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

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

  1. 1 2 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. 1 2 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. 1 2 3 4 5 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. 1 2 3 4 5 6 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. ↑ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
  6. ↑ Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) (PDF), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026
  7. ↑ "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.
source: https://en.wikipedia.org/wiki/Dimemebfe