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Substituted methylenedioxyphenethylamine

Class of psychoactive drugs

The substituted methylenedioxyphenethylamines (abbreviated as MDxx) represent a diverse chemical class of compounds derived from phenethylamines. This category encompasses numerous psychoactive substances with entactogenic, psychedelic, and/or stimulant properties, in addition to entheogens. These compounds find application as research chemicals, designer drugs, and recreational drugs.

The base compound of the MDxx class is 3,4-methylenedioxyphenethylamine (MDPEA), and the prototypical agent of this class is 3,4-methylenedioxy-N-methylamphetamine (MDMA; "ecstasy"). Other notable MDxx class substances include 3,4-methylenedioxyamphetamine (MDA), 3,4-methylenedioxy-N-ethylamphetamine (MDEA; "Eve"), N-methyl-1,3-benzodioxolylbutanamine (MBDB; "Eden"), and 3,4-methylenedioxy-N-methylcathinone (βk-MDMA; "Methylone"). There are also cyclized phenethylamine MDxx compounds, such as MDAI, MDAT, MDPV, MDPM, and MDMAR.

Use and effects

Compound	Chemical name	Dose	Duration
MDPEA	3,4-Methylenedioxyphenethylamine	300 mg	Unknown
Lophophine (MMDPEA; 2C-MMDA)	3-Methoxy-4,5-methylenedioxyphenethylamine	≥150–250 mg	Unknown
2C-MMDA-2 (2C-2; MMDPEA-2)	2-Methoxy-4,5-methylenedioxyphenethylamine	2.6 mg	Unknown
2C-MMDA-3a (2C-3a; MMDPEA-3a)	2-Methoxy-3,4-methylenedioxyphenethylamine	≥40–120 mg	Unknown
2C-MMDA-3b (2C-3b; MMDPEA-3b)	4-Methoxy-2,3-methylenedioxyphenethylamine	Unknown	Unknown
2C-MMDA-4 (MMDPEA-4)	5-Methoxy-2,3-methylenedioxyphenethylamine	Unknown	Unknown
MDMPEA	3,4-Methylenedioxy-N-methylphenethylamine	30 mg	Unknown
MDPEA-NBOMe	N-(2-Methoxybenzyl)-3,4-methylenedioxyphenethylamine	Unknown	Unknown
Lophophine-NBOMe	N-(2-Methoxybenzyl)-3-methoxy-4,5-methylenedioxyphenethylamine	Unknown	Unknown
2C2-NBOMe	N-(2-Methoxybenzyl)-2-methoxy-4,5-methylenedioxyphenethylamine	Unknown	Unknown
BOH (β-methoxy-MDPEA)	3,4-Methylenedioxy-β-methoxyphenethylamine	80–120 mg	6–8 hours
MDA	3,4-Methylenedioxyamphetamine	80–160 mg (20–200 mg+)	4–8 hours
(S)-MDA	(S)-3,4-Methylenedioxyamphetamine	160–225 mg	3 hours
(R)-MDA	(R)-3,4-Methylenedioxyamphetamine	70–200 mg	4–8 hours
ORTHO-MDA (2,3-MDA)	2,3-Methylenedioxyamphetamine	50 mg	"All night"
ORTHO-MDMA (2,3-MDMA)	2,3-Methylenedioxy-N-methylamphetamine	Unknown	Unknown
2-Methyl-MDA	2-Methyl-3,4-methylenedioxyamphetamine	≥40–100 mg	12–20 hours
5-Methyl-MDA	5-Methyl-3,4-methylenedioxyamphetamine	Unknown	Unknown
6-Methyl-MDA	6-Methyl-3,4-methylenedioxyamphetamine	160 mg	8 hours
MMDA (5-methoxy-MDA)	3-Methoxy-4,5-methylenedioxyamphetamine	100–250 mg	"Moderate"
MMDA-2 (6-methoxy-MDA)	2-Methoxy-4,5-methylenedioxyamphetamine	25–50 mg	8–12 hours
MMDA-3a (2-methoxy-MDA)	2-Methoxy-3,4-methylenedioxyamphetamine	20–80 mg	10–16 hours
MMDA-3b	4-Methoxy-2,3-methylenedioxyamphetamine	≥60–80 mg	Unknown
MMDA-4	5-Methoxy-2,3-methylenedioxyamphetamine	Unknown	Unknown
MMDA-5	6-Methoxy-2,3-methylenedioxyamphetamine	≥30 mg	Unknown
DMMDA (2,5-dimethoxy-MDA)	2,5-Dimethoxy-3,4-methylenedioxyamphetamine	30–75 mg	6–8 hours
DMMDA-2 (5,6-dimethoxy-MDA)	2,3-Dimethoxy-4,5-methylenedioxyamphetamine	~50 mg	Unknown
DMMDA-3	4,5-Dimethoxy-2,3-methylenedioxyamphetamine	Unknown	Unknown
DMMDA-4 (2,6-dimethoxy-MDA)	2,6-Dimethoxy-3,4-methylenedioxyamphetamine	Unknown	Unknown
DMMDA-5	4,6-Dimethoxy-2,3-methylenedioxyamphetamine	Unknown	Unknown
DMMDA-6	2,3-Dimethoxy-5,6-methylenedioxyamphetamine	Unknown	Unknown
EMDA-2 (6-ethoxy-MDA)	2-Ethoxy-4,5-methylenedioxyamphetamine	135–185 mg	10–12 hours
6-Chloro-MDA	2-Chloro-4,5-methylenedioxyamphetamine	160 mg	8 hours
6-Bromo-MDA	2-Bromo-4,5-methylenedioxyamphetamine	350 mg	Unknown
2T-MMDA-3a	2-Methylthio-3,4-methylenedioxyamphetamine	12 mg	Unknown
EIDA (EDA; 7-methyl-MDA)	3,4-Ethylidenedioxyamphetamine	150 mg	Unknown
IDA (7,7-dimethyl-MDA)	3,4-Isopropylidenedioxyamphetamine	Unknown	Unknown
DFMDA (7,7-difluoro-MDA)	3,4-(Difluoromethylenedioxy)amphetamine	≥250 mg	Unknown
MDMA (Ecstasy; Molly; Adam)	3,4-Methylenedioxy-N-methylamphetamine	80–150 mg (25–200 mg+)	3–6 hours
(S)-MDMA	(S)-3,4-Methylenedioxy-N-methylamphetamine	60–125 mg	5 hours
(R)-MDMA	(R)-3,4-Methylenedioxy-N-methylamphetamine	250–300 mg	4–5 hours
MDEA (MDE; Eve)	3,4-Methylenedioxy-N-ethylamphetamine	100–200 mg (30–225 mg+)	3–5 hours
MDPR	3,4-Methylenedioxy-N-propylamphetamine	200 mg	Unknown
MDIP	3,4-Methylenedioxy-N-isopropylamphetamine	250–350 mg	Unknown
MDBU	3,4-Methylenedioxy-N-butylamphetamine	40 mg	Unknown
MDCPM	3,4-Methylenedioxy-N-cyclopropylmethylamphetamine	10 mg	Unknown
MDAL	3,4-Methylenedioxy-N-allylamphetamine	180 mg	Unknown
MDPL	3,4-Methylenedioxy-N-propargylamphetamine	150–200 mg	Unknown
MDBZ	3,4-Methylenedioxy-N-benzylamphetamine	150 mg	Unknown
MDOH	3,4-Methylenedioxy-N-hydroxyamphetamine	100–160 mg	3–6 hours
MDMEO (MDME)	3,4-Methylenedioxy-N-methoxyamphetamine	180 mg	Unknown
MDHOET	3,4-Methylenedioxy-N-(β-hydroxyethyl)amphetamine	50 mg	Unknown
MDMEOET	3,4-Methylenedioxy-N-(β-methoxyethyl)amphetamine	180 mg	Unknown
MDTFEA (MDTFE)	3,4-Methylenedioxy-N-(2,2,2-trifluoroethyl)amphetamine	500 mg	Unknown
MDDM (MDDMA)	3,4-Methylenedioxy-N,N-dimethylamphetamine	150 mg	Unknown
FLEA (MDMOH, MDHMA)	3,4-Methylenedioxy-N-hydroxy-N-methylamphetamine	100–160 mg	4–8 hours
Lys-MDA	N-(L-Lysinamidyl)-3,4-methylenedioxyamphetamine	~164 mg	~6 hours
Lys-MDMA	N-(L-Lysinamidyl)-3,4-methylenedioxy-N-methylamphetamine	Inactiveb	Inactiveb
N-t-BOC-MDMA	N-tert-Butoxycarbonyl-3,4-methylenedioxy-N-methylamphetamine	Unknown	Unknown
MADAM-6 (6-methyl-MDMA)	2-Methyl-4,5-methylenedioxy-N-methylamphetamine	280 mg	Unknown
MMDMA (5-methoxy-MDMA)	3-Methoxy-4,5-methylenedioxy-N-methylamphetamine	Unknown	Unknown
Methyl-MMDA-2 (6-methoxy-MDMA)	2-Methoxy-4,5-methylenedioxy-N-methylamphetamine	70 mg	Unknown
DFMDMA (7,7-difluoro-MDMA)	3,4-(Difluoromethylenedioxy)-N-methylamphetamine	120 mg	Unknown
BDB (J)	3,4-Methylenedioxy-α-ethylphenethylamine	150–230 mg	4–8 hours
MBDB (methyl-J; Eden)	3,4-Methylenedioxy-N-methyl-α-ethylphenethylamine	180–210 mg (150–250 mg+)	4–6 hours
Ethyl-J (EBDB)	3,4-Methylenedioxy-N-ethyl-α-ethylphenethylamine	90 mg	"Short"
BDP (K)	3,4-Methylenedioxy-α-propylphenethylamine	Unknown	Unknown
Methyl-K (MBDP)	3,4-Methylenedioxy-N-methyl-α-propylphenethylamine	100 mg	Unknown
Ethyl-K (EBDP)	3,4-Methylenedioxy-N-ethyl-α-propylphenethylamine	40 mg	Unknown
MPAP (propyl-K; PDBP)	3,4-methylenedioxy-N-propyl-α-propylphenethylamine	Unknown	Unknown
MDPH	3,4-Methylenedioxy-α,α-dimethylphenethylamine	160–240 mg	3–5 hours
MDMP (MDMPH)	3,4-Methylenedioxy-N-methyl-α,α-dimethylphenethylamine	110 mg	~6 hours
3C-BOH (β-methoxy-MDA)	3,4-Methylenedioxy-β-methoxyamphetamine	40–70 mg	3–6 hours
MDC (βk-MDA)	3,4-Methylenedioxy-β-ketoamphetamine	Unknown	Unknown
Methylone (βk-MDMA)	3,4-Methylenedioxy-N-methyl-β-ketoamphetamine	100–250 mg (60–325 mg+)	2–5 hours
Ethylone (βk-MDEA)	3,4-Methylenedioxy-N-ethyl-β-ketoamphetamine	150–250 mg (80–400 mg)	2–6 hours
Dimethylone (βk-MDDMA)	3,4-Methylenedioxy-N,N-dimethyl-β-ketoamphetamine	Unknown	Unknown
Butylone (βk-MBDB)	3,4-Methylenedioxy-N-methyl-α-ethyl-β-ketophenethylamine	100–250 mg (20–250 mg)	2–5 hours
Eutylone (βk-EBDB)	3,4-Methylenedioxy-N-ethyl-α-ethyl-β-ketophenethylamine	Unknown	Unknown
Putylone (βk-PBDB)	3,4-Methylenedioxy-N-propyl-α-ethyl-β-ketophenethylamine	Unknown	Unknown
Dibutylone (βk-DMBDB)	3,4-Methylenedioxy-N,N-dimethyl-α-ethyl-β-ketophenethylamine	Unknown	Unknown
Pentylone (βk-MBDP)	3,4-Methylenedioxy-N-methyl-α-propyl-β-ketophenethylamine	30 mg (10–80 mg)	Unknown
Ephylone (βk-EBDP)	3,4-Methylenedioxy-N-ethyl-α-propyl-β-ketophenethylamine	Unknown	Unknown
Dipentylone (βk-DMBDP)	3,4-Methylenedioxy-N,N-dimethyl-α-propyl-β-ketophenethylamine	Unknown	Unknown
Isohexylone	3,4-Methylenedioxy-N-methyl-α-isobutyl-β-ketophenethylamine	Unknown	Unknown
N-Ethylhexylone	3,4-Methylenedioxy-N-ethyl-α-butyl-β-ketophenethylamine	Unknown	Unknown
N-Ethylheptylone	3,4-Methylenedioxy-N-ethyl-α-pentyl-β-ketophenethylamine	Unknown	Unknown
5-Methoxymethylone (βk-MMDMA)	3,4-Methylenedioxy-5-methoxy-N-methyl-β-ketoamphetamine	Unknown	Unknown
5-Methylethylone	3,4-Methylenedioxy-5-methyl-N-ethyl-β-ketoamphetamine	Unknown	Unknown
Benzylone	3,4-Methylenedioxy-N-benzyl-β-ketoamphetamine	Unknown	Unknown
MDPPP	3′,4′-Methylenedioxy-α-(pyrrolidin-1-yl)propanophenone	Unknown	Unknown
MDPBP	3′,4′-Methylenedioxy-α-(pyrrolidin-1-yl)butanophenone	Unknown	Unknown
MDPV (MD-α-PVP; Monkey Dust)	3′,4′-Methylenedioxy-α-(pyrrolidin-1-yl)valerophenone	5–10 mg (2–25 mg+)	3–5 hours
MDPHP	3′,4′-Methylenedioxy-α-(pyrrolidin-1-yl)hexanophenone	Unknown	Unknown
MDPEP	3′,4′-Methylenedioxy-α-(pyrrolidin-1-yl)heptanophenone	Unknown	Unknown
MDPM	3-Methyl-3′,4′-methylenedioxy-2-phenylmorpholine	Unknown	Unknown
MDMAR		Unknown	Unknown
MDAI (MDA-AI)	5,6-Methylenedioxy-2-aminoindane	100–200 mg (20–300 mg+)	2–5 hours
MDMAI (MDMA-AI)	5,6-Methylenedioxy-N-methyl-2-aminoindane	Unknown	Unknown
MDAT (MDA-AT)	6,7-Methylenedioxy-2-aminotetralin	Unknown	Unknown
MDMAT (MDMA-AT)	6,7-Methylenedioxy-N-methyl-2-aminotetralin	Unknown	Unknown
Footnotes: a = Methylenedioxyphenethylamines (MDxx compounds) variably act as psychedelics, entactogens, and/or stimulants. Examples of psychedelics include lophophine, MDA, MMDA, and MMDA-2; examples of entactogens include MDA, MDMA, MBDB, methylone, and MDAI; and examples of stimulants include ORTHO-MDA, MDPV, MDPM, and MDMAR. b = Lys-MDMA, unlike lys-MDA, is inactive, because it does not hydrolyze into and hence act as a prodrug of MDMA. Refs: Individual:

Interactions

List of substituted methylenedioxyphenethylamines

Structure	Chemical Name	Abbreviations	Other Names	CAS #	Ref
[[File:Methylenedioxyphenethylamine.svg	120px	class=skin-invert-image]]	3,4-Methylenedioxyphenethylamine	MDPEA	Homopiperonylamine	1484-85-1
[[File:MDMPEA chemical structure.svg	120px	class=skin-invert-image]]	3,4-Methylenedioxy-N-methylphenethylamine	MDMPEA	Homarylamine	451-77-4
[[File:BNDM-MDPEA_structure.png	120px	class=skin-invert-image]]	β,N-Dimethyl-3,4-methylenedioxyphenethylamine	β,N-DM-MDPEA	MDDMPEA	83329-26-4
[[File:Lophophine.png	120px	class=skin-invert-image]]	4,5-Methylendioxy-3-methoxy-phenethylamine	MMDPEA	Lophophine, Homomyristicylamine, 2C-MMDA, 5-Methoxy-MDPEA	23693-38-1
[[File:MMDMPEA_structure.png	120px	class=skin-invert-image]]	4,5-Methylenedioxy-3-methoxy-N-methylphenethylamine	MMDMPEA	N-Methyllophophine
[[File:2C-MMDA-2.svg	120px	class=skin-invert-image]]	2-Methoxy-4,5-methylenedioxyphenethylamine	2C-MMDA-2	MMDPEA-2; 6-Methoxy-MDPEA	497096-69-2
[[File:2C-MMDA-3a.svg	120px	class=skin-invert-image]]	2-Methoxy-3,4-methylenedioxyphenethylamine	2C-MMDA-3a	MMDPEA-3a; 2-Methoxy-MDPEA	2220-19-1
[[File:MDPEA-NBOMe_structure.png	120px	class=skin-invert-image]]	3,4-Methylenedioxy-N-(2-methoxybenzyl)phenethylamine	NBOMe-MDPEA	MDPEA-NBOMe
[[File:NBOMe-Lophophine structure.png	120px	class=skin-invert-image]]	3-Methoxy-4,5-methylenedioxy-N-(2-methoxybenzyl)phenethylamine	Lophophine-NBOMe	MMDPEA-NBOMe; 5-Methoxy-MDPEA-NBOMe
[[File:2C2-NBOMe structure.png	120px	class=skin-invert-image]]	N-(2-Methoxybenzyl)-2-methoxy-4,5-methylenedioxyphenethylamine	2C2-NBOMe	2C-MMDA-2-NBOMe; NBOMe-MMDPEA-2; 6-Methoxy-MDPEA-NBOMe
[[File:MDA-2D-skeletal.svg	120px	class=skin-invert-image]]	3,4-Methylenedioxyamphetamine	MDA	"Sally, Sass, Sass-a-frass or Mellow Drug of America"	4764-17-4
[[File:2,3-MDA.svg	120px	class=skin-invert-image]]	2,3-Methylenedioxyamphetamine	2,3-MDA	ORTHO-MDA	23693-17-6
[[File:2,3-MDMA.svg	120px	class=skin-invert-image]]	2,3-Methylenedioxymethamphetamine	2,3-MDMA	ORTHO-MDMA	168967-99-5
[[File:MDMA (simple).svg	120px	class=skin-invert-image]]	3,4-Methylenedioxy-N-methylamphetamine	MDMA, MDM	"Molly", "Ecstasy", "Adam", etc.	42542-10-9
[[File:MDEA.svg	120px	class=skin-invert-image]]	3,4-Methylenedioxy-N-ethylamphetamine	MDEA, MDE	"Eve"	82801-81-8
[[File:Methylenedioxypropylamphetamine.svg	120px	class=skin-invert-image]]	3,4-Methylenedioxy-N-propylamphetamine	MDPR, MDPA		74698-36-5
[[File:MDIP.svg	120px	class=skin-invert-image]]	3,4-Methylenedioxy-N-isopropylamphetamine	MDIP, MDIPR, MDIPA		74698-37-6
[[File:MDBU.svg	120px	class=skin-invert-image]]	3,4-Methylenedioxy-N-butylamphetamine	MDBU, MDBA		74698-38-7
[[File:MDIB_structure.png	120px	class=skin-invert-image]]	3,4-Methylenedioxy-N-isobutylamphetamine	MDIB, MDIBA
[[File:MDAL.svg	120px	class=skin-invert-image]]	3,4-Methylenedioxy-N-allylamphetamine	MDAL, MDAA		74698-45-6
[[File:MDBZ.svg	120px	class=skin-invert-image]]	3,4-Methylenedioxy-N-benzylamphetamine	MDBZ, MDBZA		65033-29-6
[[File:MDCPM.svg	120px	class=skin-invert-image]]	3,4-Methylenedioxy-N-cyclopropylmethylamphetamine	MDCPM, MDCPMA, MDCA		22698-08-4
[[File:3,4-MDOH.png	120px	class=skin-invert-image]]	3,4-Methylenedioxy-N-hydroxyamphetamine	MDOH, MDHA, MDH		74698-47-8
[[File:MDHOET svg.svg	120px	class=skin-invert-image]]	3,4-Methylenedioxy-N-(2-hydroxyethyl)amphetamine	MDHOET, MDHEA		74698-43-4
[[File:MDMEO.svg	120px	class=skin-invert-image]]	3,4-Methylenedioxy-N-methoxyamphetamine	MDMEO, MDMEOA		74698-48-9
[[File:MDMEOET.svg	120px	class=skin-invert-image]]	3,4-Methylenedioxy-N-(2-methoxyethyl)amphetamine	MDMEOET, MDMEA		74698-44-5
[[File:MDPL.svg	120px	class=skin-invert-image]]	3,4-Methylenedioxy-N-propargylamphetamine	MDPL, MDPLA		74698-46-7
[[File:Lys-MDA_structure.png	120px	class=skin-invert-image]]	N-(L-Lysinamidyl)-3,4-methylenedioxyamphetamine	Lys-MDA		1391487-26-5
[[File:Lys-MDMA structure.png	120px	class=skin-invert-image]]	N-(L-Lysinamidyl)-3,4-methylenedioxy-N-methylamphetamine	Lys-MDMA		2763054-67-5
[[File:2-Methyl-MDA skeletal.svg	120px	class=skin-invert-image]]	3,4-Methylenedioxy-2-methylamphetamine	2-Methyl-MDA		691876-73-0
[[File:5-Methyl-MDA.svg	120px	class=skin-invert-image]]	4,5-Methylenedioxy-3-methylamphetamine	5-Methyl-MDA		749191-14-8
[[File:6-Methyl-MDA.png	120px	class=skin-invert-image]]	4,5-Methylenedioxy-2-methylamphetamine	6-Methyl-MDA		246861-21-2
[[File:5-methoxy-MDA.svg	120px	class=skin-invert-image]]	4,5-Methylenedioxy-3-methoxy-amphetamine	MMDA	5-Methoxy-MDA	13674-05-0
[[File:MMDMA.svg	120px	class=skin-invert-image]]	4,5-Methylenedioxy-3-methoxy-N-methylamphetamine	MMDMA	N-Methyl-MMDA; 5-Methoxy-MDMA	172518-52-4
[[File:MMDA-2.svg	120px	class=skin-invert-image]]	2-Methoxy-4,5-methylenedioxyamphetamine	MMDA-2	6-Methoxy-MDA	23693-18-7
[[File:EMDA-2.svg	120px	class=skin-invert-image]]	2-Ethoxy-4,5-methylenedioxyamphetamine	EDMA-2
[[File:MDDM.png	120px	class=skin-invert-image]]	3,4-Methylenedioxy-N,N-dimethylamphetamine	MDDM, MDDMA		74698-50-3
[[File:Methylenedioxytrimethylamphetamine.svg	120px	class=skin-invert-image]]	3,4-Methylenedioxy-N,N,N-trimethylamphetamine	MDTMA
[[File:FLEA chemical structure.svg	120px	class=skin-invert-image]]	3,4-Methylenedioxy-N-methyl-N-hydroxyamphetamine	MDMOH, MDMHA, MDHMA	FLEA	214414-88-7
[[File:MDEOH_structure.png	120px	class=skin-invert-image]]	3,4-Methylenedioxy-N-ethyl-N-hydroxyamphetamine	MDEOH, MDEHA, MDHEA		866417-59-6
[[File:DMMDA.svg	120px	class=skin-invert-image]]	3,4-Methylenedioxy-2,5-dimethoxyamphetamine	DMMDA		15183-13-8
[[File:DMMDA-2.svg	120px	class=skin-invert-image]]	4,5-Methylenedioxy-2,3-dimethoxyamphetamine	DMMDA-2		15183-26-3
[[File:6-Cl-MDA.svg	120px	class=skin-invert-image]]	2-Chloro-4,5-methylenedioxyamphetamine	6-Chloro-MDA	2-Cl-4,5-MDA	46319-44-2
[[File:6-Cl-MDMA Structure.svg	120px	class=skin-invert-image]]	2-Chloro-4,5-methylenedioxy-N-methylamphetamine	6-Chloro-MDMA	2-Cl-4,5-MDMA	319920-71-3
[[File:2-Bromo-MDA.svg	120px	class=skin-invert-image]]	2-Bromo-4,5-methylenedioxyamphetamine	6-Bromo-MDA	2-Br-4,5-MDA	151920-03-5
[[File:6-Br-MDMA.svg	120px	class=skin-invert-image]]	2-Bromo-4,5-methylenedioxy-N-methylamphetamine	6-Bromo-MDMA	2-Br-4,5-MDMA	2170110-34-4
[[File:Methylenedioxyphentermine.svg	120px	class=skin-invert-image]]	3,4-Methylenedioxyphentermine	MDPH		39235-63-7
[[File:MDMP.svg	120px	class=skin-invert-image]]	3,4-Methylenedioxy-N-methylphentermine	MDMP		81262-69-3
[[File:Methylenedioxycathinone.svg	120px	class=skin-invert-image]]	3,4-Methylenedioxycathinone	βk-MDA, MDC		80535-73-5
[[File:MDMC.svg	120px	class=skin-invert-image]]	3,4-Methylenedioxy-N-methylcathinone	βk-MDMA, MDMC	Methylone	186028-79-5
[[File:Bk-MDEA.svg	120px	class=skin-invert-image]]	3,4-Methylenedioxy-N-ethylcathinone	βk-MDEA, MDEC	Ethylone	1112937-64-0
[[File:5-Methylethylone.svg	120px	class=skin-invert-image]]	3,4-Methylenedioxy-5-methyl-N-ethylcathinone	5-Me-βk-MDEA	5-Methylethylone	1364933-82-3
[[File:BDB.svg	120px	class=skin-invert-image]]	1,3-Benzodioxolylbutanamine	BDB	J	42542-07-4
[[File:MBDB.svg	120px	class=skin-invert-image]]	N-Methyl-1,3-benzodioxolylbutanamine	MBDB	Methyl-J; "Eden"	135795-90-3
[[File:Ethyl-J_svg.svg	120px	class=skin-invert-image]]	N-Ethyl-1,3-benzodioxolylbutanamine	EBDB	Ethyl-J	167394-39-0
[[File:3,4-methylenedioxy-beta-methoxy-phenethylamine.png	120px	class=skin-invert-image]]	3,4-Methylenedioxy-β-methoxyphenethylamine	BOH	β-MeO-MDPEA	73304-06-0
[[File:3C-BOH.svg	120px	class=skin-invert-image]]	3,4-Methylenedioxy-β-methoxyamphetamine	3C-BOH	β-MeO-MDA	?
[[File:Bk-MBDB.svg	120px	class=skin-invert-image]]	β-Keto-N-methyl-1,3-benzodioxolylbutanamine	βk-MBDB	Butylone	802575-11-7
[[File:Eutylone.svg	120px	class=skin-invert-image]]	β-Keto-N-ethyl-1,3-benzodioxolylbutanamine	βk-EBDB	Eutylone	802855-66-9
[[File:Dibutylone.svg	120px	class=skin-invert-image]]	β-Keto-N,N-dimethyl-1,3-benzodioxolylbutanamine	βk-DMBDB	Dibutylone	802286-83-5
[[File:BDP_structure.png	120px	class=skin-invert-image]]	1,3-Benzodioxolylpentanamine	BDP	K	220491-69
[[File:MBDP.svg	120px	class=skin-invert-image]]	N-Methyl-1,3-benzodioxolylpentanamine	MBDP	Methyl-K	952016-78-3
[[File:EBDP.svg	120px	class=skin-invert-image]]	N-Ethyl-1,3-benzodioxolylpentanamine	EBDP	Ethyl-K	952016-47-6
[[File:Methylenedioxyphenylpropylaminopentane.svg	120px	class=skin-invert-image]]	1-(3,4-Methylenedioxyphenyl)-2-propylaminopentane	MPAP	PBDP
[[File:UWA-104_structure.png	120px	class=skin-invert-image]]	2-(1,3-Benzodioxol-5-yl)-1-(propan-2-yl)-N-methylethanamine	α-iPr-MDMPEA	UWA-104
[[File:UWA-101.svg	120px	class=skin-invert-image]]	2-(1,3-Benzodioxol-5-yl)-1-cyclopropyl-N-methylethanamine	α-cPr-MDMPEA	UWA-101	1350821-24-7
[[File:UWA-001 structure.svg	120px	class=skin-invert-image]]	2-(1,3-Benzodioxol-5-yl)-N-methyl-1-phenylethanamine	α-Ph-MDMPEA	UWA-001	1350821-28-1
[[File:Pentylone.svg	120px	class=skin-invert-image]]	β-Keto-N-methyl-1,3-benzodioxolylpentanamine	βk-MBDP, βk-Methyl-K	Pentylone	698963-77-8
[[File:N-Ethylpentylone.svg	120px	class=skin-invert-image]]	β-Keto-N-ethyl-1,3-benzodioxolylpentanamine	βk-EBDP	Ephylone	727641-67-0

Related compounds

In addition, there are a number of other compounds that have some structural and pharmacological similarities to the methylenedioxyphenethylamines, and are useful for comparison. These can be broadly divided into (i) compounds where the methylenedioxyphenyl ring is retained but the phenethyl portion is modified, or (ii) compounds which retain the 3,4-cyclised amphetamine core common to the MDxx compounds, but have the 1,3-benzodioxole ring replaced by related heterocycles. In addition to the (i) and (ii) compounds, MDxx compounds are closely related to the other two main phenylethylamine classes, those being substituted amphetamines and substituted cathinones. Like amphetamines and cathinones, MDxx compounds derive most if not all of their stimulant effects from the phenylethylamine core, in fact most MDxx compounds can also be grouped with cathinones and or amphetamines due to having similar functional groups, but in most cases any compound with a methylenedioxy group attached will be grouped as an MDxx compound due to the unique hallucinogenic and empathogenic/entactogenic effects that are not present in most other amphetamines and present to a lesser extent in most cathinones.

Structure	Chemical Name	Abbreviations	Other Names	CAS #	Ref
[[File:3,4-Dimethoxyamphetamine.svg	120px	class=skin-invert-image]]	3,4-Dimethoxyamphetamine	3,4-DMA		120-26-3
[[File:3,4-Dimethoxymethamphetamine Structure.svg	120px	class=skin-invert-image]]	3,4-Dimethoxymethamphetamine	3,4-DMMA		33236-61-2
[[File:Isosafrole acsv.svg	120px	class=skin-invert-image]]	3,4-Methylenedioxyphenyl-1-propene		Isosafrole	120-58-1
[[File:safrole-Line-Structure.png	120px	class=skin-invert-image]]	3,4-Methylenedioxyphenyl-2-propene		Safrole, Shikimol	94-59-7
[[File:Myristicin.svg	120px	class=skin-invert-image]]	4,5-Methylenedioxyphenyl-3-methoxy-2-propene		Myristicin	607-91-0
[[File:Methylenedioxypropiophenone.svg	120px	class=skin-invert-image]]	3,4-Methylenedioxyphenyl-1-propanone	MDP1P		28281-49-4
[[File:MDP2P.svg	120px	class=skin-invert-image]]	3,4-Methylenedioxyphenyl-2-propanone	MDP2P		4676-39-5
[[File:Piperonal structure.png	120px	class=skin-invert-image]]	3,4-Methylenedioxybenzaldehyde		Piperonal	120-57-0
[[File:Sesamol.png	120px	class=skin-invert-image]]	3,4-Methylenedioxyphenol		Sesamol	533-31-3
[[File:piperin.svg	120px	class=skin-invert-image]]	5-(3,4-Methylenedioxyphenyl)-2,4-pentadienoyl-2-piperidine		Piperine (also chavicine)	94-62-2
[[File:Ilepcimide.png	120px	class=skin-invert-image]]	3,4-Methylenedioxycinnamylpiperidine		Ilepcimide	23434-86-8
[[File:MDM1EA.svg	120px	class=skin-invert-image]]	3,4-methylenedioxy-α,N-dimethylbenzylamine	MDM1EA	α,N-DMMDBA	121734-65-4
[[File:ALPHA.png	120px	class=skin-invert-image]]	3,4-methylenedioxy-α-ethylbenzylamine	ALPHA		127292-42-6
[[File:M-ALPHA structure.png	120px	class=skin-invert-image]]	3,4-methylenedioxy-α-ethyl-N-methylbenzylamine	M-ALPHA		127292-43-7
[[File:Homo-MDA.svg	120px	class=skin-invert-image]]	4-(1,3-Benzodioxol-5-yl)butan-2-amine		Homo-MDA, HMDA	40742-32-3
[[File:HMDMA.svg	120px	class=skin-invert-image]]	4-(1,3-Benzodioxol-5-yl)-N-methylbutan-2-amine		Homo-MDMA, HMDMA	108248-08-4
[[File:Paroxetine-2D-skeletal.svg	120px	class=skin-invert-image]]	trans-4-(4-Fluorophenyl)-3-[(3,4-methylenedioxy)phenoxy]methylpiperidine		Paroxetine	61869-08-7
[[File:MDAI.svg	120px	class=skin-invert-image]]	5,6-Methylenedioxy-2-aminoindane	5,6-MDAI, MDAI		132741-81-2
[[File:MDMAI.svg	120px	class=skin-invert-image]]	5,6-Methylenedioxy-N-methyl-2-aminoindane	5,6-MDMAI, MDMAI		132741-82-3
[[File:6,7-Methylenedioxy-2-aminotetralin.svg	120px	class=skin-invert-image]]	6,7-Methylenedioxy-2-aminotetralin	6,7-MDAT		101625-35-8
[[File:MDMAT-structure.png	120px	class=skin-invert-image]]	6,7-Methylenedioxy-2-methylaminotetralin	6,7-MDMAT		34620-52-5
[[File:MDBZP.svg	120px	class=skin-invert-image]]	3,4-Methylenedioxy-1-benzylpiperazine	MDBZP	Piperonylpiperazine	32231-06-4
[[File:MDPPP.svg	120px	class=skin-invert-image]]	3,4-Methylenedioxy-α-pyrrolidinopropiophenone	MDPPP		783241-66-7
[[File:3',4'-Methylenedioxy-α-pyrrolidinobutiophenone.svg	120px	class=skin-invert-image]]	3',4'-Methylenedioxy-α-pyrrolidinobutiophenone	MDPBP		784985-33-7
[[File:MDPV.svg	120px	class=skin-invert-image]]	3,4-Methylenedioxy-α-pyrrolidinopentiophenone	MDPV	"Monkey Dust"	687603-66-3
[[File:MDPHP.svg	120px	class=skin-invert-image]]	3,4-Methylenedioxy-α-pyrrolidinohexiophenone	MDPHP	Also known as "Monkey Dust"	776994-64-0
[[File:Methylenedioxyphenmetrazine.svg	120px	class=skin-invert-image]]	Methylenedioxyphenmetrazine	MDPM	3,4-Methylenedioxyphenmetrazine		vauthors = Świst M, Wilamowski J, Zuba D, Kochana J, Parczewski A	title = Determination of synthesis route of 1-(3,4-methylenedioxyphenyl)-2-propanone (MDP-2-P) based on impurity profiles of MDMA	journal = Forensic Science International	volume = 149	issue = 2–3	pages = 181–92	date = May 2005	pmid = 15749360	doi = 10.1016/j.forsciint.2004.06.016 }}
[[File:methylenedioxymethylphenidate_structure.png	120px	class=skin-invert-image]]	Methyl (1,3-benzodioxol-5-yl)(piperidin-2-yl)acetate	MDMPH	3,4-Methylenedioxymethylphenidate
[[File:MD4MAR_structure.png	120px	class=skin-invert-image]]	4-Methyl-5-(1,3-benzodioxol-5-yl)-4,5-dihydro-1,3-oxazol-2-amine	MDMAR	3',4'-Methylenedioxy-4-methylaminorex	1445573-16-9
[[File:GYKI 52895.svg	120px	class=skin-invert-image]]	1-(4-Aminophenyl)-4-methyl-7,8-methylenedioxy-2,3-benzodiazepine	GYKI-52895		869360-93-0
[[File:EDA.svg	120px	class=skin-invert-image]]	3,4-Ethylidenedioxyamphetamine	EIDA		125299-84-5
[[File:IDA.svg	120px	class=skin-invert-image]]	3,4-Isopropylidenedioxyamphetamine	IDA
[[File:DFMDA.svg	120px	class=skin-invert-image]]	1-(2,2-Difluoro-1,3-benzodioxol-5-yl)propan-2-amine	DFMDA		910393-51-0
[[File:3,4-Ethylenedioxyamphetamine.svg	120px	class=skin-invert-image]]	3,4-Ethylenedioxyamphetamine	EDA	EDA-6	15033-67-7
[[File:EDMA.svg	120px	class=skin-invert-image]]	3,4-Ethylenedioxy-N-methylamphetamine	EDMA		133787-66-3
[[File:MEDA chemical structure.svg	120px	class=skin-invert-image]]	3-Methoxy-4,5-ethylenedioxyamphetamine	MEDA	5-Methoxy-EDA	23693-25-6
[[File:MTDA.svg	120px	class=skin-invert-image]]	3-Methoxy-4,5-trimethylenedioxyamphetamine	MTDA	5-Methoxy-TDA
[[File:3-desoxy-MDA.svg	120px	class=skin-invert-image]]	1-(2,3-Dihydro-1-benzofuran-5-yl)propan-2-amine	5-APDB		152624-03-8
[[File:IBF5MAP_structure.png	120px	class=skin-invert-image]]	1-(1,3-Dihydro-2-benzofuran-5-yl)-N-methylpropan-2-amine	IBF5MAP		201407-56-9
[[File:4-desoxy-MDA.svg	120px	class=skin-invert-image]]	1-(2,3-Dihydro-1-benzofuran-6-yl)propan-2-amine	6-APDB		152623-93-3
[[File:5-APB.svg	120px	class=skin-invert-image]]	1-(1-Benzofuran-5-yl)propan-2-amine	5-APB		286834-81-9
[[File:5-MAPB.svg	120px	class=skin-invert-image]]	N-Methyl-1-(1-benzofuran-5-yl)propan-2-amine	5-MAPB		1354631-77-8
[[File:1-(benzofuran-5-yl)-N-ethylpropan-2-amine.png	120px	class=skin-invert-image]]	N-Ethyl-1-(1-benzofuran-5-yl)propan-2-amine	5-EAPB		1445566-01-7
[[File:5-MBPB_structure.png	120px	class=skin-invert-image]]	N-Methyl-1-(1-benzofuran-5-yl)butan-2-amine	5-MBPB	5-MABB
[[File:6-APB.svg	120px	class=skin-invert-image]]	1-(1-Benzofuran-6-yl)propan-2-amine	6-APB		286834-85-3
[[File:6-MAPB.svg	120px	class=skin-invert-image]]	N-Methyl-1-(1-benzofuran-6-yl)propan-2-amine	6-MAPB		1354631-79-0
[[File:6MBPB structure.png	120px	class=skin-invert-image]]	6-(2-Methylaminobutyl)benzofuran	6-MBPB	6-MABB
[[File:Indanylaminopropane.svg	120px	class=skin-invert-image]]	1-(2,3-Dihydro-1H-inden-5-yl)propan-2-amine	5-APDI	IAP	13396-94-6
[[File:5-MAPDI_structure.png	120px	class=skin-invert-image]]	1-(2,3-Dihydro-1H-inden-5-yl)-N-methylpropan-2-amine	5-MAPDI	IMP	1310153-27-5
[[File:Tetralinylaminopropane.svg	120px	class=skin-invert-image]]	1-(5,6,7,8-Tetrahydronaphthalen-2-yl)propan-2-amine	6-APT	TAP	3160-20-1
[[File:TH-PVP.svg	120px	class=skin-invert-image]]	2-(Pyrrolidin-1-yl)-1-(5,6,7,8-tetrahydronaphthalen-2-yl)pentan-1-one	TH-PVP		2304915-07-7
[[File:Naphthylisopropylamine.svg	120px	class=skin-invert-image]]	1-(Naphthalen-2-yl)propan-2-amine	NAP	PAL-287	18085-03-5
[[File:Methamnetamine.svg	120px	class=skin-invert-image]]	N-Methyl-1-(naphthalen-2-yl)propan-2-amine	MNAP	Methamnetamine; PAL-1046	1178720-66-5
[[File:Ethylnaphthylaminopropane.svg	120px	class=skin-invert-image]]	N-Ethyl-1-naphthalen-2-ylpropan-2-amine	ENAP	PAL-1045
[[File:Bk-methamnetamine.svg	120px	class=skin-invert-image]]	2-(Methylamino)-1-(naphthalene-2-yl) propan-1-one	BMAPN	βk-Methamnetamine; 2-Naphthylmethcathinone	109453-73-8
[[File:5-APBTP_structure.png	120px	class=skin-invert-image]]	1-(1-Benzothiophen-5-yl)propan-2-amine	5-APBT		1368128-53-3
[[File:5-MAPBT.svg	120px	class=skin-invert-image]]	1-(Benzo[b]thiophen-5-yl)-N-methylpropan-2-amine	5-MAPBT	MY400	2613382-32-2	title=Novel short-acting psychoactive compounds of the mdma class	website=Google Patents	date=5 January 2024	url=https://patents.google.com/patent/US20240197679A1/	access-date=23 October 2024	author = Mydecine}}
[[File:6-APBT.svg	120px	class=skin-invert-image]]	1-(1-Benzothiophen-6-yl)propan-2-amine	6-APBT
[[File:6-MAPBT.svg	120px	class=skin-invert-image]]	1-(Benzo[b]thiophen-6-yl)-N-methylpropan-2-amine	6-MAPBT	MY300		title=1-(1-benzothiophen-6-yl)-N-methylpropan-2-amine	website=PubChem	url=https://pubchem.ncbi.nlm.nih.gov/compound/166478938	access-date=23 October 2024}}
[[File:BK-5-MAPBT.svg	120px	class=skin-invert-image]]	1-(1-Benzothiophen-5-yl)-2-(methylamino)propan-1-one	BK-5-MAPBT		2106849-09-4
[[File:5-IT_structure.png	120px	class=skin-invert-image]]	1-(1H-Indol-5-yl)propan-2-amine	5-API	5-IT	3784-30-3
[[File:5-APBDZ_structure.png	120px	class=skin-invert-image]]	1-(1H-1,3-Benzodiazol-5-yl)propan-2-amine			752145-76-9
[[File:5-MAPBDZ_structure.png	120px	class=skin-invert-image]]	1-(1,3-Benzodiazol-5-yl)-N-methylpropan-2-amine
[[File:5-APBOX_structure.png	120px	class=skin-invert-image]]	1-(1,3-Benzoxazol-5-yl)propan-2-amine			1368557-51-0
[[File:5-BZT-MDA_structure.png	120px	class=skin-invert-image]]	1-(1,3-Benzothiazol-5-yl)propan-2-amine	5-BZT-MDA
[[File:5-BZT-MDMA_structure.png	120px	class=skin-invert-image]]	1-(Benzo[d]thiazol-5-yl)-N-methylpropan-2-amine	5-BZT-MDMA			title=Short-acting 3,4-methylenedioxymethamphetamine (mdma) analogs incorporating benzothiazole	website=Google Patents	date=13 June 2023	url=https://patents.google.com/patent/WO2024054279A1/	access-date=23 October 2024	author=Mydecine}}
[[File:6-APBTZ_structure.png	120px	class=skin-invert-image]]	1-(1,3-Benzothiazol-6-yl)propan-2-amine	6-BZT-MDA		1896565-11-9
[[File:6-BZT-MDMA_structure.png	120px	class=skin-invert-image]]	1-(Benzo[d]thiazol-6-yl)-N-methylpropan-2-amine	6-BZT-MDMA			title=1-(1,3-benzothiazol-6-yl)-N-methylpropan-2-amine	website=PubChem	url=https://pubchem.ncbi.nlm.nih.gov/compound/171055384	access-date=23 October 2024}}
[[File:SDA.svg	120px	class=skin-invert-image]]	1-(Benzo[d][1,3]oxathiol-5-yl)propan-2-amine	SDA; 3T-MDA
[[File:SDMA structure.svg	120px	class=skin-invert-image]]	1-(Benzo[d][1,3]oxathiol-5-yl)-N-methylpropan-2-amine	SDMA; 3T-MDMA	MY100
[[File:MY101_structure.png	120px	class=skin-invert-image]]	1-(Benzo[d][1,3]oxathiol-5-yl)-N,N-dimethylpropan-2-amine		MY101		title=1-(1,3-benzoxathiol-5-yl)-N,N-dimethylpropan-2-amine	website=PubChem	url=https://pubchem.ncbi.nlm.nih.gov/compound/169291099	access-date=23 October 2024}}
[[File:MY200_structure.png	120px	class=skin-invert-image]]	1-(Benzo[d][1,3]oxathiol-6-yl)-N-methylpropan-2-amine		MY200		title=1-(1,3-benzoxathiol-6-yl)-N-methylpropan-2-amine	website=PubChem	url=https://pubchem.ncbi.nlm.nih.gov/compound/169149640	access-date=23 October 2024}}
[[File:4T-MMDA-2_structure.png	120px	class=skin-invert-image]]	6-(2-Aminopropyl)-5-methoxy-1,3-benzoxathiol	4T-MMDA-2		133787-69-6
[[File:6-APIPY_structure.png	120px	class=skin-invert-image]]	1-(Imidazo[1,2-a]pyridin-6-yl)propan-2-amine			1337128-11-6
[[File:5-APBTDZ_structure.png	120px	class=skin-invert-image]]	1-(1,2,3-Benzothiadiazol-5-yl)propan-2-amine			1380044-39-2
[[File:6-APQOX_structure.png	120px	class=skin-invert-image]]	1-(Quinoxalin-6-yl)propan-2-amine			910407-54-4
[[File:5-APBXDZ_structure.png	120px	class=skin-invert-image]]	1-(2,1,3-Benzoxadiazol-5-yl)propan-2-amine			910413-33-1
[[File:ODMA.svg	120px	class=skin-invert-image]]	1-(2,1,3-Benzoxadiazol-5-yl)-N-methylpropan-2-amine	ODMA		2567501-96-4
[[File:TDMA structure.svg	120px	class=skin-invert-image]]	1-(2,1,3-Benzothiadiazol-5-yl)-N-methylpropan-2-amine	TDMA		2302389-87-1
[[File:SeDMA.svg	120px	class=skin-invert-image]]	1-(2,1,3-Benzoselenadiazol-5-yl)-N-methylpropan-2-amine	SeDMA

References

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"1-(1-Benzothiophen-5-yl)propan-2-ylamine".
"1-(1-benzothiophen-6-yl)-N-methylpropan-2-amine".
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"1-(1,3-benzoxathiol-5-yl)-N,N-dimethylpropan-2-amine".
"1-(1,3-benzoxathiol-6-yl)-N-methylpropan-2-amine".

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