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Names | |
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Preferred IUPAC name 3-[2-(Pyrrolidin-1-yl)ethyl]-1H-indol-4-ol | |
Other names 4-Hydroxy-N,N-tetramethylenetryptamine | |
Identifiers | |
3D model (JSmol) | |
ChEMBL | |
ChemSpider | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C14H18N2O | |
Molar mass | 230.311 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
4-HO-pyr-T (4-hydroxy-N,N-tetramethylenetryptamine) is a lesser-known psychedelic drug. It is the 4-hydroxyl analog of pyr-T. 4-HO-pyr-T was first synthesized by Alexander Shulgin. In his book TiHKAL (Tryptamines I Have Known and Loved), neither the dosage nor the duration are reported. [1] 4-HO-pyr-T produces few to no effects. Very little data exists about the pharmacological properties, metabolism, and toxicity of 4-HO-pyr-T.
2C-B (4-bromo-2,5-dimethoxyphenethylamine), also known as Nexus, is a synthetic psychedelic drug of the 2C family, mainly used as a recreational drug. It was first synthesized by Alexander Shulgin in 1974 for use in psychotherapy. To date, there is limited scientific information regarding the drug's pharmacokinetics and pharmacological effects in humans. The existing studies primarily classify 2C-B as a stimulant and hallucinogen, and less commonly an entactogen and empathogen.
2C-C is a psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin, sometimes used as an entheogen. In his book PiHKAL , Shulgin lists the dosage range as 20–40 mg. 2C-C is usually taken orally, but may also be insufflated. 2C-C is schedule I of section 202(c) of the Controlled Substances Act in the United States, signed into law as of July, 2012 under the Food and Drug Administration Safety and Innovation Act.
5-MeO-αMT, or 5-methoxy-α-methyltryptamine, also known as α,O-dimethylserotonin (Alpha-O), is a serotonergic psychedelic of the tryptamine family. It is a derivative of α-methyltryptamine (αMT) and an analogue of 5-MeO-DMT.
4-Hydroxy-N,N-diisopropyltryptamine is a synthetic psychedelic drug. It is a higher homologue of psilocin, 4-HO-DET, and is a positional isomer of 4-HO-DPT and has a tryptamine molecular sub-structure.
DET, also known under its chemical name N,N-diethyltryptamine and as T-9, is a psychedelic drug closely related to DMT and 4-HO-DET. However, despite its structural similarity to DMT, its activity is induced by an oral dose of around 50–100 mg, without the aid of MAO inhibitors, and the effects last for about 2–4 hours.
4-HO-DET, also known as 4-hydroxy-diethyl-tryptamine, CZ-74, is a hallucinogenic drug and psychedelic compound of moderate duration. 4-HO-DET is a substituted tryptamine, structurally related to psilocin, ethocybin, and 4-HO-DIPT.
4-Acetoxy-DET (4-Acetoxy-N,N-diethyltryptamine), also known as ethacetin, ethylacybin or 4-AcO-DET, is a psychedelic tryptamine. It was first synthesized in 1958 by Albert Hofmann in the Sandoz lab.
4-Acetoxy-DiPT is a synthetic psychedelic tryptamine. It is relatively uncommon and has only a short history of human use.
4-HO-MiPT is a synthetic substituted aromatic compound and a lesser-known psychedelic tryptamine. It is thought to be a serotonergic psychedelic, similar to magic mushrooms, LSD and mescaline. Its molecular structure and pharmacological effects somewhat resemble those of the tryptamine psilocin, which is the primary psychoactive chemical in magic mushrooms.
2C-B-FLY is a psychedelic phenethylamine and designer drug of the 2C family. It was first synthesized in 1996 by Aaron Monte, Professor of Chemistry at UW-La Crosse.
4-Hydroxy-N-methyl-N-propyltryptamine, commonly known as 4-HO-MPT or meprocin, is a psychedelic drug in the tryptamine class of chemical compounds and is a higher homologue of the naturally occurring substituted tryptamine psilocin as well as being the 4-hydroxyl analog of MPT.
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.
5-MeO-pyr-T (5-methoxy-N,N-tetramethylenetryptamine) is a lesser-known psychedelic drug. It is the 5-methoxy analog of pyr-T. 5-MeO-pyr-T was first synthesized by Hunt & Brimblecombe, who credited S. Mitzal for characterization of chemical properties. Later human tests were reported by Alexander Shulgin, in his book TiHKAL. An oral dosage of 0.5 to 2 mg, and an inhaled dosage of 2–3 mg are reported. 5-MeO-pyr-T causes varying reactions, such as amnesia, tinnitus, vomiting, and a 5-MeO-DMT-like rushing sensation. At the highest dosage reported in TiHKAL, the subject describes awakening from an apparent fugue state during which they were wandering the streets, with complete amnesia upon awakening.
4-HO-MPMI (also known as 4-Hydroxy-N-methyl-(α,N-trimethylene)-tryptamine or lucigenol) is a tryptamine derivative that is a psychedelic drug. It was developed by the team led by David Nichols from Purdue University in the late 1990s. This compound produces hallucinogen-appropriate responding in animal tests with a similar potency to the amphetamine-derived psychedelic DOI, and has two enantiomers, with only the (R)-enantiomer being active.
5-MeO-MPMI (also known as 5-Methoxy-N-methyl-(α,N-trimethylene)tryptamine) is a tryptamine derivative that is a psychedelic drug. It was first developed by the team led by JE Macor in 1992, and subsequently investigated by the team led by David Nichols from Purdue University in the late 1990s. This compound produces psychedelic-appropriate responding in animal tests with a similar potency to the amphetamine-derived psychedelic DOI, and has two enantiomers, with only the (R)-enantiomer being active.
4-HO-McPeT (4-hydroxy-N-methyl-N-cyclopentyltryptamine) is a tryptamine derivative which has serotonergic effects.
4-Acetyloxy-N,N-dipropyltryptamine is a tryptamine derivative. 4-AcO-DPT has been sold as a designer drug. It is an ester of 4-HO-DPT, a psychedelic tryptamine first synthesized by Alexander Shulgin. Anecdotal reports indicate that 4-AcO-DPT exerts psychoactive effects in humans, however, the pharmacology of 4-AcO-DPT has not been examined.
N-t-Butyltryptamine (NTBT) is a tryptamine derivative which has serotonergic effects. It is described by Alexander Shulgin as producing "a light-headed intoxication that is a totally pleasant buzz, but nothing more profound than that" at a dosage range of 5 to 20 mg, along with the related sec-butyl isomer NSBT which is similar in effects but slightly less potent.
3-(N-methylpyrrolidin-3-ylmethyl)indole (MPMI) is a tryptamine derivative which acts as a serotonin receptor agonist. It has been studied as an analogue and trace impurity of the anti-migraine drug eletriptan but is otherwise little known.