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Revision as of 17:38, 19 April 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (← Previous edit Latest revision as of 07:24, 11 December 2024 edit undoAlyInWikiWonderland (talk | contribs)Autopatrolled, Extended confirmed users81,809 edits Synonyms. 
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{{redirect|MDDM|the opioid known as 6-MDDM|6-Methylenedihydrodesoxymorphine}}
{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 379478064
| Watchedfields = changed
⚫ | verifiedrevid = 424887836
| ImageFile1 = MDDM.png | ImageFile1 = MDDM.png
| Name=Methylenedioxydimethyl{{shy}}amphetamine
| ImageSize1 = 200px | ImageSize1 =
| ImageFile2 = | ImageFile2 =
| ImageSize2 = 200px | ImageSize2 =
| IUPACName = (2-Benzodioxol-5-yl-1-methyl-ethyl)-dimethyl-amine | PIN = 1-(2''H''-1,3-Benzodioxol-5-yl)-''N'',''N''-dimethylpropan-2-amine
| OtherNames = 3,4-Methylenedioxy-N,N-dimethylamphetamine<br>3,4-Methylenedioxy-(alpha,N,N-trimethyl)-1-ethane | OtherNames = 3,4-Methylenedioxy-''N'',''N''-dimethylamphetamine<br />3,4-Methylenedioxy-(α,''N'',''N''-trimethyl)-1-ethane; MDDM; MDDMA
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 74698-50-3 | CASNo = 74698-50-3
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | PubChem =
| UNII = L6K8DR1S8O
| SMILES = C1=C2C(=CC=C1CC(C)N(C)C)OCO2
⚫ | PubChem = 551630
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 479880
| SMILES = CC(Cc1ccc2c(c1)OCO2)N(C)C
| InChI = 1/C12H17NO2/c1-9(13(2)3)6-10-4-5-11-12(7-10)15-8-14-11/h4-5,7,9H,6,8H2,1-3H3
| InChIKey = JEJGUIDNYBAPGN-UHFFFAOYAU
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C12H17NO2/c1-9(13(2)3)6-10-4-5-11-12(7-10)15-8-14-11/h4-5,7,9H,6,8H2,1-3H3
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = JEJGUIDNYBAPGN-UHFFFAOYSA-N

}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>12</sub>H<sub>17</sub>NO<sub>2</sub> | Formula = C<sub>12</sub>H<sub>17</sub>NO<sub>2</sub>
| MolarMass = 207.27 g/mol | MolarMass = 207.27 g/mol
| Appearance = | Appearance =
| Density = | Density =
| MeltingPt = 172-173 °C | MeltingPtC = 172 to 173
| MeltingPt_notes =
| BoilingPt = | BoilingPt =
| Solubility = }} | Solubility = }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = }} | AutoignitionPt =
}}
}} }}


'''3,4-]-''N'',''N''-di]]''' ('''MDDM''') is a lesser-known ]. It is also the ]-dimethyl analogue of ]. MDDM was first synthesized by ]. In his book '']'', the dosage is unspecified, and the duration unknown. MDDM produces only mild effects that are not well characterised in PiHKAL. Very little data exists about the pharmacological properties, metabolism, and toxicity of MDDM. This compound is however occasionally encountered as an impurity in ] which has been synthesized by methylation of ] using methylating reagents such as ], as an excess of reagent or too high a reaction temperature results in some double methylation of the amine nitrogen, yielding MDDM as well as MDMA. Presence of MDDM as an impurity can thus reveal which synthetic route was used to manufacture seized samples of MDMA. MDDM is also known as MDMMA, or as "sass" on the streets. This is in reference to the sassafrass plant from which MDDM can be derived. '''3,4-Methylenedioxy-''N'',''N''-dimethylamphetamine''' ('''MDDM''', '''MDDMA''') is a lesser-known ]. It is also the ''N'',''N''-dimethyl analog of ] (MDA). MDDM was first synthesized by ]. In his book '']'', the dosage is unspecified and the duration unknown. MDDM produces only mild effects that are not well characterized in ''PiHKAL''. Very little data exists about the pharmacological properties, metabolism, and toxicity of MDDM. This compound is however occasionally encountered as an impurity in ] (MDMA) which has been synthesized by methylation of MDA using methylating reagents such as ]. An excess of reagent or a reaction temperature that is too high results in some double methylation of the amine nitrogen, yielding MDDM as well as MDMA. The presence of MDDM as an impurity can thus reveal which synthetic route was used to manufacture seized samples of MDMA.<ref>Casteele SR, Bouche MP, Van Bocxlaer JF. LC-MS/MS in the elucidation of an isomer of the recreational drug methylenedioxy ethylamphetamine: methylenedioxy dimethylamphetamine. ''J Sep Sci''. 2005 Sep;28(14):1729-34. {{doi|10.1002/jssc.200500108}} {{PMID|16224967}}</ref><ref>De Letter EA, Lambert WE, Bouche MP, Cordonnier JA, Van Bocxlaer JF, Piette MH. Postmortem distribution of 3,4-methylenedioxy-N,N-dimethyl-amphetamine (MDDM or MDDA) in a fatal MDMA overdose. ''Int J Legal Med''. 2007 Jul;121(4):303-7. {{doi|10.1007/s00414-006-0094-x}} {{PMID|16636864}}</ref><ref>Awad T, Belal T, Maher HM, DeRuiter J, Clark CR. GC-MS studies on side chain regioisomers related to substituted methylenedioxyphenethylamines: MDEA, MDMMA, and MBDB. ''J Chromatogr Sci''. 2010 Oct;48(9):726-32. {{doi|10.1093/chromsci/48.9.726}} {{PMID|20875234}}</ref>


== See also == ==Legality==


===United Kingdom===
This substance is a Class A drug in the ].<ref>{{cite web | title = UK Misuse of Drugs act 2001 Amendment summary | url = http://isomerdesign.com/Cdsa/scheduleUK.php?schedule=1&ion=30&structure=C | accessdate = 12 March 2014 | publisher = Isomer Design | archive-date = 22 October 2017 | archive-url = https://web.archive.org/web/20171022085110/http://isomerdesign.com/Cdsa/scheduleUK.php?schedule=1&ion=30&structure=C | url-status = dead }}</ref>

== See also ==
* ] * ]
* ]
* ]
* ] * ]
* ]

==References==
{{Reflist}}


== External links == == External links ==
* *
*


{{Methylenedioxyphenethylamines}} {{Methylenedioxyphenethylamines}}
{{PiHKAL}}


] ]
] ]