Pyrrolidinylmethylindoles
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Pyrrolidinylmethylindoles
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. See also * α,N,N-Trimethyltryptamine * Dimethyltryptamine * 4-HO-MPMI * 5F-MPMI * 5-MeO-MPMI * NTBT * 10,11-Secoergoline (α,''N''-Pip-T) * Pyr-T * SN-22 SN-22 is a chemical compound which acts as a moderately selective agonist at the 5-HT2 family of serotonin receptors, with a Ki of 19 nM at 5-HT2 subtypes versus 514 nM at 5-HT1A receptors. Many related derivatives are known, most of ... References Alpha-Alkyltryptamines Designer drugs N,N-Dialkyltryptamines Psychedelic tryptamines Pyrrolidinylmethylindoles Serotonin receptor agonists {{nervous-system-drug-stub ...
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Eletriptan
Eletriptan, sold under the brand name Relpax and used in the form of eletriptan hydrobromide, is a second-generation triptan medication intended for treatment of migraine headaches. It is used as an abortive medication, blocking a migraine attack which is already in progress. Eletriptan is marketed and manufactured by Pfizer Inc. Approval and availability Eletriptan was approved by the US Food and Drug Administration (FDA) in December 2002, for the acute treatment of migraine with or without aura in adults. It is available only by prescription in the United States, Canada and Australia. It is not intended for the prophylactic therapy of migraine or for use in the management of hemiplegic or basilar migraine. It is available in 20 mg and 40 mg strengths. Eletriptan was covered by and ; both now expired. Mechanism of action Eletriptan is believed to reduce swelling of the blood vessels surrounding the brain. This swelling is associated with the head pain of a m ...
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4-HO-MPMI
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 enantiomer In chemistry, an enantiomer (Help:IPA/English, /ɪˈnænti.əmər, ɛ-, -oʊ-/ Help:Pronunciation respelling key, ''ih-NAN-tee-ə-mər''), also known as an optical isomer, antipode, or optical antipode, is one of a pair of molecular entities whi ...s, with only the (''R'')-enantiomer being active. The binding affinity for 5-HT2A receptor is 13 ± 2 nM (Ki 25IOI). It is reported at doses starting at 0.5 mg and 1.0-1.5 mg seem to be psychedelic doses. The duration it is reported between six and eight hours. Available (anecdotal) data on subjective effects report ...
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5F-MPMI
5F-MPMI is a tryptamine derivative which acts as a serotonin receptor agonist, selective for the 5-HT2 subtypes but with similar affinity to all three receptors, having strongest activity at 5-HT2B and weakest at 5-HT2A. Retrieved 2025-05-14 See also * 4-HO-MPMI * 5-MeO-MPMI 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 ... * MPMI References Designer drugs N,N-Dialkyltryptamines Fluoroarenes 5-Halotryptamines Pyrrolidinylmethylindoles Serotonin receptor agonists {{psychoactive-stub ...
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5-MeO-MPMI
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 enantiomer In chemistry, an enantiomer (Help:IPA/English, /ɪˈnænti.əmər, ɛ-, -oʊ-/ Help:Pronunciation respelling key, ''ih-NAN-tee-ə-mər''), also known as an optical isomer, antipode, or optical antipode, is one of a pair of molecular entities whi ...s, with only the (''R'')-enantiomer being active. See also * 5-MeO-pyr-T * 5F-MPMI * 4-HO-MPMI * 4-HO-pyr-T * CP-135,807 * MPMI References {{Tryptamines Alpha-Alkyltryptamines Designer drugs N,N-Dialkyltryptamines 5-Methoxytryptamines Pyrrolidinylmethyli ...
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Alpha-Alkyltryptamines
Substituted tryptamines, or simply tryptamines, also known as serotonin analogues (i.e., 5-hydroxytryptamine analogues), are organic compounds which may be thought of as being derived from tryptamine itself. The molecular structures of all tryptamines contain an indole ring, joined to an amino group, amino (NH2) group via an ethyl (−CH2–CH2−) side chain, sidechain. In substituted tryptamines, the indole ring, sidechain, and/or amino group are modified by substituting another group for one of the hydrogen (H) atoms. Well-known tryptamines include serotonin, an important neurotransmitter, and melatonin, a hormone involved in regulating the sleep-wake cycle. Tryptamine alkaloids are found in fungi, plants and animals; and sometimes used by humans for the neurological or psychotropic effects of the substance. Prominent examples of tryptamine alkaloids include psilocybin (from "psilocybin mushrooms") and dimethyltryptamine, DMT. In South America, dimethyltryptamine is obtained f ...
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SN-22
SN-22 is a chemical compound which acts as a moderately selective agonist at the 5-HT2 family of serotonin receptors, with a Ki of 19 nM at 5-HT2 subtypes versus 514 nM at 5-HT1A receptors. Many related derivatives are known, most of which are ligands for 5-HT1A, 5-HT6 or dopamine D2 receptors or show SSRI activity. See also * BRL-54443 * LY-334370 * LY-367,265 * MPMI * MPTP * Naratriptan * N,N-Dimethyltryptamine * RU-24969 * Sertindole Sertindole, sold under the brand name Serdolect among others, is an antipsychotic medication. Sertindole was developed by the Danish pharmaceutical company Lundbeck and marketed under license by Abbott Labs. Like other atypical antipsychotics, ... References Piperidinylindoles Serotonin receptor agonists {{pharm-stub ...
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Psychedelic Tryptamines
Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary mental states (known as psychedelic experiences or "trips") and a perceived "expansion of consciousness". Also referred to as classic hallucinogens or serotonergic hallucinogens, the term ''psychedelic'' is sometimes used more broadly to include various other types of hallucinogens as well, such as those which are atypical or adjacent to psychedelia like salvia and MDMA, respectively. Classic psychedelics generally cause specific psychological, visual, and auditory changes, and oftentimes a substantially altered state of consciousness. They have had the largest influence on science and culture, and include mescaline, LSD, psilocybin, and DMT. There are a large number of both naturally occurring and synthetic serotonergic psychedelics. Most psychedelic drugs fall into one of the three families of chemical compounds: tryptamines, phenethylamines, or lysergamides. They produce t ...
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Designer Drugs
A designer drug is a structural or functional analog of a controlled substance that has been designed to mimic the pharmacological effects of the original drug, while avoiding classification as illegal and/or detection in standard drug tests. Designer drugs include psychoactive substances that have been designated by the European Union, Australia, and New Zealand, as new psychoactive substances (NPS) as well as analogs of performance-enhancing drugs such as designer steroids. Some of these designer drugs were originally synthesized by academic or industrial researchers in an effort to discover more potent derivatives with fewer side effects and shorter duration (and possibly also because it is easier to apply for patents for new molecules) and were later co-opted for recreational use. Other designer drugs were prepared for the first time in clandestine laboratories. Because the efficacy and safety of these substances have not been thoroughly evaluated in animal and human tr ...
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Tryptamine
Tryptamine is an indolamine metabolite of the essential amino acid tryptophan. The chemical structure is defined by an indole—a fused benzene and pyrrole ring, and a 2-aminoethyl group at the second carbon (third aromatic atom, with the first one being the heterocyclic nitrogen). The structure of tryptamine is a shared feature of certain aminergic neuromodulators including melatonin, serotonin, bufotenin and psychedelic derivatives such as dimethyltryptamine (DMT), psilocybin, psilocin and others. Tryptamine has been shown to activate serotonin receptors and trace amine-associated receptors expressed in the mammalian brain, and regulates the activity of dopaminergic, serotonergic and glutamatergic systems. In the human gut, bacteria convert dietary tryptophan to tryptamine, which activates 5-HT4 receptors and regulates gastrointestinal motility. Multiple tryptamine-derived drugs have been developed to treat migraines, while trace amine-associated receptors are bei ...
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Pyr-T
Pyr-T, also known as ''N'',''N''-tetramethylenetryptamine or as 3-(2-pyrrolidinoethyl)indole, is a lesser-known serotonin receptor modulator of the tryptamine family. It is the cyclized derivative of diethyltryptamine (DET) in which the ''N'',''N''-diethyl groups have been fused into a pyrrolidine ring. Use and effects In his 1997 book ''TiHKAL'' (''Tryptamines I Have Known and Loved''), Alexander Shulgin reported neither the dose range nor the duration of the drug. However, individual experiments employed 25 to 50mg orally and 70mg smoked. Pyr-T produced effects including malaise, feeling sick, unpleasantness, salivation, muscle and joint pains, dizziness, feeling high, and uncomfortableness. Hallucinogenic effects, for instance visuals, were either absent or minor. Pharmacology Pyr-T has been found to show affinity for serotonin receptors, including the serotonin 5-HT1A, 5-HT2A and 5-HT2C receptors. Its affinities () for these receptors were 30nM for the serotonin 5-HT ...
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