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

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).

- Empathogen–entactogen

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Hallucinogens are a large and diverse class of psychoactive drugs that can produce altered states of consciousness characterized by substantial alterations in thought, mood, and perception.

One "Blotter" sheet of 900 LSD doses.
Salvia divinorum
Datura innoxia in flower.
Attractive but highly toxic berry of Atropa belladonna
Flowers and foliage of Nicotiana tabacum, the cultivated tobacco.
Single fruiting body of Amanita muscaria
Myristica fragrans fruit, halved, showing within the red seed (nutmeg) enclosed in its brown aril (mace).

Entactogens and cannabinoids are also sometimes considered hallucinogens.


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

Entactogenic effects—increased empathy or feelings of closeness with others and oneself

Substituted phenethylamine

Composed of all the derivative compounds of phenethylamine which can be formed by replacing, or substituting, one or more hydrogen atoms in the phenethylamine core structure with substituents.

The structural formula of phenethylamine with marked substitution points. Phenethylamine is obtained when R2=R3=R4=R5=R6=RN=Rα=Rβ=H.
The structural formula of phenethylamine

Many substituted phenethylamines are psychoactive drugs which belong to a variety of different drug classes, including central nervous system stimulants (e.g., amphetamine), hallucinogens (e.g., dl-2,5-dimethoxy-4-methylamphetamine DOM), entactogens (e.g., 3,4-methylenedioxyamphetamine MDA), appetite suppressants (e.g. phentermine), nasal decongestants and bronchodilators (e.g., levomethamphetamine and pseudoephedrine), antidepressants (e.g. bupropion and phenelzine), antiparkinson agents (e.g., selegiline), and vasopressors (e.g., ephedrine), among others.

Psychedelic drug

To trigger non-ordinary states of consciousness .

Synthetic mescaline. Normally biosynthesized from peyote and some other cacti, mescaline was the first psychedelic compound to be extracted and isolated.
5-HT2A receptor
Doses of lysergic acid diethylamide (LSD)
Lysergic acid diethylamide (LSD)
Psilocybin session at Johns Hopkins
Preparation of Ayahuasca, Province of Pastaza, Ecuador.
Psychedelic rock band Jefferson Airplane in 1967

2C-B (2,5-dimethoxy-4-bromophenethylamine) is a substituted phenthylamine first synthesised in 1974 by Alexander Shulgin. 2C-B is both a psychedelic and a mild entactogen, with its psychedelic effects increasing and its entactogenic effects decreasing with dosage. 2C-B is the most well known compound in the 2C family, their general structure being discovered as a result of modifying the structure of mescaline.

Alexander Shulgin

American medicinal chemist, biochemist, organic chemist, pharmacologist, psychopharmacologist, and author.

With Ann Shulgin at book signing in Oakland, California, December 2011
Zectran-containing pesticide manufactured by Dow; photo taken at the Farm on July 26, 2009.
Shulgin at the home-based lab on his property, known as "the Farm", 2009

He is credited with introducing 3,4-methylenedioxymethamphetamine (MDMA, commonly known as "ecstasy") to psychologists in the late 1970s for psychopharmaceutical use and for the discovery, synthesis and personal bioassay of over 230 psychoactive compounds for their psychedelic and entactogenic potential.


Structural similarities between some amphetamine-like stimulants and their 3,4-methylenedioxy- derivatives.
Left: amphetamine, methamphetamine and methcathinone.
Right: MDA, MDMA, and methylone
Bottles of Explosion

Methylone (also known as "3,4-methylenedioxy-N-methylcathinone", "MDMC", "βk-MDMA" and by the slang term "M1") is an empathogen and stimulant psychoactive drug.


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

3,4-Methylenedioxy-N-ethylamphetamine (MDEA; also called MDE and colloquially, Eve) is an empathogenic psychoactive drug.


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

1,3-Benzodioxolyl-N-methylbutanamine (N-methyl-1,3-benzodioxolylbutanamine, MBDB, 3,4-methylenedioxy-N-methyl-α-ethylphenylethylamine) is an entactogen of the phenethylamine chemical class.

Substituted amphetamine

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.

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

The compounds in this class span a variety of pharmacological subclasses, including stimulants, empathogens, and hallucinogens, among others.


Synthesis of MDA and related analogs from safrole
MDA as prepared for recreational use

3,4-Methylenedioxyamphetamine (also known as MDA and sass) is an empathogen-entactogen, psychostimulant, and psychedelic drug of the amphetamine family that is encountered mainly as a recreational drug.