Substituted methylenedioxyphenethylamine

Substituted methylenedioxy- phenethylamines (MDxx) are a large chemical class of derivatives of the phenethylamines, which includes many psychoactive drugs that act as entactogens, psychedelics, and/or stimulants, as well as entheogens. These agents are used as research chemicals, designer drugs and as recreational substances.

When referring to MDMA and its counterparts, the term 'MDxx' is often used with the exception of MDPV.^{[citation needed]}

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 mentionables 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 (bk-MDMA; "Methylone").

List of substituted methylenedioxyphenethylamines

The compounds most commonly regarded as comprising the family of MDxx derivatives include:

Chemical Name	Abbreviations	Other Names	Chemical Class
3,4-Methylenedioxyphenethylamine	MDPEA	Homopiperonylamine	Phenylethylamine
3,4-Methylenedioxy-N-methylphenethylamine	MDMPEA	Homarylamine	Phenylethylamine
4,5-Methylendioxy-3-methoxy-phenethylamine	MMDPEA	Lophophine, Homomyristicylamine	Phenylethylamine
4,5-Methylenedioxy-3-methoxy-N-methylphenethylamine	MMDMPEA		Phenylethylamine
3,4-Methylenedioxyamphetamine	MDA	"Sally, Sass, Sass-a-frass or Mellow Drug of America"	Phenylpropylamine
2,3-Methylenedioxyamphetamine	2,3-MDA	"Love"	Phenylpropylamine
3,4-Methylenedioxy-N-methylamphetamine	MDMA, MDM	"Molly", "Ecstasy", "Adam", etc.	Phenylpropylamine
3,4-Methylenedioxy-N-ethylamphetamine	MDEA, MDE	"Eve"	Phenylpropylamine
3,4-Methylenedioxy-N-propylamphetamine	MDPR, MDPA		Phenylpropylamine
3,4-Methylenedioxy-N-isopropylamphetamine	MDIP, MDIPR, MDIPA		Phenylpropylamine
3,4-Methylenedioxy-N-butylamphetamine	MDBU, MDBA		Phenylpropylamine
3,4-Methylenedioxy-N-isobutylamphetamine	MDIB, MDIBA		Phenylpropylamine
3,4-Methylenedioxy-N-allylamphetamine	MDAL, MDAA		Phenylpropylamine
3,4-Methylenedioxy-N-benzylamphetamine	MDBZ, MDBZA		Phenylpropylamine
3,4-Methylenedioxy-N-cyclopropylmethylamphetamine	MDCPM, MDCPMA, MDCA		Phenylpropylamine
3,4-Methylenedioxy-N-hydroxyamphetamine	MDOH, MDHA, MDH		Phenylpropylamine
3,4-Methylenedioxy-N-(2-hydroxyethyl)amphetamine	MDHOET, MDHEA		Phenylpropylamine
3,4-Methylenedioxy-N-methoxyamphetamine	MDMEO, MDMEOA		Phenylpropylamine
3,4-Methylenedioxy-N-(2-methoxyethyl)amphetamine	MDMEOET, MDMEA		Phenylpropylamine
3,4-Methylenedioxy-N-propargylamphetamine	MDPL, MDPLA		Phenylpropylamine
3,4-Methylenedioxy-2-methylamphetamine	2-Methyl-MDA		Phenylpropylamine
4,5-Methylenedioxy-3-methylamphetamine	5-Methyl-MDA		Phenylpropylamine
4,5-Methylenedioxy-2-methylamphetamine	6-Methyl-MDA		Phenylpropylamine
4,5-Methylenedioxy-3-methoxy-amphetamine	MMDA		Phenylpropylamine
4,5-Methylenedioxy-3-methoxy-N-methylamphetamine	MMDMA		Phenylpropylamine
3,4-Methylenedioxy-N,N-dimethylamphetamine	MDDM, MDDMA		Phenylpropylamine
3,4-Methylenedioxy-N-methyl-N-hydroxyamphetamine	MDMOH, MDMHA, MDHMA	FLEA	Phenylpropylamine
3,4-Methylenedioxy-N-ethyl-N-hydroxyamphetamine	MDEOH, MDEHA, MDHEA	TESS, "Nextasy"	Phenylpropylamine
3,4-Methylenedioxy-2,5-dimethoxyamphetamine	DMMDA		Phenylpropylamine
4,5-Methylenedioxy-2,3-dimethoxyamphetamine	DMMDA-2		Phenylpropylamine
3,4-Methylenedioxyphentermine	MDPH		Phenylpropylamine
3,4-Methylenedioxy-N-methylphentermine	MDMP, MDMPH		Phenylpropylamine
3,4-Methylenedioxycathinone	bk-MDA, MDC		Phenylpropylamine
3,4-Methylenedioxy-N-methylcathinone	bk-MDMA	Methylone	Phenylpropylamine
3,4-Methylenedioxy-N-ethylcathinone	bk-MDEA, MDEC	Ethylone	Phenylpropylamine
1,3-Benzodioxolylbutanamine	BDB	J	Phenylbutylamine
N-Methyl-1,3-benzodioxolylbutanamine	MBDB	Methyl-J; "Eden"	Phenylbutylamine
N-Ethyl-1,3-benzodioxolylbutanamine	EBDB	Ethyl-J	Phenylbutylamine
β-Hydroxy-1,3-benzodioxolylbutanamine	HBDB, BOH	Hydroxy-J	Phenylbutylamine
β-Keto-N-methyl-1,3-benzodioxolylbutanamine	bk-MBDB	Butylone	Phenylbutylamine
β-Keto-N,N-dimethyl-1,3-benzodioxolylbutanamine	bk-DMBDB	Dibutylone	Phenylbutylamine
1,3-Benzodioxolylpentanamine	BDP	K	Phenylpentylamine
N-Methyl-1,3-benzodioxolylpentanamine	MBDP	Methyl-K	Phenylpentylamine
N-Ethyl-1,3-benzodioxolylpentanamine	EBDP	Ethyl-K	Phenylpentylamine
β-Keto-N-methyl-1,3-benzodioxolylpentanamine	bk-MBDP, bk-Methyl-K	Pentylone	Phenylpentylamine

In addition, there are a number of other compounds that, while in the technical sense not phenethylamine derivatives, still have some structural and pharmacological similarities to the methylenedioxyphenethylamines. This makes them useful for comparison.

Chemical Name	Abbreviations	Other Names	Chemical Class
3,4-Methylenedioxyphenyl-1-propene		Isosafrole	Phenylpropene
3,4-Methylenedioxyphenyl-2-propene		Safrole, Shikimol	Phenylpropene
4,5-Methylenedioxyphenyl-3-methoxy-2-propene		Myristicin	Phenylpropene
3,4-Methylenedioxyphenyl-1-propanone	MDP1P		Phenylpropanone
3,4-Methylenedioxyphenyl-2-propanone	MDP2P		Phenylpropanone
5,6-Methylenedioxy-2-aminoindane	5,6-MDAI, MDAI		Aminoindane
5,6-Methylenedioxy-N-methyl-2-aminoindane	5,6-MDMAI, MDMAI		Aminoindane
6,7-Methylenedioxy-2-aminotetralin	6,7-MDAT		Aminotetralin
3,4-Methylenedioxybenzaldehyde		Piperonal	Benzaldehyde
3,4-Methylenedioxyphenol		Sesamol	Phenols
5-(3,4-Methylenedioxyphenyl)-2,4-pentadienoyl-2-piperidine		Piperine (also chavicine)	Piperidine
3,4-Methylenedioxycinnamylpiperidine		Ilepcimide	Piperidine
trans-4-(4-Fluorophenyl)-3-[(3,4-methylenedioxy)phenoxy]methylpiperidine		Paroxetine	Piperidine
3,4-Methylenedioxy-1-benzylpiperazine	MDBZP	Piperonylpiperazine	Piperazine
3,4-Methylenedioxy-1-benzyl chloride	MDBZC	Piperonyl chloride	Benzyl halide
3,4-Methylenedioxy-α-pyrrolidinopropiophenone	MDPPP		Pyrrolidinoalkylphenone
3',4'-Methylenedioxy-α-pyrrolidinobutiophenone	MDPBP		Pyrrolidinoalkylphenone
1-(4-aminophenyl)-4-methyl-7,8-methylenedioxy-2,3-benzodiazepine	GYKI-52895		2,3-Benzodiazepine

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v t e 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	3-MMC 4-EMC BK-5-MAPB Brephedrone Butylone Dimethylone Ethylone Eutylone Flephedrone Mephedrone Methedrone Methylone TH-PVP
Tryptamines	4-Methyl-αET αET αMT
Chemical classes	Substituted amphetamine Sub. benzofuran Sub. cathinone Sub. MDPEA Sub. PEA Sub. tryptamine

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

List of substituted methylenedioxyphenethylamines

See also

External links