Methylenedioxymethylamphetamine
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Methylenedioxymethylamphetamine
3,4-Methylenedioxymethamphetamine (MDMA), commonly known as ecstasy (tablet form), and molly (crystal form), is an empathogen–entactogenic drug with stimulant and minor psychedelic properties. In studies, it has been used alongside psychotherapy in the treatment of post-traumatic stress disorder (PTSD) and social anxiety in autism spectrum disorder. The purported pharmacological effects that may be prosocial include altered sensations, increased energy, empathy, and pleasure. When taken by mouth, effects begin in 30 to 45 minutes and last three to six hours. MDMA was first synthesized in 1912 by Merck chemist Anton Köllisch. It was used to enhance psychotherapy beginning in the 1970s and became popular as a street drug in the 1980s. MDMA is commonly associated with dance parties, raves, and electronic dance music. Tablets sold as ecstasy may be mixed with other substances such as ephedrine, amphetamine, and methamphetamine. In 2016, about 21 million people between t ...
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United States National Library Of Medicine
The United States National Library of Medicine (NLM), operated by the United States federal government, is the world's largest medical library. Located in Bethesda, Maryland, the NLM is an institute within the National Institutes of Health. Its collections include more than seven million books, journals, technical reports, manuscripts, microfilms, photographs, and images on medicine and related sciences, including some of the world's oldest and rarest works. the acting director of the NLM was Stephen Sherry. History The precursor of the National Library of Medicine, established in 1836, was the Library of the Surgeon General's Office, a part of the office of the Surgeon General of the United States Army. The Armed Forces Institute of Pathology and its Medical Museum were founded in 1862 as the Army Medical Museum. Throughout their history the Library of the Surgeon General's Office and the Army Medical Museum often shared quarters. From 1866 to 1887, they were ho ...
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Oral Administration
Oral administration is a route of administration whereby a substance is taken through the Human mouth, mouth, swallowed, and then processed via the digestive system. This is a common route of administration for many medications. Oral administration can be easier and less painful than other routes of administration, such as Injection (medicine), injection. However, the onset of action is relatively low, and the effectiveness is reduced if it is not absorbed properly in the digestive system, or if it is broken down by digestive enzymes before it can reach the bloodstream. Some medications may cause gastrointestinal side effects, such as nausea or vomiting, when taken orally. Oral administration can also only be applied to conscious patients, and patients able to swallow. Terminology ''Per os'' (; ''P.O.'') is an adverbial phrase meaning literally from Latin "through the mouth" or "by mouth". The expression is used in medicine to describe a treatment that is taken orally (but not ...
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(R)-MDMA
(''R'')-3,4-Methylenedioxy-''N''-methylamphetamine ((''R'')-MDMA), also known as (''R'')-midomafetamine or as ''levo''-MDMA, is the (''R'')- or levorotatory (''l''-) enantiomer of MDMA, 3,4-methylenedioxy-''N''-methylamphetamine (MDMA; midomafetamine; "ecstasy"), a racemic mixture of (''R'')-MDMA and (''S'')-MDMA. Like MDMA, (''R'')-MDMA is an entactogen or empathogen. It is taken oral administration, by mouth. The drug is a serotonin–norepinephrine releasing agent (SNRA) and weak serotonin 5-HT2A receptor, 5-HT2A receptor agonist. It has substantially less or no significant dopamine releasing agent, dopamine-releasing activity compared to MDMA and (''S'')-MDMA. In preclinical research, preclinial studies, (''R'')-MDMA shows equivalent therapeutic-like effects to MDMA, such as increased prosocial behavior, but shows reduced psychostimulant-like effects, addictive potential, and serotonergic neurotoxin, serotonergic neurotoxicity. In clinical study, clinical studies, (''R'')-MD ...
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Methylenedioxyhydroxyamphetamine
3,4-Methylenedioxy-''N''-hydroxyamphetamine (MDOH, MDH, N-hydroxytenamphetamine) is an entactogen, psychedelic, and stimulant of the phenethylamine and amphetamine chemical classes. It is the ''N''- hydroxy homologue of MDA, and the ''N''- desmethyl homologue of MDHMA. MDOH was first synthesized and assayed by Alexander Shulgin. In his book ''PiHKAL'' (''Phenethylamines i Have Known And Loved''), Shulgin listed the dosage range as 100–160 mg, and the duration as approximately 3–6 hours. He describes MDOH as being very psychedelic and producing increased pleasure in beauty and nature. He also mentioned several negative side effects also seen with MDMA 3,4-Methylenedioxymethamphetamine (MDMA), commonly known as ecstasy (tablet form), and molly (crystal form), is an empathogen–entactogenic drug with stimulant and minor Psychedelic drug, psychedelic properties. In studies, it has been used ... ("Ecstasy") such as difficulty urinating and internal dryness. Ref ...
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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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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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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 ...
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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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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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