3-APBT

{{Infobox drug

| drug_name =

| image = 3-APBT.svg

| width =

| caption =

| pronounce =

| tradename =

| Drugs.com =

| MedlinePlus =

| licence_CA =

| licence_EU =

| DailyMedID =

| licence_US =

| pregnancy_AU =

| pregnancy_category =

| dependency_liability =

| addiction_liability =

| routes_of_administration =

| class = Serotonin–norepinephrine–dopamine releasing agent; Serotonin 5-HT₂ receptor agonist; Entactogen; Serotonergic psychedelic

| ATC_prefix =

| ATC_suffix =

| legal_status =

| bioavailability =

| protein_bound =

| metabolism =

| metabolites =

| onset =

| elimination_half-life =

| duration_of_action =

| excretion =

| CAS_number = 1201-27-0

| CAS_supplemental =

| PubChem = 517826

| PubChemSubstance =

| IUPHAR_ligand =

| DrugBank =

| ChemSpiderID = 451800

| UNII =

| KEGG =

| ChEBI =

| ChEMBL =

| NIAID_ChemDB =

| PDB_ligand =

| synonyms = SKF-6678; SK&F-6678; 3-(2-Aminopropyl)benzo[β]thiophene; α-Methylbenzo[b]thiophene-3-ethylamine

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

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

| SMILES = CC(CC1=CSC2=CC=CC=C21)N

| StdInChI = 1S/C11H13NS/c1-8(12)6-9-7-13-11-5-3-2-4-10(9)11/h2-5,7-8H,6,12H2,1H3

| StdInChIKey = NJJBOBSLFFUELD-UHFFFAOYSA-N

}}

3-APBT (former developmental code name SKF-6678), also known as 3-(2-aminopropyl)benzo[β]thiophene, is a monoamine releasing agent and serotonin receptor agonist of the benzothiophene group.{{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 Testing and Analysis | volume = 12 | issue = 8 | pages = 1109–1125 | date = August 2020 | pmid = 32372465 | doi = 10.1002/dta.2813 }}{{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 }} It is an analogue of α-methyltryptamine (AMT) in which the indole ring has been replaced with a benzothiophene ring.

The drug acts as a potent and well-balanced serotonin–norepinephrine–dopamine releasing agent (SNDRA). It is also a full agonist of the serotonin 5-HT₂ receptors, including of the serotonin 5-HT_2A, 5-HT_2B, and 5-HT_2C receptors. 3-APBT produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents. It does not stimulate locomotor activity in rodents, suggesting that it does not possess stimulant-type effects. The drug has been reported be a weak monoamine oxidase inhibitor (MAOI), specifically of monoamine oxidase A (MAO-A) ({{Abbrlink|IC₅₀|half-maximal inhibitory concentration}} = 16,200{{nbsp}}nM).{{cite journal | vauthors = Vallejos G, Fierro A, Rezende MC, Sepúlveda-Boza S, Reyes-Parada M | title = Heteroarylisopropylamines as MAO inhibitors | journal = Bioorganic & Medicinal Chemistry | volume = 13 | issue = 14 | pages = 4450–4457 | date = July 2005 | pmid = 15908219 | doi = 10.1016/j.bmc.2005.04.045 }}

3-APBT was developed by Smith, Kline & French (SKF) as a potential pharmaceutical drug in the late 1950s.{{cite patent | country = GB | number = 855115A | title=Improvements in or relating to β-aminoalkylthianaphthene and β-aminoalkylbenzofuran derivatives | fdate=29 May 1959 | url=https://patents.google.com/patent/GB855115A/ | assign = Smith Kline and French Laboratories Ltd. }} The drug and its positional isomer 2-APBT were reported to produce various central nervous system (CNS) effects and to be useful as a "ataractics, psychic energizers, and analgetics". 3-APBT has also been reported to have appetite suppressant effects in rodents, but to have considerably lower potency than AMT as an "analeptic" in rodents.{{cite journal | vauthors = Campaigne E, Neiss ES, Pfeiffer CC, Beck RA | title = Benzo[b]thiophen derivatives. XII. Synthesis of some 3-benzo[b]thienylalkylamines and comparison of their central nervous system activity with tryptamine isosteres | journal = Journal of Medicinal Chemistry | volume = 11 | issue = 5 | pages = 1049–1054 | date = September 1968 | pmid = 5697069 | doi = 10.1021/jm00311a031 }}