Diisopropyltryptamine is a psychedelic hallucinogenic drug of the tryptamine family that has a unique effect. While the majority of hallucinogens affect the visual sense, DiPT is primarily aural.
5-MeO-MiPT is a psychedelic and hallucinogenic drug, used by some as an entheogen. It has structural and pharmacodynamic properties similar to the drugs 5-MeO-DiPT, DiPT, and MiPT. It is commonly used as a "substitute" for 5-MeO-DiPT because of the very similar structure and effects.
5-MeO-DET or 5-methoxy-N,N-diethyltryptamine is a hallucinogenic tryptamine.
Ethylisopropyltryptamine (EiPT) is a chemical of the tryptamine family that and produces psychedelic and hallucinogenic effects. It was probably first synthesized by American psychopharmacologist, Alexander Shulgin.
2,N,N-trimethyltryptamine, 2,N,N-TMT, or 2-Me-DMT is a tryptamine derivative that is a psychedelic drug. It was invented by Alexander Shulgin and reported in his book TiHKAL (#34). It is claimed to show psychoactive effects at a dosage of 50–100 mg orally, but these are relatively mild compared to other similar drugs, suggesting that while the 2-methyl group has blocked the binding of metabolic enzymes, it is also interfering with binding to the 5HT2A receptor target that mediates the hallucinogenic effects of these drugs.
5-Methoxy-2,N,N-trimethyltryptamine is a psychoactive drug of the tryptamine chemical class which acts as a psychedelic. It was first synthesized by Alexander Shulgin and reported in his book TiHKAL. 5-MeO-TMT is claimed to show psychoactive effects at a dosage of 75–150 mg orally, but these are relatively mild compared to those of other similar compounds. This suggests that while the methyl group on the 2-position of the molecule has impaired the binding of metabolic enzymes like monoamine oxidase (MAO), it is also interfering with binding to and/or activation of the serotonin 5-HT2A receptor, the target responsible for mediating the hallucinogenic effects of such compounds.
Aleph is a psychedelic hallucinogenic drug and a substituted amphetamine of the phenethylamine class of compounds, which can be used as an entheogen. It was first synthesized by Alexander Shulgin, who named it after the first letter of the Hebrew alphabet. In his book PiHKAL, Shulgin lists the dosage range as 5–10 mg, with effects typically lasting for 6 to 8 hours.
2,5-Dimethoxy-4-butylamphetamine (DOBU) is a lesser-known psychedelic drug and a substituted Amphetamine. DOBU was first synthesized by Alexander Shulgin. In his book PiHKAL (Phenethylamines i Have Known And Loved), only low dosages of 2–3 mg were tested, with the duration simply listed as "very long". DOBU produces paresthesia and difficulty sleeping, but with few other effects. Compared to shorter chain homologues such as DOM, DOET and DOPR which are all potent hallucinogens, DOBU has an even stronger 5-HT2 binding affinity but fails to substitute for hallucinogens in animals or produce hallucinogenic effects in humans, suggesting it has low efficacy and is thus an antagonist or weak partial agonist at the 5-HT2A receptor.
Dimethoxy-4-amylamphetamine (DOAM) is a lesser-known psychedelic drug and a substituted amphetamine. DOAM was first synthesized by Alexander Shulgin. In his book PiHKAL (Phenethylamines i Have Known And Loved), the minimum dosage is listed as 10 mg, and the duration is unknown. DOAM produces a bare threshold and tenseness. As the 4-alkyl chain length is increased from shorter homologues such as DOM, DOET and DOPR which are all potent hallucinogens, the 5-HT2 binding affinity increases, rising to a maximum with the 4-(n-hexyl) derivative before falling again with even longer chains, but compounds with chain length longer than n-propyl, or with other bulky groups such as isopropyl, t-butyl or γ-phenylpropyl at the 4- position, fail to substitute for hallucinogens in animals or produce hallucinogenic effects in humans, suggesting these have low efficacy and are thus antagonists or partial agonists at the 5-HT2A receptor.
Pyr-T (N,N-tetramethylenetryptamine) is a lesser-known, possible psychedelic drug. Pyr-T was first characterized by S. Mitzal. Toxicity testing was later performed by Hunt and Brimblecombe, and although a lethal dosage was found in rats, a value is not given. In the book TiHKAL, neither the dosage nor the duration are reported.
4-MeO-MiPT, or 4-methoxy-N-methyl-N-isopropyltryptamine, is a lesser-known psychedelic drug. It is the 4-methoxy analog of MiPT. 4-MeO-MiPT was first synthesized by Alexander Shulgin and is mentioned in his book TiHKAL. Subsequent testing by Shulgin on human test subjects showed the effective dose as 20-30 mg ; the onset time between ingestion and the first noticeable effects was 45-60 min, with sensations lasting between 2-2.5 hours. The sensation were significantly milder than those of 4-HO-MiPT, with 4-MeO-MiPT producing erotic-enhancing effects, and few of the visuals common with tryptamines. Very little data exists about the pharmacological properties, metabolism, and toxicity of 4-MeO-MiPT.
5-MeS-DMT (5-methylthio-N,N-dimethyltryptamine) is a lesser-known psychedelic drug. It is the 5-methylthio analog of dimethyltryptamine (DMT). 5-MeS-DMT was first synthesized by Alexander Shulgin. In his book TiHKAL, the minimum dosage is listed as 15-30 mg. The duration listed as very short, just like DMT. 5-MeS-DMT produces similar effects to DMT, but weaker. Shulgin describes his feelings while on a low dose of this drug as "pointlessly stoned", although at a higher dose of 20 mg he says it is "quite intense" and suggests that a higher dose still might have full activity.
6-MeO-THH, or 6-methoxy-1,2,3,4-tetrahydroharman, is a β-carboline derivative and a structural isomer of tetrahydroharmine (7-MeO-THH). 6-MeO-THH is mentioned in Alexander Shulgin's book TiHKAL, stating that 6-MeO-THH is very similar to the other carbolines. Limited testing suggests that it possesses mild psychoactive effects at 1.5 mg/kg and is said to be about one-third as potent as 6-methoxyharmalan. It has been isolated from certain plants of the Virola family.
4-Substituted-2,5-dimethoxyamphetamines (DOx) is a chemical class of substituted amphetamine derivatives featuring methoxy groups at the 2- and 5- positions of the phenyl ring, and a substituent such as alkyl or halogen at the 4- position of the phenyl ring. Most compounds of this class are potent and long-lasting psychedelic drugs, and act as highly selective 5-HT2A, 5-HT2B, and 5-HT2C receptor partial agonists. A few bulkier derivatives such as DOAM have similarly high binding affinity for 5-HT2 receptors but instead act as antagonists, and so do not produce psychedelic effects though they retain amphetamine-like stimulant effects.
5-Fluoro-N,N-dimethyltryptamine is a tryptamine derivative related to compounds such as 5-bromo-DMT and 5-MeO-DMT. Fluorination of psychedelic tryptamines either reduces or has little effect on 5-HT2A/C receptor affinity or intrinsic activity, although 6-fluoro-DET is inactive as a psychedelic despite acting as a 5-HT2A agonist, while 4-fluoro-5-methoxy-DMT is a much stronger agonist at 5-HT1A than 5-HT2A.
Dimemebfe (5-MeO-BFE) is a recreational drug and research chemical. It acts as an agonist for the 5-HT1A and 5-HT2 family of serotonin receptors. It is related in structure to the psychedelic tryptamine derivative 5-MeO-DMT, but with the indole nitrogen replaced by oxygen, making dimemebfe a benzofuran derivative. It is several times less potent as a serotonin agonist than 5-MeO-DMT and with relatively more activity at 5-HT1A, but still shows strongest effects at the 5-HT2 family of receptors.
5-Methoxy-7,N,N-trimethyltryptamine (5-MeO-7,N,N-TMT, 5-MeO-7-TMT), 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 high 5-HT2 receptor binding affinity, suggesting these may be antagonists or weak partial agonists for the 5-HT2 receptors. The related compound 7-MeO-MiPT (cf. 5-MeO-MiPT) was also found to be inactive, suggesting that the 7-position has poor tolerance for bulky groups at this position, at least if agonist activity is desired.
5-MeO-DiBF is a psychedelic that has been sold online as a designer drug and was first definitively identified in December 2015 by a forensic laboratory in Slovenia. It is thought to act as an agonist for the 5-HT1A and 5-HT2 family of serotonin receptors. It is related in structure to the psychedelic tryptamine derivative 5-MeO-DiPT, but with the indole nitrogen replaced by oxygen, making 5-MeO-DiBF a benzofuran derivative. It is several times less potent as a serotonin agonist than 5-MeO-DiPT and with relatively more activity at 5-HT1A, but still shows strongest effects at the 5-HT2 family of receptors.
4C-B is a lesser-known psychedelic drug which is related to 2C-B and DOB. It is a reasonably potent 5-HT2A receptor partial agonist with a Ki of 7.6nM, but has relatively low efficacy. It is briefly mentioned in Alexander Shulgin's book PiHKAL but was never tested by him, however it has subsequently been tested by other researchers and was found to be active in a dose range of 50-80mg with a duration of around 8 hours, though with generally milder effects than 2C-B or DOB.
O-Acetylbufotenine is a tryptamine derivative which produces psychedelic-appropriate responding in animal studies. It is an acylated derivative of bufotenine with higher lipophilicity that allows it to cross the blood–brain barrier; once inside the brain, it is metabolised to bufotenine. It also acts directly as an agonist at 5-HT1A and 5-HT1D receptors.
