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3-methoxy-4-hydroxyamphetamine
4-Hydroxy-3-methoxyamphetamine (HMA), also known as 3-''O''-methyl-α-methyldopamine, is an active metabolite of 3,4-methylenedioxymethamphetamine (MDMA). It is substantially less potent than MDMA or 3,4-methylenedioxyamphetamine (MDA) as a monoamine releasing agent ''in vitro''. Nonetheless, HMA has been found to induce the release of serotonin, norepinephrine, and dopamine with values of 897nM, 694nM, and 1450–3423nM, respectively, and hence acts as a lower-potency serotonin–norepinephrine–dopamine releasing agent (SNDRA). The predicted log P of HMA is 0.6. See also * 4-Hydroxy-3-methoxymethamphetamine (HMMA) * 3,4-Dihydroxyamphetamine (HHA; α-methyldopamine) * 3,4-Dihydroxymethamphetamine (HHMA; α-methylepinine) * 2,4,5-Trihydroxyamphetamine (THA) * 2,4,5-Trihydroxymethamphetamine (THMA) * 3,4-Dimethoxyamphetamine 3,4-Dimethoxyamphetamine (3,4-DMA), or simply dimethoxyamphetamine (DMA), is a psychedelic drug of the phenethylamine and amphetamine families. It i ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
3,4-Dimethoxyamphetamine
3,4-Dimethoxyamphetamine (3,4-DMA), or simply dimethoxyamphetamine (DMA), is a psychedelic drug of the phenethylamine and amphetamine families. It is one of the dimethoxyamphetamine (DMA) series of positional isomers. The drug has been assessed in various biochemical and preclinical studies. It has been tried in humans at doses of up to 700mg intravenously, with mescaline-like effects reported. 3,4-DMA is also orally active and has produced sympathomimetic effects at a dose of 160mg. Its duration of action is unknown. Its affinity (Ki) for the rat serotonin 5-HT2A receptor has been assessed and was found to be 43,300nM. For comparison, the affinity of ''para''-methoxyamphetamine (PMA) was 33,600nM, of 2,5-dimethoxyamphetamine (2,5-DMA) was 5,200nM, and of 2,5-dimethoxy-4-methylamphetamine (DOM) was 100nM in the same study. 3,4-DMA also showed affinity for the 5-HT1 receptor (Ki = 64,600nM). The drug has additionally been found to be a monoamine oxidase inhibitor (MAOI), wit ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Serotonin–norepinephrine–dopamine Releasing Agent
A serotonin–norepinephrine–dopamine releasing agent (SNDRA), also known as a triple releasing agent (TRA), is a type of drug which induces the release of serotonin, norepinephrine/epinephrine, and dopamine in the brain and body. SNDRAs produce euphoriant, entactogen, and psychostimulant effects, and are almost exclusively encountered as recreational drugs. A closely related type of drug is a serotonin–norepinephrine–dopamine reuptake inhibitor (SNDRI). Examples of SNDRAs Examples of SNDRAs include specific amphetamines such as MDMA, MDA, 4-methylamphetamine, methamphetamine (in high doses), certain substituted benzofurans such as 5-APB and 6-APB, naphthylisopropylamine; cathinones such as mephedrone and methylone; tryptamines such as αMT and αET; along with agents of other chemical classes such as 4,4'-DMAR, and 5-IAI.Bruce E. Blough, Richard Rothman, Antonio Landavazo, Kevin M. Page, Ann Marie Decker. Phenylmorpholines and analogues thereof. US Patent 2013/0 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Phenols
In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of one or more hydroxyl groups (− O H) bonded directly to an aromatic hydrocarbon group. The simplest is phenol, . Phenolic compounds are classified as simple phenols or polyphenols based on the number of phenol units in the molecule. Phenols are both synthesized industrially and produced by plants and microorganisms. Properties Acidity Phenols are more acidic than typical alcohols. The acidity of the hydroxyl group in phenols is commonly intermediate between that of aliphatic alcohols and carboxylic acids (their pKa is usually between 10 and 12). Deprotonation of a phenol forms a corresponding negative phenolate ion or phenoxide ion, and the corresponding salts are called phenolates or phenoxides (aryloxides, according to the IUPAC Gold Book). Condensation with aldehydes and ketones Phenols are susceptible to electrophilic aromatic substitutions. Condensation with ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Methoxyphenethylamines
Methoxyphenethylamine, or monomethoxyphenethylamine, may refer to: * 2-Methoxyphenethylamine (2-MPEA) * 3-Methoxyphenethylamine (3-MPEA) * 4-Methoxyphenethylamine (4-MPEA) See also * Substituted methoxyphenethylamine * Dimethoxyphenethylamine * Trimethoxyphenethylamine * Methoxyamphetamine * Dimethoxyamphetamine * Trimethoxyamphetamine {{Chemistry index Methoxyphenethylamines ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Human Drug Metabolites
Humans (''Homo sapiens'') or modern humans are the most common and widespread species of primate, and the last surviving species of the genus ''Homo''. They are great apes characterized by their hairlessness, bipedalism, and high intelligence. Humans have large brains, enabling more advanced cognitive skills that facilitate successful adaptation to varied environments, development of sophisticated tools, and formation of complex social structures and civilizations. Humans are highly social, with individual humans tending to belong to a multi-layered network of distinct social groups — from families and peer groups to corporations and political states. As such, social interactions between humans have established a wide variety of values, social norms, languages, and traditions (collectively termed institutions), each of which bolsters human society. Humans are also highly curious: the desire to understand and influence phenomena has motivated humanity's developmen ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
4-Hydroxy-3-methoxymethcathinone
4-Hydroxy-3-methoxymethcathinone (HMMC), or 3-methoxy-4-hydroxy-''N''-methylcathinone, is a monoamine releasing agent of the amphetamine and cathinone families. It is an active metabolite of methylone (3,4-methylenedioxymethcathinone; MDMC). The drug is a very low-potency serotonin–norepinephrine–dopamine releasing agent (SNDRA), with values of 7,210nM for serotonin, 6,340nM for norepinephrine, and 5,840nM for dopamine in rat brain synaptosomes. HMMC was first described in the scientific literature by 2011. See also * 3,4-Dihydroxymethcathinone (HHMC; 3,4-DHMC) * 4-Hydroxy-3-methoxyamphetamine (HMA) * 4-Hydroxy-3-methoxymethamphetamine 4-Hydroxy-3-methoxymethamphetamine (HMMA) is an active metabolite of 3,4-methylenedioxymethamphetamine (MDMA). It is a slightly more potent stimulant than MDMA in rodents. The drug is substantially less potent than MDMA as a monoamine releasi ... (HMMA) * α-Methyldopamine (3,4-dihydroxyamphetamine; HHA; 3,4-DHA) * α-Methylepinine ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
3,4-Dihydroxymethcathinone
3,4-Dihydroxymethcathinone (HHMC), or 3,4-dihydroxy-''N''-methylcathinone, is a monoamine releasing agent of the amphetamine and cathinone families. It is an active metabolite of methylone (3,4-methylenedioxymethcathinone; MDMC). The drug is a norepinephrine–dopamine releasing agent (NDRA), with values of 110nM for norepinephrine, 90nM for dopamine, and 14,100nM for serotonin in rat brain synaptosomes. HHMC was first described in the scientific literature by 2017. See also * 4-Hydroxy-3-methoxymethcathinone (HMMC; 4-HO-3-MeO-MC) * α-Methyldopamine (3,4-dihydroxyamphetamine; HHA; 3,4-DHA) * α-Methylepinine (3,4-dihydroxymethamphetamine; HHMA, 3,4-DHMA) * 4-Hydroxy-3-methoxyamphetamine (HMA) * 4-Hydroxy-3-methoxymethamphetamine 4-Hydroxy-3-methoxymethamphetamine (HMMA) is an active metabolite of 3,4-methylenedioxymethamphetamine (MDMA). It is a slightly more potent stimulant than MDMA in rodents. The drug is substantially less potent than MDMA as a monoamine releasi ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
2,4,5-Trihydroxymethamphetamine
2,4,5-Trihydroxymethamphetamine (THMA or THM) is a neurotoxin and a metabolite of MDMA. It has structural similarity to the dopamine neurotoxin 6-hydroxydopamine, and produces lasting serotonin deficits when administered centrally. See also * 2,4,5-Trihydroxyamphetamine (THA) * 3,4-Dihydroxyamphetamine (HHA; α-methyldopamine) * 3,4-Dihydroxymethamphetamine (HHMA; α-methylepinine) * 4-Hydroxy-3-methoxyamphetamine (HMA) * 4-Hydroxy-3-methoxymethamphetamine 4-Hydroxy-3-methoxymethamphetamine (HMMA) is an active metabolite of 3,4-methylenedioxymethamphetamine (MDMA). It is a slightly more potent stimulant than MDMA in rodents. The drug is substantially less potent than MDMA as a monoamine releasi ... (HMMA) References Human pathological metabolites Methamphetamines Monoaminergic neurotoxins Recreational drug metabolites {{Neurotoxin-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
2,4,5-Trihydroxyamphetamine
2,4,5-Trihydroxyamphetamine (THA) is a neurotoxin and a metabolite of MDMA. It comes from the ring-hydroxylation of 3,4-methylenedioxyamphetamine (MDA). In one paper, it was shown to reduce hippocampal tryptophan hydroxylase activity by 54% after short-term treatment. In another study, it was shown to significantly reduce striatal tyrosine hydroxylase activity. See also * 2,4,5-Trihydroxymethamphetamine (THMA) * 3,4-Dihydroxyamphetamine (HHA; α-methyldopamine) * 3,4-Dihydroxymethamphetamine (HHMA; α-methylepinine) * 4-Hydroxy-3-methoxyamphetamine (HMA) * 4-Hydroxy-3-methoxymethamphetamine 4-Hydroxy-3-methoxymethamphetamine (HMMA) is an active metabolite of 3,4-methylenedioxymethamphetamine (MDMA). It is a slightly more potent stimulant than MDMA in rodents. The drug is substantially less potent than MDMA as a monoamine releasi ... (HMMA) References Human pathological metabolites Monoaminergic neurotoxins Substituted amphetamines Recreational drug metabolites ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
3,4-Dihydroxymethamphetamine
3,4-Dihydroxymethamphetamine (HHMA, 3,4-DHMA), or 3,4-dihydroxy-''N''-methylamphetamine, also known as α-methylepinine or α,''N''-dimethyldopamine, is the major metabolite of 3,4-methylenedioxy-''N''-methylamphetamine (MDMA). It is formed from MDMA by ''O''-demethylation via cytochrome P450 enzymes including CYP2D6 as well as CYP1A2 and CYP3A4. Like MDMA, HHMA is a monoamine releasing agent. Along with 3,4-dihydroxyamphetamine (HHA; α-methyldopamine), HHMA may be involved in the serotonergic neurotoxicity of MDMA. However, findings in this regard are conflicting, and the neurotoxicity of MDMA and related agents may instead be based on their mechanism of action In pharmacology, the term mechanism of action (MOA) refers to the specific biochemical Drug interaction, interaction through which a Medication, drug substance produces its pharmacological effect. A mechanism of action usually includes mention o ... without involvement of metabolites. See also * 3,4-Dihydro ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
4-Hydroxy-3-methoxymethamphetamine
4-Hydroxy-3-methoxymethamphetamine (HMMA) is an active metabolite of 3,4-methylenedioxymethamphetamine (MDMA). It is a slightly more potent stimulant than MDMA in rodents. The drug is substantially less potent than MDMA as a monoamine releasing agent ''in vitro''. Nonetheless, HMMA has been found to induce the release of serotonin, norepinephrine, and dopamine with values of 589nM, 625nM, and 607–2884nM, respectively, and hence acts as a lower-potency serotonin–norepinephrine–dopamine releasing agent (SNDRA). The predicted log P of HMMA is 1.2. See also * 4-Hydroxy-3-methoxyamphetamine (HMA) * 3,4-Dihydroxyamphetamine (HHA; α-methyldopamine) * 3,4-Dihydroxymethamphetamine 3,4-Dihydroxymethamphetamine (HHMA, 3,4-DHMA), or 3,4-dihydroxy-''N''-methylamphetamine, also known as α-methylepinine or α,''N''-dimethyldopamine, is the major metabolite of 3,4-methylenedioxy-''N''-methylamphetamine (MDMA). It is formed fro ... (HHMA; α-methylepinine) * 2,4,5-Trihydro ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
