Entactogens

3,4-Methylenedioxymethamphetamine (MDMA), commonly known as ecstasy (tablet form), and molly (crystal form), is an entactogen with stimulant and minor psychedelic properties.

Mephedrone, also known as ', , or , is a synthetic stimulant drug belonging to the amphetamine and cathinone classes. It is commonly referred to by slang names such as drone, , white magic, meow meow, and bubble'. Chemically, it is similar to the cathinone compounds found in the khat plant, native to eastern Africa.

2C-B, also known as 4-bromo-2,5-dimethoxyphenethylamine or by names such as Nexus or Erox, is a psychedelic drug of the phenethylamine and 2C families. The drug is used as a recreational drug and is usually taken orally. 2C-B produces hallucinogenic, mild stimulant, and mild entactogenic-like effects. Its hallucinogenic effects at typical doses are milder than those of other psychedelics like LSD or psilocybin.

3,4-Methylenedioxyamphetamine (MDA) is an entactogen, stimulant, and psychedelic drug of the amphetamine and MDxx families that is encountered mainly as a recreational drug. It is usually taken orally.

α-Methyltryptamine (αMT, AMT) is a psychedelic, stimulant, and entactogen drug of the tryptamine and α-alkyltryptamine families. It was originally developed as an antidepressant at Upjohn in the 1960s, and was used briefly as an antidepressant in the Soviet Union under the brand name Indopan or Indopane before being discontinued.

Methylone, also known as '3,4-methylenedioxy-N-methylcathinone (MDMC'), is an entactogen and stimulant drug of the amphetamine, cathinone, and MDxx families related to 3,4-methylenedioxymethamphetamine (MDMA; "ecstasy"). It is the β-keto or cathinone analogue of MDMA. The drug is usually taken orally, but can also be administered by other routes.

'3,4-Methylenedioxy-N-ethylamphetamine (MDEA; also called MDE and colloquially, Eve') is an empathogenic psychoactive drug. MDEA is a substituted amphetamine and a substituted methylenedioxyphenethylamine. MDEA acts as a serotonin, norepinephrine, and dopamine releasing agent and reuptake inhibitor.

Entactogens, also known as empathogens or connectogens, are a class of psychoactive drugs that induce experiences of emotional communion, oneness, connectedness, emotional openness—that is, empathy—as particularly observed and reported for experiences with MDMA (ecstasy). This class of drug is distinguished from the classes of hallucinogens or psychedelics and stimulants, although entactogens, for instance MDMA, can also have these properties. Entactogens are used both as recreational drugs and are being investigated for medical use in the treatment of psychiatric disorders, for instance MDMA-

α-Ethyltryptamine (αET, AET), also known as etryptamine, is an entactogen and stimulant drug of the tryptamine family. It was originally developed and marketed as an antidepressant under the brand name Monase by Upjohn in the 1960s before being withdrawn due to toxicity.

4-Fluoroamphetamine (4-FA; 4-FMP; PAL-303; "Flux"), also known as '''para-fluoroamphetamine (PFA'''), is a psychoactive research chemical of the phenethylamine and substituted amphetamine chemical classes. It produces stimulant and entactogenic effects. As a recreational drug, 4-FA is sometimes sold along with related compounds such as 2-fluoroamphetamine and 4-fluoromethamphetamine.

MBDB, also known as '''N-methyl-1,3-benzodioxolylbutanamine or as 3,4-methylenedioxy-N-methyl-α-ethylphenylethylamine, is an entactogen of the phenethylamine, amphetamine, and phenylisobutylamine families related to MDMA. It is known by the nicknames "Eden" and "Methyl-J'''".

5-MeO-DiPT, also known as '5-methoxy-N,N-diisopropyltryptamine and sometimes as foxy methoxy or simply foxy', is an atypical psychedelic drug of the tryptamine and 5-methoxytryptamine families. It has unique and distinct effects from other serotonergic tryptamines, including some stimulant- and entactogen-like effects, robust tactile and sexual enhancement, and only light hallucinogenic effects. The drug is usually taken orally, but may also be used by other routes.

Methedrone ('''para-methoxymethcathinone, 4-methoxymethcathinone, bk-PMMA, PMMC, methoxyphedrine, 4-MeOMC') is a recreational drug of the cathinone chemical class. Chemically, methedrone is closely related to para''-methoxymethamphetamine (PMMA), methylone and mephedrone. Methedrone received media attention in 2009 after the death of two young Swedish men. In both cases toxicology analysis showed methedrone was the only drug present in both men during the time of their overdose and subsequent deaths.

group of stereoisomers

3-Methylmethcathinone (3-MMC), also known as metaphedrone, is a designer drug from the substituted cathinone family. 3-MMC is a monoamine transporter substrate (a substance acted upon by monoamine transporters in the brain) that potently releases and inhibits the reuptake of dopamine and norepinephrine, as well as displaying moderate serotonin releasing activity.

Butylone, also known as 'β-keto-N-methylbenzodioxolylbutanamine (βk-MBDB'), is a psychoactive drug of the phenethylamine, amphetamine, phenylisobutylamine, and cathinone families. It is the β-keto (substituted cathinone) analogue of MBDB and the substituted methylenedioxyphenethylamine analogue of buphedrone.

Flephedrone, also known as 4-fluoromethcathinone (4-FMC), is a stimulant drug of the cathinone chemical class that has been sold online as a designer drug starting in 2008.

6-APB, also known as 6-(2-aminopropyl)benzofuran, is an entactogen of the phenethylamine, amphetamine, and benzofuran families. 6-APB and related drugs are sometimes informally called "Benzofury" in media reports. It is similar in structure to MDA, but differs in that the 3,4-methylenedioxyphenyl ring system has been replaced with a benzofuran ring. 6-APB is also the unsaturated benzofuran derivative of 6-APDB. It may appear as a tan or brown grainy powder.

MDAI, also known as 5,6-methylenedioxy-2-aminoindane, is an entactogen of the 2-aminoindane family which is related to MDMA and produces similar subjective effects.

'3,4-Methylenedioxy-N-hydroxyamphetamine (MDOH, MDH), also known as N-hydroxy-MDA', is an entactogen, psychedelic, and stimulant of the phenethylamine, amphetamine, and MDxx families. It is the N-hydroxy homologue of MDA, and the N-desmethyl homologue of FLEA (MDMOH).

Ethylone, also known as '3,4-methylenedioxy-N-ethylcathinone (MDEC, βk-MDEA'), is a recreational designer drug of the phenethylamine, amphetamine, and cathinone chemical classes. It is the β-keto analogue of MDEA ("Eve"). Ethylone has only a short history of human use and is reported to be less potent than its relative methylone. In the United States, it began to be found in cathinone products in late 2011.

2-Methyl-3,4-methylenedioxyamphetamine (2-methyl-MDA) is an entactogen-related drug of the amphetamine class. It acts as a selective serotonin releasing agent (SSRA), with IC50 values of 93nM, 12,000nM, and 1,937nM for serotonin, dopamine, and norepinephrine efflux. 2-Methyl-MDA is more potent than MDA and 5-methyl-MDA. However, it is slightly more selective for serotonin over dopamine and norepinephrine release in comparison to 5-methyl-MDA.

5-Methyl-MDA, also known as 5-methyl-3,4-methylenedioxyamphetamine, is an entactogen and psychedelic designer drug of the amphetamine class. It is a ring-methylated homologue of MDA and a structural isomer of MDMA.

5-MAPB, also known as '5-(N-methyl-2-aminopropyl)benzofuran', is an entactogen and designer drug of the amphetamine family that is similar to MDMA in its structure and effects.

Naphthylaminopropane (NAP; code name PAL-287), also known as naphthylisopropylamine (NIPA), is an experimental drug of the amphetamine and naphthylaminopropane families that was under investigation for the treatment of alcohol and stimulant addiction.

1,3-Benzodioxolylbutanamine (BDB), also known as 3,4-methylenedioxy-α-ethylphenethylamine or as J, is an entactogen of the phenethylamine, phenylisobutylamine, and MDxx families related to MDMA.

6-Methyl-MDA, also known as 6-methyl-3,4-methylenedioxyamphetamine is an entactogen and psychedelic drug of the amphetamine and MDxx families. It was first synthesized in the late 1990s by a team including David E. Nichols at Purdue University while investigating derivatives of 3,4-methylenedioxyamphetamine (MDA) and 3,4-methylenedioxy-N-methylamphetamine (MDMA).

6-MAPB ('1-(benzofuran-6-yl)-N-methylpropan-2-amine') is an entactogen of the benzofuran family which is structurally related to 6-APB and MDMA. It is known to be a serotonin releasing agent and, unlike MDMA, a potent serotonin 5-HT1B receptor agonist. The drug is not known to have been widely sold as a "designer drug" but has been detected in analytical samples taken from individuals hospitalised after using drug combinations that included other benzofuran derivatives. 6-MAPB was first encountered as a novel designer drug in 2013 and described in the scientific literature in 2014. It was bann

'5-(2-Aminopropyl)-2,3-dihydro-1H-indene (5-APDI), also known as indanylaminopropane (IAP), 2-aminopropylindane (2-API), indanametamine, and, incorrectly, as indanylamphetamine', is an entactogen and psychedelic drug of the amphetamine family. It has been sold by online vendors through the Internet and has been encountered as a designer drug since 2003, but its popularity and availability has diminished in recent years.

4-Bromomethcathinone (4-BMC), also known as brephedrone, is a psychoactive drug and research chemical of the phenethylamine, amphetamine, and cathinone chemical classes. It acts as a serotonin-norepinephrine-dopamine releasing agent (SNDRA), and to a lesser degree, as a serotonin-norepinephrine-dopamine reuptake inhibitor (SNDRI). Cathinones, including 4-BMC, possess neurotoxic and cytotoxic properties.

3-Methoxy-4-methylamphetamine (MMA) is an entactogen and psychedelic drug of the phenethylamine and amphetamine classes. It was first synthesized in 1970 and was encountered as a street drug in Italy in the same decade. MMA was largely forgotten until being reassayed by David E. Nichols as a non-neurotoxic MDMA analogue in 1991, and has subsequently been sold as a designer drug on the internet since the late 2000s.

1-Aminomethyl-5-methoxyindane (AMMI), is a drug developed by a team led by David E. Nichols at Purdue University, which acts as a selective serotonin releasing agent (SSRA) and binds to the serotonin transporter (SERT) with similar affinity relative to DFMDA.

4-Methylmethamphetamine (4-MMA), also known as mephedrine, is a putative stimulant and entactogen drug of the amphetamine family. It acts as a serotonin–norepinephrine–dopamine releasing agent (SNDRA). The drug is the β-deketo analogue of mephedrone (4-methylmethcathinone; 4-MMC) and the N-methyl analogue of 4-methylamphetamine (4-MA).

'3,4-Methylenedioxy-N-hydroxy-N-methylamphetamine, also known as MDMOH, MDHMA, or FLEA', is an entactogen, psychedelic, and stimulant of the phenethylamine, amphetamine, and MDxx families. It is the N-hydroxy homologue of MDMA ("Ecstasy"), and the N-methyl homologue of MDOH.

MDMAT, also known as '6,7-methylenedioxy-N-methyl-2-aminotetralin', is a serotonin releasing agent (SRA) and possible entactogen of the 2-aminotetralin family. It is the N-methylated derivative of MDAT, similarly to the relationship of MDMA to MDA. It has been theorized to have less long-term neurotoxicity and less hallucinogenic effects than other MDxx derivatives, but no formal scientific research has been conducted specifically on MDMAT.

4-Fluoromethamphetamine (4-FMA) is a stimulant drug related to methamphetamine and 4-fluoroamphetamine. It has been reported to be sold as a designer drug, but little is known about its pharmacology or toxicology.

MEAI, also known as 5-methoxy-2-aminoindane (5-MeO-AI) and by its developmental code name CMND-100, is an entactogen-like psychoactive drug of the 2-aminoindane family. It is a cyclized phenethylamine and is the 2-aminoindane analogue of 3-methoxyamphetamine. The drug acts as a serotonin–norepinephrine releasing agent (SNRA) or as a modestly selective serotonin releasing agent (SSRA), with about 6-fold preference for induction of serotonin over norepinephrine release. MEAI has been encountered as a novel designer recreational drug. It is also under development for potential medical use in the

'''N-Ethyl-5-trifluoromethyl-2-aminoindane (ETAI''') is a drug of the 2-aminoindane family with putative entactogenic effects. It functions as a serotonin releasing agent (SRA). ETAI is the 2-aminoindane analogue of fenfluramine and has approximately 50% of the serotonergic neurotoxicity in comparison.

MDAT, also known as 6,7-methylenedioxy-2-aminotetralin, is a drug of the 2-aminotetralin family developed in the 1990s by a team at Purdue University led by David E. Nichols. It appears to act as a serotonin releasing agent based on rodent drug discrimination assays comparing it to MDMA, in which it fully substitutes for, and additionally lacks any kind of serotonergic neurotoxicity. Hence, MDAT is considered likely to be a non-neurotoxic, putative entactogen in humans.

5-APB, also known as 5-(2-aminopropyl)benzofuran, is an entactogen of the phenethylamine, amphetamine, and benzofuran families. 5-APB and related drugs have sometimes been informally called "Benzofury".