Substituted benzofuran explained

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]

StructureCompoundCAS numberR2R3R4R5R6R7Other modification
2-APB 30455-73-3 2-aminopropyl H H H H H -
806596-15-6 2-(methylamino)propyl H H H H H -
2-EAPB 2-(ethylamino)propyl H H H H H -
260550-89-8 2-(propylamino)pentyl H H H H H -
63638-91-5 4-piperidinyl H H methoxy H bromo -
3-APB 105909-13-5 H 2-aminopropyl H H H H -
140853-58-3 H 2-(dimethylamino)ethyl H methoxy H H -
Mebfap 140853-59-4 H 2-aminopropyl H methoxy H H -
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
286834-81-9 H H H 2-aminopropyl H H -
1354631-77-8 H H H 2-(methylamino)propyl H H -
1445566-01-7 H H H 2-(ethylamino)propyl H H -
5-APB-NBOMe H H H 2-[(2-methoxybenzyl)amino]propyl H H -
286834-85-3 H H H H 2-aminopropyl H -
1354631-79-0 H H H H 2-(methylamino)propyl H -
1632539-47-9 H H H H 2-(ethylamino)propyl H -
5-AEDB H H H 2-aminoethyl H H 2,3-dihydro
152624-03-8 H H H 2-aminopropyl H H 2,3-dihydro
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
1354631-78-9 H H H H 2-aminopropyl H 2,3-dihydro
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
H H H 1-oxo-2-(methylamino)propyl H H -
bk-6-MAPB H H H H 1-oxo-2-(methylamino)propyl H -
H H H 2-(methylamino)butyl H H -
6-MBPB H H H H 2-(methylamino)butyl H -
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
99355-74-5 methyl H H methoxy 2-aminopropyl H 2,3-dihydro
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
1951-25-3propyl3,5-diiodo-4-(2-diethylaminoethoxy)benzoylHHHH-
733720-95-1HH2-aminoethyl5,6-dihydrofuro[5,6-f]-bromo2,3-dihydro
260809-98-1HH2-aminoethylfuro[5,6-f]-bromo-
2C-C-FLY 1354633-83-2HH2-aminoethyl5,6-dihydrofuro[5,6-f]-chloro2,3-dihydro
2C-I-FLY 1354633-88-7HH2-aminoethyl5,6-dihydrofuro[5,6-f]-iodo2,3-dihydro
2C-D-FLY 1354634-07-3HH2-aminoethyl5,6-dihydrofuro[5,6-f]-methyl2,3-dihydro
HH2-aminoethyl5,6-dihydrofuro[5,6-f]-ethyl2,3-dihydro
2C-EF-FLY HH2-aminoethyl5,6-dihydrofuro[5,6-f]-2-fluoroethyl2,3-dihydro
2C-T-7-FLY 1354633-05-8HH2-aminoethyl5,6-dihydrofuro[5,6-f]-n-propylthio2,3-dihydro
219986-75-1HH2-aminopropyl5,6-dihydrofuro[5,6-f]-bromo2,3-dihydro
502759-67-3HH2-aminopropylfuro[5,6-f]-bromo-
1043541-82-7HH2-aminopropyl5,6-dihydropyrano-bromo-
DOM-FLY 748748-08-5HH2-aminopropyl5,6-dihydrofuro[5,6-f]-methyl2,3-dihydro
DOMOM-FLY [20] HH2-aminopropyl5,6-dihydrofuro[5,6-f]-methoxymethyl2,3-dihydro
1335331-42-4HH2-[(2-methoxybenzyl)amino]ethyl5,6-dihydrofuro[5,6-f]-bromo2,3-dihydro
2C-B-DRAGONFLY-NBOH 1335331-45-7HH2-[(2-hydroxybenzyl)amino]ethylfuro[5,6-f]-bromo-
780744-19-6HH2-aminopropyl5,6-dihydrofuro[5,6-f]-trifluoromethyl2,3-dihydro
Mescaline-FLY HH2-aminoethyl5,6-dihydrofuro[5,4-b]-methoxy2,3-dihydro
372163-84-3ethylH1-(2-aminopropyl)pyrazol[4,5-f]-HH-
2-desethyl-YM-348 748116-94-1HH1-(2-aminopropyl)pyrazol[4,5-f]-HH-

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

Notes and References

  1. Dawood KM . Benzofuran derivatives: a patent review . Expert Opinion on Therapeutic Patents . 23 . 9 . 1133–56 . September 2013 . 23683135 . 10.1517/13543776.2013.801455 . 24425145 .
  2. Nevagi RJ, Dighe SN, Dighe SN . Biological and medicinal significance of benzofuran . European Journal of Medicinal Chemistry . 97 . 561–81 . June 2015 . 26015069 . 10.1016/j.ejmech.2014.10.085 .
  3. Khanam H . Bioactive Benzofuran derivatives: A review . European Journal of Medicinal Chemistry . 97 . 483–504 . June 2015 . 25482554 . 10.1016/j.ejmech.2014.11.039 .
  4. Nugteren-van Lonkhuyzen JJ, van Riel AJ, Brunt TM, Hondebrink L . Pharmacokinetics, pharmacodynamics and toxicology of new psychoactive substances (NPS): 2C-B, 4-fluoroamphetamine and benzofurans . Drug and Alcohol Dependence . 157 . 18–27 . December 2015 . 26530501 . 10.1016/j.drugalcdep.2015.10.011 .
  5. Liu C, Jia W, Qian Z, Li T, Hua Z . Identification of five substituted phenethylamine derivatives 5-MAPDB, 5-AEDB, MDMA methylene homolog, 6-Br-MDMA, and 5-APB-NBOMe . Drug Testing and Analysis . 9 . 2 . 199–207 . February 2017 . 26856255 . 10.1002/dta.1955 .
  6. Barcelo B, Gomila I . Pharmacology and Literature Review Based on Related Death and Non-Fatal Case Reports of the Benzofurans and Benzodifurans Designer Drugs . Current Pharmaceutical Design . 23 . 36 . 5523–5529 . 2017 . 28714411 . 10.2174/1381612823666170714155140 .
  7. Halberstadt AL, Chatha M, Stratford A, Grill M, Brandt SD . Comparison of the behavioral responses induced by phenylalkylamine hallucinogens and their tetrahydrobenzodifuran ("FLY") and benzodifuran ("DragonFLY") analogs . Neuropharmacology . 144 . 368–376 . January 2019 . 30385253 . 6863604 . 10.1016/j.neuropharm.2018.10.037 .
  8. Roque Bravo R, Carmo H, Carvalho F, Bastos ML, Dias da Silva D . Benzo fury: A new trend in the drug misuse scene . Journal of Applied Toxicology . 39 . 8 . 1083–1095 . August 2019 . 30723925 . 10.1002/jat.3774 . 73433890 .
  9. Tomaszewski Z, Johnson MP, Huang X, Nichols DE . Benzofuran bioisosteres of hallucinogenic tryptamines . Journal of Medicinal Chemistry . 35 . 11 . 2061–4 . May 1992 . 1534585 . 10.1021/jm00089a017 .
  10. Monte AP, Marona-Lewicka D, Cozzi NV, Nichols DE . Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4-(methylenedioxy)amphetamine . Journal of Medicinal Chemistry . 36 . 23 . 3700–6 . November 1993 . 8246240 . 10.1021/jm00075a027 .
  11. US . 7045545 . patent . Aminoalkylbenzofurans as serotonin (5-HT(2c)) agonists . 19 January 2000 . 16 May 2006 . Karin Briner, Joseph Paul Burkhart, Timothy Paul Burkholder, Matthew Joseph Fisher, William Harlan Gritton, Daniel Timothy Kohlman, Sidney Xi Liang, Shawn Christopher Miller, Jeffrey Thomas Mullaney, Yao-Chang Xu, Yanping Xu.
  12. Web site: Temporary class drug order report on 5-6APB and NBOMe compounds . 2016-08-23 . 4 Jun 2013 . UK Home Office.
  13. Stanczuk A, Morris N, Gardner EA, Kavanagh P . Identification of (2-aminopropyl)benzofuran (APB) phenyl ring positional isomers in internet purchased products . Drug Testing and Analysis . 5 . 4 . 270–6 . April 2013 . 23349125 . 10.1002/dta.1451 .
  14. 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 . Journal of Medicinal Chemistry . 29 . 2 . 302–4 . February 1986 . 3950910 . 10.1021/jm00152a022 .
  15. Nichols DE, Snyder SE, Oberlender R, Johnson MP, Huang XM . 2,3-Dihydrobenzofuran analogues of hallucinogenic phenethylamines . Journal of Medicinal Chemistry . 34 . 1 . 276–81 . January 1991 . 1992127 . 10.1021/jm00105a043 .
  16. Monte AP, Marona-Lewicka D, Parker MA, Wainscott DB, Nelson DL, Nichols DE . Dihydrobenzofuran analogues of hallucinogens. 3. Models of 4-substituted (2,5-dimethoxyphenyl)alkylamine derivatives with rigidified methoxy groups . Journal of Medicinal Chemistry . 39 . 15 . 2953–61 . July 1996 . 8709129 . 10.1021/jm960199j .
  17. Liu C, Jia W, Qian Z, Li T, Hua Z . Identification of five substituted phenethylamine derivatives 5-MAPDB, 5-AEDB, MDMA methylene homolog, 6-Br-MDMA, and 5-APB-NBOMe . Drug Testing and Analysis . 9 . 2 . 199–207 . February 2017 . 26856255 . 10.1002/dta.1955 .
  18. Wagmann L, Brandt SD, Stratford A, Maurer HH, Meyer MR . Interactions of phenethylamine-derived psychoactive substances of the 2C-series with human monoamine oxidases . Drug Testing and Analysis . 11 . 2 . 318–324 . February 2019 . 30188017 . 10.1002/dta.2494 . 52166076 .
  19. Wagmann L, Hempel N, Richter LH, Brandt SD, Stratford A, Meyer MR . Phenethylamine-derived new psychoactive substances 2C-E-FLY, 2C-EF-FLY, and 2C-T-7-FLY: Investigations on their metabolic fate including isoenzyme activities and their toxicological detectability in urine screenings . Drug Testing and Analysis . 11 . 10 . 1507–1521 . October 2019 . 31299701 . 10.1002/dta.2675 . free .
  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.
  21. Web site: The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014 . 2016-08-23 . UK Home Office . 2014-03-05 . UK Government.
  22. Web site: 关于印发《非药用类麻醉药品和精神药品列管办法》的通知 . China Food and Drug Administration . 27 September 2015 . zh . 23 August 2016 . 1 October 2015 . https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html . dead .
  23. Web site: 指定薬物名称・構造式一覧（平成27年9月16日現在） . 厚生労働省 . 16 September 2015 . ja . 23 August 2016.

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