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词条 Substituted benzofuran
释义

  1. List of substituted benzofurans

  2. Legislation

  3. See also

  4. References

{{Use dmy dates|date=March 2014}}

The substituted benzofurans are a class of chemical compounds based on the heterocyclyc and polycyclic compound benzofuran. Some compounds in this class are psychoactive drugs including stimulants, psychedelics and empathogens. Some psychoactive derivatives from this family have been sold under the name Benzofury.

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:[1][2][3][4][5][6][7][8][9]

CompoundR2R3R4R5R6R7Other modification
2-APB 2-aminopropyl H H H H H -
2-MAPB 2-(methylamino)propyl H H H H H -
2-EAPB 2-(ethylamino)propyl H H H H H -
3-APB H 2-aminopropyl H H H H -
Dimemebfe H 2-(dimethylamino)ethyl H methoxy H H -
Mebfap H 2-aminopropyl H methoxy H H -
5-MeO-DiBF H 2-(diisopropylamino)ethyl H methoxy H H -
4-APB H H 2-aminopropyl H H H -
5-MeO-7-Br-4-APDB H H 2-aminopropyl methoxy H bromo 2,3-dihydro
5-APB H H H 2-aminopropyl H H -
5-MAPB H H H 2-(methylamino)propyl H H -
5-EAPB H H H 2-(ethylamino)propyl H H -
5-APB-NBOMe H H H 2-[(2-methoxybenzyl)amino]propyl H H -
6-APB H H H H 2-aminopropyl H -
6-MAPB H H H H 2-(methylamino)propyl H -
6-EAPB H H H H 2-(ethylamino)propyl H -
5-APDB H H H 2-aminopropyl H H 2,3-dihydro
5-MAPDB 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 H H H H 2-aminopropyl H 2,3-dihydro
6-MAPDB 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-AEDB H H H 2-aminoethyl H H 2,3-dihydro
5-MBPB H H H 2-(methylamino)butyl H H -
6-MBPB H H H H 2-(methylamino)butyl H -
5-DBFPV 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 methyl H H methoxy 2-aminopropyl H 2,3-dihydro
F-22 dimethyl H H methoxy 2-aminopropyl H 2,3-dihydro
7-APB H H H H H 2-aminopropyl -
4-I-5-MeO-7-APDB H H iodo methoxy H 2-aminopropyl 2,3-dihydro
2C-B-FLYHH2-aminoethyl5,6-dihydrofuro[5,6-f] -bromo2,3-dihydro
Bromo-DragonFLYHH2-aminopropylfuro[5,6-f] -bromo -
2C-B-FLY-NBOMeHH2-[(2-methoxybenzyl)amino]ethyl5,6-dihydrofuro[5,6-f] -bromo2,3-dihydro
TFMFlyHH2-aminopropyl5,6-dihydrofuro[5,6-f] -trifluoromethyl2,3-dihydro
YM-348ethylH1-aminopropylpyrazol[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 on June 2013 as temporary class drugs, while others have been made permanently illegal in various jurisdictions.[10][11][12]

See also

  • 5-IT
  • Bromo-dragonfly
  • Substituted amphetamines
  • Substituted cathinones
  • Substituted methylenedioxyphenethylamines
  • Substituted phenethylamines

References

1. ^{{ cite journal | last1 = Tomaszewski | first1 = Z. | last2 = Johnson | first2 = M. P. | last3 = Huang | first3 = X. | last4 = Nichols | first4 = D. E. | title = Benzofuran bioisosteres of hallucinogenic tryptamines | journal = Journal of Medicinal Chemistry | year = 1992 | volume = 35 | issue = 11 | pages = 2061–2064 | pmid = 1534585 | doi = 10.1021/jm00089a017 }}
2. ^{{cite journal |vauthors=Monte AP, Marona-Lewicka D, Cozzi NV, Nichols DE | title = Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4-(methylenedioxy)amphetamine | journal = Journal of Medicinal Chemistry | volume = 36 | issue = 23 | pages = 3700–6 |date=November 1993 | pmid = 8246240 | doi = 10.1021/jm00075a027| url = }}
3. ^{{cite patent | country = US | number = 7045545 | status = patent | title = Aminoalkylbenzofurans as serotonin (5-HT(2c)) agonists | pubdate = 19 January 2000 | gdate = 16 May 2006 | inventor = 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}}
4. ^{{cite web | url = https://www.gov.uk/government/publications/temporary-class-drug-order-report-on-benzofury-and-nbome-compounds | title = Temporary class drug order report on 5-6APB and NBOMe compounds | accessdate = 2016-08-23 | date = 4 Jun 2013 | publisher = UK Home Office}}
5. ^Stanczuk A, Morris N, Gardner EA, Kavanagh P. Identification of (2-aminopropyl)benzofuran (APB) phenyl ring positional isomers in internet purchased products. Drug Test Anal. 2013 Apr;5(4):270-6. doi: 10.1002/dta.1451. {{PMID|23349125}}
6. ^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}}
7. ^Nichols DE, Snyder SE, Oberlender R, Johnson MP, Huang XM. 2,3-Dihydrobenzofuran analogues of hallucinogenic phenethylamines. J Med Chem 1991; 34:276–281. DOI: 10.1021/jm00105a043
8. ^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. J Med Chem 1996, 39:2953–2961. DOI: 10.1021/jm960199j
9. ^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: Identification of five substituted phenethylamine derivatives. Drug Test Analysis, 1 Jan 2016. doi: 10.1002/dta.1955
10. ^{{cite web | url = http://www.legislation.gov.uk/ukdsi/2014/9780111110904 | title = The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014 | accessdate = 2016-08-23 | author = UK Home Office | date = 2014-03-05 | publisher = UK Government}}
11. ^{{cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html | title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | publisher=China Food and Drug Administration | date=27 September 2015 | language=Chinese | accessdate=23 August 2016}}
12. ^{{cite web | url=http://www.mhlw.go.jp/seisakunitsuite/bunya/kenkou_iryou/iyakuhin/yakubuturanyou/dl/meisho.pdf | title=指定薬物名称・構造式一覧（平成27年9月16日現在） | publisher=厚生労働省 | date=16 September 2015 | language=Japanese | accessdate=23 August 2016}}
{{Entactogens|state=expanded}}{{Serotonergics}}{{Adrenergics}}{{Dopaminergics}}{{Phenethylamines}}

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