Arylalkylamines
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Arylalkylamines
Substituted arylalkylamines, also alternatively known in many cases as substituted arylethylamines, are a group of chemical compounds. These compounds are divided into two main categories: indolylalkylamines and phenylalkylamines. * Indolylalkylamines include substances like tryptamines, which are found in some natural compounds and can affect mood and perception. * Phenylalkylamines include substances like phenethylamines and amphetamines, which are found in both natural and synthetic forms. These compounds are related to monoamine neurotransmitters, which are chemicals in the brain that transmit signals between nerve cells. Because of this, substituted arylalkylamines can have a wide range of effects on the body and mind. They are used in many medications, including: * Psychostimulants, which increase alertness and energy. * Anorectics, which suppress appetite. * Wakefulness-promoting agents, which help people stay awake. * Bronchodilators, which make breathing easier. * Decon ...
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2-Furylethylamine
2-Furylethylamine (2-FEA or FEA) is a drug of the arylalkylamine family related to the substituted phenethylamines such as β-phenethylamine (PEA) and amphetamine. It is known to have similar pressor effects as amphetamine and strong constricting effects on the uterus in animals. The psychoactive effects of FEA in humans are unknown. Derivatives of FEA include α-Me-FEA (furylisopropylamine) and α,''N''-Me-FEA, among others. α-Me-FEA was less several-fold potent than amphetamine in animals and showed limited effects in humans. Analogues of FEA, besides β-phenethylamine (PEA) and amphetamine (α-Me-PEA), include TH-FEA, α-Me-TH-FEA, ThEA, thiopropamine (α-Me-ThEA), 3-ThEA, 2-(2-pyrrolyl)ethylamine (NEA), and α-Me-NEA, among others. Some of them are known to be active. FEA was first synthesized by 1920. FEA and analogues were studied by Gordon Alles and colleagues, who discovered its pressor effects. FEA is not a controlled substance in the United States Th ...
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Chemical Compound
A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element is therefore not a compound. A compound can be transformed into a different substance by a chemical reaction, which may involve interactions with other substances. In this process, bonds between atoms may be broken or new bonds formed or both. There are four major types of compounds, distinguished by how the constituent atoms are bonded together. Molecular compounds are held together by covalent bonds; ionic compounds are held together by ionic bonds; intermetallic compounds are held together by metallic bonds; coordination complexes are held together by coordinate covalent bonds. Non-stoichiometric compounds form a disputed marginal case. A chemical formula specifies the number of atoms of each element in a compound molecule, usin ...
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Phenethylamine
Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine, which acts as a central nervous system stimulant in humans. In the brain, phenethylamine regulates monoamine neurotransmission by binding to trace amine-associated receptor 1 (TAAR1) and inhibiting vesicular monoamine transporter 2 (VMAT2) in monoamine neurons. To a lesser extent, it also acts as a neurotransmitter in the human central nervous system. In mammals, phenethylamine is produced from the amino acid L-phenylalanine by the enzyme aromatic L-amino acid decarboxylase via enzymatic decarboxylation. In addition to its presence in mammals, phenethylamine is found in many other organisms and foods, such as chocolate, especially after microbial fermentation. Phenethylamine is sold as a dietary supplement for purported mood and weight loss-related therapeutic benefits; however, in orally ingested phenethylamine, a significant amount is metabolized in the small intestine by mon ...
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Methylhexanamine
Methylhexanamine (also known as methylhexamine, 1,3-dimethylamylamine, 1,3-DMAA, dimethylamylamine, and DMAA; trade names Forthane and Geranamine) is an indirect sympathomimetic drug invented and developed by Eli Lilly and Company and marketed as an inhaled nasal decongestant from 1948 until it was voluntarily withdrawn from the market in the 1980s. Since 2006 methylhexanamine has been sold extensively under many names as a stimulant or energy-boosting dietary supplement under the claim that it is similar to certain compounds found in geraniums, but its safety has been questioned as a number of adverse events and at least five deaths have been associated with methylhexanamine-containing supplements. It is banned by many sports authorities and governmental agencies. Despite multiple warning letters from the FDA, as of 2019, the stimulant remains available in sports and weight loss supplements in the US. History In April 1944, Eli Lilly and Company introduced methylhexanamine ...
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3-APBT
3-APBT (former developmental code name SKF-6678), also known as 3-(2-aminopropyl)benzo ²hiophene, is a monoamine releasing agent and serotonin receptor agonist of the benzothiophene group. It is an analogue of α-methyltryptamine (AMT) in which the indole ring has been replaced with a benzothiophene ring. The drug acts as a potent and well-balanced serotonin–norepinephrine–dopamine releasing agent (SNDRA). It is also a full agonist of the serotonin 5-HT2 receptors, including of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors. 3-APBT produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents. It does not stimulate locomotor activity in rodents, suggesting that it does not possess stimulant-type effects. The drug has been reported be a weak monoamine oxidase inhibitor (MAOI), specifically of monoamine oxidase A (MAO-A) ( = 16,200nM). 3-APBT was developed by Smith, Kline & French (SKF) as a potential pharmaceutical drug in the late 1950s. ...
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3-APB
3-APB, also known as 3-(2-aminopropyl)benzofuran, is a drug of the benzofuran family related to α-methyltryptamine (AMT). It is an analogue of AMT in which the indole ring has been replaced with a benzofuran ring. The properties of 3-APB do not yet appear to have been reported. However, derivatives of 3-APB have been studied and described. An example is its 5-methoxy analogue mebfap (5-MeO-3-APB; a benzofuran analogue of 5-MeO-AMT), which is known to have high affinity for the serotonin 5-HT2 receptors. In addition, 3-APBT, the analogue of 3-APB with a sulfur atom instead of an oxygen atom, is a highly potent serotonin–norepinephrine–dopamine releasing agent (SNDRA) and serotonin receptor agonist, with psychedelic-like but not stimulant-like effects in animals. Positional isomers of 3-APB such as 5-APB and 6-APB are monoamine releasing agents and entactogens of the amphetamine and benzofuran families. Besides 3-APBT, all of the possible positional isomers of the APBTs ...
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1ZP2MA
1ZP2MA, also known as -(indolizin-1-yl)propan-2-ylmethyl)amine or as 1-(indolizin-1-yl)-''N''-methylpropan-2-amine, is a monoamine releasing agent and an indolizine derivative. It is the analogue and positional isomer of the stimulant-like drug α,''N''-dimethyltryptamine (α,''N''-DMT or ''N''-methyl-α-methyltryptamine (''N''-methyl-αMT)) in which the indole ring has been replaced with an indolizine ring. 1ZP2MA has been found to be a potent dopamine releasing agent, with an of 62nM. It is the α-methyl and ''N''-desmethyl analogue of (2-(indolizin-1-yl)ethyl)dimethylamine (TACT908; the indolizine analogue of dimethyltryptamine (DMT)). 1ZP2MA and 2ZEDMA were patented by Tactogen in 2023. See also * 1Z2MAP1O * α-Methylisotryptamine (isoAMT) * BK-NM-AMT * 3-APBT 3-APBT (former developmental code name SKF-6678), also known as 3-(2-aminopropyl)benzo ²hiophene, is a monoamine releasing agent and serotonin receptor agonist of the benzothiophene group. It is an analogue o ...
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Isotryptamine
Isotryptamine, also known as 2-(1-indolyl)ethylamine, is a chemical compound and positional isomer of tryptamine (2-(3-indolyl)ethylamine). A variety of isotryptamine chemical derivative, derivatives, or chemical substituent, substituted isotryptamines, have been developed, including serotonergic psychedelics and psychoplastogens like 6-MeO-isoDMT; non-hallucinogenic psychoplastogens like isoDMT, 5-MeO-isoDMT, and zalsupindole (DLX-001; AAZ-A-154); serotonin 5-HT2C receptor, 5-HT2C receptor agonists like 5,6-difluoro-isoAMT, (''S'')-5,6-difluoro-isoAMT, Ro60-0175 ((''S'')-5-fluoro-6-chloro-isoAMT), and PNU-181731; serotonin 5-HT6 receptor, 5-HT6 receptor receptor modulator, modulators; and dual monoamine releasing agents and serotonin receptor agonists like α-methylisotryptamine, isoAMT (PAL-569). JRT (drug), JRT is the isotryptamine analogue of LSD and may be considered a cyclic compound, cyclized isotryptamine. References

Isotryptamines, Serotonin receptor modulato ...
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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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Propylhexedrine
Propylhexedrine, sold under the brand name Benzedrex among others, is an alkylamine primarily utilized as a topical nasal decongestant. Its main indications are relief of congestion due to colds, allergies, and allergic rhinitis. Propylhexedrine was first used medically in 1949, with the release of Benzedrex by Smith, Kline & French, and it has been used, mainly within the United States, since then. Medical use Propylhexedrine is used to treat acute nasal congestion related to the common cold, allergies, and hay fever. For nasal congestion, the dosage is listed as four inhalations (two inhalations per nostril) every two hours for adults and children 6–12 years of age. Each inhalation delivers 0.4 to 0.5 mg (400 to 500 ''μ''g) in 800 mL of air. Use is not to exceed three days. Historically, it has also been used for weight loss in oral tablet preparations at a dose of 25 mg. No medications containing propylhexedrine are currently approved for weight loss in any country sin ...
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Cyclopentamine
Cyclopentamine (trade names Clopane, Cyclonarol, Cyclosal, Cyklosan, Nazett, Sinos, among others) is a sympathomimetic and vasoconstrictor drug of the alkylamine family and related to the arylalkylamines. Cyclopentamine was indicated in the past as an over-the-counter (OTC) medication for use as a nasal decongestant, notably in Europe and Australia, but has now been largely discontinued. Pharmacology Cyclopentamine acts as a releasing agent of the catecholamine neurotransmitters norepinephrine (noradrenaline), epinephrine (adrenaline), and dopamine. Its effects on norepinephrine and epinephrine mediate its decongestant effects, while its effects on all three neurotransmitters are responsible for its stimulant properties. When ingested orally in sufficient quantities, cyclopentamine produces similar effects to amphetamine, methamphetamine, and propylhexedrine. Chemistry Cyclopentamine is the cyclopentane homolog of propylhexedrine, differing only in terms of the contracted ...
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