 | |
| Identifiers | |
|---|---|
| |
| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| ChEMBL | |
| CompTox Dashboard (EPA) | |
| Chemical and physical data | |
| Formula | C14H20N2 |
| Molar mass | 216.328 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
  (what is this?) (verify) | |
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. [1]
N,N-Dimethyltryptamine is a substituted tryptamine that occurs in many plants and animals and which is both a derivative and a structural analog of tryptamine. It is used as a recreational psychedelic drug and prepared by various cultures for ritual purposes as an entheogen.
Psilocin is a substituted tryptamine alkaloid and a serotonergic psychedelic substance. It is present in most psychedelic mushrooms together with its phosphorylated counterpart psilocybin. Psilocin is a Schedule I drug under the Convention on Psychotropic Substances. The mind-altering effects of psilocin are highly variable, subjective and resemble those of LSD and DMT.
A serotonin receptor agonist is an agonist of one or more serotonin receptors. They activate serotonin receptors in a manner similar to that of serotonin, a neurotransmitter and hormone and the endogenous ligand of the serotonin receptors.
5-hydroxytryptamine (serotonin) receptor 1F, also known as HTR1F is a 5-HT1 receptor protein and also denotes the human gene encoding it.
AL-38022A is an indazole derivative drug which is one of a range of similar drugs developed for scientific research and with some possible clinical applications. It acts as a potent and selective agonist for the 5-HT2 family of serotonin receptors, with highest binding affinity for the 5-HT2C subtype and around 4x less affinity for 5-HT2A and 5-HT2B. In drug discrimination tests on animals, it fully substituted for both DOM and 5-MeO-DMT.
AL-37350A (4,5-DHP-AMT) is a tryptamine derivative which acts as a potent and selective agonist for the serotonin receptor 5-HT2A, with a Ki of 2.0 nM, and moderate selectivity over the related 5-HT2B and 5-HT2C receptors. It has been shown to have ocular hypotensive activity in animal models, suggesting it may be useful for the treatment of glaucoma.
5-Fluoro-N,N-dimethyltryptamine (5-fluoro-DMT) 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 an agonist at the 5-HT2 serotonin receptors. 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.
7,N,N-Trimethyltryptamine (7-methyl-DMT, 7-TMT), is a tryptamine derivative which acts as an agonist of 5-HT2 receptors. In animal tests, both 7-TMT and its 5-methoxy derivative 5-MeO-7-TMT produced behavioural responses similar to those of psychedelic drugs such as DMT, but the larger 7-ethyl and 7-bromo derivatives of DMT did not produce psychedelic responses despite having higher 5-HT2 receptor affinity in vitro (cf. DOBU, DOAM). 7-TMT also weakly inhibits reuptake of serotonin but with little effect on dopamine or noradrenaline reuptake.
5-(Nonyloxy)tryptamine is a tryptamine derivative which acts as a selective agonist at the 5-HT1B receptor. Increasing the O-alkoxy chain length in this series gives generally increasing potency and selectivity for 5-HT1B, with highest activity found for the nonyloxy derivative, having a 5-HT1B binding affinity of 1.0 nM, and around 300-fold selectivity over the related 5-HT1A receptor.
1-(2-Dimethylaminoethyl)dihydropyrano(3,2-e)indole (4,5-DHP-DMT) is a tricyclic tryptamine derivative which acts as a potent and reasonably selective partial agonist for the serotonin receptor 5-HT2A, with a Ki of 17.0 nM, and moderate selectivity over related serotonin receptors. It has lower 5-HT2 affinity and efficacy than the related compound AL-37350A, but higher lipophilicity.
RU-28306 is a tricyclic tryptamine derivative which acts as a serotonin receptor agonist, with selectivity for 5-HT1 and 5-HT2 subtypes. It can be regarded either as a conformationally constrained derivative of DMT, or a structurally simplified analogue of LSD, but the binding affinity of racemic RU-28306 is closer to that of DMT, though with relatively higher affinity for 5-HT2 subtypes and lower for 5-HT1. It has been sold as a designer drug and was first reported to the EMCDDA by a forensic laboratory in Slovenia in 2017.
O-4310 (1-isopropyl-6-fluoro-psilocin) is a tryptamine derivative developed by Organix Inc which acts as a serotonin receptor agonist. It is claimed to have an EC50 of 5nM at 5-HT2A with 89% efficacy vs 5-HT, and 100x selectivity over 5-HT2C, while being apparently inactive at the 5-HT2B antitarget.
5-HO-DiPT (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 5-HT2A affinity and good selectivity over 5-HT1A, while being more lipophilic than the related drug bufotenine (5-HO-DMT), which produces mainly peripheral effects.
CP-132,484 is a tryptamine derivative which acts as a potent and selective agonist for the 5-HT2 family of serotonin receptors. It has reasonable selectivity for 5-HT2A and 5-HT2C subtypes over 5-HT2B, but is only slightly selective for 5-HT2A over 5-HT2C. This compound and several related analogues have been shown to have ocular hypotensive activity in animal models, suggesting they may be useful for the treatment of glaucoma.
Acetryptine (INN), also known as 5-acetyltryptamine (5-AT), is a drug described as an antihypertensive agent which was never marketed. Structurally, acetryptine is a substituted tryptamine, and is closely related to other substituted tryptamines like serotonin (5-hydroxytryptamine). It was developed in the early 1960s. The binding of acetryptine to serotonin receptors does not seem to have been well-investigated, although it was assessed at the 5-HT1A and 5-HT1D receptors and found to bind to them with high affinity. The drug may also act as a monoamine oxidase inhibitor (MAOI); specifically, as an inhibitor of MAO-A.
Amesergide is a serotonin receptor antagonist of the ergoline and lysergamide families related to methysergide which was under development by Eli Lilly and Company for the treatment of a variety of conditions including depression, anxiety, schizophrenia, male sexual dysfunction, migraine, and thrombosis but was never marketed. It reached phase II clinical trials for the treatment of depression, erectile dysfunction, and premature ejaculation prior to the discontinuation of its development.
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.
7-Chloro-α-methyltryptamine (7-Cl-AMT) is a tryptamine derivative with stimulant effects, invented in the 1960s. It is a weak monoamine oxidase inhibitor but its pharmacology has not otherwise been studied by modern techniques, though several closely related compounds are known to act as serotonin–dopamine releasing agents and agonists of the 5-HT2A receptor.
 | This drug article relating to the nervous system is a stub. You can help Wikipedia by expanding it. |
