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Substituted benzofuran

Topic: Chemistry

 From HandWiki - Reading time: 12 min

Short description: Class of chemical compounds
General chemical structure of substituted benzofurans

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

Chemical structures of selected APBs

Use and effects

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Oral doses and durations of benzofurans and dihydrobenzofurans
Compound Chemical name Dose Duration
2-APB 2-(2-Aminopropyl)benzofuran Unknown Unknown
3-APB 3-(2-Aminopropyl)benzofuran Unknown Unknown
4-APB 4-(2-Aminopropyl)benzofuran Unknown Unknown
5-APB 5-(2-Aminopropyl)benzofuran 60–80 mg (20–100 mg+) 3–8 hours
5-MAPB 5-(2-(Methylamino)propyl)benzofuran 30–70 mg (10–120 mg+) 4–8 hours
5-EAPB 5-(2-(Ethylamino)propyl)benzofuran 80 mg (50–150 mg+) Unknown
5-MBPB 6-(2-(Methylamino)butyl)benzofuran Unknown Unknown
BK-5-MAPB 5-[2-(Methylamino)propanoyl]benzofuran Unknown Unknown
5-APDB 5-(2-Aminopropyl)-2,3-dihydrobenzofuran 100 mg (50–200 mg+) Unknown
5-MAPDB 5-(2-(Methylamino)propyl)-2,3-dihydrobenzofuran 100 mg (50–150 mg+) Unknown
6-APB 6-(2-Aminopropyl)benzofuran 80–100 mg (15–125 mg+) 6–9 hours
6-MAPB 6-(2-(Methylamino)propyl)benzofuran 50–100 mg (20–130 mg+) 6–8 hours
6-EAPB 6-(2-(Ethylamino)propyl)benzofuran Unknown Unknown
6-MBPB 6-(2-(Methylamino)butyl)benzofuran Unknown Unknown
BK-6-MAPB 6-[2-(Methylamino)propanoyl]benzofuran Unknown Unknown
6-APDB 6-(2-Aminopropyl)-2,3-dihydrobenzofuran 70 mg (20–130 mg+) 6–8 hours
6-MAPDB 6-(2-(Methylamino)propyl)-2,3-dihydrobenzofuran Unknown Unknown
7-APB 7-(2-Aminopropyl)benzofuran Unknown Unknown
Refs: [9][10][11][12]

Interactions

Pharmacology

Benzofurans like 5-APB and 6-APB act as serotonin–norepinephrine–dopamine releasing agents and as serotonin 5-HT2 receptor agonists.[9][11][13] In addition, some benzofurans, including 5-MAPB, 6-MAPB, BK-5-MAPB, and BK-6-MAPB, have unexpectedly been found to be potent serotonin 5-HT1B receptor agonists.[14] Along with serotonin release and other actions, this property may be involved may be involved in their entactogenic effects.[14] Conversely, MDMA is inactive as a direct agonist of the serotonin 5-HT1B receptor.[14]

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:[15][16][17][18][19][20][21][22][23][24][25]

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Structure Compound CAS # R2 R3 R4 R5 R6 R7 Other
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-(dimethyl-amino)ethyl H methoxy H H -
Mebfap 140853-59-4 H 2-aminopropyl H methoxy H H -
5-MeO-DiBF H 2-(diisopropyl-amino)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 (F-1) 99355-77-8 H H H methoxy 2-aminopropyl 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-diethylamino-ethoxy)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
2C-MeTriox H H 2-aminoethyl 5,6-methylenedioxy[5,6-f] - methyl 2,3-dihydro
MeTriox H H 2-aminopropyl 5,6-methylenedioxy[5,6-f] - methyl 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 [26] 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 -

Society and culture

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.[27][28][29]

See also

References

  1. ↑ "Benzofuran derivatives: a patent review". Expert Opinion on Therapeutic Patents 23 (9): 1133–56. September 2013. doi:10.1517/13543776.2013.801455. PMID 23683135. 
  2. ↑ "Biological and medicinal significance of benzofuran". European Journal of Medicinal Chemistry 97: 561–81. June 2015. doi:10.1016/j.ejmech.2014.10.085. PMID 26015069. 
  3. ↑ "Bioactive Benzofuran derivatives: A review". European Journal of Medicinal Chemistry 97: 483–504. June 2015. doi:10.1016/j.ejmech.2014.11.039. PMID 25482554. 
  4. ↑ "Pharmacokinetics, pharmacodynamics and toxicology of new psychoactive substances (NPS): 2C-B, 4-fluoroamphetamine and benzofurans". Drug and Alcohol Dependence 157: 18–27. December 2015. doi:10.1016/j.drugalcdep.2015.10.011. PMID 26530501. 
  5. ↑ "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. doi:10.1002/dta.1955. PMID 26856255. 
  6. ↑ "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. doi:10.2174/1381612823666170714155140. PMID 28714411. 
  7. ↑ "Comparison of the behavioral responses induced by phenylalkylamine hallucinogens and their tetrahydrobenzodifuran ("FLY") and benzodifuran ("DragonFLY") analogs". Neuropharmacology 144: 368–376. January 2019. doi:10.1016/j.neuropharm.2018.10.037. PMID 30385253. 
  8. ↑ "Benzo fury: A new trend in the drug misuse scene". Journal of Applied Toxicology 39 (8): 1083–1095. August 2019. doi:10.1002/jat.3774. PMID 30723925. 
  9. ↑ 9.0 9.1 "Beyond ecstasy: Alternative entactogens to 3,4-methylenedioxymethamphetamine with potential applications in psychotherapy". J Psychopharmacol 35 (5): 512–536. May 2021. doi:10.1177/0269881120920420. PMID 32909493. 
  10. ↑ "Monoamine Transporter and Receptor Interaction Profiles in Vitro Predict Reported Human Doses of Novel Psychoactive Stimulants and Psychedelics". Int J Neuropsychopharmacol 21 (10): 926–931. October 2018. doi:10.1093/ijnp/pyy047. PMID 29850881. 
  11. ↑ 11.0 11.1 "Designer drugs: mechanism of action and adverse effects". Arch Toxicol 94 (4): 1085–1133. April 2020. doi:10.1007/s00204-020-02693-7. PMID 32249347. 
  12. ↑ "Benzo fury: A new trend in the drug misuse scene". J Appl Toxicol 39 (8): 1083–1095. August 2019. doi:10.1002/jat.3774. PMID 30723925. 
  13. ↑ "Pharmacological profile of novel psychoactive benzofurans". Br J Pharmacol 172 (13): 3412–3425. July 2015. doi:10.1111/bph.13128. PMID 25765500. 
  14. ↑ 14.0 14.1 14.2 Matthew Baggott, "Advantageous benzofuran compositions for mental disorders or enhancement", US patent 20230150963, published 2023 May 18, assigned to Tactogen
  15. ↑ "Benzofuran bioisosteres of hallucinogenic tryptamines". Journal of Medicinal Chemistry 35 (11): 2061–4. May 1992. doi:10.1021/jm00089a017. PMID 1534585. 
  16. ↑ "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. doi:10.1021/jm00075a027. PMID 8246240. 
  17. ↑ 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, "Aminoalkylbenzofurans as serotonin (5-HT(2c)) agonists", US patent 7045545, published 19 January 2000, issued 16 May 2006
  18. ↑ "Temporary class drug order report on 5-6APB and NBOMe compounds". UK Home Office. 4 Jun 2013. https://www.gov.uk/government/publications/temporary-class-drug-order-report-on-benzofury-and-nbome-compounds. 
  19. ↑ "Identification of (2-aminopropyl)benzofuran (APB) phenyl ring positional isomers in internet purchased products". Drug Testing and Analysis 5 (4): 270–6. April 2013. doi:10.1002/dta.1451. PMID 23349125. 
  20. ↑ "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. doi:10.1021/jm00152a022. PMID 3950910. 
  21. ↑ "2,3-Dihydrobenzofuran analogues of hallucinogenic phenethylamines". Journal of Medicinal Chemistry 34 (1): 276–81. January 1991. doi:10.1021/jm00105a043. PMID 1992127. 
  22. ↑ "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. doi:10.1021/jm960199j. PMID 8709129. 
  23. ↑ "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. doi:10.1002/dta.1955. PMID 26856255. 
  24. ↑ "Interactions of phenethylamine-derived psychoactive substances of the 2C-series with human monoamine oxidases". Drug Testing and Analysis 11 (2): 318–324. February 2019. doi:10.1002/dta.2494. PMID 30188017. http://researchonline.ljmu.ac.uk/id/eprint/9155/1/DTA-18-0224.R1.pdf. 
  25. ↑ "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. doi:10.1002/dta.2675. PMID 31299701. 
  26. ↑ "Novel benzodifuran analogs as potent 5-HT2A receptor agonists with ocular hypotensive activity". Bioorg Med Chem Lett 17 (11): 2998–3002. Jun 2007. doi:10.1016/j.bmcl.2007.03.073. PMID 17419053. 
  27. ↑ UK Home Office (2014-03-05). "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Government. http://www.legislation.gov.uk/ukdsi/2014/9780111110904. 
  28. ↑ "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 zh). China Food and Drug Administration. 27 September 2015. http://www.sfda.gov.cn/WS01/CL0056/130753.html. 
  29. ↑ "指定薬物名称・構造式一覧（平成27年9月16日現在）" (in ja). 厚生労働省. 16 September 2015. http://www.mhlw.go.jp/seisakunitsuite/bunya/kenkou_iryou/iyakuhin/yakubuturanyou/dl/meisho.pdf. 

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