DMMDA-2

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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

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 3,4-methylenedioxy-1-α-methylphenylethylamine.^[1] DMMDA-2 can be synthesized from dillapiole.^[1]

See also
References
Further reading

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

References

1 2 3 "#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.

"#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.

Phenethylamines

Entactogens: Lophophine
MDPEA
MDMPEA

Amphetamines

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) Bicyclo(4.2.0)octa-1,3,5-trienes (e.g., 2CBCB-NBOMe, S33005, TCB-2, tomscaline) 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-DMBA Tooltip 1,3-dimethylbutylamine, 1,4-DMAA Tooltip 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, mCPP Tooltip meta-chlorophenylpiperazine, TFMPP Tooltip trifluoromethylphenylpiperazine, oMPP Tooltip ortho-methylphenylpiperazine, pFPP Tooltip para-fluorophenylpiperazine, pMeOPP Tooltip para-methoxyphenylpiperazine)
Phenylpropylamines (e.g., phenylpropylamine, homo-MDA, homo-MDMA)
Thienylaminopropanes (thiopropamines) (e.g., thiopropamine, methiopropamine, thiothinone)

See also: Tryptamines
Ergolines and lysergamides

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DMMDA-2

Contents

See also

References

Further reading