Substituted benzofuran

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General chemical structure of substituted benzofurans

The substituted benzofurans are a class of chemical compounds based on the

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
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-(dimethylamino)ethyl H methoxy H H -
Mebfap 140853-59-4 H 2-aminopropyl H methoxy H H -
5-MeO-DiBF H 2-(diisopropylamino)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-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
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 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
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 -

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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  12. ^ "Temporary class drug order report on 5-6APB and NBOMe compounds". UK Home Office. 4 June 2013. Retrieved 23 August 2016.
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  21. ^ UK Home Office (5 March 2014). "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Government. Retrieved 23 August 2016.
  22. ^ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 23 August 2016.
  23. ^ "指定薬物名称・構造式一覧（平成27年9月16日現在）" (PDF) (in Japanese). 厚生労働省. 16 September 2015. Retrieved 23 August 2016.
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