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Description

5-APB Also known as:

  • 5-(2-aminopropyl)benzofuran
  • 1-(1-Benzofuran-5-yl)-2-propanamin[German][ACD/IUPAC Name]
  • 1-(1-Benzofuran-5-yl)-2-propanamine[ACD/IUPAC Name]
  • 1-(1-Benzofuran-5-yl)-2-propanamine[French][ACD/IUPAC Name]
  • 1-benzofuran-5-ylpropan-2-amine
  • 2M3825704H
  • 5-Benzofuranethanamine, α-methyl-[ACD/Index Name]
  • UNII:2M3825704H

A triple monoamine reuptake inhibitor. This agonism for 5-HT2B makes it likely that 5-APB would be cardiotoxic with long term use, as seen in other 5-HT2B agonists such as fenfluramine and MDMA.

Summary

It is structurally related to entactogens like 5-MAPB, 6-APB, and MDA. 5-APB was first synthesized in 1993 by psychedelic chemist and researcher David E. Nichols as a potential non-neurotoxic alternative to MDMA.

However, it did not come into popular recreational use until over a decade later, where it briefly entered the rave scene and global research chemicals market. It was sold along with other novel benzofuran entactogens under the name “Benzofury” before its sale and import were subsequently banned. Compared to other members of its family such as 6-APB and 5-MAPB, this compound in particular is known for its stimulating and euphoric effects which has resulted in its rise in popularity as a product which is easily accessible through the use of online research chemical vendors.

It has been commercially distributed as a designer drug alternative to MDMA since 2010. Very little data exists about the pharmacological properties, metabolism, and toxicity of 5-APB in humans, and it has only a brief history of human usage. It is highly advised that one take proper precautions, conduct independent research, and use proper harm reduction practices if choosing to use with this substance.

History

The synthesis of 5-APB was first reported by a team led by the medicinal chemist and psychedelic researcher David E. Nichols at Purdue University. They were examining the role of the MDA dioxle ring structure in interacting with serotonergic neurons.

It was also partly an effort to find an alternative to MDMA, which was gaining recognition as a potentially useful adjunct in psychotherapy, but was also being linked to neurotoxic effects. Human usage was not documented until 2010, when it emerged for sale on the research chemical market. It was particularly prominent in the UK “legal highs” market, where it was sold under the name “Benzofury”. On June 10, 2013 5-APB and a number of analogues were classified as Temporary Class Drugs in the UK following an ACMD recommendation. On November 28, 2013 the ACMD recommended that 5-APB and related benzofurans should become Class B, Schedule 1 substances.

On March 5, 2014 the UK Home Office announced that 6-APB would be made a class B drug on 10 June 2014 alongside every other benzofuran entactogen and many structurally related drugs.

Chemistry

5-APB

5-APB

It can also be classified as an amphetamine derivative because the ethylamine chain is alpha methylated.

Molecules of the amphetamine class contain a phenethylamine core featuring a phenyl ring bound to an amino (NH2) group through an ethyl chain with an additional methyl substitution at Rα.

The oxygen in the furan ring is placed at the 5 position, which generally constitutes more stimulating effects than when the oxygen is placed at the 6 position, which is usually described as being more psychedelic in effects.

5-APB is commonly found as the succinate and hydrochloride salt.

The hydrochloride salt is 10% more potent by mass so doses should be adjusted accordingly.

Common Name5-(2-aminopropyl)benzofuran
Systematic name5-(2-aminopropyl)benzofuran
FormulaC_{11}H_{13}NO
SMILESo2c1ccc(cc1cc2)CC(N)C
Std. InChiInChI=1S/C11H13NO/c1-8(12)6-9-2-3-11-10(7-9)4-5-13-11/h2-5,7-8H,6,12H2,1H3
Std. InChiKeyVKUMKUZDZWHMQU-UHFFFAOYSA-N
Avg. Mass175.227 Da
Molecular Weight175.227
Monoisotopic Mass175.099716 Da
Nominal Mass175
ChemSpider ID8012953

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Dose Chart

Oral
Light40-60mg
Common70-100mg
Strong100mg+

Duration Chart

5-APB Duration Data
Onset45 minutes
Duration7-8 hours
After-effectssmooth

Interactions

Caution

  1. Mushrooms
    • Stimulants increase anxiety levels and the risk of thought loops which can lead to negative experiences
  2. LSD
    • Stimulants increase anxiety levels and the risk of thought loops which can lead to negative experiences
  3. DMT
    • Stimulants increase anxiety levels and the risk of thought loops which can lead to negative experiences
  4. Mescaline
    • The focus and anxiety caused by stimulants is magnified by psychedelics and results in an increased risk of thought loops
  5. 2C-x
    • The anxiogenic and focusing effects of stimulants increase the chance of unpleasant thought loops. The combination is generally uneccessary because of the stimulating effects of psychedelics. Combination of the stimulating effects may be uncomfortable.
  6. Cannabis
    • Stimulants increase anxiety levels and the risk of thought loops which can lead to negative experiences
  7. Ketamine
    • No unexpected interactions, though likely to increase blood pressure but not an issue with sensible doses. Moving around on high doses of this combination may be ill advised due to risk of physical injury.
  8. MXE
    • Risk of tachycardia, hypertension, and manic states
  9. Cocaine
    • This combination of stimulants will increase strain on the heart. It is not generally worth it as cocaine has a mild blocking effect on dopamine releasers like amphetamine
  10. Caffeine
    • This combination of stimulants is not generally necessary and may increase strain on the heart, as well as potentially causing anxiety and greater physical discomfort.
  11. Alcohol
    • Drinking on stimulants is risky because the sedative effects of the alcohol are reduced, and these are what the body uses to gauge drunkenness. This typically leads to excessive drinking with greatly reduced inhibitions, high risk of liver damage and increased dehydration. They will also allow you to drink past a point where you might normally pass out, increasing the risk. If you do decide to do this then you should set a limit of how much you will drink each hour and stick to it, bearing in mind that you will feel the alcohol and the stimulant less. Extended release formulations may severely impede sleep, further worsening the hangover.
  12. GHB/GBL
    • Stimulants increase respiration rate allowing a higher dose of sedatives. If the stimulant wears off first then the opiate may overcome the patient and cause respiratory arrest.
  13. Opioids
    • Stimulants increase respiration rate allowing a higher dose of opiates. If the stimulant wears off first then the opiate may overcome the patient and cause respiratory arrest.

Dangerous

  1. DOx
    • The combined stimulating effects of the two can lead to an uncomfortable body-load, while the focusing effects of amphetamine can easily lead to thought loops. Coming down from amphetamines while the DOx is still active can be quite anxiogenic.
  2. NBOMes
    • Amphetamines and NBOMes both provide considerable stimulation. When combined they can result in tachycardia, hypertension, vasoconstriction and in extreme cases heart failure. The anxiogenic and focusing effects of stimulants are also not good in combination with psychedelics as they can lead to unpleasant thought loops. NBOMes are known to cause seizures and stimulants can increase this risk.
  3. 2C-T-x
    • Stimulants increase anxiety levels and the risk of thought loops which can lead to negative experiences. In extreme cases, they can result in severe vasoconstriction, tachycardia, hypertension, and in extreme cases heart failure.
  4. 5-MeO-xxT
    • The anxiogenic and focusing effects of stimulants increase the chance of unpleasant thought loops. The combination is generally unnecessary because of the stimulating effects of psychedelics.
  5. DXM
    • Both substances raise heart rate, in extreme cases, panic attacks caused by these drugs have led to more serious heart issues.
  6. PCP
    • This combination can easily lead to hypermanic states

Low Synergy

  1. Benzodiazepines
    • Both can dull each other's effects, so if one wears off before the other it's possible to overdose due to the lack of counteraction

No Synergy

  1. SSRIs

High Synergy

  1. N2O
  2. MDMA
    • Amphetamines increase the neurotoxic effects of MDMA

Psychological Effects

Pharmacological Effects

5-APB is a triple reuptake inhibitor for norepinephrine, dopamine and serotonin as well as being an agonist for the 5-HT2A and 5-HT2B receptors. It has also been speculated that 5-APB acts as a releasing agent for the previously mentioned neurotransmitters. This means it effectively boosts the levels of the serotonin, norepinephrine and dopamine neurotransmitters in the brain by binding to and partially blocking the transporter proteins that normally remove those monoamines from the synaptic cleft. This allows dopamine and norepinephrine to accumulate within the brain, resulting in stimulating and euphoric effects.

Physical Effects

Subjective Effects

Legal Status

  • Brazil: Possession, production and sale is illegal as it is listed on Portaria SVS/MS nº 344.
  • Germany: 5-APB is controlled under Anlage II BtMG (Narcotics Act, Schedule II) as of July 17, 2013. It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.
  • United Kingdom: 5-APB is a Class B drug.
  • United States: 5-APB could be considered an analogue of MDA and therefore would be covered under the Federal Analogue Act if intended for human consumption.
  • Sources

    References

    1. Monte, A. P., Marona-Lewicka, D., Cozzi, N. V., & Nichols, D. E. (1993). Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogs of 3, 4-(methylenedioxy) amphetamine. Journal of Medicinal Chemistry, 36(23), 3700-3706. https://doi.org/10.1021/jm00075a027
    2. EMCDDA–Europol 2010 Annual Report on the implementation of Council Decision 2005/387/JHA | http://www.emcdda.europa.eu/publications/implementation-reports/2010
    3. Advisory Council on the Misuse of Drugs, Jeremy Browne (4 June 2013). "Temporary class drug order on benzofury and NBOMe compounds - letter from ACMD". GOV.UK.
    4. UK Home Office (28 April 2014). "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". The National Archives.
    5. The effects of benzofury (5-APB) on the dopamine transporter and 5-HT2-dependent vasoconstriction in the rat (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/24012617?dopt=Abstract
    6. Neurochemical profiles of some novel psychoactive substances (ScienceDirect) | http://www.sciencedirect.com/science/article/pii/S0014299912010114
    7. Talaie, H., Panahandeh, R., Fayaznouri, M. R., Asadi, Z., & Abdollahi, M. (2009). Dose-independent occurrence of seizure with tramadol. Journal of Medical Toxicology, 5(2), 63-67. https://doi.org/10.1007/BF03161089
    8. Gillman, P. K. (2005). Monoamine oxidase inhibitors, opioid analgesics and serotonin toxicity. British Journal of Anaesthesia, 95(4), 434-441. https://doi.org/10.1093/bja/aei210
    9. Gillman, P. K. (2005). Monoamine oxidase inhibitors, opioid analgesics and serotonin toxicity. British Journal of Anaesthesia, 95(4), 434-441. https://doi.org/10.1093/bja/aei210
    10. http://portal.anvisa.gov.br/documents/10181/3115436/(1)RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7
    11. "Anlage II BtMG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 18, 2019.
    12. "Siebenundzwanzigste Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften" (in German). Bundesanzeiger Verlag. Retrieved December 18, 2019.
    13. "§ 29 BtMG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 18, 2019.

    Information made possible with:

    1. PsychonautWiki is a community-driven online encyclopedia that aims to document the field of psychonautics in a comprehensive, scientifically-grounded manner.
    2. Erowid is a non-profit educational & harm-reduction resource with 60 thousand pages of online information about psychoactive drugs
    3. PubChem National Center for Bio Informatics
    4. Chemspider is a free chemical structure database providing fast access to over 34 million structures, properties and associated information.
    5. Wikipedia

    Additional APIs were used to construct this information. Thanks to ChemSpider, NCBI, PubChem etc.

    Data is constantly updated so please check back later to see if there is any more available information on this substance.