Methylenedioxydimethylamphetamine

Methylenedioxydimethylamphetamine
IUPAC name

(2-Benzo[1,3]dioxol-5-yl-1-methyl-ethyl)-dimethyl-amine
Other names

3,4-Methylenedioxy-N,N-dimethylamphetamine
3,4-Methylenedioxy-(alpha,N,N-trimethyl)-1-ethane
Identifiers
CAS number 74698-50-3
Jmol-3D images Image 1
Properties
Molecular formula C12H17NO2
Molar mass 207.27 g/mol
Melting point

172-173 °C
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

3,4-Methylenedioxy-N,N-dimethylamphetamine (MDDM) is a lesser-known psychedelic drug. It is also the N,N-dimethyl analogue of MDA. MDDM was first synthesized by Alexander Shulgin. In his book PiHKAL (Phenethylamines i Have Known And Loved), 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 MDMA which has been synthesized by methylation of MDA using methylating reagents such as methyl iodide, 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.

See also

External links

Phenethylamines
Psychedelics: 2C-B • 2C-B-FLY • 2C-C • 2C-D • 2C-E • 2C-F • 2C-G • 2C-I • 2C-N • 2C-P • 2C-SE • 2C-T • 2C-T-2 • 2C-T-4 • 2C-T-7 • 2C-T-8 • 2C-T-9 • 2C-T-13 • 2C-T-15 • 2C-T-17 • 2C-T-21 • 2C-TFM • 2C-YN • Allylescaline • DESOXY • Escaline • Isoproscaline • Jimscaline • Macromerine • MEPEA • Mescaline • Metaescaline • Methallylescaline • Proscaline • Psi-2C-T-4 • TCB-2
Stimulants: 2-OH-PEA • β-Me-PEA • Hordenine • N-Me-PEA • Phenethylamine (PEA)
Entactogens: Lophophine • MDPEA • MDMPEA
Others: BOH • DMPEA
Amphetamines
Phenylisopropylamines
Psychedelics: 3C-BZ • 3C-E • 3C-P • Aleph • Beatrice • Bromo-DragonFLY • D-Deprenyl • DMA • DMCPA • DMMDA • DOB • DOC • DOEF • DOET • DOI • DOM • DON • DOPR • DOTFM • Ganesha • MMDA • MMDA-2 • Psi-DOM • TMA • TeMA
Stimulants: 4-MA • 4-MMA • 4-MTA • 5-IT • Alfetamine • Amfecloral • Amfepentorex • Amphetamine (Dextroamphetamine, Levoamphetamine) • Amphetaminil • Benfluorex • Benzphetamine • Cathine • Clobenzorex • Dimethylamphetamine • Ephedrine (EPH) • Ethylamphetamine • Fencamfamine • Fencamine • Fenethylline • Fenfluramine (Dexfenfluramine) • Fenproporex • Fludorex • Furfenorex • Isopropylamphetamine • Lefetamine • Mefenorex • Methamphetamine (Dextromethamphetamine, Levomethamphetamine) • Methoxyphenamine • MMA • Norfenfluramine • Oxilofrine • Ortetamine • PBA • PCA • Phenpromethamine • PFA • PFMA • PIA • PMA • PMEA • PMMA • Phenylpropanolamine (PPA) • Prenylamine • Propylamphetamine • Pseudoephedrine (PSE) • Sibutramine • Tiflorex (Flutiorex) • Tranylcypromine • Xylopropamine • Zylofuramine
Entactogens: 5-APDB • 6-APB • 6-APDB • EDA • IAP • MDA • MDEA • MDHMA (FLEA) • MDMA ("Ecstasy") • MDOH • MMDMA • NAP • TAP
Others: Amiflamine • DFMDA • D-Deprenyl • L-Deprenyl (Selegiline)
Phentermines
Stimulants: Chlorphentermine • Cloforex • Clortermine • Etolorex • Mephentermine • Pentorex (Phenpentermine) • Phentermine
Entactogens: MDPH • MDMPH
Cathinones
Stimulants: Amfepramone • Brephedrone • Buphedrone • Bupropion (Amfebutamone) • Cathinone (Propion) • Dimethylcathinone (Dimethylpropion, Metamfepramone) • Ethcathinone (Ethylpropion) • Flephedrone • Methcathinone (Methylpropion) • Mephedrone • Methedrone
Entactogens: Ethylone • Methylone
Phenylisobutylamines
Entactogens: 4-CAB • 4-MAB • Ariadne (α-Et-DOM) • BDB (J) • Butylone (bk-MBDB) • EBDB (Ethyl-J) • Eutylone (bk-EBDB) • MBDB (Methyl-J)
Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines
Stimulants: α-PBP • α-PPP • α-PVP • MDPBP • MDPPP • MDPV • MOPPP • MPBP • MPHP • MPPP • Naphyrone • PEP • Prolintane • Pyrovalerone
Catecholamines
(and relatives..)
6-FNE • 6-OHDA • α-Me-DA • α-Me-TRA • Adrenochrome • Ciladopa • D-DOPA (Dextrodopa) • Dopamine • Epinephrine (Adrenaline) • Epinine • Fenclonine • Ibopamine • L-DOPA (Levodopa) • L-DOPS (Droxidopa) • L-Phenylalanine • L-Tyrosine • meta-Octopamine • meta-Tyramine • Metanephrine • Metirosine • Methyldopa • Nordefrin (Levonordefrin) • Norepinephrine (Noradrenaline) • Normetanephrine • para-Octopamine • para-Tyramine
Miscellaneous
Drugs from PiHKAL

AEM • AL • Aleph • Aleph-2 • Aleph-4 • Aleph-6 • Aleph-7 • Ariadne • Asymbescaline • Buscaline • Beatrice • Bis-TOM • BOB • BOD • BOH • BOHD • BOM • 4-Bromo-3,5-dimethoxyamphetamine • 2-Bromo-4,5-methylenedioxyamphetamine • 2C-B • 3C-BZ • 2C-C • 2C-D • 2C-E • 3C-E • 2C-F • 2C-G • 2C-G-3 • 2C-G-4 • 2C-G-5 • 2C-G-N • 2C-H • 2C-I • 2C-N • 2C-O • 2C-O-4 • 2C-P • CPM • 2C-SE • 2C-T • 2C-T-2 • 2C-T-4 • psi-2C-T-4 • 2C-T-7 • 2C-T-8 • 2C-T-9 • 2C-T-13 • 2C-T-15 • 2C-T-17 • 2C-T-21 • 4-D • beta-D • DESOXY • 2,4-DMA • 2,5-DMA • 3,4-DMA • DMCPA • DME • DMMDA • DMMDA-2 • DMPEA • DOAM • DOB • DOBU • DOC • DOEF • DOET • DOI • DOM • psi-DOM • DON • DOPR • Escaline • EEE • EEM • EME • EMM • Ethyl-J (EBDB) • Ethyl-K • F-2 • F-22 • Flea • G-3 • G-4 • G-5 • G-N • Ganesha • HOT-2 • HOT-7 • HOT-17 • IDNNA • Isomescaline • Isoproscaline • Iris • J (BDB) • Lophophine • PMA • Mescaline • Madam-6 • Methallylescaline • MDA • MDAL • MDBU • MDBZ • MDCPM • MDDM • MDE • MDHOET • MDIP • MDMA • MDMC (EDMA) • MDMEO • MDMEOET • MDMP • MDOH • MDPEA • MDPH • MDPL • MDPR • Metaescaline • MEDA • MEE • MEM • MEPEA • Meta-DOB • Meta-DOT • Methyl-DMA • Methyl-DOB • Methyl-J (MBDB) • Methyl-K • Methyl-MA (PMMA) • Methyl-MMDA-2 • MMDA • MMDA-2 • MMDA-3a • MMDA-3b • MME • Metaproscaline • MPM • Ortho-DOT • Proscaline • Phenescaline • Phenethylamine • Propynyl • Symbescaline • 2,3,4,5-Tetramethoxyamphetamine • 3-TASB • 4-TASB • 5-TASB • Thiobuscaline • 3-TE • 4-TE • 3-TIM • 4-TIM • 5-TIM • 3-TM • 4-TM • TMA • TMA-2 • TMA-3 • TMA-4 • TMA-5 • TMA-6 • 3-TME • 4-TME • 5-TME • 2T-MMDA-3a • 4T-MMDA-2 • 2-TOET • 5-TOET • 2-TOM • 5-TOM • TOMSO • Thioproscaline • Trisescaline • 3-TSB • 4-TSB • 3-T-Trisescaline • 4-T-Trisescaline