5-APB
| Summary sheet: 5-APB |
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| Chemical Nomenclature | |||||||||||||||||||||||||||||||||
| Common names | 5-APB | ||||||||||||||||||||||||||||||||
| Substitutive name | 5-(2-Aminopropyl)benzofuran | ||||||||||||||||||||||||||||||||
| Systematic name | 1-(Benzofuran-5-yl)-propan-2-amine | ||||||||||||||||||||||||||||||||
| Class Membership | |||||||||||||||||||||||||||||||||
| Psychoactive class | Entactogen / Stimulant | ||||||||||||||||||||||||||||||||
| Chemical class | Amphetamine / Benzofuran | ||||||||||||||||||||||||||||||||
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| Alcohol | |||||||||||||||||||||||||||||||||
| MXE | |||||||||||||||||||||||||||||||||
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| DXM | |||||||||||||||||||||||||||||||||
| MDMA | |||||||||||||||||||||||||||||||||
| Stimulants | |||||||||||||||||||||||||||||||||
| 25x-NBOMe | |||||||||||||||||||||||||||||||||
| 25x-NBOH | |||||||||||||||||||||||||||||||||
| Tramadol | |||||||||||||||||||||||||||||||||
| MAOIs | |||||||||||||||||||||||||||||||||
| SNRIs | |||||||||||||||||||||||||||||||||
| Serotonin releasers | |||||||||||||||||||||||||||||||||
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| 5-HTP | |||||||||||||||||||||||||||||||||
5-(2-Aminopropyl)benzofuran (commonly known as 5-APB) is a lesser-known novel entactogen of the benzofuran class that produces MDA-like entactogenic and stimulating effects when administered. 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.[1] 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.[citation needed]
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.[2]
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 and culture
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This History and culture section is a stub. As a result, it may contain incomplete or wrong information. You can help by expanding it. |
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.[1]
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".[citation needed]
On June 10, 2013 5-APB and a number of analogues were classified as Temporary Class Drugs in the UK following an ACMD recommendation.[3] 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.[4]
Chemistry
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This chemistry section is incomplete. You can help by adding to it. |
5-(2-aminopropyl)benzofuran, also known as 5-APB, is a benzofuran and phenethylamine, meaning it has an ethylamine chain and a furan ring attached to the core benzene ring. 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.[citation needed] The hydrochloride salt is 10% more potent by mass so doses should be adjusted accordingly.
Pharmacology
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This pharmacology section is incomplete. You can help by adding to it. |
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.[5][6] 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.
Subjective effects
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This subjective effects section is a stub. As such, it is still in progress and may contain incomplete or wrong information. You can help by expanding or correcting it. |
Disclaimer: The effects listed below cite the Subjective Effect Index (SEI), an open research literature based on anecdotal user reports and the personal analyses of PsychonautWiki contributors. As a result, they should be viewed with a healthy degree of skepticism.
It is also worth noting that these effects will not necessarily occur in a predictable or reliable manner, although higher doses are more liable to induce the full spectrum of effects. Likewise, adverse effects become increasingly likely with higher doses and may include addiction, severe injury, or death ☠.
Physical effects 
After effects 
- The effects which occur during the offset of a stimulant experience generally feel negative and uncomfortable in comparison to the effects which occurred during its peak. This is often referred to as a "comedown" and occurs because of neurotransmitter depletion. Its effects commonly include:
Experience reports
Anecdotal reports which describe the effects of this compound within our experience index include:
Additional experience reports can be found here:
Toxicity and harm potential
The toxicity and long-term health effects of recreational 5-APB use do not seem to have been studied in any scientific context and the exact toxic dosage is unknown. This is because 5-APB has very little history of human usage.
Anecdotal evidence from people who have tried 5-APB within the community suggest that there do not seem to be any negative health effects attributed to simply trying this drug at low to moderate doses by itself and using it sparingly (but nothing can be completely guaranteed).
5-APB's high affinity for the 5-HT2b receptor 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.
It is strongly recommended that one use harm reduction practices when using this substance.
Tolerance and addiction potential
As with other stimulants, the chronic use of 5-APB can be considered moderately addictive with a high potential for abuse and is capable of causing psychological dependence among certain users. When addiction has developed, cravings and withdrawal effects may occur if a person suddenly stops their usage.
Tolerance to many of the effects of 5-APB develops with prolonged and repeated use. This results in users having to administer increasingly large doses to achieve the same effects. After that, it takes about 3 - 7 days for the tolerance to be reduced to half and 1 - 2 weeks to be back at baseline (in the absence of further consumption). 5-APB presents cross-tolerance with all dopaminergic stimulants, meaning that after the consumption of 5-APB all stimulants will have a reduced effect.
Psychosis
Abuse of compounds within the amphetamine chemical class at high dosages for prolonged periods of time can potentially result in a stimulant psychosis that may present with a variety of symptoms (e.g., paranoia, hallucinations, or delusions). A review on treatment for amphetamine, dextroamphetamine, and methamphetamine abuse-induced psychosis states that about 5–15% of users fail to recover completely. The same review asserts that, based upon at least one trial, antipsychotic medications effectively resolve the symptoms of acute amphetamine psychosis. Psychosis very rarely arises from therapeutic use.
Dangerous interactions
Warning: Many psychoactive substances that are reasonably safe to use on their own can suddenly become dangerous and even life-threatening when combined with certain other substances. The following list provides some known dangerous interactions (although it is not guaranteed to include all of them).
Always conduct independent research (e.g. Google, DuckDuckGo, PubMed) to ensure that a combination of two or more substances is safe to consume. Some of the listed interactions have been sourced from TripSit.
- 25x-NBOMe & 25x-NBOH - 25x compounds are highly stimulating and physically straining. Combinations with 5-APB should be strictly avoided due to the risk of excessive stimulation and heart strain. This can result in increased blood pressure, vasoconstriction, panic attacks, thought loops, seizures, and heart failure in extreme cases.
- Alcohol - Combining alcohol with stimulants can be dangerous due to the risk of accidental over-intoxication. Stimulants mask alcohol's depressant effects, which is what most people use to assess their degree of intoxication. Once the stimulant wears off, the depressant effects will be left unopposed, which can result in blackouts and severe respiratory depression. If mixing, the user should strictly limit themselves to only drinking a certain amount of alcohol per hour.
- DXM - Combinations with DXM should be avoided due to its inhibiting effects on serotonin and norepinephrine reuptake. There is an increased risk of panic attacks and hypertensive crisis, or serotonin syndrome with serotonin releasers (MDMA, methylone, mephedrone, etc.). Monitor blood pressure carefully and avoid strenuous physical activity.
- MDMA - Any neurotoxic effects of MDMA are likely to be increased when other stimulants are present. There is also a risk of excessive blood pressure and heart strain (cardiotoxicity).
- MXE - Some reports suggest combinations with MXE may dangerously increase blood pressure and increase the risk of mania and psychosis.
- Dissociatives - Both classes carry a risk of delusions, mania and psychosis, and these risk may be multiplied when combined.
- Stimulants - 5-APB may be dangerous to combine with other stimulants like cocaine as they can increase one's heart rate and blood pressure to dangerous levels.
- Tramadol - Tramadol is known to lower the seizure threshold[7] and combinations with stimulants may further increase this risk.
- MAOIs - This combination may increase the amount of neurotransmitters such as dopamine to dangerous or even fatal levels. Examples include syrian rue, banisteriopsis caapi, and some antidepressants.[8]
Serotonin syndrome risk
Combinations with the following substances can cause dangerously high serotonin levels. Serotonin syndrome requires immediate medical attention and can be fatal if left untreated.
- MAOIs - Such as banisteriopsis caapi, syrian rue, phenelzine, selegiline, and moclobemide.[9]
- Serotonin releasers - Such as MDMA, 4-FA, methamphetamine, methylone and αMT.
- SSRIs - Such as citalopram and sertraline
- SNRIs - Such as tramadol and venlafaxine
- 5-HTP
Legal status
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This legality section is a stub. As such, it may contain incomplete or wrong information. You can help by expanding it. |
- Brazil: Possession, production and sale is illegal as it is listed on Portaria SVS/MS nº 344.[10]
- Germany: 5-APB is controlled under Anlage II BtMG (Narcotics Act, Schedule II)[11] as of July 17, 2013.[12] It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.[13]
- Japan: 5-APB is a controlled substance in Japan effective September 16th, 2015.[14]
- The Netherlands: 5-APB is currently legal, but it is part of a substance group that may be banned soon as part of a recently passed law on New Psychoactive Substances (NPS). [15]
- Switzerland: 5-APB is a controlled substance specifically named under Verzeichnis E.[16]
- United Kingdom: 5-APB is a Class B drug.[citation needed]
- 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.[citation needed]
See also
External links
Community
Literature
- Greene, S. L. (2013). Benzofurans and benzodifurans. In Novel Psychoactive Substances (pp. 383-392). https://doi.org/10.1016/B978-0-12-415816-0.00016-X
References
- ↑ 1.0 1.1 Monte, A. P., Marona-Lewicka, D., Cozzi, N. V., Nichols, D. E. (November 1993). "Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogs of 3,4-(methylenedioxy)amphetamine". Journal of Medicinal Chemistry. 36 (23): 3700–3706. doi:10.1021/jm00075a027. ISSN 0022-2623.
- ↑ EMCDDA–Europol 2010 Annual Report on the implementation of Council Decision 2005/387/JHA
- ↑ 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.
- ↑ The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014
- ↑ Dawson, P., Opacka-Juffry, J., Moffatt, J. D., Daniju, Y., Dutta, N., Ramsey, J., Davidson, C. (3 January 2014). "The effects of benzofury (5-APB) on the dopamine transporter and 5-HT2-dependent vasoconstriction in the rat". Progress in Neuro-Psychopharmacology & Biological Psychiatry. 48: 57–63. doi:10.1016/j.pnpbp.2013.08.013. ISSN 1878-4216.
- ↑ Iversen, L., Gibbons, S., Treble, R., Setola, V., Huang, X.-P., Roth, B. L. (30 January 2013). "Neurochemical profiles of some novel psychoactive substances". European Journal of Pharmacology. 700 (1): 147–151. doi:10.1016/j.ejphar.2012.12.006. ISSN 0014-2999.
- ↑ 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. doi:10.1007/BF03161089. eISSN 1937-6995. ISSN 1556-9039. OCLC 163567183.
- ↑ Gillman, P. K. (2005). "Monoamine oxidase inhibitors, opioid analgesics and serotonin toxicity". British Journal of Anaesthesia. 95 (4): 434–441. doi:10.1093/bja/aei210
. eISSN 1471-6771. ISSN 0007-0912. OCLC 01537271. PMID 16051647.
- ↑ Gillman, P. K. (2005). "Monoamine oxidase inhibitors, opioid analgesics and serotonin toxicity". British Journal of Anaesthesia. 95 (4): 434–441. doi:10.1093/bja/aei210 . eISSN 1471-6771. ISSN 0007-0912. OCLC 01537271. PMID 16051647.
- ↑ http://portal.anvisa.gov.br/documents/10181/3115436/%281%29RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7
- ↑ "Anlage II BtMG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 18, 2019.
- ↑ "Siebenundzwanzigste Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften" (in German). Bundesanzeiger Verlag. Retrieved December 18, 2019.
- ↑ "§ 29 BtMG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 18, 2019.
- ↑ "危険ドラッグの成分４物質を新たに指定薬物に指定" (in Japanese). 厚生労働省 [Ministry of Health, Labour and Welfare (MHLW)]. Retrieved May 2, 2022.
- ↑ Wijziging van de Opiumwet in verband met het toevoegen van een derde lijst met als doel het tegengaan van de productie van en de handel in nieuwe psychoactieve stoffen en enkele andere wijzigingen (Dutch), 2024
- ↑ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Bundeskanzlei [Federal Chancellery of Switzerland]. Retrieved January 1, 2020.