Dimemebfe

Psychedelic drug From Wikipedia, the free encyclopedia

Dimemebfe, also known as 5-methoxy-N,N-dimethyl-3-(2-aminoethyl)benzofuran (5-MeO-BFE or 5-MeO-DMBF) or as 1-oxa-5-MeO-DMT, is a psychedelic drug of the benzofuran family related to the psychedelic tryptamine 5-MeO-DMT.[1][2][3][4] It is the analogue and bioisostere of 5-MeO-DMT in which the nitrogen atom of the indole ring has been replaced with an oxygen atom, making dimemebfe a benzofuran rather than tryptamine derivative.[1][2][3][4] The drug has been encountered as a novel designer drug.[3]

Other names5-Methoxy-N,N-dimethyl-3-(2-aminoethyl)benzofuran; N,N-Dimethyl-5-methoxy-benzofuranylethylamine; 5-MeO-BFE; 5-MeO-DMBF; 1-Oxa-5-MeO-DMT; O-5-MeO-DMT; "Head f--k"; "Head fuck"
Drug classSerotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
  • US: Unscheduled and not FDA approved
Quick facts Clinical data, Other names ...
Dimemebfe
Clinical data
Other names5-Methoxy-N,N-dimethyl-3-(2-aminoethyl)benzofuran; N,N-Dimethyl-5-methoxy-benzofuranylethylamine; 5-MeO-BFE; 5-MeO-DMBF; 1-Oxa-5-MeO-DMT; O-5-MeO-DMT; "Head f--k"; "Head fuck"
Drug classSerotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
  • US: Unscheduled and not FDA approved
Identifiers
  • 2-(5-Methoxy-1-benzofuran-3-yl)-N,N-dimethylethanamine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H17NO2
Molar mass219.284 g·mol−1
3D model (JSmol)
  • CN(C)CCc1coc(c1c2)ccc2OC
  • InChI=1S/C13H17NO2/c1-14(2)7-6-10-9-16-13-5-4-11(15-3)8-12(10)13/h4-5,8-9H,6-7H2,1-3H3 ☒N
  • Key:WBPQJTBOQCCTFX-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)
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Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

Pharmacodynamics

Dimemebfe acts as an agonist of the serotonin 5-HT1A and 5-HT2 family of serotonin receptors.[4] It is several times less potent as a serotonin receptor agonist than 5-MeO-DMT and with relatively more activity at the serotonin 5-HT1A receptor, but still shows strongest actions at the 5-HT2 family of receptors.[4]

Chemistry

Synthesis

The chemical synthesis of dimemembfe has been described.[4]

Analogues

Analogues of dimemebfe include the benzofurans 5-MeO-DiBF (1-oxa-5-MeO-DiPT), 3-APB (1-oxa-AMT), and mebfap (5-MeO-3-APB; 1-oxa-5-MeO-AMT), the benzothiophene S-DMT (1-thia-DMT), and the tryptamine 5-MeO-DMT, among others.

History

Dimemebfe was first described in the scientific literature by David E. Nichols and colleagues in 1992.[3][4] Subsequently, it emerged as a novel designer drug by 2012.[3]

Society and culture

Canada

Dimemebfe is not a controlled substance in Canada as of 2025.[5]

United States

Dimemebfe is not an explicitly controlled substance in the United States.[6] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.

Dimemebfe is a Schedule I controlled substance in the United States state of Alabama.[7]

See also

References

External links

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