Substituted methylenedioxyphenethylamine explained

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 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:

Structure	Chemical Name	Abbreviations	Other Names	CAS number	Ref
		MDPEA	Homopiperonylamine	1484-85-1
		MDMPEA	Homarylamine	451-77-4
	β,N-Dimethyl-3,4-methylenedioxyphenethylamine	β,N-DM-MDPEA	MDDMPEA	83329-26-4
		MMDPEA	Lophophine, Homomyristicylamine	23693-38-1
	4,5-Methylenedioxy-3-methoxy-N-methylphenethylamine	MMDMPEA
	3,4-Methylenedioxy-N-(2-methoxybenzyl)phenethylamine	NBOMe-MDPEA
		MDA	"Sally, Sass, Sass-a-frass or Mellow Drug of America"	4764-17-4
		2,3-MDA	"Love"	23693-17-6
		MDMA, MDM	"Molly", "Ecstasy", "Adam", etc.	42542-10-9
		MDEA, MDE	"Eve"	82801-81-8
		MDPR, MDPA		74698-36-5
		MDIP, MDIPR, MDIPA		74698-37-6
		MDBU, MDBA		74698-38-7
		MDIB, MDIBA
		MDAL, MDAA		74698-45-6
		MDBZ, MDBZA		65033-29-6
		MDCPM, MDCPMA, MDCA		22698-08-4
		MDOH, MDHA, MDH		74698-47-8
		MDHOET, MDHEA		74698-43-4
		MDMEO, MDMEOA		74698-48-9
		MDMEOET, MDMEA		74698-44-5
		MDPL, MDPLA		74698-46-7
	N-(L-lysinamidyl)-3,4-methylenedioxyamphetamine			1391487-26-5	[2]
		2-Methyl-MDA		691876-73-0
		5-Methyl-MDA		749191-14-8
		6-Methyl-MDA		246861-21-2
		MMDA		13674-05-0
		MMDMA		172518-52-4
		MDDM, MDDMA		74698-50-3
		MDMOH, MDMHA, MDHMA	FLEA	214414-88-7
		MDEOH, MDEHA, MDHEA	TESS, "Nextasy"
		DMMDA		15183-13-8
		DMMDA-2		15183-26-3
		MDPH		39235-63-7
		MDMP		81262-69-3
		βk-MDA, MDC		80535-73-5
		βk-MDMA, MDMC	Methylone	186028-79-5
		βk-MDEA, MDEC	Ethylone	1112937-64-0
		5-Me-βk-MDEA	5-Methylethylone	1364933-82-3
		BDB	J	42542-07-4
		MBDB	Methyl-J; "Eden"	135795-90-3
		EBDB	Ethyl-J	167394-39-0
		BOH		73304-06-0
		βk-MBDB	Butylone	802575-11-7
		βk-EBDB	Eutylone	802855-66-9
		βk-DMBDB	Dibutylone	802286-83-5
		BDP	K
		MBDP	Methyl-K	952016-78-3
		EBDP	Ethyl-K	952016-47-6
	2-(1,3-Benzodioxol-5-yl)-1-(propan-2-yl)-N-methylethanamine	α-iPr-MDMPEA	UWA-104
		α-cPr-MDMPEA	UWA-101	1350821-24-7
		α-Ph-MDMPEA	UWA-001
		βk-MBDP, βk-Methyl-K	Pentylone	698963-77-8
		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.

Structure	Chemical Name	Abbreviations	Other Names	CAS number	Ref
			Isosafrole	120-58-1
			Safrole, Shikimol	94-59-7
			Myristicin	607-91-0
		MDP1P		28281-49-4
		MDP2P		4676-39-5
			Piperonal	120-57-0
			Sesamol	533-31-3
			Piperine (also chavicine)	94-62-2
			Ilepcimide	23434-86-8
			Paroxetine	61869-08-7
		5,6-MDAI, MDAI		132741-81-2
		5,6-MDMAI, MDMAI		132741-82-3
		6,7-MDAT		101625-35-8
		6,7-MDMAT		34620-52-5
		MDBZP	Piperonylpiperazine	32231-06-4
		MDPPP		783241-66-7
		MDPBP		784985-33-7
		MDPV		687603-66-3
		MDPHP		776994-64-0
		MDPM	3,4-Methylenedioxyphenmetrazine		[3]
	Methyl (1,3-benzodioxol-5-yl)(piperidin-2-yl)acetate	MDMPH	3,4-Methylenedioxymethylphenidate
		MDMAR	3',4'-Methylenedioxy-4-methylaminorex	1445573-16-9
		GYKI-52895		869360-93-0
		EIDA		125299-84-5
	3,4-isopropylidenedioxyamphetamine	IDA
		DFMDA		910393-51-0
	6-(2-aminopropyl)-5-methoxy-1,3-benzoxathiol	4T-MMDA-2		133787-69-6
		EDMA		133787-66-3
		5-APDB		152624-03-8
		IBF5MAP		201407-56-9
		6-APDB		152623-93-3
		5-APB		286834-81-9
		5-MAPB		1354631-77-8
		5-EAPB		1445566-01-7
		5-MBPB
		6-APB		286834-85-3
		6-MAPB		1354631-79-0
		5-APDI	IAP	13396-94-6
		5-MAPDI	IMP	1310153-27-5
		6-APT	TAP	3160-20-1
		NAP	PAL-287	18085-03-5
		MNAP	Methamnetamine (PAL-1046)	1178720-66-5
	1-(1-benzothiophen-5-yl)propan-2-amine	5-APBT		1368128-53-3
		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-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-(1,3-Benzodiazol-5-yl)-N-methylpropan-2-amine
		ODMA		2567501-96-4
		TDMA		2302389-87-1
		SeDMA
	1-(Benzo[d][1,3]oxathiol-5-yl)-N-methylpropan-2-amine		MY100		[4] [5]
	1-(Benzo[d][1,3]oxathiol-5-yl)-N,N-dimethylpropan-2-amine		MY101		[6]
	1-(Benzo[d][1,3]oxathiol-6-yl)-N-methylpropan-2-amine		MY200		[7]
	1-(Benzo[b]thiophen-6-yl)-N-methylpropan-2-amine		MY300		[8]
		5-MAPBT	MY400	2613382-32-2	[9]
	1-(Benzo[d]thiazol-5-yl)-N-methylpropan-2-amine	5-BZT-MDMA	MYCO-006?		[10] [11] [12] [13]
	1-(Benzo[d]thiazol-6-yl)-N-methylpropan-2-amine	6-BZT-MDMA	MYCO-007?		[14]
	?		MYCO-002		[15] [16] [17]

See also

• 2Cs, DOx, 25-NB
• Substituted amphetamines
• Substituted benzofurans
• Substituted cathinones
• Substituted phenethylamines
• Substituted phenmetrazines
• Substituted tryptamines

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)

Notes and References

1. Book: Daniel . Trachsel . David . Lehmann . Christoph . Enzensperger . vanc . Phenethylamine: From Structure to Function . Nachtschatten Verlag AG . 2013 . 978-3-03788-700-4.
2. https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2022053696&_cid=P20-L10J3Y-27843-1 Dr. Matthias Grill, Novel Safrylamine derivates having prodrug properties. Patent WO 2022/053696
3. Świst M, Wilamowski J, Zuba D, Kochana J, Parczewski A . 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 . May 2005 . 15749360 . 10.1016/j.forsciint.2004.06.016 .
4. Web site: Novel short-acting psychoactive compounds of the mdma class . Google Patents . 5 January 2024 . 23 October 2024 . Mydecine.
5. Web site: 1-(1,3-benzoxathiol-5-yl)-N-methylpropan-2-amine . PubChem . 23 October 2024.
6. Web site: 1-(1,3-benzoxathiol-5-yl)-N,N-dimethylpropan-2-amine . PubChem . 23 October 2024.
7. Web site: 1-(1,3-benzoxathiol-6-yl)-N-methylpropan-2-amine . PubChem . 23 October 2024.
8. Web site: 1-(1-benzothiophen-6-yl)-N-methylpropan-2-amine . PubChem . 23 October 2024.
9. Web site: [1-(1-Benzothiophen-5-yl)propan-2-yl](methyl)amine ]. PubChem . 23 October 2024.
10. Web site: Short-acting 3,4-methylenedioxymethamphetamine (mdma) analogs incorporating benzothiazole . Google Patents . 13 June 2023 . 23 October 2024 . Mydecine.
11. Web site: 1-(1,3-benzothiazol-5-yl)-N-methylpropan-2-amine . PubChem . 23 October 2024.
12. Web site: 2309151616480990.pdf . 23 October 2024 . MYCO - 006 and 007 represent families of molecules that are based on MDMA molecules. MYCO -006 and MYCO – 007 have been developed in order to reduce the overall acute experience time of Generation 1 MDMA by increasing the metabolism properties of the drug..
13. Web site: Mydecine Innovations Group . Mydecine Files Full Patent Application Covering MYCO-006 Family of Novel Short-Acting MDMA Analogs . GlobeNewswire News Room . 19 July 2022 . 23 October 2024 . Mydecine [...] announced it has successfully synthesized multiple short-acting MDMA analogs. This family of analogs have been specifically designed by experts at Mydecine to have a shorter half life than traditional MDMA. The Company has named this family of novel molecules MYCO-006 and have applied for patent coverage with the World Intellectual Property Organization..
14. Web site: 1-(1,3-benzothiazol-6-yl)-N-methylpropan-2-amine . PubChem . 23 October 2024.
15. Web site: MYCO 002 . AdisInsight . 28 November 2021 . 23 October 2024.
16. Web site: Delving into the Latest Updates on MYCO-002 with Synapse . Synapse . 19 September 2024 . 23 October 2024.
17. Web site: Mydecine Innovations Group . Mydecine Announces Four Lead Novel Drug Candidates and Prepares for Pre-IND Meetings with the FDA and Health Canada To Prepare For Human Clinical . GlobeNewswire News Room . 7 April 2021 . 23 October 2024 . MYCO - 002 is an entactogenic compound that has been created with the goal of reducing harm and improving the safety profile vs. traditional MDMA..