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| Formula | C13H18N2O |
| Molar mass | 218.300 g·mol−1 |
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5-Ethoxy-alpha-methyltryptamine (5-EtO-AMT) is a tryptamine derivative closely related to 5-MeO-AMT. It has an LD50 in mice of 56mg/kg, [1] but its pharmacology has otherwise been little studied. [2]
Alexander Theodore "Sasha" Shulgin was an American biochemist, broad researcher of synthetic psychoactive compounds, and author of works regarding these, who independently explored the organic chemistry and pharmacology of such agents—in his mid-life and later, many through preparation in his home laboratory, and testing on himself. He is acknowledged to have introduced to broader use, in the late 1970s, the prior synthesized compound MDMA ("ecstasy"), in research psychopharmacology and in combination with conventional therapy, the latter through presentations and academic publications, including to psychologists; and for the rediscovery, occasional discovery, and regular synthesis and personal use and distribution, of possibly hundreds of psychoactive compounds. As such, Shulgin is seen both as a pioneering and a controversial participant in the emergence of the broad use of psychedelics.
α-Methyltryptamine is a psychedelic, stimulant, and entactogen drug of the tryptamine family. 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.
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.
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 hallucinogen of the tryptamine family. It 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-DALT or N,N-diallyl-5-methoxytryptamine is a psychedelic tryptamine first synthesized by Alexander Shulgin.
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-T is a psychedelic and hallucinogenic drug of the 2C family. It is used by some as an entheogen. It has structural and pharmacodynamic properties similar to the drugs mescaline and 2C-T-2.
N-Methyltryptamine (NMT), also known as monomethyltryptamine, is a chemical compound of the tryptamine family and a naturally occurring compound found in the human body and certain plants.
5-Methoxy-α-ethyltryptamine (5-MeO-α-ET) is a psychoactive drug and member of the tryptamine chemical class. It reportedly produces psychedelic and stimulant effects.
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.
2C-O-4 (4-isopropoxy-2,5-dimethoxyphenethylamine) is a phenethylamine of the 2C family. It is also a positional isomer of isoproscaline and was probably first synthesized by Alexander Shulgin. It produces hallucinogenic, psychedelic, and entheogenic effects. Because of the low potency of 2C-O-4, and the inactivity of 2C-O, Shulgin felt that the 2C-O series would not be an exciting area for research, and did not pursue any further analogues.
4-Hydroxy-5-methoxydimethyltryptamine, also known as 4-HO-5-MeO-DMT or psilomethoxin, is a hypothetical novel psychedelic drug.
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.
N,N-Dibutyltryptamine (DBT) is a psychedelic drug belonging to the tryptamine family. It is found either as its crystalline hydrochloride salt or as an oily or crystalline base. DBT was first synthesized by the chemist Alexander Shulgin and reported in his book TiHKAL . Shulgin did not test DBT himself, but reports a human dosage of "1 mg/kg i.m." being active, but less so than DMT or DET. This suggests that an active dosage of DBT will be in the 100 mg range. This compound has been sold as a "research chemical" and has been confirmed to be an active hallucinogen although somewhat weaker than other similar tryptamine derivatives. It produces a head-twitch response in mice.
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.
5-MeO-NMT (5-methoxy-N-methyltryptamine) is an organic chemical compound, being the 5-methoxy analog of N-methyltryptamine (NMT). It was first isolated from Phalaris arundinacea. It has also been synthesized by Alexander Shulgin and reported in his book TiHKAL.
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.
5-Ethoxy-DMT is a tryptamine derivative which has been previously synthesized as a chemical intermediate, but has not been studied to determine its pharmacology.
O-Acetylbufotenine, or bufotenine O-acetate, also known as 5-acetoxy-N,N-dimethyltryptamine (5-AcO-DMT) or O-acetyl-N,N-dimethylserotonin, is a synthetic tryptamine derivative and putative serotonergic psychedelic. It is the O-acetylated analogue of the naturally occurring peripherally selective serotonergic tryptamine bufotenine and is thought to act as a centrally penetrant prodrug of bufotenine.
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