Thesubstituted benzofurans are a class ofchemical compounds based on theheterocyclic andpolycyclic compoundbenzofuran. Many medicines use the benzofuran core as a scaffold,^[1][2][3] but most commonly the term is used to refer to the simpler compounds in this class which include numerouspsychoactive drugs, includingstimulants,psychedelics andempathogens. In general, these compounds have a benzofuran core to which a 2-aminoethyl group is attached (at any position), and combined with a range of other substituents.^[4][5][6][7] Some psychoactive derivatives from this family have been sold under the nameBenzofury.^[8]

The derivatives may be produced by substitutions at six locations of the benzofuran molecule, as well as saturation of the 2,3- double bond.

The following table displays notable derivatives that have been reported:^{[9][10][11][12][13][14][15][16][17][18][19]}

Structure	Compound	CAS #	R2	R3	R4	R5	R6	R7	Other
	2-APB	30455-73-3	2-aminopropyl	H	H	H	H	H	-
	2-MAPB	806596-15-6	2-(methylamino)propyl	H	H	H	H	H	-
	2-EAPB		2-(ethylamino)propyl	H	H	H	H	H	-
	BPAP	260550-89-8	2-(propylamino)pentyl	H	H	H	H	H	-
	Brofaromine	63638-91-5	4-piperidinyl	H	H	methoxy	H	bromo	-
	3-APB	105909-13-5	H	2-aminopropyl	H	H	H	H	-
	Dimemebfe	140853-58-3	H	2-(dimethyl-amino)ethyl	H	methoxy	H	H	-
	Mebfap	140853-59-4	H	2-aminopropyl	H	methoxy	H	H	-
	5-MeO-DiBF		H	2-(diisopropyl-amino)ethyl	H	methoxy	H	H	-
	4-APB	286834-82-0	H	H	2-aminopropyl	H	H	H	-
	DOB-5-HEMIFLY (5-MeO-7-Br-4-APDB)		H	H	2-aminopropyl	methoxy	H	bromo	2,3-dihydro
	5-APB	286834-81-9	H	H	H	2-aminopropyl	H	H	-
	5-MAPB	1354631-77-8	H	H	H	2-(methylamino)propyl	H	H	-
	5-EAPB	1445566-01-7	H	H	H	2-(ethylamino)propyl	H	H	-
	5-APB-NBOMe		H	H	H	2-[(2-methoxybenzyl)-amino]propyl	H	H	-
	6-APB	286834-85-3	H	H	H	H	2-aminopropyl	H	-
	6-MAPB	1354631-79-0	H	H	H	H	2-(methylamino)propyl	H	-
	6-EAPB	1632539-47-9	H	H	H	H	2-(ethylamino)propyl	H	-
	5-AEDB		H	H	H	2-aminoethyl	H	H	2,3-dihydro
	5-APDB	152624-03-8	H	H	H	2-aminopropyl	H	H	2,3-dihydro
	5-MAPDB	1354631-78-9	H	H	H	2-(methylamino)propyl	H	H	2,3-dihydro
	5-EAPDB		H	H	H	2-(ethylamino)propyl	H	H	2,3-dihydro
	6-APDB	1354631-78-9	H	H	H	H	2-aminopropyl	H	2,3-dihydro
	6-MAPDB	1354631-81-4	H	H	H	H	2-(methylamino)propyl	H	2,3-dihydro
	6-EAPDB		H	H	H	H	2-(ethylamino)propyl	H	2,3-dihydro
	bk-5-MAPB		H	H	H	1-oxo-2-(methylamino)propyl	H	H	-
	bk-6-MAPB		H	H	H	H	1-oxo-2-(methylamino)propyl	H	-
	5-MBPB		H	H	H	2-(methylamino)butyl	H	H	-
	6-MBPB		H	H	H	H	2-(methylamino)butyl	H	-
	5-DBFPV	2117405-32-8	H	H	H	1-oxo-2-(pyrrolidin-1-yl)pentyl	H	H	2,3-dihydro
	6-MeO-5-APDB		H	H	H	2-aminopropyl	methoxy	H	2,3-dihydro
	F (F-1)	99355-77-8	H	H	H	methoxy	2-aminopropyl	H	2,3-dihydro
	F-2	99355-74-5	methyl	H	H	methoxy	2-aminopropyl	H	2,3-dihydro
	F-22	952016-51-2	dimethyl	H	H	methoxy	2-aminopropyl	H	2,3-dihydro
	7-APB	286834-86-4	H	H	H	H	H	2-aminopropyl	-
	DOI-2-HEMIFLY (4-I-5-MeO-7-APDB)		H	H	iodo	methoxy	H	2-aminopropyl	2,3-dihydro
	Amiodarone	1951-25-3	propyl	3,5-diiodo-4-(2-diethylamino-ethoxy)benzoyl	H	H	H	H	-
	2C-B-FLY	733720-95-1	H	H	2-aminoethyl	5,6-dihydrofuro[5,6-f]	-	bromo	2,3-dihydro
	2C-B-DRAGONFLY	260809-98-1	H	H	2-aminoethyl	furo[5,6-f]	-	bromo	-
	2C-C-FLY	1354633-83-2	H	H	2-aminoethyl	5,6-dihydrofuro[5,6-f]	-	chloro	2,3-dihydro
	2C-I-FLY	1354633-88-7	H	H	2-aminoethyl	5,6-dihydrofuro[5,6-f]	-	iodo	2,3-dihydro
	2C-D-FLY	1354634-07-3	H	H	2-aminoethyl	5,6-dihydrofuro[5,6-f]	-	methyl	2,3-dihydro
	2C-E-FLY		H	H	2-aminoethyl	5,6-dihydrofuro[5,6-f]	-	ethyl	2,3-dihydro
	2C-EF-FLY		H	H	2-aminoethyl	5,6-dihydrofuro[5,6-f]	-	2-fluoroethyl	2,3-dihydro
	2C-T-7-FLY	1354633-05-8	H	H	2-aminoethyl	5,6-dihydrofuro[5,6-f]	-	n-propylthio	2,3-dihydro
	2C-MeTriox		H	H	2-aminoethyl	5,6-methylenedioxy[5,6-f]	-	methyl	2,3-dihydro
	MeTriox		H	H	2-aminopropyl	5,6-methylenedioxy[5,6-f]	-	methyl	2,3-dihydro
	DOB-FLY	219986-75-1	H	H	2-aminopropyl	5,6-dihydrofuro[5,6-f]	-	bromo	2,3-dihydro
	Bromo-DragonFLY	502759-67-3	H	H	2-aminopropyl	furo[5,6-f]	-	bromo	-
	DOB-2-DRAGONFLY-5-BUTTERFLY	1043541-82-7	H	H	2-aminopropyl	5,6-dihydropyrano	-	bromo	-
	DOM-FLY	748748-08-5	H	H	2-aminopropyl	5,6-dihydrofuro[5,6-f]	-	methyl	2,3-dihydro
	DOMOM-FLY[20]		H	H	2-aminopropyl	5,6-dihydrofuro[5,6-f]	-	methoxymethyl	2,3-dihydro
	2C-B-FLY-NBOMe	1335331-42-4	H	H	2-[(2-methoxybenzyl)-amino]ethyl	5,6-dihydrofuro[5,6-f]	-	bromo	2,3-dihydro
	2C-B-DRAGONFLY-NBOH	1335331-45-7	H	H	2-[(2-hydroxybenzyl)-amino]ethyl	furo[5,6-f]	-	bromo	-
	TFMFly	780744-19-6	H	H	2-aminopropyl	5,6-dihydrofuro[5,6-f]	-	trifluoromethyl	2,3-dihydro
	Mescaline-FLY		H	H	2-aminoethyl	5,6-dihydrofuro[5,4-b]	-	methoxy	2,3-dihydro
	YM-348	372163-84-3	ethyl	H	1-(2-aminopropyl)-pyrazol[4,5-f]	-	H	H	-
	2-Desethyl-YM-348	748116-94-1	H	H	1-(2-aminopropyl)-pyrazol[4,5-f]	-	H	H	-

Substituted benzofurans saw widespread use asrecreational drugs by being sold asresearch chemicals making them exempt from drug legislation. Many of the more common compounds were banned in the UK in June 2013 astemporary class drugs, while others have been made permanently illegal in various jurisdictions.^[21][22][23]

• 2-Aminoethoxydiphenyl borate (an unrelated compound also known as 2-APB)
• 2C-B-BUTTERFLY
• 5-IT
• AL-38022A
• IBF5MAP
• Jimscaline
• Oxa-noribogaine
• Substituted amphetamine
• Substituted benzothiophene
• Substituted cathinone
• Substituted methylenedioxyphenethylamine
• Substituted methoxyphenethylamine
• Substituted naphthylethylamine
• Substituted phenethylamine
• Substituted tryptamines

• Benzofurans
• Chemical classes of psychoactive drugs
• Designer drugs
• Stimulants

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• CS1 Japanese-language sources (ja)
• Articles with short description
• Short description is different from Wikidata
• Use dmy dates from March 2014