Ensiklopedia Dunia

From Wikipedia, the free encyclopedia

DMMDA-2
Identifiers

IUPAC name 1-(6,7-dimethoxy-2H-1,3-benzodioxol-5-yl)propan-2-amine
CAS Number	15183-26-3^{Y[chemspider]}
PubChem CID	16766527
ChemSpider	21106292^Y
UNII	EPG4XUJ647
ChEMBL	ChEMBL424156^Y
CompTox Dashboard (EPA)	DTXSID00587947
Chemical and physical data
Formula	C₁₂H₁₇NO₄
Molar mass	239.271 g·mol⁻¹
3D model (JSmol)	Interactive image
Melting point	178 to 180 °C (352 to 356 °F)
SMILES CC(N)Cc1cc2OCOc2c(OC)c1OC
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
^NY (what is this?) (verify)

DMMDA-2 is a bioactive 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]

DMMDA-2 is equivalent to 5 mescaline units. DMMDA-2's isomer DMMDA is equivalent to 12 mescaline units.^[2]

References

^ ^a ^b ^c "#59 DMMDA-2". PiHKAL: a chemical love story. Erowid. Retrieved 22 November 2011.
^ Clare, Brian W. (1990). "Structure-Activity Correlations for Psychotomimetics. 1. Phenylalkylamines: Electronic, Volume, and Hydrophobicity Parameters" (PDF). Journal of Medicinal Chemistry. 33 (7): 687–702. Retrieved 2025-01-07.

External links

No ring subs.	CYB004 (deuDMT) DALT DBT DCPT DET (T-9) DiPT DMT DPT EiPT EPT iPALT (ALiPT) MALT MET MiPT MPT NBoc-DMT NMT PALT PiPT Tryptamine (T)
4-Hydroxytryptamines	4-HO-DALT (daltocin) 4-HO-DBT 4-HO-DET (ethocin; CZ-74) 4-HO-DiPT (iprocin) 4-HO-DPT (deprocin) 4-HO-EPT 4-HO-MALT 4-HO-McPT 4-HO-MET (metocin) 4-HO-MiPT (miprocin) 4-HO-MPT (meprocin) 4-HO-NALT 4-HO-T 4-HO-TMT 4-HO-5-MeO-DMT CYB003 (deupsilocin) Psilocin (4-HO-DMT; CX-59) 4-Phosphoryloxytryptamines: Aeruginascin (4-PO-TMT) Baeocystin (4-PO-NMT) Ethocybin (4-PO-DET; CEY-19) Norbaeocystin (4-PO-T) Psilocybin (4-PO-DMT; CY-39) 4-Acetoxytryptamines: 4-AcO-DALT (daltacetin) 4-AcO-DET (ethacetin) 4-AcO-DiPT (ipracetin) 4-AcO-DMT (psilacetin) 4-AcO-DPT (depracetin) 4-AcO-MET (metocetin) 4-AcO-MiPT (mipracetin) 4-GO-DiPT (RE-104, FT-104) 4-GO-DMT (RE-109) 4-PrO-DMT
5-Hydroxytryptamines	Bufotenin (5-HO-DMT) Serotonin (5-HT; 5-HO-T) 5-Acetoxytryptamines: O-Acetylbufotenine (5-AcO-DMT) O-Pivalylbufotenine (5-(t-BuCO)-DMT)
5-Methoxytryptamines	4-HO-5-MeO-DMT 5-MeO-2,N,N-TMT 5-MeO-4,N,N-TMT 5-MeO-DALT 5-MeO-DET 5-MeO-DiPT 5-MeO-DMT (mebufotenin) 5-MeO-DPT 5-MeO-EiPT 5-MeO-MALT 5-MeO-MET 5-MeO-MiPT 5-MeO-NiPT 5-MeO-NMT ASR-3001 (5-MeO-iPALT)
Other ring subs.	2,N,N-TMT 4,N,N-TMT 5-Bromo-DMT 5-N,N-TMT 7,N,N-TMT 5-Fluoro-DMT 5-MeO-2,N,N-TMT 5-MeO-4,N,N-TMT 6-Fluoro-DMT Bretisilocin (GM-2505; 5-fluoro-MET)
α-Alkyltryptamines	4-HO-AMT 4-Methyl-AMT 5-Fluoro-AMT 6-Fluoro-AMT AMT (Indopan) α-Methylserotonin (5-HO-αMT) 5-Methoxy-α-alkyltryptamines: 5-MeO-AET 5-MeO-AMT (α,O-DMS; Alpha-O) α,N,O-TMS (5-MeO-α,N-DMT) α,N,N,O-TeMS (5-MeO-α,N,N-TMT)
Others	N-DEAOP-Ts (e.g., N-DEAOP-NET, N-DEAOP-NMT, 5-MeO-N-DEAOP-NMT, 5-MeO-N-DEAOP-NET) Structure undisclosed: CT-4201 EB-002 (EB-373) MSP-1014 MYCO-004
Cyclized	Ergolines/lysergamides (e.g., LSD) Harmala alkaloids and β-carbolines (e.g., harmine, harmaline) Iboga alkaloids (e.g., 18-MAC, 18-MC, coronaridine, ibogaine, ibogamine, ME-18-MC, noribogaine, tabernanthine, voacangine) Ibogalogs (e.g., ibogainalog) Partial ergolines (e.g., NDTDI, RU-28306, DEIMDHPCA, CT-5252) Piperidinylethylindoles (e.g., Pip-T) Pyrrolidinylethylindoles (e.g., Pyr-T, 5-MeO-pyr-T) Pyrrolidinylmethylindoles (e.g., MPMI, 4-HO-MPMI (lucigenol), 5-MeO-MPMI)
Bioisosteres	Benzofurans (e.g., 5-MeO-DiBF, dimemebfe (5-MeO-BFE), mebfap) Benzothiophenes (e.g., 3-APBT) Indazoles (e.g., AL-38022A, O-methyl-AL-34662) Indenes (e.g., C-DMT) Isotryptamines (e.g., 6-MeO-isoDMT, Ro60-0175) MYCO-005 Quinolinylethylamines (e.g., mefloquine)

Scalines	2-Bromomescaline 3-TE 3-TM 4-Desoxymescaline (DESOXY) 4-TE 4-TM Allylescaline Beta-D Cyclopropylmescaline Difluoroescaline Difluoromescaline Escaline Fluoroproscaline Isobuscaline Isoproscaline Jimscaline Mescaline (3,4,5-TMPEA) Metaescaline Methallylescaline NBOMe-escaline NBOMe-mescaline Proscaline Thioproscaline Tomscaline Trifluoroescaline Trifluoromescaline
2C-x	2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-H 2C-I 2C-iBu 2C-iP 2C-N 2C-NH2 2C-P 2C-SE 2C-tBu 2C-TFE 2C-TFM 2C-YN 2C-V 2C-T-x: 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 CYB210010 (2C-T-TFM, 2C-T-36) 2C-O-x: 2C-O 2C-O-2 2C-O-4 Others: 2C-G-x (e.g., 2C-G-3, 2C-G-5) β-Keto-2C-B (βk-2C-B) β-Keto-2C-I (βk-2C-I) β-Methyl-2C-B (BMB) BOx (e.g., BOB, BOD, BOH-2C-B) HOT-x (e.g., HOT-2, HOT-7, HOT-17) N-Ethyl-2C-B TWEETIOs (e.g., 2CD-2-ETO, 2CD-5-ETO, 2CE-5-ETO, 2CE-5iPrO, 2CT2-5-ETO, ASR-2001 (2CB-5PrO))
3C-x	3C-AL 3C-BZ 3C-DFE 3C-E 3C-MAL 3C-P TMA
DOx	DOB DOC DOEF DOET DOI DOiPR DOM DON DOPR DOTFM Aleph-x (DOT-x): Aleph (DOT) Aleph-2 Aleph-4 Aleph-6 Aleph-7 TMA-2 and derivatives (Mxx): MALM MEM MDFEM MFEM MIPM MMALM MPM MTFEM TMA-2 Others: Ganeshas (G-x) (e.g., Ganesha (G, G-1)
4C-x	4C-B 4C-C 4C-D (Ariadne) 4C-E 4C-I 4C-N 4C-P 4C-T-2
MDxx	5-Methyl-MDA 6-Methyl-MDA DMMDA DMMDA-2 EIDA IDA Lophophine (MMDPEA) Lys-MDA Lys-MDMA MDA (tenamfetamine) MDHMA MDMA (midomafetamine; ecstasy) MDOH MMDA MMDA-2 MMDA-3a MMDMA N-t-BOC-MDMA (R)-MDMA
FLY	2C-B-FLY 2C-B-BUTTERFLY 2C-B-DragonFLY 2C-B-DragonFLY-NBOH 2C-B-FLY-NB2EtO5Cl 2CB-5-hemifly 2CBFly-NBOMe Bromo-DragonFLY DOB-FLY TFMFly
25x-NB (NBOMes)	25x-NBOMe: 25B-NBOMe • 25C-NBOMe • 25CN-NBOMe • 25D-NBOMe • 25E-NBOMe • 25H-NBOMe • 25I-NBOMe • 25N-NBOMe • 25P-NBOMe • 25T2-NBOMe • 25T4-NBOMe • 25T7-NBOMe • 25TFM-NBOMe 25x-NBOH: 25B-NBOH 25C-NBOH 25CN-NBOH 25D-NBOH 25E-NBOH 25I-NBOH 25P-NBOH Others: 25B-NB (N-benzyl-2C-B) 2CBCB-NBOMe 2CBFly-NBOMe NBOMe-mescaline
Others	2-TOET 2-TOM 25B-NAcPip 4-HA 5-TOET 5-TOM Benzofurans (e.g., 5-APB, 5-APDB, 6-APB, 6-APDB, F-2, F-22) Benzothiophenes (e.g., 5-APBT, 6-APBT) DMAs (e.g., 2,4-DMA, 3,4-DMA) Fenfluramine MMA (3-MeO-4-MA) Norfenfluramine PEA-NDEPAs (e.g., 25D-NM-NDEAOP, DOB-NDEPA, DOI-NDEPA, DOM-NDEPA, DOTFM-NDEPA, M-NDEPA, TMA-2-NDEPA) PMA (4-MA) TMAs (e.g., TMA-3, TMA-4, TMA-5, TMA-6) TOMSO ZDCM-04 Structure undisclosed: CYB005
Cyclized	1-Aminomethylindanes (e.g., 2CB-Ind, jimscaline) 2-Aminoindanes (e.g., DOM-AI) 2-Aminotetralins (e.g., DOM-AT) 3-Phenylpiperidines (e.g., LPH-5, LPH-48) Benzazepines (e.g., lorcaserin) Benzocyclobutenes (e.g., 2CBCB-NBOMe, TCB-2, tomscaline) Benzoxepins (e.g., BBOX, IBOX, TFMBOX) DMBMPP (juncosamine) Ergolines/lysergamides (e.g., LSD) Glaucine IHCH-7113 Partial ergolines (e.g., NDTDI, DEIMDHPCA, DEMPDHPCA, DEMTMPDHPCA, DEMNDHPCA) Phenylcyclopropylamines (e.g., DMCPA, TMT) Phenylmorpholines (phenmetrazines) (e.g., 2C-B-morpholine) Phenyloxazolamines (aminorexes) (e.g., 2C-B-aminorex) Z3517967757 ZC-B

1-Alkyllysergamides (prodrugs): Methysergide (1-methylmethylergonovine; UML-491)
MLA-74 (1-methyl-LAE)
MLD-41 (1-methyl-LSD)
MPD-75 (1-methyl-LPD)
OML-632 (1-hydroxymethyl-LSD)

Other ring system-substituted lysergamides: 12-Hydroxy-LSD
12-Methoxy-LSD

Bioisosteres: JRT

Others

Arylpiperazines (e.g., 2C-B-PP, 2-NP, mCPP, MK-212, ORG-12962, pCPP, pFPP, quipazine, TFMPP)
Efavirenz
ORG-37684
RH-34

Natural sources

Cyclized tryptamines: Banisteriopsis caapi (yagé)
Peganum harmala (Syrian rue)
Silene undulata
Tabernanthe iboga (iboga)

Phenethylamines: Peyote (Lophophora williamsii; peyotl)
Trichocereus cacti (e.g., San Pedro, Peruvian torch)

Phenethylamines

Entactogens: Lophophine
MDPEA
MDMPEA

Amphetamines

Stimulants: 2-FA
2-FMA
3-FA
3-FMA
β-Phenylmethamphetamine
Acridorex
Alfetamine
Amfecloral
Amfepentorex
Amphetamine
- Dextroamphetamine
- Levoamphetamine
Amphetaminil
Benfluorex
Benzphetamine
Cathine
Clobenzorex
Dimethylamphetamine
Ephedrine
Ephenidine
Etafedrine
Etilamfetamine
Famprofazone
Fencamfamin
Fencamine
Fenethylline
Fenfluramine
- Dexfenfluramine
- Levofenfluramine
Fenproporex
Flucetorex
Fludorex
Formetorex
Furfenorex
Gepefrine
4-Hydroxyamphetamine
Iofetamine
Isopropylamphetamine
Lefetamine
Lisdexamfetamine
Mefenorex
Metaraminol
Methamphetamine
- Dextromethamphetamine
- Levomethamphetamine
Methoxamine
Methoxyphenamine
MMA
Morforex
Norfenfluramine
L-Norpseudoephedrine
α,N-Diethylphenylethylamine
Oxifentorex
Oxilofrine
Ortetamine
PBA
PBMA
PCA
PCMA
PFA
PFMA
PIA
PIMA
PMA
PMEA
PMMA
Phenylpropanolamine
Pholedrine
Prenylamine
Propylamphetamine
Pseudoephedrine
Sibutramine
Tiflorex
Xylopropamine
Zylofuramine

Others: 3,4-DCA
Amiflamine
Cafedrine
Deprenyl
- D-Deprenyl
- Selegiline (L-deprenyl)
DiFMDA
Thiamphenicol
UWA-101 (α-cPr-MDMA)

Phentermines

Entactogens: MDPH
MDMPH

Others: Cericlamine

Cathinones

Phenylisobutylamines
(and further-extended)

Stimulants: α-Propylphenethylamine
Hexapradol
Phenylisobutylamine (α-ethylphenethylamine)

Catecholamines
(and close relatives)

Cyclized
phenethylamines

Phenylalkylpyrrolidines	α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP Fluorolintane MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
2-Benzylpiperidines (phenidates)	2-Benzylpiperidine 3-Bromomethylphenidate 3-Chloromethylphenidate 3-Methylmethylphenidate 3,4-Dichloro-2-benzylpiperidine 3,4-Dichloroethylphenidate 3,4-Dichloromethylphenidate 4-Bromoethylphenidate 4-Bromomethylphenidate 4-Chloromethylphenidate 4-Fluoroethylphenidate 4-Fluoroisopropylphenidate 4-Fluoromethylphenidate 4-Methyl-2-benzylpiperidine 4-Methylisopropylphenidate 4-Methylmethylphenidate 4-Nitromethylphenidate α-Acetyl-2-benzylpiperidine α-Keto-2-benzylpiperidine CPMBP Desoxypipradrol (2-DPMP) Difemetorex Ethylnaphthidate (HDEP-28) Ethylphenidate Isopropylnaphthidate Isopropylphenidate MDMPH Methylnaphthidate (HDMP-28) Methylphenidate Phacetoperane Pipradrol Propylphenidate Rimiterol Ritalinamide Ritalinic acid SCH-5472 Serdexmethylphenidate
Phenylmorpholines (phenmetrazines)	(2R,3R)-Hydroxybupropion 2-(2,5-Dimethoxy-4-bromophenyl)morpholine 2-Fluorophenmetrazine 2-Methylphenmetrazine 2-Phenylmorpholine 2-Phenyl-3,6-dimethylmorpholine 3-Chlorophenmetrazine (PAL-594) 3-Fluorophenetrazine 3-Fluorophenmetrazine (PAL-593) 3-Methoxyphenmetrazine 3-Methylphenmetrazine (PAL-773) 4-Fluorophenmetrazine (PAL-748) 4-Methylphendimetrazine 4-Methylphenmetrazine (PAL-747) 2C-B-morpholine Fenbutrazate Fenmetramide Flumexadol G-130 Isophenmetrazine Manifaxine Methylenedioxyphenmetrazine Morazone N-Ethylphenmetrazol Naphthylmetrazine (PAL-704) Naphthylmorpholine (PAL-678) Oxaflozane PDM-35 PF-219,061) Phendimetrazine Phenetrazine Phenmetetrazine Phenmetrazine Phenmetrazol Pseudophenmetrazine Radafaxine ((2S,3S)-hydroxybupropion)
Phenyloxazolamines (aminorexes)	3-Methylaminorex 4-Ethylaminorex (4-EAR) 4'-Fluoroaminorex 4-Methylaminorex (4-MAR) 4,4'-Dimethylaminorex (4,4'-DMAR) 2C-B-aminorex 2F-MAR 4B-MAR 4C-MAR 4F-MAR Aminorex Clominorex Cyclazodone Ephedroxane Fenozolone Fluminorex MDMAR Methylenedioxyaminorex (MDAR) N-Methylcyclazodone N,N-Dimethylaminorex Pemoline Thozalinone
Isoquinolines and tetrahydroisoquinolines	Anhalamine Anhalidine Anhalinine Anhalonidine Calycotomine Debrisoquine Deutetrabenazine Diclofensine Esproquin Gigantine Hedycarine Lophophorine Lophotine Nomifensine Norsalsolinol Pellotine Perafensine Peyophorine Peyotine Quinisocaine Reticuline Salsoline Salsolinol Tetrabenazine Tetrahydroisoquinoline Tetrahydropapaveroline Tilisolol Tretoquinol Valbenazine Zelandopam
2-Aminoindanes	2-Aminoindane (2-AI) 5-IAI Aprindine BFAI BFMAI DHAI DOM-AI ETAI Indanorex Indantadol MDAI MDMAI MEAI (5-MeO-AI) MMAI NM-2-AI PNU-99,194 TAI
2-Aminotetralins	2-Aminotetralin (2-AT) 5-OH-DPAT 6-CAT 7-OH-DPAT 8-OH-DPAT AS-19 DOM-AT MDAT MDMAT UH-232
Others / unsorted	1-Aminomethylindanes (e.g., 2CB-Ind, AMMI, jimscaline) 2-ADN 2-Benzhydrylpyrrolidine 3-Benzhydrylmorpholine 3-Phenylpiperidines (e.g., 3-phenylpiperidine, OSU-6162 (PNU-96391), LPH-5, LPH-48) 6-AB AL-1095 Benzazepines (e.g., fenoldopam, lorcaserin, SCHEMBL5334361) Benzocyclobutenes (e.g., 2CBCB-NBOMe, S33005, TCB-2, tomscaline) Benzoxepins (e.g., BBOX, IBOX, TFMBOX) Butyltolylquinuclidine Cypenamine (trans-2-phenylcyclopentylamine) Diphenidine Diphenylprolinol DMBMPP Ergolines (e.g., LSD) GYKI-52895 HDMP-29 Ivabradine Lumateperone and analogues (e.g., IHCH-7079, IHCH-7086, IHCH-7113, ITI-1549) Methoxphenidine Methylmorphenate Milnacipran MT-45 2-Naphthylamine Org 6582 Partial ergolines (e.g., NDTDI, RU-27849, DEIMDHPCA, DEMPDHPCA, RU-27251) PF-592,379 Phenylcyclopropylamines (e.g., DMCPA, TMT, tranylcypromine) Tricyclics (e.g., benzoctamine, dizocilpine) Z3517967757 ZC-B

Related compounds

2-Furylethylamine
2-Pyrrolylethylamine
3-Pyrrolylethylamine
3-Pyrrolylpropylamine
2-Tetrahydrofurylethylamine
4-Benzylpiperidine
7-AB
Alkylamines (e.g., 1,3-DMBATooltip 1,3-dimethylbutylamine, 1,4-DMAATooltip 1,4-dimethylamylamine, heptaminol, iproheptine, isometheptene, methylhexanamine/1,3-DMAA, octodrine, oenethyl, tuaminoheptane)
Benzylamines (e.g., benzylamine, α-methylbenzylamine, MDM1EA, ALPHA, M-ALPHA, pargyline)
Benzylpiperazines (e.g., benzylpiperazine, MDBZP, fipexide)
Cyclohexylaminopropanes (e.g., propylhexedrine, norpropylhexedrine)
Cyclopentylaminopropanes (e.g., isocyclamine, cyclopentamine)
Phenylalkenylamines (e.g., phenylbutenamine)
Phenylalkynylamines (e.g., phenylbutynamine)
Phenylpiperazines (e.g., 1-phenylpiperazine, mCPPTooltip meta-chlorophenylpiperazine, TFMPPTooltip trifluoromethylphenylpiperazine, oMPPTooltip ortho-methylphenylpiperazine, pFPPTooltip para-fluorophenylpiperazine, pMeOPPTooltip para-methoxyphenylpiperazine)
Phenylpropylamines (e.g., phenylpropylamine, homo-MDA, homo-MDMA)
Thienylaminopropanes (thiopropamines) (e.g., thiopropamine, methiopropamine, thiothinone)

Categories:

Hidden categories:

See also

References

External links