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| Formula | C11H14N2O |
| Molar mass | 190.246 g·mol−1 |
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2-Hydroxy-N-methyltryptamine (2-HO-NMT) is a tryptamine and is the 2-hydroxy analog of N-methyltryptamine (NMT). It is briefly mentioned in Alexander Shulgin's book TiHKAL (Tryptamines I Have Known and Loved) under the DMT entry and is stated to be found in Desmanthus illinoensis . [1]
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.
N-Ethyltryptamine (NET) is a tryptamine that is structurally related to N-methyltryptamine (NMT) and the psychedelic drugs N,N-dimethyltryptamine (DMT) and N,N-diethyltryptamine (DET).
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.
Baeocystin, also known as norpsilocybin or 4-phosphoryloxy-N-methyltryptamine (4-PO-NMT), is a zwitterionic alkaloid and analog of psilocybin. It is found as a minor compound in most psilocybin mushrooms together with psilocybin, norbaeocystin, aeruginascin, and psilocin. Baeocystin is an N-demethylated derivative of psilocybin, and a phosphorylated derivative of 4-HO-NMT (4-hydroxy-N-methyltryptamine). The structures at right illustrate baeocystin in its zwitterionic form.
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.
4-Hydroxy-5-methoxydimethyltryptamine, also known as 4-HO-5-MeO-DMT or psilomethoxin, is a hypothetical novel psychedelic drug.
α,N,N-Trimethyltryptamine is a psychoactive drug of the tryptamine chemical class which acts as a psychedelic hallucinogen. It is similar in structure to the other psychedelics of the tryptamine class such as dimethyltryptamine (DMT) and α-methyltryptamine (α-MT).
MBT, or N-methyl-N-butyltryptamine, is a lesser-known psychedelic drug. MBT was first synthesized by Alexander Shulgin. In his book TiHKAL, the minimum dosage is listed as 250-400 mg, and the duration listed as 4–6 hours. MBT produces a heavy body load with dehydration, and causes visuals similar to those of DMT. Very little data exists about the pharmacological properties, metabolism, and toxicity of MBT.
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.
α,N-Dimethyltryptamine (α,N-DMT; developmental code names SK&F-7024, Ro 3-1715), also known as N-methyl-α-methyltryptamine (N-methyl-αMT), is a lesser-known substituted tryptamine and psychoactive drug. It is the α,N-dimethyl positional isomer of N,N-dimethyltryptamine (N,N-DMT).
5-Fluoro-α-methyltryptamine, also known as PAL-544, is a putative stimulant, entactogen, and psychedelic tryptamine derivative related to α-methyltryptamine (αMT). It has been found to act as a well-balanced serotonin-norepinephrine-dopamine releasing agent, a 5-HT2A receptor agonist, and a potent and specific MAO-A inhibitor. which suggests that 5-fluoro-αMT could be an active psychedelic in humans, although it is not known to have been tested in humans and could be dangerous due to its strong inhibition of MAO-A.
Desmanthus illinoensis, commonly known as Illinois bundleflower, prairie-mimosa or prickleweed, is a common plant in the central and southern United States.
4-Hydroxy-α-methyltryptamine (4-HO-αMT) is a psychedelic drug of the tryptamine class. It is a close structural analogue of α-methyltryptamine (αMT) and produces similar effects to it, but with exacerbated side effects similarly to 5-MeO-αMT. Alexander Shulgin describes 4-HO-αMT briefly in his book TiHKAL:
The 4-hydroxy analogue of αMT has been looked at in human subjects. It is reported to be markedly visual in its effects, with some subjects reporting dizziness and a depressed feeling. There were, however, several toxic signs at doses of 15 to 20 milligrams orally, including abdominal pain, tachycardia, increased blood pressure and, with several people, headache and diarrhea.
5-Chloro-α-methyltryptamine (5-Chloro-αMT), also known as PAL-542, is a tryptamine derivative related to α-methyltryptamine (αMT) and one of only a few known specific serotonin-dopamine releasing agents (SDRAs). It has been investigated in animals as a potential treatment for cocaine dependence. The EC50 values of 5-chloro-αMT in evoking the in vitro release of serotonin (5-HT), dopamine (DA), and norepinephrine (NE) in rat synaptosomes were reported as 16 nM, 54 nM, and 3434 nM, with an NE/DA ratio of 63.6 and a DA/5-HT ratio of 3.38, indicating that it is a highly specific and well-balanced SDRA. However, 5-chloro-αMT has also been found to act as a potent full agonist of the 5-HT2A receptor, with an EC50 value of 6.27 nM and an efficacy of 105%. It is likely to act as a potent agonist of other serotonin receptors as well.
Norpsilocin, also known as 4-hydroxy-N-methyltryptamine (4-HO-NMT), is a tryptamine alkaloid recently discovered in 2017 in the psychedelic mushroom Psilocybe cubensis. It is hypothesized to be a dephosphorylated metabolite of baeocystin.
5,6-Dibromo-N-methyltryptamine (5,6-Dibromo-NMT) is a substituted tryptamine alkaloid that occurs naturally in marine sponges.
5,6-Dibromo-DMT is a substituted tryptamine alkaloid found in some marine sponges. It is briefly mentioned in Alexander Shulgin's book TiHKAL under the DMT entry and is stated to be found, along with other tryptamines, in Smenospongia aurea and other sponges.
A neurotransmitter prodrug, or neurotransmitter precursor, is a drug that acts as a prodrug of a neurotransmitter. A variety of neurotransmitter prodrugs have been developed and used in medicine. They can be useful when the neurotransmitter itself is not suitable for use as a pharmaceutical drug owing to unfavorable pharmacokinetic or physicochemical properties, for instance high susceptibility to metabolism, short elimination half-life, or lack of blood–brain barrier permeability. Besides their use in medicine, neurotransmitter prodrugs have also been used as recreational drugs in some cases.
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