3-APB

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| image = 3-APB.svg

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| CAS_number = 105909-13-5

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| PubChem = 57014554

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| ChemSpiderID = 45884773

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| synonyms = 3-(2-Aminopropyl)benzofuran

| IUPAC_name = 1-(1-benzofuran-3-yl)propan-2-amine

| C=11 | H=13 | N=1 | O=1

| SMILES = CC(CC1=COC2=CC=CC=C21)N

| StdInChI = 1S/C11H13NO/c1-8(12)6-9-7-13-11-5-3-2-4-10(9)11/h2-5,7-8H,6,12H2,1H3

| StdInChIKey = YOSBGWAOEQRQMP-UHFFFAOYSA-N

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3-APB, also known as 3-(2-aminopropyl)benzofuran, is a drug of the benzofuran family related to α-methyltryptamine (AMT).{{cite journal | vauthors = Rudin D, McCorvy JD, Glatfelter GC, Luethi D, Szöllősi D, Ljubišić T, Kavanagh PV, Dowling G, Holy M, Jaentsch K, Walther D, Brandt SD, Stockner T, Baumann MH, Halberstadt AL, Sitte HH | title = (2-Aminopropyl)benzo[β]thiophenes (APBTs) are novel monoamine transporter ligands that lack stimulant effects but display psychedelic-like activity in mice | journal = Neuropsychopharmacology | volume = 47 | issue = 4 | pages = 914–923 | date = March 2022 | pmid = 34750565 | pmc = 8882185 | doi = 10.1038/s41386-021-01221-0 | url = | quote = 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. }}{{cite web | title=I+/--Methyl-3-benzofuranethanamine | work = PubChem | publisher = U.S. National Library of Medicine | url=https://pubchem.ncbi.nlm.nih.gov/compound/57014554 | access-date=31 January 2025}} It is an analogue of AMT in which the indole ring has been replaced with a benzofuran ring.

The properties of 3-APB do not yet appear to have been reported. However, derivatives of 3-APB have been studied and described.{{cite journal | vauthors = Tomaszewski Z, Johnson MP, Huang X, Nichols DE | title = Benzofuran bioisosteres of hallucinogenic tryptamines | journal = J Med Chem | volume = 35 | issue = 11 | pages = 2061–4 | date = May 1992 | pmid = 1534585 | doi = 10.1021/jm00089a017 | url = }} 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.{{cite book | vauthors = Nichols DE | title=Behavioral Neurobiology of Psychedelic Drugs | chapter=Chemistry and Structure–Activity Relationships of Psychedelics | publisher=Springer Berlin Heidelberg | publication-place=Berlin, Heidelberg | volume=36 | date=2017 | isbn=978-3-662-55878-2 | doi=10.1007/7854_2017_475 | page=1–43}}{{cite journal | vauthors =Nichols DE | title=Structure–activity relationships of serotonin 5‐HT 2A agonists | journal=Wiley Interdisciplinary Reviews: Membrane Transport and Signaling | volume=1 | issue=5 | date=2012 | issn=2190-460X | doi=10.1002/wmts.42 | doi-access=free | pages=559–579 | url=https://onlinelibrary.wiley.com/doi/pdfdirect/10.1002/wmts.42 | access-date=31 January 2025}} 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.{{cite journal | vauthors = Brandt SD, Carlino L, Kavanagh PV, Westphal F, Dreiseitel W, Dowling G, Baumann MH, Sitte HH, Halberstadt AL | title = Syntheses and analytical characterizations of novel (2-aminopropyl)benzo[b]thiophene (APBT) based stimulants | journal = Drug Test Anal | volume = 12 | issue = 8 | pages = 1109–1125 | date = August 2020 | pmid = 32372465 | doi = 10.1002/dta.2813 | url = }}

Positional isomers of 3-APB such as 5-APB and 6-APB are monoamine releasing agents and entactogens of the amphetamine and benzofuran families.{{cite journal | vauthors = Oeri HE | title = Beyond ecstasy: Alternative entactogens to 3,4-methylenedioxymethamphetamine with potential applications in psychotherapy | journal = J Psychopharmacol | volume = 35 | issue = 5 | pages = 512–536 | date = May 2021 | pmid = 32909493 | pmc = 8155739 | doi = 10.1177/0269881120920420 | url = }}{{cite book | vauthors = Lapoint J, Welker KL | title=Novel Psychoactive Substances | chapter=Synthetic amphetamine derivatives, benzofurans, and benzodifurans | publisher=Elsevier | date=2022 | isbn=978-0-12-818788-3 | doi=10.1016/b978-0-12-818788-3.00007-3 | page=247–278}}{{cite journal | vauthors = Brandt SD, Walters HM, Partilla JS, Blough BE, Kavanagh PV, Baumann MH | title = The psychoactive aminoalkylbenzofuran derivatives, 5-APB and 6-APB, mimic the effects of 3,4-methylenedioxyamphetamine (MDA) on monoamine transmission in male rats | journal = Psychopharmacology (Berl) | volume = 237 | issue = 12 | pages = 3703–3714 | date = December 2020 | pmid = 32875347 | pmc = 7686291 | doi = 10.1007/s00213-020-05648-z | url = }} 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.