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Substituted benzofuran

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] Some psychoactive derivatives from this family have been sold under the name Benzofury.[7]

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:[8][9][10][11][12][13][14][15][16][17][18]

Structure Compound R2 R3 R4 R5 R6 R7 Other modification
2APB structure.png 2-APB 2-aminopropyl H H H H H -
2MAPB structure.png 2-MAPB 2-(methylamino)propyl H H H H H -
2EAPB structure.png 2-EAPB 2-(ethylamino)propyl H H H H H -
BPAP.svg BPAP 2-(propylamino)pentyl H H H H H -
Brofaromine.svg Brofaromine 4-piperidinyl H H methoxy H bromo -
3APB structure.png 3-APB H 2-aminopropyl H H H H -
Dimemebfe.png Dimemebfe H 2-(dimethylamino)ethyl H methoxy H H -
Mebfap structure.png Mebfap 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 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 H H H 2-aminopropyl H H -
5-MAPB.svg 5-MAPB H H H 2-(methylamino)propyl H H -
1-(benzofuran-5-yl)-N-ethylpropan-2-amine.png 5-EAPB 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 H H H H 2-aminopropyl H -
6-MAPB structure.png 6-MAPB H H H H 2-(methylamino)propyl H -
6-EAPB structure.svg 6-EAPB 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 H H H 2-aminopropyl H H 2,3-dihydro
5-MAPDB structure.png 5-MAPDB 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 H H H H 2-aminopropyl H 2,3-dihydro
6-MAPDB structure.png 6-MAPDB 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 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 methyl H H methoxy 2-aminopropyl H 2,3-dihydro
F-22 (psychedelic).png F-22 dimethyl H H methoxy 2-aminopropyl H 2,3-dihydro
7APB structure.png 7-APB 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
2C-B-FLY structure.svg 2C-B-FLY H H 2-aminoethyl 5,6-dihydrofuro[5,6-f] - bromo 2,3-dihydro
2CB-DRAGONFLY structure.png 2C-B-DRAGONFLY H H 2-aminoethyl furo[5,6-f] - bromo -
2CC-FLY structure.png 2C-C-FLY H H 2-aminoethyl 5,6-dihydrofuro[5,6-f] - chloro 2,3-dihydro
2CI-FLY structure.png 2C-I-FLY H H 2-aminoethyl 5,6-dihydrofuro[5,6-f] - iodo 2,3-dihydro
2CD-FLY structure.png 2C-D-FLY 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 H H 2-aminoethyl 5,6-dihydrofuro[5,6-f] - n-propylthio 2,3-dihydro
DOB-FLY structure.png DOB-FLY H H 2-aminopropyl 5,6-dihydrofuro[5,6-f] - bromo 2,3-dihydro
R-Bromo-DragonFLY.svg Bromo-DragonFLY H H 2-aminopropyl furo[5,6-f] - bromo -
DOB-2-DRAGONFLY-5-BUTTERFLY structure.png DOB-2-DRAGONFLY
-5-BUTTERFLY
H H 2-aminopropyl 5,6-dihydropyrano - bromo -
DOM-FLY structure.png DOM-FLY H H 2-aminopropyl 5,6-dihydrofuro[5,6-f] - methyl 2,3-dihydro
2CBFly-NBOMe.svg 2C-B-FLY-NBOMe 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 H H 2-[(2-hydroxybenzyl)amino]ethyl furo[5,6-f] - bromo -
TFMFly.svg TFMFly 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 ethyl H 1-(2-aminopropyl)pyrazol[4,5-f] - H H -
2-desethyl-YM348 structure.png 2-desethyl-YM-348 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 on June 2013 as temporary class drugs, while others have been made permanently illegal in various jurisdictions.[19][20][21]

See also

References

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  13. ^ Nichols DE, Hoffman AJ, Oberlender RA, Riggs RM. Synthesis and evaluation of 2,3-dihydrobenzofuran analogues of the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane: drug discrimination studies in rats. J Med Chem. 1986 Feb;29(2):302-4. PMID 3950910
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