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Dimemebfe

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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)

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]

Interactions

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

Pharmacology

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Pharmacodynamics

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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

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Synthesis

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

Analogues

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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

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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

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United States

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Dimemebfe is a Schedule I controlled substance in the United States state of Alabama.[5]

See also

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References

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  1. ^ a b Nichols, David E. (2012). "Structure–activity relationships of serotonin 5‐HT 2A agonists". Wiley Interdisciplinary Reviews: Membrane Transport and Signaling. 1 (5): 559–579. doi:10.1002/wmts.42. ISSN 2190-460X. Retrieved 7 January 2026.
  2. ^ a b Nichols DE (2018). "Chemistry and Structure-Activity Relationships of Psychedelics". Curr Top Behav Neurosci. 36: 1–43. doi:10.1007/7854_2017_475. PMID 28401524.
  3. ^ a b c d e Casale JF, Hays PA (2012). "The Characterization of 2-(5-Methoxy-1-benzofuran-3-yl)-N,N-dimethylethanamine (5-MeO-BFE) and Differentiation from its N-Ethyl Analog" (PDF). Microgram Journal. 9 (1): 39–45. Archived from the original (PDF) on 2017-05-13. Retrieved 2015-02-23.
  4. ^ a b c d e f Tomaszewski Z, Johnson MP, Huang X, Nichols DE (May 1992). "Benzofuran bioisosteres of hallucinogenic tryptamines". Journal of Medicinal Chemistry. 35 (11): 2061–2064. doi:10.1021/jm00089a017. PMID 1534585.
  5. ^ "Alabama Senate Bill 333 - Controlled substances, Schedule I, additional synthetic controlled substances and analogue substances included in, trafficking in controlled substance analogues, requisite weight increased, Secs. 13A-12-231, 20-2-23 am'd". March 2014. Retrieved 28 September 2015.
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