Empathogen-entactogen
Encyclopedia
The terms empathogen and entactogen are used to describe a class of psychoactive drug
s that produce distinctive emotional and social effects similar to those of MDMA. Putative members of this class include 2C-B
, 2C-I
, MDMA, MDA
, MDEA
, MBDB
, 2C-T-7
, and 2C-T-2
, among others. The chemical structure
of many entactogens contains a substituted amphetamine
core, and most belong to the phenethylamine
class of psychoactive drugs, although several (AET and AMT) are tryptamine
s. When referring to MDMA and its counterparts, the term 'MDxx' is often used with the exception of MDPV
. Entactogens are sometimes incorrectly referred to as major hallucinogens or stimulant
s, which is often thought to be incorrect although their effects are often somewhat similar.
to denote chemical agents inducing feelings of empathy
. "Entactogen" was coined by David E. Nichols
as an alternative to "empathogen", attempting to avoid the potential for improper association of the latter with negative connotations related to the Greek root "pathos" (suffering); Nichols also thought the word was limiting, and did not cover other therapeutic uses for the drugs that go beyond instilling feelings of empathy. The word "entactogen" is derived from the roots "en" , "tactus" and "gen" (Greek: produce) (Nichols 1986: 308). Neither term is dominant in usage, and, despite their difference in connotation, they are essentially interchangeable, as they refer to precisely the same chemicals.
and amphetamine
or from major psychedelic drug
s such as LSD
or psilocybin
. As implied by the category names, users of entactogens say the drugs often produce feelings of empathy, love, and emotional closeness to others. However, there have been only very preliminary comparisons of these different drugs in humans in properly-controlled laboratory studies.
, serotonin
, and norepinephrine
—closely resemble those of methamphetamine. In a study of rodents, MDMA was recently shown to induce release of oxytocin
, a hormone and neurotransmitter involved in social bonding. This may contribute to the emotional effects of MDMA. However, many other serotonergic
drugs also increase oxytocin without producing the unusual effects of MDMA . Entactogens other than MDMA have received relatively little scientific attention, making it difficult to draw conclusions about the mechanisms of entactogens in general.
effects, stimulant
effects, antidepressant
effects, anxiolytic
effects, and psychedelic
effects.
Psychoactive drug
A psychoactive drug, psychopharmaceutical, or psychotropic is a chemical substance that crosses the blood–brain barrier and acts primarily upon the central nervous system where it affects brain function, resulting in changes in perception, mood, consciousness, cognition, and behavior...
s that produce distinctive emotional and social effects similar to those of MDMA. Putative members of this class include 2C-B
2C-B
2C-B or 4-bromo-2,5-dimethoxyphenethylamine is a psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin in 1974. In Shulgin's book PiHKAL, the dosage range is listed as 16–24 mg. 2C-B is sold as a white powder sometimes pressed in tablets or gel caps and is referred...
, 2C-I
2C-I
2C-I or 2,5-dimethoxy-4-iodophenethylamine is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin. It was described in Shulgin’s book PiHKAL: A Chemical Love Story. The drug is used recreationally for its psychedelic and entactogenic effects...
, MDMA, MDA
3,4-Methylenedioxyamphetamine
3,4-Methylenedioxyamphetamine , also known as tenamfetamine , is a psychedelic and entactogenic drug of the phenethylamine and amphetamine chemical classes...
, MDEA
Methylenedioxyethylamphetamine
3,4-Methylenedioxy-N-ethylamphetamine is an entactogen, psychedelic, and stimulant of the phenethylamine and amphetamine chemical classes....
, MBDB
MBDB
Methylbenzodioxolylbutanamine is an entactogen of the phenethylamine chemical class. MBDB is a closely related chemical analogue of MDMA, with the only difference between the two molecules being an ethyl group instead of a methyl group attached to the alpha carbon.MBDB was first synthesized by...
, 2C-T-7
2C-T-7
2C-T-7 is a psychedelic phenethylamine of the 2C family. In his book PiHKAL: A Chemical Love Story, Alexander Shulgin lists the dosage range as 10 to 30 mg. 2C-T-7 is generally taken orally, and produces psychedelic and entactogenic effects that last 8 to 15 hours...
, and 2C-T-2
2C-T-2
2C-T-2, or 2,5-dimethoxy-4-ethylthiophenethylamine is a psychedelic and entactogenic phenethylamine of the 2C family. It was first synthesized in 1981 by Alexander Shulgin. The drug has structural and pharmacodynamic properties similar to the drug 2C-T-7 .-Dosage:In Alexander Shulgin's book...
, among others. The chemical structure
Chemical structure
A chemical structure includes molecular geometry, electronic structure and crystal structure of molecules. Molecular geometry refers to the spatial arrangement of atoms in a molecule and the chemical bonds that hold the atoms together. Molecular geometry can range from the very simple, such as...
of many entactogens contains a substituted amphetamine
Substituted amphetamine
Substituted amphetamines are a chemical class of stimulants, entactogens, hallucinogens, and other drugs. They feature a phenethylamine core with a methyl group attached to the alpha carbon resulting in amphetamine, along with additional substitutions...
core, and most belong to the phenethylamine
Phenethylamine
Phenylethylamine or phenethylamine is a natural monoamine alkaloid, trace amine, and also the name of a class of chemicals with many members well known for psychoactive drug and stimulant effects. Studies suggest that phenylethylamine functions as a neuromodulator or neurotransmitter in the...
class of psychoactive drugs, although several (AET and AMT) are tryptamine
Tryptamine
Tryptamine is a monoamine alkaloid found in plants, fungi, and animals. It is based around the indole ring structure, and is chemically related to the amino acid tryptophan, from which its name is derived...
s. When referring to MDMA and its counterparts, the term 'MDxx' is often used with the exception of MDPV
MDPV
Methylenedioxypyrovalerone is a psychoactive drug with stimulant properties which acts as a norepinephrine-dopamine reuptake inhibitor . Reportedly, it has been sold since around 2004 as a designer drug. It is also known as MDPK, MTV, Magic, Maddie, Black Rob, Super Coke and PV...
. Entactogens are sometimes incorrectly referred to as major hallucinogens or stimulant
Stimulant
Stimulants are psychoactive drugs which induce temporary improvements in either mental or physical function or both. Examples of these kinds of effects may include enhanced alertness, wakefulness, and locomotion, among others...
s, which is often thought to be incorrect although their effects are often somewhat similar.
Etymology
The term "empathogen" was coined in 1983 by Ralph MetznerRalph Metzner
Ralph Metzner Ph.D. , is an American psychologist, writer and researcher, who participated in psychedelic research at Harvard University in the early 1960s with Timothy Leary and Richard Alpert . Dr...
to denote chemical agents inducing feelings of empathy
Empathy
Empathy is the capacity to recognize and, to some extent, share feelings that are being experienced by another sapient or semi-sapient being. Someone may need to have a certain amount of empathy before they are able to feel compassion. The English word was coined in 1909 by E.B...
. "Entactogen" was coined by David E. Nichols
David E. Nichols
David E. Nichols is an American pharmacologist and medicinal chemist.Presently the Robert C. and Charlotte P. Anderson Distinguished Chair in Pharmacology at Purdue University, Nichols has worked in the field of psychoactive drugs since 1969...
as an alternative to "empathogen", attempting to avoid the potential for improper association of the latter with negative connotations related to the Greek root "pathos" (suffering); Nichols also thought the word was limiting, and did not cover other therapeutic uses for the drugs that go beyond instilling feelings of empathy. The word "entactogen" is derived from the roots "en" , "tactus" and "gen" (Greek: produce) (Nichols 1986: 308). Neither term is dominant in usage, and, despite their difference in connotation, they are essentially interchangeable, as they refer to precisely the same chemicals.
Psychological Effects
These drugs appear to produce a different spectrum of psychological effects from major stimulants such as methamphetamineMethamphetamine
Methamphetamine is a psychostimulant of the phenethylamine and amphetamine class of psychoactive drugs...
and amphetamine
Amphetamine
Amphetamine or amfetamine is a psychostimulant drug of the phenethylamine class which produces increased wakefulness and focus in association with decreased fatigue and appetite.Brand names of medications that contain, or metabolize into, amphetamine include Adderall, Dexedrine, Dextrostat,...
or from major psychedelic drug
Psychedelic drug
A psychedelic substance is a psychoactive drug whose primary action is to alter cognition and perception. Psychedelics are part of a wider class of psychoactive drugs known as hallucinogens, a class that also includes related substances such as dissociatives and deliriants...
s such as LSD
LSD
Lysergic acid diethylamide, abbreviated LSD or LSD-25, also known as lysergide and colloquially as acid, is a semisynthetic psychedelic drug of the ergoline family, well known for its psychological effects which can include altered thinking processes, closed and open eye visuals, synaesthesia, an...
or psilocybin
Psilocybin
Psilocybin is a naturally occurring psychedelic prodrug, with mind-altering effects similar to those of LSD and mescaline, after it is converted to psilocin. The effects can include altered thinking processes, perceptual distortions, an altered sense of time, and spiritual experiences, as well as...
. As implied by the category names, users of entactogens say the drugs often produce feelings of empathy, love, and emotional closeness to others. However, there have been only very preliminary comparisons of these different drugs in humans in properly-controlled laboratory studies.
Pharmacology
If MDMA is taken as a representative entactogen, the pharmacological mechanisms of this class—increased extracellular dopamineDopamine
Dopamine is a catecholamine neurotransmitter present in a wide variety of animals, including both vertebrates and invertebrates. In the brain, this substituted phenethylamine functions as a neurotransmitter, activating the five known types of dopamine receptors—D1, D2, D3, D4, and D5—and their...
, serotonin
Serotonin
Serotonin or 5-hydroxytryptamine is a monoamine neurotransmitter. Biochemically derived from tryptophan, serotonin is primarily found in the gastrointestinal tract, platelets, and in the central nervous system of animals including humans...
, and norepinephrine
Norepinephrine
Norepinephrine is the US name for noradrenaline , a catecholamine with multiple roles including as a hormone and a neurotransmitter...
—closely resemble those of methamphetamine. In a study of rodents, MDMA was recently shown to induce release of oxytocin
Oxytocin
Oxytocin is a mammalian hormone that acts primarily as a neuromodulator in the brain.Oxytocin is best known for its roles in sexual reproduction, in particular during and after childbirth...
, a hormone and neurotransmitter involved in social bonding. This may contribute to the emotional effects of MDMA. However, many other serotonergic
Serotonergic
Serotonergic or serotoninergic means "related to the neurotransmitter serotonin". A synapse is serotonergic if it uses serotonin as its neurotransmitter...
drugs also increase oxytocin without producing the unusual effects of MDMA . Entactogens other than MDMA have received relatively little scientific attention, making it difficult to draw conclusions about the mechanisms of entactogens in general.
Examples
The chemicals below have a varying degree of entactogenic effects. Some of the chemicals have a minimal entactogenic effect while others may have a strong entactogenic effect. These substances possess other effects including serenicSerenic
A serenic, or antiaggressive agent, is a type of drug which inhibits social feelings of irritability, aggression, and anger. Many commonly induce the opposite of effects as well, including empathy, compassion, and affection....
effects, stimulant
Stimulant
Stimulants are psychoactive drugs which induce temporary improvements in either mental or physical function or both. Examples of these kinds of effects may include enhanced alertness, wakefulness, and locomotion, among others...
effects, antidepressant
Antidepressant
An antidepressant is a psychiatric medication used to alleviate mood disorders, such as major depression and dysthymia and anxiety disorders such as social anxiety disorder. According to Gelder, Mayou &*Geddes people with a depressive illness will experience a therapeutic effect to their mood;...
effects, anxiolytic
Anxiolytic
An anxiolytic is a drug used for the treatment of anxiety, and its related psychological and physical symptoms...
effects, and psychedelic
Psychedelic
The term psychedelic is derived from the Greek words ψυχή and δηλοῦν , translating to "soul-manifesting". A psychedelic experience is characterized by the striking perception of aspects of one's mind previously unknown, or by the creative exuberance of the mind liberated from its ostensibly...
effects.
- 4-Fluoroamphetamine ("Flux")
- 4-methylthioamphetamine (4-MTA; "Flatliners")
- 5-APB5-APB5-benzofuran or 1-benzofuran-5-ylpropan-2-amine is a drug claimed to act as an agonist of the 5-HT2C receptor, which has been sold as a designer drug...
- 5-APDB
- 5-Methoxy-diisopropyltryptamine (5-MeO-DiPT; "Foxy" or "Foxy Methoxy")
- 6-APB6-APB6-benzofuran or 1-benzofuran-6-ylpropan-2-amine is thought to be a stimulant and entactogen drug although to date, no authoritative source can say even whether or not it is psychoactive. Chemically, it is of the phenethylamine and substituted amphetamine classes...
("Benzo Fury") - 6-APDB6-APDB6--2,3-dihydrobenzofuran is a stimulant and entactogen drug of the phenethylamine and amphetamine classes. It is an analogue of MDA where the heterocyclic 4-position oxygen from the 3,4-methylenedioxy ring has been replaced with a methylene group...
- alpha-ethyltryptamineAlpha-Ethyltryptamineα-ethyltryptamine , also known as etryptamine, is a psychedelic, stimulant and entactogen of the tryptamine chemical class.- History :...
(αET; Monase) - bk-MBDBBk-MBDBButylone, also known as β-keto-N-methylbenzodioxolylpropylamine , is an entactogen, psychedelic, and stimulant of the phenethylamine chemical class. It is the β-keto analogue of MBDB....
(Butylone) - indanylaminopropaneIndanylaminopropaneIndanylaminopropane , sometimes incorrectly referred to as indanylamphetamine, is an entactogen and psychedelic drug of the phenethylamine and amphetamine classes...
(IAP) - methylenedioxyaminoindane (MDAI)
- methylbenzodioxolylbutanamine (MBDB; "Eden")
- methylenedioxyamphetamine (MDA; "Mellow Drug of America"; "Sassafras")
- methylenedioxyethylamphetamineMethylenedioxyethylamphetamine3,4-Methylenedioxy-N-ethylamphetamine is an entactogen, psychedelic, and stimulant of the phenethylamine and amphetamine chemical classes....
(MDEA; "Eve") - methylenedioxymethamphetamineMethylenedioxymethamphetamineMDMA is an entactogenic drug of the phenethylamine and amphetamine class of drugs. In popular culture, MDMA has become widely known as "ecstasy" , usually referring to its street pill form, although this term may also include the presence of possible adulterants...
(MDMA; "Ecstasy"; "E", "X", "XTC", "Rolls", "Pills", "Adam", "Molly") - mephedrone ("Meow", "MCAT", "Molly's little sister", and "Shrimp")
- methylone ("Explosion", "Ease," and "Bubbles")
- methoxymethylamphetamine (MMA)
- paramethoxyamphetamine (PMA)