α-Methylepinine
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α-Methylepinine
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 without involvement of metabolites. See also * 3,4-Dihydroxyamphetamine (HHA; α-methyldopamine) * 4-Hydroxy-3-methoxyamphetamine (HMA) * 4-Hydroxy-3-methoxymethamphetamine (HMMA) * 2,4,5-Trihydroxyamphetamine (THA) * 2,4,5-Trihydroxymethamphetamine (THMA) * 3,4-Dihydroxymethcathinone (HHMC) * 4-Hydroxy-3-methoxyme ...
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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 ...
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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 ...
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Metabolite
In biochemistry, a metabolite is an intermediate or end product of metabolism. The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, catalytic activity of their own (usually as a cofactor to an enzyme), defense, and interactions with other organisms (e.g. pigments, odorants, and pheromones). A primary metabolite is directly involved in normal "growth", development, and reproduction. Ethylene exemplifies a primary metabolite produced large-scale by industrial microbiology. A secondary metabolite is not directly involved in those processes, but usually has an important ecological function. Examples include antibiotics and pigments such as resins and terpenes etc. Some antibiotics use primary metabolites as precursors, such as actinomycin, which is created from the primary metabolite tryptophan. Some sugars are metabolites, such as fructose or glucose, which ar ...
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4-Hydroxy-3-methoxyamphetamine
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 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-methylepinin ...
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Methamphetamines
Methamphetamine (contracted from ) is a potent central nervous system (CNS) stimulant that is mainly used as a recreational or performance-enhancing drug and less commonly as a second-line treatment for attention deficit hyperactivity disorder (ADHD). It has also been researched as a potential treatment for traumatic brain injury. Methamphetamine was discovered in 1893 and exists as two enantiomers: levo-methamphetamine and dextro-methamphetamine. ''Methamphetamine'' properly refers to a specific chemical substance, the racemic free base, which is an equal mixture of levomethamphetamine and dextromethamphetamine in their pure amine forms, but the hydrochloride salt, commonly called crystal meth, is widely used. Methamphetamine is rarely prescribed over concerns involving its potential for recreational use as an aphrodisiac and euphoriant, among other concerns, as well as the availability of safer substitute drugs with comparable treatment efficacy such as Adderall an ...
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Human Pathological 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 development of s ...
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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 ...
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Catecholamines
A catecholamine (; abbreviated CA), most typically a 3,4-dihydroxyphenethylamine, is a monoamine neurotransmitter, an organic compound that has a catechol (benzene with two hydroxyl side groups next to each other) and a side-chain amine. Catechol can be either a free molecule or a substituent of a larger molecule, where it represents a 1,2-dihydroxybenzene group. Catecholamines are derived from the amino acid tyrosine, which is derived from dietary sources as well as synthesis from phenylalanine. Catecholamines are water-soluble and are 50% bound to plasma proteins in circulation. Included among catecholamines are epinephrine (adrenaline), norepinephrine (noradrenaline), and dopamine. Release of the hormones epinephrine and norepinephrine from the adrenal medulla of the adrenal glands is part of the fight-or-flight response. Tyrosine is created from phenylalanine by hydroxylation by the enzyme phenylalanine hydroxylase. Tyrosine is also ingested directly from dietar ...
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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 ...
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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 ...
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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 ...
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