5-APB
1-(1-benzofuran-5-yl)propan-2-amine
Overview
5-APB belongs to Entactogens/Empathogens / Phenethylamines.
Effects
- An MDMA-like entactogen: euphoria, emotional warmth, empathy and sociability with stimulant energy, though often described as somewhat less intense than MDMA.
- A mild psychedelic/visual component (visual disturbances) can appear, reflecting its serotonin-receptor agonism.
- Notably long-lasting (≈3–8 hours), with a correspondingly drawn-out comedown.
- Common unwanted effects mirror MDMA: jaw tension, a raised heart rate and body temperature, anxiety and after-effects.
Dosing & duration
Oral. Not a recommendation. 5-APB has never been studied in controlled human trials, so these are only commonly cited recreational ranges. It is more potent and much longer-lasting than MDMA which: together with its 5-HT2B-mediated cardiotoxicity and its hyponatraemia and serotonin-toxicity risks: makes redosing especially dangerous. Note that the hydrochloride salt is about 10% more potent by mass than the succinate.
Dose ranges
≈50–75 mg
≈75–125 mg
≈125–175 mg
Duration
≈45–90 min
≈2–4 h
≈3–8 h
Chemical & Physical Properties
| Formula | C11H13NO |
| Molar mass | 175.23 g/mol |
| State | Solid (usually the succinate or hydrochloride salt, the hydrochloride is ~10% more potent by mass) |
| Melting point | Not reported |
| Boiling point | Not reported |
| Density | Not reported |
| Vapor pressure | Not reported |
| pKa | Not reported |
| LogP | 2.1 (predicted, XLogP3) |
| Solubility | Not reported |
| Refractive index | Not reported |
Identifiers & Synonyms
| CAS | 286834-81-9 |
| CAS (enantiomer) | |
| PubChem CID | 9837232 |
| InChIKey | VKUMKUZDZWHMQU-UHFFFAOYSA-N |
| InChI | InChI=1S/C11H13NO/c1-8(12)6-9-2-3-11-10(7-9)4-5-13-11/h2-5,7-8H,6,12H2,1H3 |
| SMILES | CC(CC1=CC2=C(C=C1)OC=C2)N |
Synonyms
- 5-APB
- 5-(2-Aminopropyl)benzofuran
- Benzofury
- Benzo Fury
Pharmacodynamics & Biochemistry
5-APB (5-(2-aminopropyl)benzofuran) is a benzofuran entactogen: the benzofuran analogue of MDA and one of the compounds sold as 'Benzo Fury'. It acts as a serotonin–noradrenaline–dopamine releasing agent (and reuptake inhibitor) with balanced, potent release of all three monoamines (EC50 ≈19 nM serotonin, ≈21 nM noradrenaline, ≈31 nM dopamine), giving MDMA-like entactogenic and stimulant effects. It fully substitutes for MDMA in animal drug-discrimination tests. It is also a direct serotonin-receptor agonist: potent at 5-HT2B (EC50 ≈280 nM) and 5-HT2C, with weaker, low-potency 5-HT2A agonism and 5-HT1A affinity, plus activity at TAAR1, which accounts for the mild 'psychedelic'/visual quality some users report. Its potent 5-HT2B agonism is a specific safety concern: chronic 5-HT2B activation drives cardiac valve disease, as seen with fenfluramine and (with heavy use) MDMA, so repeated 5-APB use is expected to carry a similar cardiotoxic risk.
Biological targets
- SERT
- NET
- DAT
- 5-HT2B
- 5-HT2C
Binding & functional measurements
| Target | Measurement | Species |
|---|---|---|
| Serotonin transporter | EC50 19 ± 2.0 nM Emax 104% | Rat |
| Noradrenaline transporter | EC50 21 ± 4.0 nM Emax 103% | Rat |
| Dopamine transporter | EC50 31 ± 3.0 nM Emax 103% | Rat |
| 5-HT2B | EC50 280 nM | Human |
| 5-HT2C | Ki 880 nM | Human |
| 5-HT1A | Ki 3,300 nM | Human |
| 5-HT2A | EC50 6,300 nM | Human |
| TAAR1 | Unspecified High affinity (mouse/rat TAAR1) | Rodent |
Pharmacokinetics
| Bioavailability | Oral |
| Tmax | Not well characterised (onset ≈45–90 min) |
| Half-life | Not established in humans (duration ≈3–8 h) |
| Vd | Not reported |
| Protein binding | Not reported |
| Metabolism | Hepatic |
| Excretion | Renal (presumed) |
Toxicology & Safety
Not reported
5-APB carries the serotonergic risks of an MDMA-like releaser: hyperthermia, serotonin toxicity (especially with other serotonergic drugs) and hyponatraemia (dangerously low blood sodium from drinking too much water), which has caused at least one death. Several deaths, alone and in combination, have been reported. Its long duration (up to ~8 h) encourages redosing and overexertion. The most distinctive concern is its potent 5-HT2B receptor agonism, which, as with fenfluramine and MDMA, is expected to damage heart valves (valvulopathy) with repeated use. It has never been tested in humans and its safety margin is unknown. Missing data must never be read as evidence of safety.[2][3]
Legal Status
US: Not federally scheduled. UK: Class B. DE: BtMG Anlage II
Interactions & Contraindications
Drug interactions
Contraindications
No interactions or contraindications listed.
Usage & Context
- Emerged as a 'legal high' / designer drug around 2010–2011, widely sold as 'Benzo Fury' (pellets or powder), often alongside its isomer 6-APB.
- Originally patented by Eli Lilly in 2000 as a candidate 5-HT2C agonist. Adopted recreationally as an MDMA substitute before being banned across many countries.
Sources & Evidence
- PubChem: 5-APB (CID 9837232) — identifiers & computed properties
- Wikipedia: 5-APB — pharmacology, effects, adverse effects, history & legal status CC BY-SA 4.0
- Rickli A, Kopf S, Hoener MC, et al. (2015). Pharmacological profile of novel psychoactive benzofurans. Br J Pharmacol 172:3412-25.
PMID 25765500 · doi:10.1111/bph.13128
- Brandt SD, Walters HM, Partilla JS, et al. (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) 237:3703-3714.
PMID 32875347 · doi:10.1007/s00213-020-05648-z
- DEA Diversion Control Division: Controlled Substance Schedules (5-APB — not scheduled, Federal Analogue Act may apply)
- GOV.UK: Controlled drugs list (Misuse of Drugs legislation) — 5-APB is Class B OGL v3.0
- PubChem computed properties (CID 9837232)