3,4-Dihydroxymethcathinone
   HOME





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]  


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 ...
[...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]  


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 ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  




α-Methyldopamine
α-Methyldopamine (α-Me-DA), also known as 3,4-dihydroxyamphetamine (3,4-DHA or HHA) or as catecholamphetamine, is a research chemical of the catecholamine and amphetamine families. It is a monoamine releasing agent and a metabolite of MDMA and MDA. The ''bis''- glutathionyl metabolite of α-methyldopamine is slightly neurotoxic when directly injected into the brain's ventricles. Role in MDMA-induced serotonergic neurotoxicity Interest in α-methyldopamine lies in the fact that 3,4-methylenedioxyamphetamine (MDA) and 3,4-methylenedioxy-''N''-methylamphetamine (MDMA) may not themselves be responsible for their serotonergic neurotoxicity, as an intracerebroventricular injection does not appear to cause neurotoxicity. While many studies suggest excitotoxicity or oxidative stress as likely mechanisms, which may be an effect of MDMA itself, this has led to the search for other mechanisms for the observed toxicity of serotonin axons and subsequent reduction in serotonin (5-HT) a ...
[...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]  


picture info

Norepinephrine–dopamine Releasing Agent
A norepinephrine–dopamine releasing agent (NDRA) is a type of drug which induces the synapse, release of norepinephrine (and epinephrine) and dopamine in the body and/or brain. Many of these are amphetamine type stimulants. Examples Examples of NDRAs include phenethylamine, tyramine, amphetamine, dextroamphetamine, levoamphetamine, methamphetamine, lisdexamfetamine, 4-fluoroamphetamine, cathine, cathinone, methcathinone, phentermine, phenmetrazine, aminorex, and benzylpiperazine. Amphetamine type stimulants Amphetamine type stimulants (ATS) are a group of synthetic drugs that are chemical derivatives of the parent compound alpha-methylphenethylamine, also known as amphetamine. Common ATS includes amphetamine, methamphetamine, ephedrine, pseudoephedrine, MDMA, 3,4-methylenedioxymethamphetamine (MDMA), 3,4-Methylenedioxyamphetamine, 3,4-methylenedioxyamphetamine (MDA) and 3,4-methylenedioxyethylamphetamine (MDEA). ATS when used illicitly has street names including ice, meth, cry ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

Scientific Literature
Scientific literature encompasses a vast body of academic papers that spans various disciplines within the natural and social sciences. It primarily consists of academic papers that present original empirical research and theoretical contributions. These papers serve as essential sources of knowledge and are commonly referred to simply as "the literature" within specific research fields. The process of academic publishing involves disseminating research findings to a wider audience. Researchers submit their work to reputable journals or conferences, where it undergoes rigorous evaluation by experts in the field. This evaluation, known as peer review, ensures the quality, validity, and reliability of the research before it becomes part of the scientific literature. Peer-reviewed publications contribute significantly to advancing our understanding of the world and shaping future research endeavors. Original scientific research first published in scientific journals co ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

Hydroxyarenes
Phenol (also known as carbolic acid, phenolic acid, or benzenol) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile and can catch fire. The molecule consists of a phenyl group () bonded to a hydroxy group (). Mildly acidic, it requires careful handling because it can cause chemical burns. It is acutely toxic and is considered a health hazard. Phenol was first extracted from coal tar, but today is produced on a large scale (about 7 million tonnes a year) from petroleum-derived feedstocks. It is an important industrial commodity as a precursor to many materials and useful compounds, and is a liquid when manufactured. It is primarily used to synthesize plastics and related materials. Phenol and its chemical derivatives are essential for production of polycarbonates, epoxies, explosives such as picric acid, Bakelite, nylon, detergents, herbicides such as phenoxy herbicides, and numerous pharmaceutical dru ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

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]  


picture info

Cathinones
Substituted cathinones, or simply cathinones, which include some stimulants and Empathogen-entactogen, entactogens, are chemical derivative, derivatives of cathinone. They feature a substituted phenethylamine, phenethylamine core with an alkyl functional group, group attached to the alpha and beta carbon, alpha carbon, and a ketone group attached to the alpha and beta carbon, beta carbon, along with additional Substitution reaction, substitutions. Cathinone occurs naturally in the plant khat whose leaves are chewed as a recreational drug. Substituted cathinones act as monoamine releasing agents and/or monoamine reuptake inhibitors, including of norepinephrine, dopamine, and/or serotonin. In contrast to substituted amphetamines, most substituted cathinones do not act as agonists of the human trace amine-associated receptor 1 (TAAR1). This may potentiate their stimulating and drug addiction, addictive effects. In addition, β-keto-substituted phenethylamines, such as βk-2C-B, app ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


Synaptosome
A synaptosome is an isolated synaptic terminal from a neuron. Synaptosomes are obtained by mild homogenization of nervous tissue under isotonic conditions and subsequent fractionation using differential and density gradient centrifugation. Liquid shear detaches the nerve terminals from the axon and the plasma membrane surrounding the nerve terminal particle reseals. Synaptosomes are osmotically sensitive, contain numerous small clear synaptic vesicles, sometimes larger dense-core vesicles and frequently one or more small mitochondria. They carry the morphological features and most of the chemical properties of the original nerve terminal. Synaptosomes isolated from mammalian brain often retain a piece of the attached postsynaptic membrane, facing the active zone. Synaptosomes were first isolated in an attempt to identify the subcellular compartment corresponding to the fraction of so-called bound acetylcholine that remains when brain tissue is homogenized in iso-osmotic sucrose. ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

Monoamine Releasing Agent
A monoamine releasing agent (MRA), or simply monoamine releaser, is a drug that induces the release of one or more monoamine neurotransmitters from the presynaptic neuron into the synapse, leading to an increase in the extracellular concentrations of the neurotransmitters and hence enhanced signaling by those neurotransmitters. The monoamine neurotransmitters include serotonin, norepinephrine, and dopamine; MRAs can induce the release of one or more of these neurotransmitters. MRAs work by reversing the direction of the monoamine transporters (MATs), including the serotonin transporter (SERT), norepinephrine transporter (NET), and/or dopamine transporter (DAT), causing them to promote efflux of non-vesicular cytoplasmic monoamine neurotransmitter rather than reuptake of synaptic monoamine neurotransmitter. Many, but not all MRAs, also reverse the direction of the vesicular monoamine transporter 2 (VMAT2), thereby additionally resulting in efflux of vesicular monoamine neuro ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]