca2+ ion influx in glial cells and dopamine neurons.
This illustration depicts the normal operation of the dopaminergic terminal to the left, and the dopaminergic terminal in the presence of methamphetamine to the right. Methamphetamine reverses the action of the dopamine transporter (DAT) by activating TAAR1 (not shown). TAAR1 activation also causes some of the dopamine transporters to move into the presynaptic neuron and cease transport (not shown). At VMAT2 (labeled VMAT), methamphetamine causes dopamine efflux (release).
Shards of pure methamphetamine hydrochloride, also known as crystal meth
Pervitin, a methamphetamine brand used by German soldiers during World War II, was dispensed in these tablet containers.
U.S. drug overdose related fatalities in 2017 were 70,200, including 10,333 of those related to psychostimulants (including methamphetamine).

Methamphetamine belongs to the substituted phenethylamine and substituted amphetamine chemical classes.


Man chewing khat
Mechanism of the Non-Beta Oxidation pathway for the biosynthesis of S-Cathinone in the Khat plant
Chemical structure of bupropion, a cathinone derivative

Cathinone (also known as benzoylethanamine, or β-keto-amphetamine) is a monoamine alkaloid found in the shrub Catha edulis (khat) and is chemically similar to ephedrine, cathine, methcathinone and other amphetamines.


Two pairs of enantiomers: ephedrine (top) and pseudoephedrine (bottom)
A warning at an Australian pharmacy

Pseudoephedrine (PSE) is a sympathomimetic drug of the phenethylamine and amphetamine chemical classes.


Overarching term that covers many drugs including those that increase activity of the central nervous system and the body, drugs that are pleasurable and invigorating, or drugs that have sympathomimetic effects.

Ritalin: 20 mg sustained-release (SR) tablets
A chart comparing the chemical structures of different amphetamine derivatives
Roasted coffee beans, a common source of caffeine.
Tablets containing MDMA
Lines of illicit cocaine, used as a recreational stimulant
Catha edulis

Classifying stimulants is difficult, because of the large number of classes the drugs occupy, and the fact that they may belong to multiple classes; for example, ecstasy can be classified as a substituted methylenedioxyphenethylamine, a substituted amphetamine and consequently, a substituted phenethylamine.


Medication used together with diet and exercise to treat obesity.


Chemically, phentermine is a substituted amphetamine.