Serotonin releasing agents

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, memory, and physiological processes such as vomiting and vasoconstriction. In the CNS, serotonin regulates mood, appetite, and sleep.

Psilocybin, also known as '4-phosphoryloxy-N,N-dimethyltryptamine (4-PO-DMT'), is a naturally occurring tryptamine alkaloid and investigational drug found in more than 200 species of mushrooms, with hallucinogenic and serotonergic effects. Effects include euphoria, changes in perception, a distorted sense of time, and perceived spiritual experiences. It can also cause adverse reactions such as nausea and panic attacks.

Dimethyltryptamine (DMT), also known as '''N,N-dimethyltryptamine (N,N-DMT'''), is a serotonergic hallucinogen and investigational drug of the tryptamine family that occurs naturally in many plants and animals. DMT is used as a psychedelic drug and prepared by various cultures for ritual purposes as an entheogen.

Psilocin, also known as '4-hydroxy-N,N-dimethyltryptamine (4-HO-DMT'), is a psychedelic drug and fungal alkaloid of the tryptamine and 4-hydroxytryptamine families. Along with its phosphate ester psilocybin, it is found in most species of psilocybin-containing mushrooms, such as Psilocybe cubensis and Psilocybe mexicana, and is the compound responsible for their hallucinogenic effects, although concentrations of psilocin are variably lower than those of psilocybin. The drug is taken orally and its effects include perceptual changes and visual effects, emotional changes, ego dissolution, time d

Bufotenin, also known as dimethylserotonin or as '5-hydroxy-N,N-dimethyltryptamine (5-HO-DMT'), is a serotonergic psychedelic of the tryptamine family. It is a derivative of the psychedelic dimethyltryptamine (DMT) and of the neurotransmitter serotonin (5-hydroxytryptamine; 5-HT). The compound is an alkaloid found in some species of mushrooms, plants, and toads. It is also found naturally in the human body in small amounts. Bufotenin, for instance derived from the trees Anadenanthera colubrina and Anadenanthera peregrina, has a long history of entheogenic use as a snuff in South America.

'''para-Methoxyamphetamine (PMA), also known as 4-methoxyamphetamine (4-MA'''), is a designer drug of the amphetamine class with serotonergic effects. Unlike other similar drugs of this family, PMA does not produce stimulant, euphoriant, or entactogenic effects, and behaves more like an antidepressant in comparison, though it does have some psychedelic properties.

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-

'''N-Methyltryptamine (NMT), also known as monomethyltryptamine''', is a chemical compound of the tryptamine family and a naturally occurring compound found in various plants and animals, including humans.

4-Methylthioamphetamine (4-MTA), also known as '''para-methylthioamphetamine (MTA'''), is a designer drug of the substituted amphetamine class developed in the 1990s by a team led by David E. Nichols, an American pharmacologist and medical chemist, at Purdue University. It acts as a non-neurotoxic highly selective serotonin releasing agent (SSRA) in animals. 4-MTA is the methylthio derivative of amphetamine.

8-OH-DPAT, also known as 8-hydroxy-2-(dipropylamino)tetralin, is a serotonin 5-HT1A receptor agonist of the 2-aminotetralin family which was developed in the 1980s and has been widely used to study the function of the 5-HT1A receptor. It was one of the first major 5-HT1A receptor full agonists to have been discovered.

'''meta-Chlorophenylpiperazine (mCPP''') is a psychoactive drug of the phenylpiperazine class. It was initially developed in the late-1970s and used in scientific research before being sold as a designer drug in the mid-2000s. It has been detected in pills touted as legal alternatives to illicit stimulants in New Zealand and pills sold as "ecstasy" in Europe and the United States.

3-Trifluoromethylphenylpiperazine (TFMPP) is a recreational drug of the phenylpiperazine chemical class and is a substituted piperazine. Usually in combination with benzylpiperazine (BZP) and other analogues, it is sold as an alternative to the illicit drug MDMA ("Ecstasy").

'''N-Ethyltryptamine (NET), also abbreviated as NETP', is a tryptamine that is structurally related to N-methyltryptamine (NMT) and the psychedelic drugs N,N-dimethyltryptamine (DMT) and N,N''-diethyltryptamine (DET).

group of stereoisomers

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.

'4-Acetoxy-N,N-dimethyltryptamine (4-AcO-DMT or 4-acetoxy-DMT), also known as O-acetylpsilocin or psilacetin', is a psychedelic drug of the tryptamine family related to psilocybin and psilocin. It is a synthetic derivative of psilocin (4-HO-DMT) in which the hydroxyl group has been acetylated, and is the analogue of psilocybin (4-PO-DMT) in which the phosphate ester has been replaced with an acetate ester. The drug is a prodrug of psilocin and is used orally similarly to psilocybin.

Indeloxazine (INN; trade names Elen and Noin) is an antidepressant and cerebral activator that was marketed in Japan and South Korea by Yamanouchi Pharmaceutical Co., Ltd for the treatment of psychiatric symptoms associated with cerebrovascular diseases, namely depression resulting from stroke, emotional disturbance, and avolition. It was marketed from 1988 to 1998, when it was removed from the market reportedly for lack of effectiveness.

5-Carboxamidotryptamine (5-CT), also known as 5-(aminocarbonyl)tryptamine, is a tryptamine derivative closely related to the neurotransmitter serotonin.

3,4,5-Trimethoxyamphetamine (TMA, TMA-1, or 3,4,5-TMA), also known as α-methylmescaline (3C-mescaline or 3C-M) or mescalamphetamine, is a psychedelic drug of the phenethylamine and amphetamine families. It is one of the trimethoxyamphetamine (TMA) series of positional isomers. The drug is notable in being the amphetamine (α-methylated) analogue of mescaline (3,4,5-trimethoxyphenethylamine).

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.

Chlorphentermine, sold under the brand names Apsedon, Desopimon, and Lucofen, is a serotonergic appetite suppressant of the amphetamine family. Developed in 1962, it is the para-chloro derivative of the better-known appetite suppressant phentermine, which is still in current use.

Methylethyltryptamine (MET), also known as '''N-methyl-N-ethyltryptamine (N,N-MET'''), is a psychedelic drug of the tryptamine family. It is taken orally or via inhalation.

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.

Noribogaine, also known as '''O-desmethylibogaine or 12-hydroxyibogamine', is the principal psychoactive metabolite of the oneirogen ibogaine. It is thought to be involved in the antiaddictive effects of ibogaine-containing plant extracts, such as Tabernanthe iboga''.

Viqualine (INN; developmental code PK-5078) is an antidepressant and anxiolytic drug that was never marketed. It acts as a potent and selective serotonin releasing agent (SRA) and serotonin reuptake inhibitor (SRI) similarly to para-chloroamphetamine (PCA). In addition, viqualine displaces diazepam from the GABAA receptor and produces benzodiazepine-like effects, indicating that it is also a positive allosteric modulator of the benzodiazepine site of the GABAA receptor. The drug has mainly been researched as a potential treatment for alcoholism.

'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.

DMMDA-2, also known as 2,3-dimethoxy-4,5-methylenedioxyamphetamine or as 5,6-dimethoxy-MDA, is a psychedelic drug of the phenethylamine, amphetamine, and MDxx families related to MDA. It is the derivative of MDA with methoxy groups at the 5 and 6 positions and of MMDA and MMDA-2 with an additional methoxy group at either of these positions.

'3,4-Methylenedioxy-N,N-dimethylamphetamine (MDDM, MDDMA), also known as N,N-dimethyl-MDA or N-methyl-MDMA', is a lesser-known serotonin releasing agent and psychoactive drug of the phenethylamine, amphetamine, and MDxx families. It is the N,N-dimethyl analogue of 3,4-methylenedioxyamphetamine (MDA) and the N-methyl derivative of MDMA. The drug is a known synthetic impurity of MDMA and has also been described as a possible novel designer drug in 2025.

class of compounds

5-MeO-pyr-T, also known as '5-methoxy-N,N-tetramethylenetryptamine or as 5-methoxy-3-(2-pyrrolidinoethyl)indole', is a serotonin receptor modulator and psychedelic drug of the tryptamine, 5-methoxytryptamine, and pyrrolidinylethylindole families. It is the 5-methoxy analogue of pyr-T and the derivative of 5-MeO-DMT and 5-MeO-DET in which their N,N-dialkyl groups have been cyclized into a pyrrolidine ring.

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.

Amiflamine (developmental code name FLA-336), also known '(S)-2-methyl-4-(dimethylamino)amphetamine', is a reversible inhibitor of monoamine oxidase A (MAO-A), thereby being a RIMA, and, to a lesser extent, semicarbazide-sensitive amine oxidase (SSAO) inhibitor, as well as a serotonin releasing agent (SRA). It is a derivative of the phenethylamine and amphetamine families. The (+)-enantiomer is the active stereoisomer.

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.

'''para-Methoxyethylamphetamine (PMEA''') is a stimulant drug related to PMA. PMEA reputedly produces similar effects to PMA, but is considerably less potent and seems to have slightly less tendency to produce severe hyperthermia, at least at low doses. At higher doses however the side effects and danger of death approach those of PMA itself, and PMEA should still be considered a potentially dangerous drug. Investigation of a drug-related death in Japan in 2005 showed PMEA to be present in the body and was thought to be responsible for the death.

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.

Cloforex (Oberex) is an anorectic of the amphetamine class. It is a prodrug to chlorphentermine. It never became a mass produced drug in part due to the side effects found in mice. Mice who consumed 75 mg of cloforex a day experienced weight loss along with pulmonary hypertension and hair loss.

'''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.

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.

'''para-Ethoxyamphetamine (PEtOA), also known as 4-ethoxyamphetamine (4-EA, 4-ETA, or 4-EtO-A'), is a psychoactive drug of the phenethylamine and amphetamine families which is closely related to para''-methoxyamphetamine (PMA). It has similar effects to PMA in animal studies, although with slightly weaker stimulant effects. Like PMA, it has prominent MAOI activity, and is likely to have similar dangers associated with its use.