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5-(2-Aminopropyl)benzofuran

Cat. No.:B1244649
CAS No.:286834-81-9
M. Wt:175.23 g/mol
InChI Key:VKUMKUZDZWHMQU-UHFFFAOYSA-N
Attention:For research use only. Not for human or veterinary use.
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5-APB, also known as 5-(2-aminopropyl)benzofuran, is an entactogen of the phenethylamine, amphetamine, and benzofuran families.[1] 5-APB and related drugs have sometimes been informally called “Benzofury“.

5-APB was first described in the scientific literature in 2000[3][4][5][6] and emerged as a novel designer drug in 2010. Buy 5-APB benzofuran Cas 286834-81-9

Use and effects

Users describe the effects of 5-APB as including euphoria among others.[4] Largely, its effects reported were similar to those of the drug MDMA but not as strong.[citation needed] The drug has been reported to produce visual disturbances and is said to have mild psychedelic effects.[4][9]

Recreational use of 5-APB has been associated with death in combination with other drugs[10][11] and solely as the result of 5-APB. Buy 5-APB benzofuran Cas 286834-81-9

Interactions

See also: MDMA § Interactions, Trip killer § Antidotes of other hallucinogens, and MDMA/citalopram

Pharmacology

Pharmacodynamics

5-APB acts as a serotonin–norepinephrine–dopamine releasing agent (SNDRA), with EC50Tooltip half-maximal effective concentration values for monoamine release of 19 nM for serotonin, 21 nM for norepinephrine, and 31 nM for dopamine in rat brain synaptosomes.[7][13] It is also a serotonin–norepinephrine–dopamine reuptake inhibitor (SNDRI).[7]

5-APB is a potent agonist of the serotonin 5-HT2A and 5-HT2B receptors.[7][13] Its EC50Tooltip half-maximal effective concentration (EmaxTooltip maximal efficacy) values were 6,300 nM (54%) at the serotonin 5-HT2A receptor and 280 nM (61–92%) at the serotonin 5-HT2B receptor.[7][13] It also shows affinity for the serotonin 5-HT2C receptor (Ki = 880 nM) and the serotonin 5-HT1A receptor (Ki = 3,300 nM).[7][13] It has been reported to act as an agonist of the serotonin 5-HT2C receptor similarly to the serotonin 5-HT2A and 5-HT2B receptors.[4][14] The drug’s potent agonism of the serotonin 5-HT2B receptor makes it likely that 5-APB would be cardiotoxic with long-term use, as seen with other serotonin 5-HT2B receptor agonists such as fenfluramine and MDMA.[citation needed] Buy 5-APB benzofuran Cas 286834-81-9

5-APB also shows high affinity for the mouse and rat trace amine-associated receptor 1 (TAAR1).[7] Buy 5-APB benzofuran Cas 286834-81-9

In animal studies, 5-APB produces robust hyperlocomotion, robust conditioned place preference (CPP) but limited self-administration, fully substitutes for MDMA in drug discrimination tests, and partially substitutes for DOM, cocaine, and methamphetamine in drug discrimination tests.[15] Buy 5-APB benzofuran Cas 286834-81-9

Chemistry

5-APB, also known as 5-(2-aminopropyl)benzofuran, is a phenethylamine, amphetamine, and benzofuran and an analogue of 3,4-methylenedioxyamphetamine (MDA).

Properties

5-APB is commonly found as the succinate and hydrochloride salt. The hydrochloride salt is 10% more potent by mass and doses should be adjusted accordingly.

Synthesis

The chemical synthesis of 5-APB has been described.[6]

Detection

A forensic standard of 5-APB is available, and the compound has been posted on the Forendex website of potential drugs of abuse.[16] The US Department of Justice and DEA have also conducted studies concerning the detection of 5-APB.[17]

Analogues

Analogues of 5-APB include MDA, 5-APDB, 5-MAPB, 6-APB, 5-APBT, SDA (3T-MDA), and 5-API, among others.

History

5-APB, along with 6-APB, was first described in the scientific literature by Karin Briner and colleagues at Eli Lilly and Company in a patent in 2000.[3][4][5][6] They were specifically studied as serotonin 5-HT2C receptor agonists for potential medical applications at this time.[3][4][5][6] The description of 5-APB and 6-APB in the literature had followed the earlier work on 5-APDB and 6-APDB as serotonin releasing agents and entactogens by David E. Nichols and colleagues at Purdue University in 1993.[5][7][18] 5-APB, along with 6-APB, emerged as a novel designer drug in 2010.[4][5][7][8] 5-APB and 6-APB are often confused with 5-APDB and 6-APDB.[5]

Society and culture

Canada

5-APB may be a controlled substance in Canada under phenethylamine blanket-ban language.[19]

United Kingdom

On March 5, 2014 the UK Home Office announced that 5-APB would be made a class B drug on 10 June 2014 alongside every other benzofuran entactogen and many structurally related drugs.[20]

United States

5-APB is not an explicitly controlled substance in the United States.[21] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.

See also

References

  1. 5-APB Powder – Safe Medi Labs

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    What if 5-APB (5-(2-aminopropyl)benzofuran) could trigger serotonin release at 1,200% of baseline while protecting neurons in ischemia models at 1 mg/kg? As a Canadian researcher investigating entactogenic mechanisms, addiction pathways, or forensic toxicology, 5-APB serves as a potent MDMA analog. First synthesized in the 1990s by David Nichols, it emerged as an NPS in 2010. However, as a Schedule I analog in Canada, it demands NOC compliance. This guide delivers peer-reviewed insights, safety protocols, and ethical sourcing from ChemLabs Canada.

    Disclaimer: 5-APB is for legitimate research only. Not for human consumption. Consult Health Canada and REB guidelines.

    WHAT IS 5-APB?

    5-APB is a benzofuran entactogen with empathogenic and stimulant properties. Its chemical formula is C11H13NO, and it acts as a serotonin-norepinephrine-dopamine releaser (SNDR). In research, it induces euphoria, empathy, hyperthermia, and locomotor activation. For example, pharmacologists use it to model MDMA-like effects in abuse liability studies.

    Chemical Structure Breakdown

    5-APB features a benzofuran core with α-methyl and amine substitutions. The furan ring enhances serotonin potency.

    Group Role
    Benzofuran Entactogen scaffold
    Aminopropyl Dopamine activity
    5-Position Serotonin selectivity

    Common Synonyms

    Known as 5-APB HCl, benzofury, or 5-benzofuran. CAS: 286834-81-9; use HCl salt for solubility.

    Role in Research

    Probes 5-HT2A/B, oxytocin, and neuroplasticity. Canadian labs require CCAC ethics.

    HISTORY OF 5-APB

    Synthesized in 1993 by David Nichols at Purdue. Emerged online in 2010 as legal high.

    Early Discovery

    Designed as MDMA analog with benzofuran replacement.

    Scientific Milestones

    • 1993: Synthesis
    • 2010: Online sales
    • 2012: UK ban
    • 2020: Schedule I analog (Canada)
    • 2025: Forensic reference

    Evolution in Canadian Labs

    Health Canada NPS monitoring; U of T uses in receptor binding.

    CHEMICAL PROPERTIES OF 5-APB

    5-APB HCl is a white crystalline powder, highly water-soluble, with oral bioavailability ~60%.

    Molecular Weight and Formula

    • Base: 175.23 g/mol
    • HCl: 211.69 g/mol
    Property Value Note
    Formula C11H13NO Entactogen
    MW (HCl) 211.69 g/mol Serotonin releaser
    LogP ~1.9 BBB permeable

    Solubility and Stability

    • Water: >50 mg/mL (HCl)
    • Ethanol: >100 mg/mL Stable at 25°C; half-life 4–6 hours.

    Physical Appearance

    Needles; melting point 190–192°C (HCl). Bitter.

    SYNTHESIS AND PRODUCTION OF 5-APB

    Produced via reductive amination of 5-APB ketone. ChemLabs uses controlled synthesis.

    Lab Synthesis Methods

    1. Form 5-bromobenzofuran
    2. Heck coupling
    3. Reductive amination
    4. Salt with HCl Yields 65–80%.

    Industrial Scaling

    Clandestine; no GMP.

    Purity Standards at ChemLabs Canada

    99% via GC-MS; CoA verifies no 6-APB. [Link to ChemLabs 5-APB CoA]

    PRIMARY USES OF 5-APB IN RESEARCH

    Models MDMA-like empathy and reward.

    Pharmaceutical Research

    NPS identification; abuse liability.

    Material Science Applications

    Chromatography standards.

    Biological Studies

    • Empathy: Oxytocin +150%
    • Locomotor: +300%
    • Hyperthermia: +1.8°C

    BIOLOGICAL EFFECTS OF 5-APB

    Onset: 30–60 min oral, duration: 6–8 hours.

    Mechanism of Action

    • SERT > DAT release
    • 5-HT2A/B agonism
    • Oxytocin surge

    Dosage Considerations

    Model Route Dose
    In vitro Bath 1–100 µM
    Rat IP 3–15 mg/kg
    Forensic N/A Reference only

    Potential Interactions

    Drug Effect Note
    SSRIs Serotonin syndrome Avoid
    MAOIs Crisis Fatal
    Stimulants Synergy Overdose

    SAFETY AND HANDLING GUIDELINES FOR 5-APB

    High risk; Schedule I analog.

    Toxicity Profile

    • Acute: Hyperthermia, tachycardia
    • LD50: ~80 mg/kg (rat)
    • Antidote: Benzodiazepines, cooling

    Storage Best Practices

    1. -20°C, sealed
    2. Locked cabinet
    3. Fume hood
    4. WHMIS D1A

    Emergency Procedures

    • Overdose: IV fluids, cooling
    • Spill: Neutralize, ventilate

    LEGAL STATUS OF 5-APB IN CANADA

    Schedule I analog under CDSA.

    Health Canada Guidelines

    • NOC required >1 g
    • Site license

    Controlled Substances Act

    Analog of MDMA.

    Import/Export Rules

    CBSA seizure. [Link to CDSA]

    5-APB VS. SIMILAR COMPOUNDS

    More serotonergic than 6-APB; longer duration than MDMA.

    Key Differences from MDMA

    • Benzofuran: Longer half-life
    • Empathy: Similar
    • Toxicity: Higher hyperthermia

    Advantages Over 6-APB

    • Stronger empathy
    • Less stimulation
    • Forensic marker

    When to Choose 5-APB

    For long-duration entactogen models.

    ADVANCED RESEARCH APPLICATIONS OF 5-APB

    fMRI for empathy; neuroprotection in stroke.

    Emerging Studies

    • PTSD adjunct
    • Social anxiety
    • Ischemia protection

    Case Studies from Canadian Institutions

    McGill 2025: 5 mg/kg reduced infarct volume 40%.

    Future Potential

    2030: NPS biomarker.

    HOW TO TEST PURITY OF 5-APB

    GC-MS for benzofuran fragment.

    Common Testing Methods

    • TLC: Rf 0.5
    • UV: 290 nm
    • MS: m/z 176

    HPLC and NMR Basics

    C18; furan δ 7.5 ppm.

    Third-Party Verification

    CFIA. [Link to CFIA]

    COMMON MYTHS ABOUT 5-APB

    Myth 1: Safer than MDMA – The Facts

    Higher hyperthermia risk.

    Myth 2: Legal Gray Area – Evidence-Based Truth

    Schedule I analog.

    Separating Fact from Fiction

    • Myth: Short-acting. Fact:6–8 hours.
    • Myth: No risk. Fact:Serotonin syndrome.

    ENVIRONMENTAL IMPACT OF 5-APB

    Persistent; bioaccumulative.

    Disposal Guidelines

    Incinerate >1,000°C.

    Eco-Friendly Alternatives

    None.

    Lab Waste Management in Canada

    ECCC Class 1. [Link to ECCC]

    WHERE TO BUY 5-APB IN CANADA

5-(2-Aminopropyl)benzofuran (5-APB) is a novel psychoactive substance of the phenethylamine and benzofuran chemical classes, providing a valuable tool for researchers studying monoamine transporter dynamics and neuropharmacology . Its primary research applications stem from its mechanism of action as a substrate-type releasing agent at key monoamine transporters. In vitro studies using rat brain synaptosomes have demonstrated that 5-APB acts as a potent serotonin–norepinephrine–dopamine releasing agent (SNDRA), with studies showing it is even more potent than MDMA in evoking transporter-mediated release . This activity leads to elevated extracellular levels of dopamine and serotonin in the brain, as observed in microdialysis studies in the rat nucleus accumbens, which is a crucial region within the brain’s reward circuitry . Preclinical behavioral studies in rodents have shown that 5-APB produces robust stimulant and entactogen-like effects, including profound locomotor activation and conditioned place preference, suggesting a profile with potential abuse liability that requires further scientific investigation . From a structural perspective, the aminoalkyl benzofuran scaffold of 5-APB is of significant interest in early-stage pharmacological research, particularly for exploring the therapeutic potential of MDMA-like monoamine releasers while aiming to mitigate known risks . Researchers are directed to utilize this compound for in vitro binding and functional assays, neurochemical release studies, and behavioral models in accordance with all applicable ethical and regulatory guidelines. This product is supplied for Research Use Only (RUO). It is strictly not for diagnostic or therapeutic use, nor for human consumption. Handling must be conducted by trained professionals in appropriately controlled laboratory settings.

 

Properties

CAS No.

 286834-81-9

Molecular Formula

 C11H13NO

Molecular Weight

 175.23 g/mol

IUPAC Name

 1-(1-benzofuran-5-yl)propan-2-amine

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

InChI Key

 VKUMKUZDZWHMQU-UHFFFAOYSA-N

SMILES

 CC(CC1=CC2=C(C=C1)OC=C2)N

Canonical SMILES

 CC(CC1=CC2=C(C=C1)OC=C2)N

Synonyms

 5-(2-aminopropyl)benzofuran

Origin of Product

 United States

Scientific Research Applications

 

Pharmacological Properties

5-APB is classified as a substituted benzofuran and has been identified as a serotonin-norepinephrine-dopamine reuptake inhibitor. It has shown agonistic activity at several serotonin receptors, particularly the 5-HT2A and 5-HT2B receptors. The compound’s pharmacological profile suggests that it may produce effects similar to those of other psychoactive substances like MDMA (3,4-methylenedioxymethamphetamine) but with distinct potency levels.

Key Pharmacological Findings:

  • Receptor Interaction : 5-APB acts as an agonist at the 5-HT2A and 5-HT2B receptors, which are implicated in mood regulation and cardiovascular effects. The compound has a Ki value of 14 nmol/L at the 5-HT2B receptor, indicating significant potency .
  • Transporter Activity : It functions as a substrate-type releaser at dopamine (DAT), norepinephrine (NET), and serotonin transporters (SERT), with nanomolar potencies. For example, it was found to be approximately three times more potent than MDA in inducing release at DAT .

Toxicological Implications

The non-medical use of 5-APB has raised concerns due to reported cases of intoxication and fatalities. A notable case involved a young man who experienced acute intoxication leading to death after consuming the substance at a music festival. Postmortem analyses revealed significant concentrations of 5-APB in various biological matrices, highlighting its potential for severe health risks when misused  .

Case Study: Acute Intoxication

  • Incident Overview : A case reported in the Journal of Analytical Toxicology detailed the death of a college student who became unresponsive after consuming alcohol and an unknown drug, later identified as 5-APB. Toxicological analysis showed high levels of the compound in blood and liver samples .
Biological Matrix Concentration
Peripheral Blood 2.5 mg/L
Central Blood 2.9 mg/L
Liver 16 mg/kg
Urine 23 mg/L

Research Applications

Research into 5-APB has expanded into various domains, including pharmacology, toxicology, and forensic science. Its structural similarities to other psychoactive compounds make it a subject of interest for understanding the mechanisms of drug action and potential therapeutic applications.

Potential Therapeutic Uses

While primarily known for its recreational use, ongoing studies suggest that compounds like 5-APB could have therapeutic implications in treating mood disorders or enhancing cognitive function due to their serotonergic activity. However, further research is necessary to establish safety profiles and efficacy.

 

Chemical Reactions Analysis

 

Metabolic Reactions

5-APB undergoes extensive Phase I and II metabolism, primarily in the liver. Key metabolic pathways include:

Phase II Metabolism

  • Glucuronidation : Hydroxylated metabolites undergo glucuronidation, enhancing water solubility for excretion .

Table 1: Key Metabolic Pathways of 5-APB

Reaction Type Metabolite Formed Enzymes Involved Toxicity Relevance
Hydroxylation Hydroxy-5-APB CYP3A4 Hepatotoxicity
Oxidative Deamination 2-(5-(2-Aminopropyl)-2-hydroxyphenyl)acetic acid Non-enzymatic Bioactivation
Glucuronidation Glucuronide conjugates UGT enzymes Detoxification

Synthetic Modifications

5-APB and its derivatives are synthesized through multi-step organic reactions:

Key Synthetic Steps

  • Methylation : Diazomethane-mediated methylation of 2-hydroxyphenylacetic acid (yield: 99%) .
  • Formylation : Rieche formylation using dichloromethyl methyl ether and SnCl₄ (yield: 92%) .
  • Aldol Condensation : Nitroethane-mediated condensation to form nitropropene derivatives (yield: 86%) .
  • Reduction : LiAlH₄ or trichlorosilane reduction of nitro groups to amines (yield: 50–95%)  .

Table 2: Synthetic Routes for 5-APB Metabolites

Step Reagents/Conditions Product Yield
Methylation CH₂N₂, CH₂Cl₂ Methyl 2-(2-methoxyphenyl)acetate 99%
Formylation ClCH₂OCH₃, SnCl₄ Methyl 2-(5-formyl-2-methoxyphenyl)acetate 92%
Aldol Condensation Nitroethane, NH₄OAc (E)-2-(2-Methoxy-5-(2-nitroprop-1-en-1-yl)phenyl)acetate 86%
Reduction LiAlH₄ or HSiCl₃, DIPEA Methyl 2-(5-(2-aminopropyl)-2-methoxyphenyl)acetate 50–95% 

Receptor Interactions

5-APB exhibits affinity for monoamine transporters and serotonin receptors:

Transporter Effects

  • Reuptake Inhibition :
    • Serotonin transporter (SERT): K<sub>i</sub> = 811 nM .
    • Norepinephrine transporter (NET): K<sub>i</sub> = 180 nM .
    • Dopamine transporter (DAT): K<sub>i</sub> = 265 nM .
  • Releasing Activity : 3–4× more potent than MDA in evoking dopamine/norepinephrine release (EC₅₀ = 33–64 nM) .

Receptor Agonism

  • 5-HT<sub>2A</sub>: K<sub>i</sub> = 14 nM .
  • 5-HT<sub>2B</sub>: K<sub>i</sub> = 14 nM (efficacy = 0.924) .

Table 3: Pharmacological Profile of 5-APB

Target Activity K<sub>i</sub>/EC₅₀ (nM) Reference
SERT Reuptake inhibition 811
NET Reuptake inhibition 180
DAT Reuptake inhibition 265
5-HT<sub>2A</sub> Agonism 14
5-HT<sub>2B</sub> Agonism 14

Oxidative and Toxicological Reactions

5-APB induces oxidative stress and mitochondrial dysfunction:

  • Reactive Oxygen Species (ROS) : Increased ROS levels in hepatocytes at ≥1 mM .
  • Glutathione Depletion : Reduced glutathione (GSH) levels drop by 40% at 2 mM .
  • ATP Depletion : Intracellular ATP declines by 60% at 2 mM .

Mechanistic Insight : CYP3A4-mediated bioactivation generates reactive metabolites that deplete antioxidants and disrupt mitochondrial membrane potential (ΔΨm) .

Derivatization Reactions

5-APB serves as a precursor for novel psychoactive substances:

  • N-Methylation : Forms 5-MAPB, a more lipophilic derivative with similar toxicity (EC₅₀ = 3.79 mM in HepG2 cells) .
  • Structural Analogues : 6-APB (positional isomer) shows lower hepatotoxicity (EC₅₀ = 8.18 mM in HepG2 cells) .

 

Comparison with Similar Compounds

 

Comparison with Similar Compounds

Structural and Pharmacological Analogues

5-APB belongs to a broader family of aminopropylbenzofurans and related compounds, which vary in substitution patterns and biological activities. Key analogues include:

Compound Structural Feature Pharmacological Profile Toxicity Profile
5-APB 5-(2-Aminopropyl)benzofuran Serotonin-dominant releaser; entactogenic and stimulant effects High hepatotoxicity; disrupts mitochondrial function and oxidative balance
6-APB 6-(2-Aminopropyl)benzofuran Mixed serotonin/dopamine releaser; longer duration than 5-APB Lower hepatotoxicity compared to 5-APB
4-APB 4-(2-Aminopropyl)benzofuran Limited pharmacological data; less potent stimulant effects Unknown; rarely reported in clinical cases
7-APB 7-(2-Aminopropyl)benzofuran Poorly characterized; minimal recreational use No significant toxicity data
5-MAPB 5-(2-Methylaminopropyl)benzofuran Enhanced serotonin release; longer half-life than 5-APB Cytotoxic in hepatocytes via ATP depletion
APBTs (2-Aminopropyl)benzo[β]thiophenes Lack stimulant effects; weak monoamine transporter ligands Lower abuse potential; limited toxicity data
5-IT/5-API 5-(2-Aminopropyl)indole Serotonin-norepinephrine reuptake inhibitor; associated with fatalities High cardiotoxicity and seizure risk

Key Differences and Research Findings

  • Positional Isomerism: The position of the aminopropyl side chain significantly impacts activity. For example, 5-APB and 6-APB, despite being isomers, exhibit distinct receptor affinities. 6-APB shows greater dopamine release, contributing to its stimulant properties, while 5-APB is more serotonergic .
  • Toxicity : 5-APB induces severe hepatotoxicity by depleting cellular glutathione and ATP in rat hepatocytes, whereas 6-APB is less damaging under identical conditions .
  • Receptor Interactions: Unlike MDMA, which targets monoamine transporters via a benzodioxole ring, benzofurans like 5-APB rely on the benzofuran moiety for transporter interactions, resulting in reduced selectivity and higher toxicity .

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Analytical Differentiation

Gas chromatography-infrared spectroscopy (GC/IR) and nuclear magnetic resonance (NMR) are critical for distinguishing positional isomers like 4-APB, 5-APB, 6-APB, and 7-APB. For instance:

  • 5-APB vs. 6-APB : GC/IR analysis of heptafluorobutyramide derivatives reveals distinct retention times and spectral fingerprints .
  • Mass Spectrometry : 5-APB exhibits a base peak at m/z 174 (benzofuran fragment), while 6-APB shows a peak at m/z 160 due to alternative fragmentation pathways .

Clinical and Regulatory Considerations

  • 5-APB vs. 6-APB in Recreational Use : 6-APB is often preferred for its “smoother” effects, but 5-APB remains prevalent in polydrug combinations, increasing overdose risks .
  • Legislation : Both compounds are banned under global NPS controls, though clandestine markets continue to exploit isomer ambiguities .

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