Substituted methylenedioxyphenethylamine

Methylenedioxyphenethylamine (MDPEA)

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.^[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 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 (βk-MDMA; "Methylone").

List of substituted methylenedioxyphenethylamines[]

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

Chemical Name	Abbreviations	Other Names	CAS number
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	23693-38-1
4,5-Methylenedioxy-3-methoxy-N-methylphenethylamine	MMDMPEA
3,4-Methylenedioxy-N-(2-methoxybenzyl)phenethylamine	NBOMe-MDPEA
3,4-Methylenedioxyamphetamine	MDA	"Sally, Sass, Sass-a-frass or Mellow Drug of America"	4764-17-4
2,3-Methylenedioxyamphetamine	2,3-MDA	"Love"	23693-17-6
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
	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
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		13674-05-0
4,5-Methylenedioxy-3-methoxy-N-methylamphetamine	MMDMA		172518-52-4
3,4-Methylenedioxy-N,N-dimethylamphetamine	MDDM, MDDMA		74698-50-3
3,4-Methylenedioxy-N-methyl-N-hydroxyamphetamine	MDMOH, MDMHA, MDHMA	FLEA	214414-88-7
	MDEOH, MDEHA, MDHEA	TESS, "Nextasy"
3,4-Methylenedioxy-2,5-dimethoxyamphetamine	DMMDA		15183-13-8
4,5-Methylenedioxy-2,3-dimethoxyamphetamine	DMMDA-2		15183-26-3
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
β-Methoxy-1,3-benzodioxolylbutanamine	BOH		73304-06-0
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
	BDP	K
N-Methyl-1,3-benzodioxolylpentanamine	MBDP	Methyl-K	952016-78-3
N-Ethyl-1,3-benzodioxolylpentanamine	EBDP	Ethyl-K	952016-47-6
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
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.

Chemical Name	Abbreviations	Other Names	CAS number
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
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		687603-66-3
3,4-Methylenedioxy-α-pyrrolidinohexiophenone	MDPHP		776994-64-0
3-methyl-2-(3,4-methylenedioxyphenyl)morpholine	MDPM	3,4-Methylenedioxyphenmetrazine^[2]
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	MD-4-MAR	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
1-(2,3-dihydro-1,4-benzodioxin-6-yl)-N-methylpropan-2-amine	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
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
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
1-(naphthalen-2-yl)propan-2-amine	NAP	PAL-287	18085-03-5
N-methyl-1-(naphthalen-2-yl)propan-2-amine	MNAP	Methamnetamine
1-(1-benzothiophen-5-yl)propan-2-amine	5-APBT		1368128-53-3
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-benzoxazol-5-yl)propan-2-amine			1368557-51-0
1-(1,3-benzothiazol-6-yl)propan-2-amine			1896565-11-9
1-(2,1,3-benzoxadiazol-5-yl)propan-2-amine			910413-33-1
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

References[]

^ Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine Von der Struktur zur Funktion. Nachtschatten Verlag AG. ISBN 978-3-03788-700-4.
^ 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.

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)

[1] Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine Von der Struktur zur Funktion. Nachtschatten Verlag AG. ISBN 978-3-03788-700-4.

[pmid15749360-2] 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.

[1]

[2]

v t 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 DiFMDA DMMDA DMMDA-2 EIDA MDEA MDMA (midomafetamine) MDMOH MDOH MMDA MMDA-2 MMDMA N-t-BOC-MDMA } 1-Phenylbutan-2-amines: { BDB EBDB MBDB } Phentermines: { MDMP MDPH } Benzofurans and dihydrobenzofurans: 2-MAPB 5-APB 5-APDB 5-EAPB 5-MAPB 5-MAPDB 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 ETAI MDAI MDMAI MMAI MEAI NM-2-AI TAI Aminotetralins: 6-CAT MDAT MDMAT
Cathinones	3-MMC 4-EMC 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 Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-C 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-O 2C-O-4 2C-P 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-7 2C-T-8 2C-T-9 2C-T-13 2C-T-15 2C-T-16 2C-T-17 2C-T-19 2C-T-21 2C-T-28 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

Substituted methylenedioxyphenethylamine

Contents

List of substituted methylenedioxyphenethylamines[]

Related compounds[]

See also[]

References[]

External links[]