Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and MDMAI: Difference between pages
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Saving copy of the {{drugbox}} taken from revid 448233630 of page 5,6-Methylenedioxy-N-methyl-2-aminoindane for the Chem/Drugbox validation project (updated: 'CAS_number'). |
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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:5,6-Methylenedioxy-N-methyl-2-aminoindane|oldid=448233630}} 448233630] of page [[5,6-Methylenedioxy-N-methyl-2-aminoindane]] with values updated to verified values.}} |
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{{one source|date=October 2014}} |
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{{Drugbox |
{{Drugbox |
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| Verifiedfields = changed |
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| verifiedrevid = |
| verifiedrevid = 477223870 |
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| IUPAC_name = ''N''-methyl-6,7-dihydro-5''H''-cyclopenta[''f''][1,3]benzodioxol-6-amine |
| IUPAC_name = ''N''-methyl-6,7-dihydro-5''H''-cyclopenta[''f''][1,3]benzodioxol-6-amine |
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| image = MDMAI.svg |
| image = MDMAI.svg |
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| alt = Structural formula of MDMAI |
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| image2 = MDMAI 3D ball.png |
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| alt2 = Ball-and-stick model of the MDMAI molecule |
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| width2 = 250 |
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| drug_name = 5,6-Methylenedioxy-''N''-methyl-2-aminoindane |
| drug_name = 5,6-Methylenedioxy-''N''-methyl-2-aminoindane |
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| tradename = |
| tradename = |
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| pregnancy_category = |
| pregnancy_category = |
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| legal_DE = NpSG |
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| ⚫ | |||
| legal_UK = PSA |
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| ⚫ | |||
| routes_of_administration = Oral |
| routes_of_administration = 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_Ref = {{cascite|changed|??}} |
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| CAS_number = |
| CAS_number = 132741-82-3 |
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| ATC_prefix = none |
| ATC_prefix = none |
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| ATC_suffix = |
| ATC_suffix = |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 111695 |
| ChemSpiderID = 111695 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 5N88M9ZTD8 |
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<!--Chemical data--> |
<!--Chemical data--> |
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| C=11 | H=13 | N=1 | O=2 |
| C=11 | H=13 | N=1 | O=2 |
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| molecular_weight = 191.226 g/mol |
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| smiles = C3c2cc1OCOc1cc2CC3NC |
| smiles = C3c2cc1OCOc1cc2CC3NC |
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| InChI = 1/C11H13NO2/c1-12-9-2-7-4-10-11(14-6-13-10)5-8(7)3-9/h4-5,9,12H,2-3,6H2,1H3 |
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| InChIKey = KNZKMFXEUONVMF-UHFFFAOYAU |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C11H13NO2/c1-12-9-2-7-4-10-11(14-6-13-10)5-8(7)3-9/h4-5,9,12H,2-3,6H2,1H3 |
| StdInChI = 1S/C11H13NO2/c1-12-9-2-7-4-10-11(14-6-13-10)5-8(7)3-9/h4-5,9,12H,2-3,6H2,1H3 |
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| StdInChIKey = KNZKMFXEUONVMF-UHFFFAOYSA-N |
| StdInChIKey = KNZKMFXEUONVMF-UHFFFAOYSA-N |
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}} |
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'''5,6-Methylenedioxy-''N''-methyl-2-aminoindane''' ('''MDMAI'''), is a [[drug]] developed in the 1990s by a team led by [[David E. Nichols]] at [[Purdue University]]. It acts as a non-[[neurotoxic]] and highly [[binding selectivity|selective]] [[selective serotonin releasing agent|serotonin releasing agent]] (SSRA) in animals and a putative [[empathogen-entactogen|entactogen]] in humans.<ref name="pmid1979813">{{cite journal | vauthors = Oberlender R, Nichols DE | title = (+)-N-methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine as a discriminative stimulus in studies of 3,4-methylenedioxy-methamphetamine-like behavioral activity| journal = J Pharmacol Exp Ther | volume = 255 | issue = 3 | pages = 1098–1106 | year = 1990 | pmid = 1979813 }}</ref> |
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== Chemistry == |
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MDMAI can be thought of as a cyclised [[analog (chemistry)|analogue]] of [[MDMA]] where the alpha-methyl carbon of the alkylamino side chain has been joined back round to the 6-position of the aromatic ring to form an [[indane]] ring system. This changes the core structure of the molecule from [[phenethylamine]] to [[aminoindane]], and causes the pharmacological properties of the two compounds to be substantially different.<ref name="pmid1979813" /> |
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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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{{DEFAULTSORT:Methylenedioxy-N-methyl-2-aminoindane, 5,6-}} |
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[[Category:Entactogens and empathogens]] |
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[[Category:Designer drugs]] |
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[[Category:Benzodioxoles]] |
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[[Category:Serotonin releasing agents]] |
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