Substituted methylenedioxyphenethylamine

Chemical structure of MDPEA, the parent compound of this family.

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 substances. ^[1]

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 phenethylamines MDxx compounds, such as MDAI, MDAT, MDPV, MDPM, and MDMAR.

Use and effects

See also: Entactogen § Doses and durations

Oral doses and durations of methylenedioxyphenethylamines (MDxx)^a

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-propargylampehtamine	>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	3′,4′-Methylenedioxy-4-methyl-5-phenyl-4,5-dihydro-1,3-oxazol-2-amine	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: [2] [3] [4] [5] [6] [7] [8] [9] [10] [11] [12] Individual: [13] [14] [15] [16] [17] [18] [19] [20]

Interactions

See also: MDMA § Interactions, Trip killer § Antidotes of other hallucinogens, Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

List of substituted methylenedioxyphenethylamines

Structure	Chemical Name	Abbreviations	Other Names	CAS #	Ref
	3,4-Methylenedioxyphenethylamine	MDPEA	Homopiperonylamine	1484-85-1
	3,4-Methylenedioxy-N-methylphenethylamine	MDMPEA	Homarylamine	451-77-4
	β,N-Dimethyl-3,4-methylenedioxyphenethylamine	β,N-DM-MDPEA	MDDMPEA	83329-26-4
	4,5-Methylendioxy-3-methoxy-phenethylamine	MMDPEA	Lophophine, Homomyristicylamine, 2C-MMDA, 5-Methoxy-MDPEA	23693-38-1
	4,5-Methylenedioxy-3-methoxy-N-methylphenethylamine	MMDMPEA	N-Methyllophophine
	2-Methoxy-4,5-methylenedioxyphenethylamine	2C-MMDA-2	MMDPEA-2; 6-Methoxy-MDPEA	497096-69-2
	3,4-Methylenedioxy-N-(2-methoxybenzyl)phenethylamine	NBOMe-MDPEA	MDPEA-NBOMe
	3-Methoxy-4,5-methylenedioxy-N-(2-methoxybenzyl)phenethylamine	Lophophine-NBOMe	MMDPEA-NBOMe; 5-Methoxy-MDPEA-NBOMe
	N-(2-Methoxybenzyl)-2-methoxy-4,5-methylenedioxyphenethylamine	2C2-NBOMe	2C-MMDA-2-NBOMe; NBOMe-MMDPEA-2; 6-Methoxy-MDPEA-NBOMe
	3,4-Methylenedioxyamphetamine	MDA	"Sally, Sass, Sass-a-frass or Mellow Drug of America"	4764-17-4
	2,3-Methylenedioxyamphetamine	2,3-MDA	ORTHO-MDA	23693-17-6
	2,3-Methylenedioxymethamphetamine	2,3-MDMA	ORTHO-MDMA	168967-99-5
	3,4-Methylenedioxy-N-methylamphetamine	MDMA, MDM	"Molly", "Ecstasy", "Adam", etc.	42542-10-9
	3,4-Methylenedioxy-N-ethylamphetamine	MDEA, MDE	"Eve"	82801-81-8
	3,4-Methylenedioxy-N-propylamphetamine	MDPR, MDPA		74698-36-5
	3,4-Methylenedioxy-N-isopropylamphetamine	MDIP, MDIPR, MDIPA		74698-37-6
	3,4-Methylenedioxy-N-butylamphetamine	MDBU, MDBA		74698-38-7
	3,4-Methylenedioxy-N-isobutylamphetamine	MDIB, MDIBA
	3,4-Methylenedioxy-N-allylamphetamine	MDAL, MDAA		74698-45-6
	3,4-Methylenedioxy-N-benzylamphetamine	MDBZ, MDBZA		65033-29-6
	3,4-Methylenedioxy-N-cyclopropylmethylamphetamine	MDCPM, MDCPMA, MDCA		22698-08-4
	3,4-Methylenedioxy-N-hydroxyamphetamine	MDOH, MDHA, MDH		74698-47-8
	3,4-Methylenedioxy-N-(2-hydroxyethyl)amphetamine	MDHOET, MDHEA		74698-43-4
	3,4-Methylenedioxy-N-methoxyamphetamine	MDMEO, MDMEOA		74698-48-9
	3,4-Methylenedioxy-N-(2-methoxyethyl)amphetamine	MDMEOET, MDMEA		74698-44-5
	3,4-Methylenedioxy-N-propargylamphetamine	MDPL, MDPLA		74698-46-7
	N-(L-Lysinamidyl)-3,4-methylenedioxyamphetamine	Lys-MDA		1391487-26-5	[21]
	N-(L-Lysinamidyl)-3,4-methylenedioxy-N-methylamphetamine	Lys-MDMA		2763054-67-5
	3,4-Methylenedioxy-2-methylamphetamine	2-Methyl-MDA		691876-73-0
	4,5-Methylenedioxy-3-methylamphetamine	5-Methyl-MDA		749191-14-8
	4,5-Methylenedioxy-2-methylamphetamine	6-Methyl-MDA		246861-21-2
	4,5-Methylenedioxy-3-methoxy-amphetamine	MMDA	5-Methoxy-MDA	13674-05-0
	4,5-Methylenedioxy-3-methoxy-N-methylamphetamine	MMDMA	N-Methyl-MMDA; 5-Methoxy-MDMA	172518-52-4
	2-Methoxy-4,5-methylenedioxyamphetamine	MMDA-2	6-Methoxy-MDA	23693-18-7
	2-Ethoxy-4,5-methylenedioxyamphetamine	EDMA-2
	3,4-Methylenedioxy-N,N-dimethylamphetamine	MDDM, MDDMA		74698-50-3
	3,4-Methylenedioxy-N,N,N-trimethylamphetamine	MDTMA
	3,4-Methylenedioxy-N-methyl-N-hydroxyamphetamine	MDMOH, MDMHA, MDHMA	FLEA	214414-88-7
	3,4-Methylenedioxy-N-ethyl-N-hydroxyamphetamine	MDEOH, MDEHA, MDHEA		866417-59-6
	3,4-Methylenedioxy-2,5-dimethoxyamphetamine	DMMDA		15183-13-8
	4,5-Methylenedioxy-2,3-dimethoxyamphetamine	DMMDA-2		15183-26-3
	2-Chloro-4,5-methylenedioxyamphetamine	6-Chloro-MDA	2-Cl-4,5-MDA	46319-44-2
	2-Chloro-4,5-methylenedioxy-N-methylamphetamine	6-Chloro-MDMA	2-Cl-4,5-MDMA	319920-71-3
	2-Bromo-4,5-methylenedioxyamphetamine	6-Bromo-MDA	2-Br-4,5-MDA	151920-03-5
	2-Bromo-4,5-methylenedioxy-N-methylamphetamine	6-Bromo-MDMA	2-Br-4,5-MDMA	2170110-34-4
	3,4-Methylenedioxyphentermine	MDPH		39235-63-7
	3,4-Methylenedioxy-N-methylphentermine	MDMP		81262-69-3
	3,4-Methylenedioxycathinone	βk-MDA, MDC		80535-73-5
	3,4-Methylenedioxy-N-methylcathinone	βk-MDMA, MDMC	Methylone	186028-79-5
	3,4-Methylenedioxy-N-ethylcathinone	βk-MDEA, MDEC	Ethylone	1112937-64-0
	3,4-Methylenedioxy-5-methyl-N-ethylcathinone	5-Me-βk-MDEA	5-Methylethylone	1364933-82-3
	1,3-Benzodioxolylbutanamine	BDB	J	42542-07-4
	N-Methyl-1,3-benzodioxolylbutanamine	MBDB	Methyl-J; "Eden"	135795-90-3
	N-Ethyl-1,3-benzodioxolylbutanamine	EBDB	Ethyl-J	167394-39-0
	3,4-Methylenedioxy-β-methoxyphenethylamine	BOH	β-MeO-MDPEA	73304-06-0
	3,4-Methylenedioxy-β-methoxyamphetamine	3C-BOH	β-MeO-MDA	?
	β-Keto-N-methyl-1,3-benzodioxolylbutanamine	βk-MBDB	Butylone	802575-11-7
	β-Keto-N-ethyl-1,3-benzodioxolylbutanamine	βk-EBDB	Eutylone	802855-66-9
	β-Keto-N,N-dimethyl-1,3-benzodioxolylbutanamine	βk-DMBDB	Dibutylone	802286-83-5
	1,3-Benzodioxolylpentanamine	BDP	K	220491-69
	N-Methyl-1,3-benzodioxolylpentanamine	MBDP	Methyl-K	952016-78-3
	N-Ethyl-1,3-benzodioxolylpentanamine	EBDP	Ethyl-K	952016-47-6
	1-(3,4-Methylenedioxyphenyl)-2-propylaminopentane	MPAP	PBDP
	2-(1,3-Benzodioxol-5-yl)-1-(propan-2-yl)-N-methylethanamine	α-iPr-MDMPEA	UWA-104
	2-(1,3-Benzodioxol-5-yl)-1-cyclopropyl-N-methylethanamine	α-cPr-MDMPEA	UWA-101	1350821-24-7
	2-(1,3-Benzodioxol-5-yl)-N-methyl-1-phenylethanamine	α-Ph-MDMPEA	UWA-001	1350821-28-1
	β-Keto-N-methyl-1,3-benzodioxolylpentanamine	βk-MBDP, βk-Methyl-K	Pentylone	698963-77-8
	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
	3,4-Dimethoxyamphetamine	3,4-DMA		120-26-3
	3,4-Dimethoxymethamphetamine	3,4-DMMA		33236-61-2
	3,4-Methylenedioxyphenyl-1-propene		Isosafrole	120-58-1
	3,4-Methylenedioxyphenyl-2-propene		Safrole, Shikimol	94-59-7
	4,5-Methylenedioxyphenyl-3-methoxy-2-propene		Myristicin	607-91-0
	3,4-Methylenedioxyphenyl-1-propanone	MDP1P		28281-49-4
	3,4-Methylenedioxyphenyl-2-propanone	MDP2P		4676-39-5
	3,4-Methylenedioxybenzaldehyde		Piperonal	120-57-0
	3,4-Methylenedioxyphenol		Sesamol	533-31-3
	5-(3,4-Methylenedioxyphenyl)-2,4-pentadienoyl-2-piperidine		Piperine (also chavicine)	94-62-2
	3,4-Methylenedioxycinnamylpiperidine		Ilepcimide	23434-86-8
	3,4-methylenedioxy-α,N-dimethylbenzylamine	MDM1EA	α,N-DMMDBA	121734-65-4
	3,4-methylenedioxy-α-ethylbenzylamine	ALPHA		127292-42-6
	3,4-methylenedioxy-α-ethyl-N-methylbenzylamine	M-ALPHA		127292-43-7
	4-(1,3-Benzodioxol-5-yl)butan-2-amine		Homo-MDA, HMDA	40742-32-3
	4-(1,3-Benzodioxol-5-yl)-N-methylbutan-2-amine		Homo-MDMA, HMDMA	108248-08-4
	trans-4-(4-Fluorophenyl)-3-[(3,4-methylenedioxy)phenoxy]methylpiperidine		Paroxetine	61869-08-7
	5,6-Methylenedioxy-2-aminoindane	5,6-MDAI, MDAI		132741-81-2
	5,6-Methylenedioxy-N-methyl-2-aminoindane	5,6-MDMAI, MDMAI		132741-82-3
	6,7-Methylenedioxy-2-aminotetralin	6,7-MDAT		101625-35-8
	6,7-Methylenedioxy-2-methylaminotetralin	6,7-MDMAT		34620-52-5
	3,4-Methylenedioxy-1-benzylpiperazine	MDBZP	Piperonylpiperazine	32231-06-4
	3,4-Methylenedioxy-α-pyrrolidinopropiophenone	MDPPP		783241-66-7
	3',4'-Methylenedioxy-α-pyrrolidinobutiophenone	MDPBP		784985-33-7
	3,4-Methylenedioxy-α-pyrrolidinopentiophenone	MDPV	"Monkey Dust"	687603-66-3
	3,4-Methylenedioxy-α-pyrrolidinohexiophenone	MDPHP	Also known as "Monkey Dust"	776994-64-0
	Methylenedioxyphenmetrazine	MDPM	3,4-Methylenedioxyphenmetrazine		[22]
	Methyl (1,3-benzodioxol-5-yl)(piperidin-2-yl)acetate	MDMPH	3,4-Methylenedioxymethylphenidate
	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
	1-(4-Aminophenyl)-4-methyl-7,8-methylenedioxy-2,3-benzodiazepine	GYKI-52895		869360-93-0
	3,4-Ethylidenedioxyamphetamine	EIDA		125299-84-5
	3,4-Isopropylidenedioxyamphetamine	IDA
	1-(2,2-Difluoro-1,3-benzodioxol-5-yl)propan-2-amine	DFMDA		910393-51-0
	6-(2-Aminopropyl)-5-methoxy-1,3-benzoxathiol	4T-MMDA-2		133787-69-6
	3,4-Ethylenedioxyamphetamine	EDA	EDA-6	15033-67-7
	3,4-Ethylenedioxy-N-methylamphetamine	EDMA		133787-66-3
	1-(2,3-Dihydro-1-benzofuran-5-yl)propan-2-amine	5-APDB		152624-03-8
	1-(1,3-Dihydro-2-benzofuran-5-yl)-N-methylpropan-2-amine	IBF5MAP		201407-56-9
	1-(2,3-Dihydro-1-benzofuran-6-yl)propan-2-amine	6-APDB		152623-93-3
	1-(1-Benzofuran-5-yl)propan-2-amine	5-APB		286834-81-9
	N-Methyl-1-(1-benzofuran-5-yl)propan-2-amine	5-MAPB		1354631-77-8
	N-Ethyl-1-(1-benzofuran-5-yl)propan-2-amine	5-EAPB		1445566-01-7
	N-Methyl-1-(1-benzofuran-5-yl)butan-2-amine	5-MBPB	5-MABB
	1-(1-Benzofuran-6-yl)propan-2-amine	6-APB		286834-85-3
	N-Methyl-1-(1-benzofuran-6-yl)propan-2-amine	6-MAPB		1354631-79-0
	6-(2-Methylaminobutyl)benzofuran	6-MBPB	6-MABB
	1-(2,3-Dihydro-1H-inden-5-yl)propan-2-amine	5-APDI	IAP	13396-94-6
	1-(2,3-Dihydro-1H-inden-5-yl)-N-methylpropan-2-amine	5-MAPDI	IMP	1310153-27-5
	1-(5,6,7,8-Tetrahydronaphthalen-2-yl)propan-2-amine	6-APT	TAP	3160-20-1
	2-(Pyrrolidin-1-yl)-1-(5,6,7,8-tetrahydronaphthalen-2-yl)pentan-1-one	TH-PVP		2304915-07-7
	1-(Naphthalen-2-yl)propan-2-amine	NAP	PAL-287	18085-03-5
	N-Methyl-1-(naphthalen-2-yl)propan-2-amine	MNAP	Methamnetamine; PAL-1046	1178720-66-5
	N-Ethyl-1-naphthalen-2-ylpropan-2-amine	ENAP	PAL-1045
	2-(Methylamino)-1-(naphthalene-2-yl) propan-1-one	BMAPN	βk-Methamnetamine; 2-Naphthylmethcathinone	109453-73-8
	1-(1-Benzothiophen-5-yl)propan-2-amine	5-APBT		1368128-53-3
	1-(Benzo[b]thiophen-5-yl)-N-methylpropan-2-amine	5-MAPBT	MY400	2613382-32-2	[23] [24]
	1-(1-Benzothiophen-6-yl)propan-2-amine	6-APBT
	1-(Benzo[b]thiophen-6-yl)-N-methylpropan-2-amine	6-MAPBT	MY300		[23] [25]
	1-(1H-Indol-5-yl)propan-2-amine	5-API	5-IT	3784-30-3
	1-(1H-1,3-Benzodiazol-5-yl)propan-2-amine			752145-76-9
	1-(1,3-Benzodiazol-5-yl)-N-methylpropan-2-amine
	1-(1,3-Benzoxazol-5-yl)propan-2-amine			1368557-51-0
	1-(1,3-Benzothiazol-5-yl)propan-2-amine	5-BZT-MDA
	1-(Benzo[d]thiazol-5-yl)-N-methylpropan-2-amine	5-BZT-MDMA			[26] [27]
	1-(1,3-Benzothiazol-6-yl)propan-2-amine	6-BZT-MDA		1896565-11-9
	1-(Benzo[d]thiazol-6-yl)-N-methylpropan-2-amine	6-BZT-MDMA			[26] [28]
	1-(Benzo[d][1,3]oxathiol-5-yl)-N-methylpropan-2-amine		MY100		[23] [29]
	1-(Benzo[d][1,3]oxathiol-5-yl)-N,N-dimethylpropan-2-amine		MY101		[23] [30]
	1-(Benzo[d][1,3]oxathiol-6-yl)-N-methylpropan-2-amine		MY200		[23] [31]
	1-(Imidazo[1,2-a]pyridin-6-yl)propan-2-amine			1337128-11-6
	1-(1,2,3-Benzothiadiazol-5-yl)propan-2-amine			1380044-39-2
	1-(Quinoxalin-6-yl)propan-2-amine			910407-54-4
	1-(2,1,3-Benzoxadiazol-5-yl)propan-2-amine			910413-33-1
	1-(2,1,3-Benzoxadiazol-5-yl)-N-methylpropan-2-amine	ODMA		2567501-96-4
	1-(2,1,3-Benzothiadiazol-5-yl)-N-methylpropan-2-amine	TDMA		2302389-87-1
	1-(2,1,3-Benzoselenadiazol-5-yl)-N-methylpropan-2-amine	SeDMA

See also

• Substituted methoxyphenethylamine
• 2Cs, DOx, 4Cs, 25-NB
• Substituted amphetamines
• Substituted benzofurans
• Substituted cathinones
• Substituted phenethylamines
• Substituted phenmetrazines
• Substituted tryptamines
• PiHKAL
• The Shulgin Index

References

1. Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: From Structure to Function. Nachtschatten Verlag AG. ISBN   978-3-03788-700-4.
2. Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN   0-9630096-0-5. OCLC   25627628.
3. Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. pp. 465–468, 555–557, 578–630, 659–660, 721, 745–746, 828–831, 905–906. ISBN   978-3-03788-700-4. OCLC   858805226. Archived from the original on 21 August 2025.
4. Oeri HE (May 2021). "Beyond ecstasy: Alternative entactogens to 3,4-methylenedioxymethamphetamine with potential applications in psychotherapy". J Psychopharmacol. 35 (5): 512–536. doi:10.1177/0269881120920420. PMC   8155739 . PMID   32909493.
5. Shulgin, A.; Manning, T.; Daley, P.F. (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds . Vol. 1. Berkeley: Transform Press. ISBN   978-0-9630096-3-0.
6. Jacob P, Shulgin AT (1994). "Structure-Activity Relationships of the Classic Hallucinogens and Their Analogs". In Lin GC, Glennon RA (eds.). Hallucinogens: An Update (PDF). National Institute on Drug Abuse Research Monograph Series. Vol. 146. National Institute on Drug Abuse. pp. 74–91. PMID   8742795. Archived from the original on 13 July 2025.
7. Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN   978-0-12-433951-4. Archived from the original on 13 July 2025.
8. Shulgin AT (1976). "Psychotomimetic Agents". In Gordon M (ed.). Psychopharmacological Agents: Use, Misuse and Abuse. Medicinal Chemistry: A Series of Monographs. Vol. 4. Academic Press. pp. 59–146. doi:10.1016/b978-0-12-290559-9.50011-9. ISBN   978-0-12-290559-9.
9. Shulgin AT (1978). "Psychotomimetic Drugs: Structure-Activity Relationships". In Iversen LL, Iversen SD, Snyder SH (eds.). Stimulants. Boston, MA: Springer US. pp. 243–333. doi:10.1007/978-1-4757-0510-2_6. ISBN   978-1-4757-0512-6.
10. Luethi D, Liechti ME (October 2018). "Monoamine Transporter and Receptor Interaction Profiles in Vitro Predict Reported Human Doses of Novel Psychoactive Stimulants and Psychedelics". Int J Neuropsychopharmacol. 21 (10): 926–931. doi:10.1093/ijnp/pyy047. PMC   6165951 . PMID   29850881.
11. Ballentine, Galen; Friedman, Samuel Freesun; Bzdok, Danilo (March 2022). "Trips and neurotransmitters: Discovering principled patterns across 6850 hallucinogenic experiences". Sci Adv. 8 (11) eabl6989. Bibcode:2022SciA....8L6989B. doi:10.1126/sciadv.abl6989. PMC   8926331 . PMID   35294242.
12. Luethi D, Liechti ME (April 2020). "Designer drugs: mechanism of action and adverse effects". Arch Toxicol. 94 (4): 1085–1133. doi:10.1007/s00204-020-02693-7. PMC   7225206 . PMID   32249347.
13. Liechti ME, Holze F (2022). "Dosing Psychedelics and MDMA". Curr Top Behav Neurosci. 56: 3–21. doi:10.1007/7854_2021_270. PMID   34734392.
14. Anderson GM, Braun G, Braun U, Nichols DE, Shulgin AT (1978). "Absolute Configuration and Psychotomimetic Activity" (PDF). In Barnett G, Trsic M, Willette RE (eds.). QuaSAR: Quantitative Structure Activity Relationships Of Analgesics, Narcotic Antagonists, And Hallucinogens (PDF). National Institute on Drug Abuse Research Monograph Series. Vol. 22. National Institute on Drug Abuse. pp. 8–15. PMID   101890.
15. Straumann I, Avedisian I, Klaiber A, Varghese N, Eckert A, Rudin D, et al. (August 2024). "Acute effects of R-MDMA, S-MDMA, and racemic MDMA in a randomized double-blind cross-over trial in healthy participants". Neuropsychopharmacology. 50 (2): 362–371. doi: 10.1038/s41386-024-01972-6 . PMC   11631982 . PMID   39179638.
16. Baggott MJ, Garrison KJ, Coyle JR, Galloway GP, Barnes AJ, Huestis MA, Mendelson JE (2019-03-15). "Effects of the Psychedelic Amphetamine MDA (3,4-Methylenedioxyamphetamine) in Healthy Volunteers". Journal of Psychoactive Drugs. 51 (2): 108–117. doi:10.1080/02791072.2019.1593560. PMID   30967099. S2CID   106410946.
17. Straumann I, Vizeli P, Avedisian I, Erne L, Noorshams D, Vukalovic I, Eckert A, Luethi D, Rudin D, Liechti ME (September 2025). "Acute effects of MDMA, MDA, lysine-MDMA, and lysine-MDA in a randomized, double-blind, placebo-controlled, crossover trial in healthy participants". Neuropsychopharmacology. doi: 10.1038/s41386-025-02248-3 . PMID   40999236.
18. Angerer V, Schmid Y, Franz F, Gnann H, Speer JM, Gnann A, Helmecke S, Buchwald A, Brandt SD, Passie T, Liechti ME, Auwärter V (September 2024). "Acute psychotropic, autonomic, and endocrine effects of 5,6-methylenedioxy-2-aminoindane (MDAI) compared with 3,4-methylenedioxymethamphetamine (MDMA) in human volunteers: A self-administration study". Drug Test Anal. 16 (9): 1002–1011. doi: 10.1002/dta.3622 . PMID   38056906.
19. Corkery JM, Elliott S, Schifano F, Corazza O, Ghodse AH (July 2013). "MDAI (5,6-methylenedioxy-2-aminoindane; 6,7-dihydro-5H-cyclopenta[f][1,3]benzodioxol-6-amine; 'sparkle'; 'mindy') toxicity: a brief overview and update". Hum Psychopharmacol. 28 (4): 345–355. doi:10.1002/hup.2298. PMID   23881883. Doses range from 70–300 mg; typical doses appear to be 150–200 mg of active ingredient (equivalent to half of a 300 mg capsule or a whole 200 mg capsule). A 'low' dose of 70–80 mg produces subtle but noticeable effects; a strong dose is considered to be 250–300 mg. Redosing often occurs; typically a 'booster' of 100–150 mg is administered after the initial positive effects have worn off (Drugs-Forum, 2009a; Bluelight, 2010a; Herbalhighs, 2012a; Partyvibe, 2012).
20. Zawilska JB (2015). ""Legal Highs"--An Emerging Epidemic of Novel Psychoactive Substances". Int Rev Neurobiol. 120: 273–300. doi:10.1016/bs.irn.2015.02.009. PMID   26070762. Table 2 Dosage, Onset, and Duration of Action of Psychostimulatory NPS [...] Compound: Mephedrone. Doses: [...] 150–250 mg orally [...] Duration: 2–4 h [...] Compound: MDPV. [...] Doses: 3–15 mg (typically 5–10 mg). [...] Duration: [...] up to 7 h (oral) [...] Compound: MDAI. [...] Doses: 70–300 mg. [...]
21. Dr. Matthias Grill, Novel Safrylamine derivates having prodrug properties. Patent WO 2022/053696
22. Świst M, Wilamowski J, Zuba D, Kochana J, Parczewski A (May 2005). "Determination of synthesis route of 1-(3,4-methylenedioxyphenyl)-2-propanone (MDP-2-P) based on impurity profiles of MDMA". Forensic Science International. 149 (2–3): 181–92. doi:10.1016/j.forsciint.2004.06.016. PMID   15749360.
23. Mydecine (5 January 2024). "Novel short-acting psychoactive compounds of the mdma class". Google Patents. Retrieved 23 October 2024.
24. "[1-(1-Benzothiophen-5-yl)propan-2-yl](methyl)amine". PubChem. Retrieved 23 October 2024.
25. "1-(1-benzothiophen-6-yl)-N-methylpropan-2-amine". PubChem. Retrieved 23 October 2024.
26. Mydecine (13 June 2023). "Short-acting 3,4-methylenedioxymethamphetamine (mdma) analogs incorporating benzothiazole". Google Patents. Retrieved 23 October 2024.
27. "1-(1,3-benzothiazol-5-yl)-N-methylpropan-2-amine". PubChem. Retrieved 23 October 2024.
28. "1-(1,3-benzothiazol-6-yl)-N-methylpropan-2-amine". PubChem. Retrieved 23 October 2024.
29. "1-(1,3-benzoxathiol-5-yl)-N-methylpropan-2-amine". PubChem. Retrieved 23 October 2024.
30. "1-(1,3-benzoxathiol-5-yl)-N,N-dimethylpropan-2-amine". PubChem. Retrieved 23 October 2024.
31. "1-(1,3-benzoxathiol-6-yl)-N-methylpropan-2-amine". PubChem. Retrieved 23 October 2024.

External links

• PiHKAL ("Phenethylamines i Have Known And Loved") by Alexander "Sasha" Shulgin (1991)
• Psychotomimetic Drugs: Structure-Activity Relationships by Alexander "Sasha" Shulgin (1978)
• Mescaline: The Chemistry and Pharmacology of its Analogues by Alexander "Sasha" Shulgin (1972)