Substituted benzofuran

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]

General chemical structure of substituted benzofurans

List of substituted benzofurans

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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
  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

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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

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References

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  2. ^ Nevagi RJ, Dighe SN, Dighe SN (June 2015). "Biological and medicinal significance of benzofuran". European Journal of Medicinal Chemistry. 97: 561–81. doi:10.1016/j.ejmech.2014.10.085. PMID 26015069.
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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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  14. ^ Nichols DE, Hoffman AJ, Oberlender RA, Riggs RM (February 1986). "Synthesis and evaluation of 2,3-dihydrobenzofuran analogues of the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane: drug discrimination studies in rats". Journal of Medicinal Chemistry. 29 (2): 302–4. doi:10.1021/jm00152a022. PMID 3950910.
  15. ^ Nichols DE, Snyder SE, Oberlender R, Johnson MP, Huang XM (January 1991). "2,3-Dihydrobenzofuran analogues of hallucinogenic phenethylamines". Journal of Medicinal Chemistry. 34 (1): 276–81. doi:10.1021/jm00105a043. PMID 1992127.
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  20. ^ Feng Z, Mohapatra S, Klimko PG, Hellberg MR, May JA, Kelly C, Williams G, McLaughlin MA, Sharif NA. Novel benzodifuran analogs as potent 5-HT2A receptor agonists with ocular hypotensive activity. Bioorg Med Chem Lett. 2007 Jun 1;17(11):2998-3002. doi:10.1016/j.bmcl.2007.03.073 PMID 17419053
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