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Revision as of 18:33, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,071 edits Saving copy of the {{drugbox}} taken from revid 453535330 of page 5-Methyl-MDA for the Chem/Drugbox validation project (updated: 'CAS_number').  Latest revision as of 22:12, 11 January 2025 edit Arthurfragoso (talk | contribs)Extended confirmed users, Template editors4,591 edits dark mode fix 
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{{short description|Chemical compound}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Drugbox {{Drugbox
| Verifiedfields = changed
| verifiedrevid = 407465455 | verifiedrevid = 477225266
| IUPAC_name = 1-(7-methyl-1,3-benzodioxol-5-yl)propan-2-amine | IUPAC_name = 1-(7-methyl-1,3-benzodioxol-5-yl)propan-2-amine
| image = 5-Methyl-MDA.svg | image = 5-Methyl-MDA.svg
| image_class = skin-invert-image


<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename =
| pregnancy_category = | pregnancy_category =
| legal_CA = Schedule I
| legal_status = Uncontrolled <small>(but may be covered under the ] in the ] and under similar bills in other countries)</small>
| legal_DE = NpSG
| legal_UK = Class A
| legal_US = analogue
| legal_US_comment =(possibly, if human consumption intent can be proven)
| routes_of_administration = ] | routes_of_administration = ]


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| metabolism = | metabolism =
| elimination_half-life = | elimination_half-life =
| excretion = | excretion =


<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = <!-- blanked - oldvalue: 749191-14-8 --> | CAS_number = 749191-14-8
| CAS_supplemental = <br />204916-89-2 (]) | CAS_supplemental = <br />204916-89-2 (])
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 10R3PP3FVM
| ATC_prefix = none | ATC_prefix = none
| ATC_suffix = | ATC_suffix =
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<!--Chemical data--> <!--Chemical data-->
| C=11 | H=15 | N=1 | O=2 | C=11 | H=15 | N=1 | O=2
| molecular_weight = 193.242 g/mol
| smiles = O2COc1c2cc(CC(N)C)cc1C | smiles = O2COc1c2cc(CC(N)C)cc1C
| InChI = 1/C11H15NO2/c1-7-3-9(4-8(2)12)5-10-11(7)14-6-13-10/h3,5,8H,4,6,12H2,1-2H3
| InChIKey = OLENSVFSNAULML-UHFFFAOYAY
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C11H15NO2/c1-7-3-9(4-8(2)12)5-10-11(7)14-6-13-10/h3,5,8H,4,6,12H2,1-2H3 | StdInChI = 1S/C11H15NO2/c1-7-3-9(4-8(2)12)5-10-11(7)14-6-13-10/h3,5,8H,4,6,12H2,1-2H3
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| StdInChIKey = OLENSVFSNAULML-UHFFFAOYSA-N | StdInChIKey = OLENSVFSNAULML-UHFFFAOYSA-N
}} }}

'''5-Methyl-3,4-methylenedioxyamphetamine''' ('''5-Methyl-MDA''') is an ] and ] ] of the ] class. It is a ]-]ated ] of ] and a ] of ].<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 }}</ref>

==Effects and research==
{{contradict section|date=June 2016}}
{{primary sources| section|date=June 2016}}
] studies showed that 5-methyl-MDA substitutes for MDA, ], and ], but not ], suggesting that it produces a mix of entactogen and hallucinogenic effects without any ] effects.{{cn|date=May 2019}}

5-Methyl-MDA acts as a ] (SSRA) with ] values of 107nM, 11,600nM, and 1,494nM for ], ], and ] efflux.<ref name="pmid9526575" /> It is over 5 times more potent than MDA in vitro assays, with a suitable active dose possibly in vivo being around 15–25&nbsp;mg.<ref name="pmid9526575" /> Subsequent testing in vivo, however, has found that it is not as potent as once thought and is active at at least 100&nbsp;mg. ] is also much more potent than MDA, but is not quite as potent as 5-methyl-MDA.<ref name="pmid9526575" /> ] (also known as Madam-6) is mostly inactive, likely due to ].<ref name="pmid9526575" /><ref></ref>

Recent research has used data on 2-methyl-MDA and 5-methyl-MDA to help guide computer modeling of the ] complex.<ref name="pmid18354055">{{cite journal | vauthors = Walline CC, Nichols DE, Carroll FI, Barker EL | title = Comparative molecular field analysis using selectivity fields reveals residues in the third transmembrane helix of the serotonin transporter associated with substrate and antagonist recognition | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 325 | issue = 3 | pages = 791–800 |date=June 2008 | pmid = 18354055 | pmc = 2637348 | doi = 10.1124/jpet.108.136200 }}</ref>

==Legal status==
5-Methyl-MDA is not scheduled by the ]' ].<ref name="UNCPS">{{Cite web |url=https://www.unodc.org/unodc/en/commissions/CND/conventions.html |title=Convention on Psychotropic Substances, 1971 |access-date=2016-06-09 |archive-date=2022-01-19 |archive-url=https://web.archive.org/web/20220119014500/http://www.unodc.org/unodc/en/commissions/CND/conventions.html |url-status=dead }}</ref>

===United States===
5-Methyl-MDA is not ] at the ] in the ],<ref name="PART 1308 — SCHEDULES OF CONTROLLED SUBSTANCES - 1308.11 Schedule I">{{Cite web |url=http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm |title=§1308.11 Schedule I. |access-date=2016-06-09 |archive-date=2009-08-27 |archive-url=https://web.archive.org/web/20090827043725/http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm |url-status=dead }}</ref> but it is possible that 5-Methyl-MDA could legally be considered an ] of ], in which case, sales or ] could potentially be prosecuted under the ].<ref></ref>

== References ==
{{Reflist}}

{{Entactogens}}
{{Hallucinogens}}
{{Monoamine releasing agents}}
{{Serotonin receptor modulators}}
{{Phenethylamines}}

{{DEFAULTSORT:Methyl-MDA, 5-}}
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