Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 6-Methyl-MDA: Difference between pages
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Saving copy of the {{drugbox}} taken from revid 453538705 of page 6-Methyl-MDA for the Chem/Drugbox validation project (updated: ''). |
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{{short description|Chemical compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid [{{fullurl:6-Methyl-MDA|oldid=453538705}} 453538705] of page [[6-Methyl-MDA]] with values updated to verified values.}} |
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{{Drugbox |
{{Drugbox |
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| verifiedrevid = |
| verifiedrevid = 477226006 |
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| IUPAC_name = 1-(6- |
| IUPAC_name = 1-(6-Methyl-1,3-benzodioxol-5-yl)propan-2-amine |
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| image = 6-Methyl-MDA.png |
| image = 6-Methyl-MDA.png |
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| tradename = |
| tradename = |
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| pregnancy_category = |
| pregnancy_category = |
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| legal_status = Uncontrolled <small>(but may be covered under the [[Federal Analogue Act]] in the [[United States]] and under similar |
| legal_status = Uncontrolled <small>(but may be covered under the [[Federal Analogue Act]] in the [[United States]] and under similar laws in other countries)</small> |
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| routes_of_administration = [[Mouth|Oral]] |
| routes_of_administration = [[Mouth|Oral]] |
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| metabolism = |
| metabolism = |
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| elimination_half-life = |
| elimination_half-life = |
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| excretion = |
| excretion = |
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<!--Identifiers--> |
<!--Identifiers--> |
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| CAS_number = |
| CAS_number = 246861-21-2 |
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| ATC_prefix = none |
| ATC_prefix = none |
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| ATC_suffix = |
| ATC_suffix = |
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<!--Chemical data--> |
<!--Chemical data--> |
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| C=11 | N=1 | O=2 |
| C=11 | H=15 | N=1 | O=2 |
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| molecular_weight = 193.24 g/mol |
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| smiles = O1c2cc(c(cc2OC1)CC(N)C)C |
| smiles = O1c2cc(c(cc2OC1)CC(N)C)C |
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| InChI = 1/C11H15NO2/c1-7-3-10-11(14-6-13-10)5-9(7)4-8(2)12/h3,5,8H,4,6,12H2,1-2H3 |
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| InChIKey = HCFHWXDIZOAUTQ-UHFFFAOYAQ |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C11H15NO2/c1-7-3-10-11(14-6-13-10)5-9(7)4-8(2)12/h3,5,8H,4,6,12H2,1-2H3 |
| StdInChI = 1S/C11H15NO2/c1-7-3-10-11(14-6-13-10)5-9(7)4-8(2)12/h3,5,8H,4,6,12H2,1-2H3 |
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| StdInChIKey = HCFHWXDIZOAUTQ-UHFFFAOYSA-N |
| StdInChIKey = HCFHWXDIZOAUTQ-UHFFFAOYSA-N |
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}} |
}} |
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'''6-Methyl-3,4-methylenedioxyamphetamine''' ('''6-Methyl-MDA''') is an [[entactogen]] and [[psychedelic drug|psychedelic]] [[drug]] of the [[substituted amphetamine|amphetamine]] class.<ref name="pmid9526575">{{cite journal | vauthors = Parker MA, Marona-Lewicka D, Kurrasch D, Shulgin AT, Nichols DE | title = Synthesis and pharmacological evaluation of ring-methylated derivatives of 3,4-(methylenedioxy)amphetamine (MDA) | journal = Journal of Medicinal Chemistry | volume = 41 | issue = 6 | pages = 1001–5 |date=March 1998 | pmid = 9526575 | doi = 10.1021/jm9705925 | citeseerx = 10.1.1.688.9559 }}</ref> It was first [[chemical synthesis|synthesized]] in the late 1990s by a team including [[David E. Nichols]] at [[Purdue University]] while investigating [[chemical derivative|derivative]]s of [[3,4-Methylenedioxyamphetamine|3,4-methylenedioxyamphetamine]] (MDA) and [[MDMA|3,4-methylenedioxy-''N''-methylamphetamine]] (MDMA).<ref name="pmid9526575"/> |
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6-Methyl-MDA has [[IC50|IC<sub>50</sub>]] values of 783 nM, 28,300 nM, and 4,602 nM for [[reuptake inhibitor|inhibiting]] the [[reuptake]] of [[serotonin]], [[dopamine]], and [[norepinephrine]] in rat [[synaptosome]]s.<ref name="pmid9526575"/> In animal studies it substitutes for [[MBDB]], [[MMAI]], [[lysergic acid diethylamide|LSD]], and [[2,5-Dimethoxy-4-iodoamphetamine|2,5-dimethoxy-4-iodoamphetamine]] (DOI), though not [[amphetamine]], but only partially and at high doses.<ref name="pmid9526575"/> Thus, while several-fold less [[potency (pharmacology)|potent]] than its [[structural analog|analogue]]s [[2-methyl-MDA]] and [[5-methyl-MDA]], and approximately half as potent as MDA, 6-methyl-MDA is still significantly [[activity (chemistry)|active]],<ref name="pmid9526575"/> and appropriate doses may be similar to or somewhat higher than those of MDMA.{{citation needed|date=April 2010}} |
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== References == |
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{{Reflist}} |
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{{Entactogens}} |
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{{Monoamine releasing agents}} |
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{{Phenethylamines}} |
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{{DEFAULTSORT:Methyl-MDA, 6-}} |
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[[Category:Substituted amphetamines]] |
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[[Category:Benzodioxoles]] |
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[[Category:Entactogens and empathogens]] |
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[[Category:Serotonin-norepinephrine releasing agents]] |
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[[Category:Substances discovered in the 1990s]] |
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