Chemistry:Substituted benzofuran

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Short description: Class of chemical compounds


General chemical structure of substituted benzofurans

The substituted benzofurans are a class of chemical compounds based on the heterocyclyc and polycyclic compound benzofuran. 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 numerous psychoactive drugs, including stimulants, psychedelics and empathogens. 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 name Benzofury.[8]

List of substituted benzofurans

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 number R2 R3 R4 R5 R6 R7 Other modification
2APB structure.png 2-APB 30455-73-3 2-aminopropyl H H H H H -
2MAPB structure.png 2-MAPB 806596-15-6 2-(methylamino)propyl H H H H H -
2EAPB structure.png 2-EAPB 2-(ethylamino)propyl H H H H H -
BPAP.svg BPAP 260550-89-8 2-(propylamino)pentyl H H H H H -
Brofaromine.svg Brofaromine 63638-91-5 4-piperidinyl H H methoxy H bromo -
3APB structure.png 3-APB 105909-13-5 H 2-aminopropyl H H H H -
Dimemebfe.png Dimemebfe 140853-58-3 H 2-(dimethylamino)ethyl H methoxy H H -
Mebfap structure.png Mebfap 140853-59-4 H 2-aminopropyl H methoxy H H -
5-MeO-DiBF structure.png 5-MeO-DiBF H 2-(diisopropylamino)ethyl H methoxy H H -
4APB structure.png 4-APB 286834-82-0 H H 2-aminopropyl H H H -
DOB-HEMIFLY-5 structure.png DOB-5-HEMIFLY
(5-MeO-7-Br-4-APDB)
H H 2-aminopropyl methoxy H bromo 2,3-dihydro
5-APB2DACS.svg 5-APB 286834-81-9 H H H 2-aminopropyl H H -
5-MAPB.svg 5-MAPB 1354631-77-8 H H H 2-(methylamino)propyl H H -
1-(benzofuran-5-yl)-N-ethylpropan-2-amine.png 5-EAPB 1445566-01-7 H H H 2-(ethylamino)propyl H H -
5APB-NBOMe structure.png 5-APB-NBOMe H H H 2-[(2-methoxybenzyl)amino]propyl H H -
Benzofuran2DACSL.svg 6-APB 286834-85-3 H H H H 2-aminopropyl H -
6-MAPB.svg 6-MAPB 1354631-79-0 H H H H 2-(methylamino)propyl H -
6-EAPB structure.svg 6-EAPB 1632539-47-9 H H H H 2-(ethylamino)propyl H -
5AEDB structure.png 5-AEDB H H H 2-aminoethyl H H 2,3-dihydro
3-desoxy-MDA.svg 5-APDB 152624-03-8 H H H 2-aminopropyl H H 2,3-dihydro
5-MAPDB structure.png 5-MAPDB 1354631-78-9 H H H 2-(methylamino)propyl H H 2,3-dihydro
5EAPDB structure.png 5-EAPDB H H H 2-(ethylamino)propyl H H 2,3-dihydro
4-desoxy-MDA.svg 6-APDB 1354631-78-9 H H H H 2-aminopropyl H 2,3-dihydro
6-MAPDB structure.png 6-MAPDB 1354631-81-4 H H H H 2-(methylamino)propyl H 2,3-dihydro
6EAPDB structure.png 6-EAPDB H H H H 2-(ethylamino)propyl H 2,3-dihydro
Bk5MAPB structure.png bk-5-MAPB H H H 1-oxo-2-(methylamino)propyl H H -
Bk6MAPB structure.png bk-6-MAPB H H H H 1-oxo-2-(methylamino)propyl H -
5-MBPB structure.png 5-MBPB H H H 2-(methylamino)butyl H H -
6MBPB structure.png 6-MBPB H H H H 2-(methylamino)butyl H -
5-DBFPV.svg 5-DBFPV 2117405-32-8 H H H 1-oxo-2-(pyrrolidin-1-yl)pentyl H H 2,3-dihydro
6MeO5APDB structure.png 6-MeO-5-APDB H H H 2-aminopropyl methoxy H 2,3-dihydro
F-2.png F-2 99355-74-5 methyl H H methoxy 2-aminopropyl H 2,3-dihydro
F-22 (psychedelic).svg F-22 952016-51-2 dimethyl H H methoxy 2-aminopropyl H 2,3-dihydro
7APB structure.png 7-APB 286834-86-4 H H H H H 2-aminopropyl -
DOI-HEMIFLY-2 structure.png DOI-2-HEMIFLY
(4-I-5-MeO-7-APDB)
H H iodo methoxy H 2-aminopropyl 2,3-dihydro
The chemical structure of amiodarone, a class III antiarrhythmic drug. Amiodarone 1951-25-3 propyl 3,5-diiodo-4-(2-diethylaminoethoxy)benzoyl H H H H -
2C-B-FLY structure.svg 2C-B-FLY 733720-95-1 H H 2-aminoethyl 5,6-dihydrofuro[5,6-f] - bromo 2,3-dihydro
2CB-DRAGONFLY structure.png 2C-B-DRAGONFLY 260809-98-1 H H 2-aminoethyl furo[5,6-f] - bromo -
2CC-FLY structure.png 2C-C-FLY 1354633-83-2 H H 2-aminoethyl 5,6-dihydrofuro[5,6-f] - chloro 2,3-dihydro
2CI-FLY structure.png 2C-I-FLY 1354633-88-7 H H 2-aminoethyl 5,6-dihydrofuro[5,6-f] - iodo 2,3-dihydro
2CD-FLY structure.png 2C-D-FLY 1354634-07-3 H H 2-aminoethyl 5,6-dihydrofuro[5,6-f] - methyl 2,3-dihydro
2CE-FLY structure.png 2C-E-FLY H H 2-aminoethyl 5,6-dihydrofuro[5,6-f] - ethyl 2,3-dihydro
2CEF-FLY structure.png 2C-EF-FLY H H 2-aminoethyl 5,6-dihydrofuro[5,6-f] - 2-fluoroethyl 2,3-dihydro
2CT7-FLY structure.png 2C-T-7-FLY 1354633-05-8 H H 2-aminoethyl 5,6-dihydrofuro[5,6-f] - n-propylthio 2,3-dihydro
DOB-FLY structure.png DOB-FLY 219986-75-1 H H 2-aminopropyl 5,6-dihydrofuro[5,6-f] - bromo 2,3-dihydro
R-Bromo-DragonFLY.svg Bromo-DragonFLY 502759-67-3 H H 2-aminopropyl furo[5,6-f] - bromo -
DOB-2-DRAGONFLY-5-BUTTERFLY structure.png DOB-2-DRAGONFLY
-5-BUTTERFLY
1043541-82-7 H H 2-aminopropyl 5,6-dihydropyrano - bromo -
DOM-FLY structure.png DOM-FLY 748748-08-5 H H 2-aminopropyl 5,6-dihydrofuro[5,6-f] - methyl 2,3-dihydro
DOMOM-Fly structure.png DOMOM-FLY [20] H H 2-aminopropyl 5,6-dihydrofuro[5,6-f] - methoxymethyl 2,3-dihydro
2CBFly-NBOMe.svg 2C-B-FLY-NBOMe 1335331-42-4 H H 2-[(2-methoxybenzyl)amino]ethyl 5,6-dihydrofuro[5,6-f] - bromo 2,3-dihydro
2CB-DRAGONFLY-NBOH structure.png 2C-B-DRAGONFLY-NBOH 1335331-45-7 H H 2-[(2-hydroxybenzyl)amino]ethyl furo[5,6-f] - bromo -
TFMFly.svg TFMFly 780744-19-6 H H 2-aminopropyl 5,6-dihydrofuro[5,6-f] - trifluoromethyl 2,3-dihydro
Mescaline-FLY structure.png Mescaline-FLY H H 2-aminoethyl 5,6-dihydrofuro[5,4-b] - methoxy 2,3-dihydro
YM-348 structure.png YM-348 372163-84-3 ethyl H 1-(2-aminopropyl)pyrazol[4,5-f] - H H -
2-desethyl-YM348 structure.png 2-desethyl-YM-348 748116-94-1 H H 1-(2-aminopropyl)pyrazol[4,5-f] - H H -

Legislation

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

See also

References

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