DMMDA-2

DMMDA-2
Names

Preferred IUPAC name 1-(6,7-Dimethoxy-2H-1,3-benzodioxol-5-yl)propan-2-amine
Identifiers
CAS Number	15183-26-3^{Y[chemspider]}
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL424156^Y
ChemSpider	21106292^Y
PubChem CID	16766527
UNII	EPG4XUJ647^Y
CompTox Dashboard (EPA)	DTXSID00587947
InChI InChI=1S/C12H17NO4/c1-7(13)4-8-5-9-11(17-6-16-9)12(15-3)10(8)14-2/h5,7H,4,6,13H2,1-3H3^Y Key: UQXNREZPUUGSKM-UHFFFAOYSA-N^Y InChI=1/C12H17NO4/c1-7(13)4-8-5-9-11(17-6-16-9)12(15-3)10(8)14-2/h5,7H,4,6,13H2,1-3H3 Key: UQXNREZPUUGSKM-UHFFFAOYAC
SMILES CC(N)Cc1cc2OCOc2c(OC)c1OC
Properties
Chemical formula	C₁₂H₁₇NO₄
Molar mass	239.27 g/mol
Melting point	178 to 180 °C (352 to 356 °F; 451 to 453 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Chemical compound

DMMDA-2 is a psychedelic phenethylamine discussed by Alexander Shulgin in his book PiHKAL (Phenethylamines i Have Known And Loved); however, he was not the first to synthesize it.^[1] Shulgin comments in his book that a 50 milligram dose of DMMDA-2 produces similar effects to MDA.^[1] DMMDA-2 can be synthesized from dillapiole.^[1]

References

^ ^a ^b ^c "#59 DMMDA-2". PiHKAL: a chemical love story. Erowid. Retrieved 22 November 2011.

"#59 DMMDA-2: 2,3-Dimethoxy-4,5-methylenedioxyamphetamine". PiHKAL • info. 10 November 2009. Retrieved 20 November 2011.
Shulgin, A. T.; Sargent, T. (1967). "Psychotropic Phenylisopropylamines derived from Apiole and Dillapiole". Nature. 215 (5109): 1494–5. Bibcode:1967Natur.215.1494S. doi:10.1038/2151494b0. PMID 4861200. S2CID 26334093.

Empathogens/entactogens

Phenylalkyl-
amines
(other than
cathinones)

Unfused benzene ring: 3-CMA
4-CAB
4-FA
4-MA
4-MMA
4-FMA
4-MTA
4,4'-DMAR
Ariadne
Metaescaline
MMA
PMA
PMEA
PMMA
mMMA
Benzodioxine: EDMA
Benzodioxoles: Phenethylamine: { Lophophine }
Amphetamines: { 2-Methyl-MDA
2,3-MDA
3,4-MDA (tenamfetamine)
5-Methyl-MDA
6-Methyl-MDA
DFMDA
DMMDA
DMMDA-2
EIDA
Lys-MDA
MDEA
MDMA (midomafetamine)
MDMOH
MDOH
MMDA
MMDA-2
MMDMA
N-t-BOC-MDMA }
1-Phenylbutan-2-amines: { BDB
EBDB
MBDB }
Phentermines: { MDMP
MDPH }
Benzofurans, dihydrobenzofurans and benzothiophenes: 2-MAPB
5-APB
5-APDB
5-EAPB
5-MAPB
5-MAPDB
5-MAPBT
5-MBPB
6-APB
6-APDB
6-EAPB
6-MAPB
6-MAPDB
IBF5MAP
Indanes: 5-APDI
5-MAPDI
Indoles: 5-IT
6-API
Naphthalenes: Methamnetamine
Naphthylaminopropane
Tetralin: 6-APT

Cyclized phenyl-
alkylamines

Aminoindanes: 5-IAI
AMMI
BFAI
ETAI
MDAI
MDMAI
MMAI
MEAI
NM-2-AI
TAI
Aminotetralins: 6-CAT
MDAT
MDMAT

Cathinones

Tryptamines

Chemical classes

v t e Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine Phenpromethamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-AL 3C-BZ 3C-E 3C-MAL 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 ZDCM-04 Stimulants: 2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L-Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DiFMDA Selegiline (also D-Deprenyl)
Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH Others: Cericlamine
Cathinones	Stimulants: 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB N-Ethylhexedrone N-Ethylpentedrone Pentedrone Pentylone Radafaxine Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone
Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants: α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D-DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L-DOPA (Levodopa) L-DOPS (Droxidopa) L-Phenylalanine L-Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Solriamfetol Theodrenaline Thiamphenicol UWA-101 Venlafaxine