Dimemebfe

Dimemebfe
Clinical data
Other names	5-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 class	Serotonin 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
	IUPAC name 2-(5-Methoxy-1-benzofuran-3-yl)-N,N-dimethylethanamine;
CAS Number	140853-58-3 Y;
PubChem CID	126589;
ChemSpider	112474 N;
UNII	9JXZ3RM7Y9;
CompTox Dashboard (EPA)	DTXSID80161481 ;
Chemical and physical data
Formula	C13H17NO2
Molar mass	219.284 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN(C)CCc1coc(c1c2)ccc2OC;
	InChI 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;
	NY (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.¹²³⁴ 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.¹²³⁴ The drug has been encountered as a novel designer drug.³

Interactions

Pharmacology

Pharmacodynamics

Dimemebfe acts as an agonist of the serotonin 5-HT_1A 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-HT_1A 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 1992.³⁴ Subsequently, it emerged as a novel designer drug by 2012.³

Society and culture

Legal status

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

References

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.
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.
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.
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.
"Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
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
"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.

External links

Dimemebfe - Isomer Design

[Nichols2012-1] 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.

[Nichols2018-2] 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.

[CasaleHays2012-3] 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.

[TomaszewskiJohnsonHuang1992-4] 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.

[CDSA-5] "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.

[OrangeBook2026-6] 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.

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