N,N-Dialkyltryptamines

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

Sumatriptan, sold under the brand name Imitrex among others, is a medication used to treat migraine headaches and cluster headaches. It is taken orally, intranasally, or by subcutaneous injection. Therapeutic effects generally occur within three hours. Sumatriptan is a serotonin (5-HT1B/1D) receptor agonist (triptan).

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.

5-MeO-DMT, also known as '5-methoxy-N,N-dimethyltryptamine, as well as O-methylbufotenin or mebufotenin', is an atypical psychedelic drug, entheogen, and alkaloid of the tryptamine and 5-methoxytryptamine families. It is found naturally in a wide variety of plant species, and is also secreted by the glands of at least one toad species, the Colorado River toad (Incilius alvarius, formerly Bufo alvarius). It may occur naturally in humans as well. Like its close relatives dimethyltryptamine (DMT) and bufotenin (5-HO-DMT), it has been used as an entheogen in South America. Slang terms include five

Rizatriptan, sold under the brand name Maxalt among others, is a medication used for the treatment of migraine headaches. It is taken by mouth. It can also be applied on the tongue. It is a serotonin (5-HT) 1B/1D receptor agonist (triptan).

Zolmitriptan, sold under the brand name Zomig among others, is a serotonergic medication which is used in the acute treatment of migraine attacks with or without aura and cluster headaches. It is taken by mouth as a swallowed or disintegrating tablet or as a nasal spray.

Almotriptan, sold under the brand names Axert and Almogran among others, is a triptan medication used in the treatment of heavy migraine headache.

Dipropyltryptamine (DPT), also known as '''N,N-dipropyltryptamine or as "The Light'''", is a psychedelic drug of the tryptamine family related to dimethyltryptamine (DMT). It is taken orally or by other routes.

Diethyltryptamine (DET), also known as '''N,N-diethyltryptamine or T-9''', is a psychedelic drug of the tryptamine family closely related to dimethyltryptamine (DMT). It is taken orally, but can also be used by parenteral routes.

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.

Diisopropyltryptamine (DiPT), also known as '''N,N-diisopropyltryptamine''', is a psychedelic drug of the tryptamine family related to dimethyltryptamine (DMT). It is unusual among psychedelics in that at usual doses it primarily or exclusively produces strong auditory changes, including decreased pitch, harmonic distortion, and sound unfamiliarity, but produces no other hallucinogenic effects such as visuals. However, the drug may produce more classically psychedelic effects at very high doses. It is taken orally, but can also be smoked.

Eletriptan, sold under the brand name Relpax and used in the form of eletriptan hydrobromide, is a second-generation triptan medication intended for treatment of migraine headaches. It is used as an abortive medication, blocking a migraine attack which is already in progress. Eletriptan is marketed and manufactured by Pfizer.

Indoramin (trade names Baratol and Doralese) is a piperidine antiadrenergic agent.

Metralindole (Inkazan) is a reversible inhibitor of monoamine oxidase A (RIMA) which was investigated in Russia as a potential antidepressant. It is structurally and pharmacologically related to pirlindole.

4-HO-MET, also known as '4-hydroxy-N-methyl-N-ethyltryptamine, as well as metocin or methylcybin', is a psychedelic drug of the tryptamine and 4-hydroxytryptamine families related to psilocin (4-HO-DMT). It is taken orally.

4-HO-DiPT, also known as '4-hydroxy-N,N-diisopropyltryptamine or as iprocin', is a psychedelic drug of the tryptamine and 4-hydroxytryptamine families related to psilocin (4-HO-DMT). It is taken orally. The drug has an unusually fast onset, short duration, and narrow dose range. Among orally administered psychedelics, it is one of the shortest-acting compounds known.

Yuremamine is a phytoindole alkaloid which was isolated from the bark of Mimosa tenuiflora in 2005, and erroneously assigned a pyrrolo[1,2-a]indole structure that was thought to represent a new class of indole alkaloids. However, in 2015, the bioinspired total synthesis of yuremamine revealed its structure to be a flavonoid derivative. It was also noted in the original isolation of yuremamine that the alkaloid occurs naturally as a purple solid, but total synthesis revealed that yuremamine as a free base is colorless, and the formation of a trifluoroacetate salt during HPLC purification is wha

'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.

Methylisopropyltryptamine (MiPT), also known as '''N-methyl-N-isopropyltryptamine''', is a psychedelic drug of the tryptamine family related to other psychedelics like dimethyltryptamine (DMT) and diisopropyltryptamine (DiPT). It is taken orally.

5-MeS-DMT, also known as '5-methylthio-N,N-dimethyltryptamine or as 5-methylthio-DMT', is a lesser-known psychedelic drug of the tryptamine family. It is the 5-methylthio derivative of dimethyltryptamine (DMT) and is an analogue of 5-MeO-DMT.

chemical compound

4-AcO-DiPT, also known as '4-acetoxy-N,N-diisopropyltryptamine or as ipracetin', is a psychedelic drug of the tryptamine and 4-hydroxytryptamine families related to 4-AcO-DMT (psilacetin). It is taken orally.

4-AcO-DET, also known as '4-acetoxy-N,N-diethyltryptamine as well as ethacetin or ethylacybin', is a psychedelic tryptamine. It was first synthesized in 1958 by Albert Hofmann in the Sandoz lab.

4-AcO-MiPT, also known as '4-acetoxy-N-methyl-N-isopropyltryptamine or as mipracetin', is a psychedelic tryptamine. It is closely related to 4-AcO-DMT and methylisopropyltryptamine (MiPT).

Pyr-T, also known as '''N,N-tetramethylenetryptamine or as 3-(2-pyrrolidinoethyl)indole', is a lesser-known serotonin receptor modulator of the tryptamine and pyrrolidinylethylindole families. It is the cyclized derivative of diethyltryptamine (DET) in which the N,N''-diethyl groups have been fused into a pyrrolidine ring.

5-Bromo-DMT, or 5-Br-DMT, also known as '5-bromo-N,N-dimethyltryptamine or by informal names like sea DMT or SpongeBob DMT', is a psychedelic drug and brominated indole alkaloid of the tryptamine family related to dimethyltryptamine (DMT). It is the 5-bromo derivative of DMT. The drug is naturally occurring in the sponges Smenospongia aurea and Smenospongia echina, as well as in Verongula rigida (0.00142% dry weight) alongside 5,6-dibromo-DMT (0.35% dry weight) and seven other alkaloids. It has been encountered as a novel designer drug.

4-MeO-MiPT, also known as '4-methoxy-N-methyl-N-isopropyltryptamine', is a lesser-known psychedelic drug of the tryptamine and 4-methoxytryptamine families. It is the 4-methoxy analogue of MiPT and the O-methyl ether of 4-HO-MiPT. The drug is taken orally.

2-Me-DET, or 2-methyl-DET, also known as '2-methyl-N,N-diethyltryptamine', is a psychedelic drug of the tryptamine family. It is the 2-methyl derivative of diethyltryptamine (DET). The drug is taken orally.

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.

4-HO-MiPT, also known as '4-hydroxy-N-methyl-N-isopropyltryptamine or as miprocin', is a psychedelic drug of the tryptamine and 4-hydroxytryptamine families related to psilocin (4-HO-DMT). It appears to be similar to psilocin in terms of onset, duration, and effects. The drug is taken orally.

Carbazocine is an opioid analgesic of the benzomorphan family which was never marketed.

4-AcO-DALT, also known as '4-acetoxy-N,N-diallyltryptamine or as dalcetin', is a tryptamine derivative. It has been sold as a designer drug, but little other information is available. It was first officially identified in seized drug samples in 2012.

4-HO-DET, also known as '4-hydroxy-N,N-diethyltryptamine as well as ethocin or CZ-74', is a psychedelic drug of the tryptamine and 4-hydroxytryptamine families related to psilocin (4-HO-DMT). It is taken orally.

Ethocybin also known as '4-phosphoryloxy-N,N-diethyltryptamine (4-PO-DET) or as CEY-19', is a psychedelic drug of the tryptamine and 4-hydroxytryptamine families related to the psilocybin-containing mushroom alkaloid psilocybin. It is assumed to act as a prodrug of 4-HO-DET (CZ-74) analogously to how psilocybin (4-PO-DMT) acts as a prodrug of psilocin (4-HO-DMT). The drug was first described in the literature by Albert Hofmann and colleagues at Sandoz by 1963.

Dibutyltryptamine (DBT), also known as '''N,N-dibutyltryptamine (N,N-DBT'''), is a psychedelic drug of the tryptamine family related to dimethyltryptamine (DMT).

5-MeO-DET, also known as '5-methoxy-N,N-diethyltryptamine' is a psychedelic drug of the tryptamine family related to 5-MeO-DMT. It is taken orally but can also be used parenterally.

4-HO-pyr-T, also known as '4-hydroxy-N,N-tetramethylenetryptamine', is a serotonin receptor modulator of the tryptamine, 4-hydroxytryptamine, and pyrrolidinylethylindole families. It is the 4-hydroxyl analogue of pyr-T and the analogue of psilocin (4-HO-DMT) and 4-HO-DET in which the N,N-dialkyl moiety has been cyclized into a pyrrolidine ring.

FGIN-1-27 is an anxiolytic drug which acts as a selective agonist at the peripheral benzodiazepine receptor, also known as the mitochondrial 18 kDa translocator protein or TSPO. It is thought to produce anxiolytic effects by stimulating steroidogenesis of neuroactive steroids such as allopregnanolone.

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.

5-MeO-DALT, also known as '''N,N-diallyl-5-methoxytryptamine or as foxtrot''', is a psychedelic drug of the tryptamine and 5-methoxytryptamine families. It is taken orally.

5-MeO-MiPT, also known as '5-methoxy-N-methyl-N-isopropyltryptamine or by its nickname Moxy', is an atypical psychedelic drug of the tryptamine and 5-methoxytryptamine families. It has unique and unusual effects compared to other psychedelic tryptamines. At low doses, its effects include stimulation, tactile and sexual enhancement, some MDMA-like entactogenic effects, and introspective and mild perceptual changes with few or no psychedelic visuals or time dilation, whereas at higher doses, it produces 5-MeO-DMT-like classical psychedelic effects. It is usually taken orally or smoked.

Flucindole (, ; developmental code name WIN-35150) is an antipsychotic of the tetrahydrocarbazolamine family with a tricyclic cyclized tryptamine structure that was never marketed. It is the 6,8-difluoro derivative of ciclindole. The drug is about 5 to 10times more potent than ciclindole both in vitro and in vivo.

5-HO-DiPT, also known as '5-hydroxy-N,N-di-iso-propyltryptamine', is a tryptamine derivative which acts as a serotonin receptor agonist. It is primarily known as a metabolite of the better known psychoactive drug 5-MeO-DiPT, but 5-HO-DiPT has also rarely been encountered as a designer drug in its own right. Tests in vitro show 5-HO-DiPT to have high serotonin 5-HT2A receptor affinity and good selectivity over the serotonin 5-HT1A receptor, while being more lipophilic than the related drug bufotenine (5-HO-DMT), which produces primarily peripheral effects.

'7,N,N-trimethyltryptamine (7,N,N-TMT or 7-TMT), also known as 7-methyl-DMT', is a serotonin receptor modulator and psychedelic drug of the tryptamine family related to dimethyltryptamine (DMT). It was first described by 1978 and was encountered online as a novel designer drug in 2024.

LY-293284, also known as 4,α-methylene-5-acetyl-DPT, is a research chemical developed by the pharmaceutical company Eli Lilly and used for scientific studies. It acts as a potent and selective 5-HT1A receptor full agonist. It was derived through structural simplification of the ergoline based psychedelic LSD, but is far more selective for 5-HT1A with over 1000× selectivity over other serotonin receptor subtypes and other targets. It has anxiogenic effects in animal studies.

E-6837 is an orally active, 5-HT6 agonist developed in an attempt to create an anti-obesity medication.

4-MeO-DMT, or 4-methoxy-DMT, also known as '4-methoxy-N,N-dimethyltryptamine or as O-methylpsilocin (PSOM'), is a serotonin receptor modulator and possible psychedelic drug of the tryptamine and 4-hydroxytryptamine families. It is the O-methylated analogue of psilocin (4-HO-DMT) and a positional isomer of 5-MeO-DMT.

'5-Methoxy-7,N,N-trimethyltryptamine (5-MeO-7,N,N-TMT, 5-MeO-7-TMT), also known as 7-Me-5-MeO-DMT', is a tryptamine derivative which acts as a partial agonist at the 5-HT2 serotonin receptors, with an EC50 of 63.9 nM and an efficacy of 66.2% at 5-HT2A (vs 5-HT), and weaker activity at 5-HT2B and 5-HT2C. In animal tests, both 7,N,N-TMT and 5-MeO-7,N,N-TMT produced behavioural responses similar to those of psychedelic drugs such as DMT and 5-MeO-DMT, but compounds with larger 7-position substituents such as 7-ethyl-DMT and 7-bromo-DMT did not produce psychedelic-appropriate responding despite hi

5,6-MeO-MiPT, also known as '5,6-dimethoxy-N-methyl-N-isopropyltryptamine', is a chemical compound of the tryptamine family. It is the 5,6-dimethoxy derivative of methylisopropyltryptamine (MiPT) and is an analogue of 5-MeO-MiPT. In his 1991 book TiHKAL (Tryptamines I Have Known and Loved), Alexander Shulgin listed the dose as greater than 75mg orally and the duration as unknown. The drug produced few to no effects at doses of up to 75mg orally. Very little data exists about the pharmacological properties, metabolism, and toxicity of 5,6-MeO-MiPT. However, the drug has been found to have aboli

'5,N,N-Trimethyltryptamine (5,N,N-TMT; 5-TMT), also known as 5-methyl-DMT', is a tryptamine derivative that may be a psychedelic drug. It was first made in 1958 by Edwin H. P. Young. In animal experiments it was found to be in between DMT and 5-MeO-DMT in potency.

4-HO-DBT, also known as '4-hydroxy-N,N-dibutyltryptamine', is a psychedelic drug of the tryptamine family related to psilocin (4-HO-DMT). It is taken orally.

4-HO-DPT, also known as '4-hydroxy-N,N-dipropyltryptamine or as deprocin', is a psychedelic drug of the tryptamine and 4-hydroxytryptamine families related to psilocin (4-HO-DMT). It is taken orally.

Diallyltryptamine (DALT), also known as '''N,N-diallyltryptamine''', is a tryptamine derivative which has been identified as a designer drug.

E-6801 is a partial agonist of the 5-HT6 receptor. It enhanced recognition memory and reversed the memory deficits of scopolamine in an object recognition task in a rat model. The mechanism of memory enhancement is due to a combined modulation of cholinergic and glutamatergic neurotransmission.

'5-Ethyl-N,N-dimethyltryptamine' is a tryptamine derivative which acts as an agonist at the 5-HT1A and 5-HT1D serotonin receptors, with around 3x selectivity for 5-HT1D.

5-Fluoro-DMT, or 5-F-DMT, also known as '5-fluoro-N,N-dimethyltryptamine', is a psychedelic drug of the tryptamine family related to dimethyltryptamine (DMT) and to other psychedelic tryptamines like 5-chloro-DMT and 5-bromo-DMT.