Article · Wikipedia archive · Last revised Jun 14, 2026

3-APB

3-APB, also known as 3-(2-aminopropyl)benzofuran or as 1-oxa-α-methyltryptamine (1-oxa-AMT), is a drug of the benzofuran family related to the psychedelic tryptamine α-methyltryptamine (AMT). It is the analogue and bioisostere of AMT in which the nitrogen atom of the indole ring has been replaced with an oxygen atom, resulting in the drug being a benzofuran rather than tryptamine derivative.

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3-APB
Clinical data
Other names3-(2-Aminopropyl)benzofuran; 3-APB; 1-Oxa-α-methyltryptamine; 1-Oxa-AMT
Identifiers
  • 1-(1-benzofuran-3-yl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H13NO
Molar mass175.231 g·mol−1
3D model (JSmol)
  • CC(CC1=COC2=CC=CC=C21)N
  • InChI=1S/C11H13NO/c1-8(12)6-9-7-13-11-5-3-2-4-10(9)11/h2-5,7-8H,6,12H2,1H3
  • Key:YOSBGWAOEQRQMP-UHFFFAOYSA-N

3-APB, also known as 3-(2-aminopropyl)benzofuran or as 1-oxa-α-methyltryptamine (1-oxa-AMT), is a drug of the benzofuran family related to the psychedelic tryptamine α-methyltryptamine (AMT).12 It is the analogue and bioisostere of AMT in which the nitrogen atom of the indole ring has been replaced with an oxygen atom, resulting in the drug being a benzofuran rather than tryptamine derivative.12

The properties of 3-APB do not yet appear to have been reported.1 However, derivatives of 3-APB have been studied and described.1345 An example is its 5-methoxy analogue mebfap (5-MeO-3-APB; a benzofuran analogue of 5-MeO-AMT), which is known to have high affinity for the serotonin 5-HT2 receptors.1345 In addition, 3-APBT, the analogue of 3-APB with a sulfur atom instead of an oxygen atom, is a highly potent serotonin–norepinephrine–dopamine releasing agent (SNDRA) and serotonin receptor agonist, with psychedelic-like but not stimulant-like effects in animals.61

Positional isomers of 3-APB such as 5-APB and 6-APB are monoamine releasing agents and entactogens of the amphetamine and benzofuran families.789 Besides 3-APBT, all of the possible positional isomers of the APBTs (i.e., 2-APBT through 7-APBT) are active as potent SNDRAs and at least some also as serotonin 5-HT2 receptor agonists.16

See also

See also

References

References

  1. Rudin D, McCorvy JD, Glatfelter GC, Luethi D, Szöllősi D, Ljubišić T, et al. (March 2022). "(2-Aminopropyl)benzo[β]thiophenes (APBTs) are novel monoamine transporter ligands that lack stimulant effects but display psychedelic-like activity in mice". Neuropsychopharmacology. 47 (4): 914–923. doi:10.1038/s41386-021-01221-0. PMC 8882185. PMID 34750565. The 5-HT2A receptor is the primary target for LSD, psilocybin, and other hallucinogenic drugs in the brain [76, 77]. Other hallucinogenic drugs acting strongly at 5-HT2A include 3-API [78, 79], while, by contrast, 5-API displays a much lower potency and efficacy [18]. Hence, the interaction of APIs with the 5-HT2A receptor is dependent on the position of the alkylamine side chain on the indole ring. Although relevant data have not been reported for 3-APB, the 5-methoxy-substituted derivative 5-methoxy-3-(2-aminopropyl)benzofuran has high affinity for 5-HT2A sites [80]. In line with the activity of 5-API, both 5-APB and 6-APB have been shown to be active at 5-HT2A with relatively low potency and efficacy [20]. Given those previous findings, it is notable that 3-APBT, 5-APBT, and 6-APBT are highly efficacious 5-HT2A agonists. Hence, compared to APIs and APBs, the ability of APBTs to activate the 5-HT2A receptor does not depend on side chain position.
  2. "I+/--Methyl-3-benzofuranethanamine". PubChem. U.S. National Library of Medicine. Retrieved 31 January 2025.
  3. Nichols DE (2017). "Chemistry and Structure–Activity Relationships of Psychedelics". Behavioral Neurobiology of Psychedelic Drugs. Current Topics in Behavioral Neurosciences. Vol. 36. Berlin, Heidelberg: Springer Berlin Heidelberg. pp. 1–43. doi:10.1007/7854_2017_475. ISBN 978-3-662-55878-2. PMID 28401524.
  4. Nichols DE (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.
  5. Tomaszewski Z, Johnson MP, Huang X, Nichols DE (May 1992). "Benzofuran bioisosteres of hallucinogenic tryptamines". J Med Chem. 35 (11): 2061–4. doi:10.1021/jm00089a017. PMID 1534585.
  6. Brandt SD, Carlino L, Kavanagh PV, Westphal F, Dreiseitel W, Dowling G, et al. (August 2020). "Syntheses and analytical characterizations of novel (2-aminopropyl)benzo[b]thiophene (APBT) based stimulants". Drug Test Anal. 12 (8): 1109–1125. doi:10.1002/dta.2813. PMC 8281332. PMID 32372465.
  7. Oeri HE (May 2021). "Beyond ecstasy: Alternative entactogens to 3,4-methylenedioxymethamphetamine with potential applications in psychotherapy". J Psychopharmacol. 35 (5): 512–536. doi:10.1177/0269881120920420. PMC 8155739. PMID 32909493.
  8. Lapoint J, Welker KL (2022). "Synthetic amphetamine derivatives, benzofurans, and benzodifurans". Novel Psychoactive Substances. Elsevier. pp. 247–278. doi:10.1016/b978-0-12-818788-3.00007-3. ISBN 978-0-12-818788-3.
  9. Brandt SD, Walters HM, Partilla JS, Blough BE, Kavanagh PV, Baumann MH (December 2020). "The psychoactive aminoalkylbenzofuran derivatives, 5-APB and 6-APB, mimic the effects of 3,4-methylenedioxyamphetamine (MDA) on monoamine transmission in male rats". Psychopharmacology (Berl). 237 (12): 3703–3714. doi:10.1007/s00213-020-05648-z. PMC 7686291. PMID 32875347.
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