Substituted methylenedioxyphenethylamine

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]

Methylenedioxyphenethylamine (MDPEA)

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").

List of substituted methylenedioxyphenethylamines

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

Structure	Chemical Name	Abbreviations	Other Names	CAS number	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	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	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	[2]
	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		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,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
	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
	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 number	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
	1-(1,3-Benzodioxol-5-yl)-N-methylethanamine	MDM1EA	α,N-DMMDBA	121734-65-4
	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		[3]
	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	[4][5]
	1-(1-Benzothiophen-6-yl)propan-2-amine	6-APBT
	1-(Benzo[b]thiophen-6-yl)-N-methylpropan-2-amine	6-MAPBT	MY300		[4][6]
	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			[7][8]
	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			[7][9]
	1-(Benzo[d][1,3]oxathiol-5-yl)-N-methylpropan-2-amine		MY100		[4][10]
	1-(Benzo[d][1,3]oxathiol-5-yl)-N,N-dimethylpropan-2-amine		MY101		[4][11]
	1-(Benzo[d][1,3]oxathiol-6-yl)-N-methylpropan-2-amine		MY200		[4][12]
	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

• 2Cs, DOx, 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. Dr. Matthias Grill, Novel Safrylamine derivates having prodrug properties. Patent WO 2022/053696
3. 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.
4. Mydecine (5 January 2024). "Novel short-acting psychoactive compounds of the mdma class". Google Patents. Retrieved 23 October 2024.
5. "[1-(1-Benzothiophen-5-yl)propan-2-yl](methyl)amine". PubChem. Retrieved 23 October 2024.
6. "1-(1-benzothiophen-6-yl)-N-methylpropan-2-amine". PubChem. Retrieved 23 October 2024.
7. Mydecine (13 June 2023). "Short-acting 3,4-methylenedioxymethamphetamine (mdma) analogs incorporating benzothiazole". Google Patents. Retrieved 23 October 2024.
8. "1-(1,3-benzothiazol-5-yl)-N-methylpropan-2-amine". PubChem. Retrieved 23 October 2024.
9. "1-(1,3-benzothiazol-6-yl)-N-methylpropan-2-amine". PubChem. Retrieved 23 October 2024.
10. "1-(1,3-benzoxathiol-5-yl)-N-methylpropan-2-amine". PubChem. Retrieved 23 October 2024.
11. "1-(1,3-benzoxathiol-5-yl)-N,N-dimethylpropan-2-amine". PubChem. Retrieved 23 October 2024.
12. "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)