5-MAPB
| Summary sheet: 5-MAPB |
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| Chemical Nomenclature | |||||||||||||||||||||||||||||||||
| Common names | 5-MAPB | ||||||||||||||||||||||||||||||||
| Substitutive name | 5-(2-methylaminopropyl)benzofuran | ||||||||||||||||||||||||||||||||
| Systematic name | (1-(benzofuran-5-yl)-N-methylpropan-2-amine) | ||||||||||||||||||||||||||||||||
| Class Membership | |||||||||||||||||||||||||||||||||
| Psychoactive class | Entactogen | ||||||||||||||||||||||||||||||||
| Chemical class | Amphetamine / Benzofuran | ||||||||||||||||||||||||||||||||
| Routes of Administration | |||||||||||||||||||||||||||||||||
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| Alcohol | |||||||||||||||||||||||||||||||||
| MXE | |||||||||||||||||||||||||||||||||
| Dissociatives | |||||||||||||||||||||||||||||||||
| DXM | |||||||||||||||||||||||||||||||||
| MDMA | |||||||||||||||||||||||||||||||||
| Stimulants | |||||||||||||||||||||||||||||||||
| 25x-NBOMe | |||||||||||||||||||||||||||||||||
| 25x-NBOH | |||||||||||||||||||||||||||||||||
| Tramadol | |||||||||||||||||||||||||||||||||
| MAOIs | |||||||||||||||||||||||||||||||||
| SNRIs | |||||||||||||||||||||||||||||||||
| Serotonin releasers | |||||||||||||||||||||||||||||||||
| SSRIs | |||||||||||||||||||||||||||||||||
| 5-HTP | |||||||||||||||||||||||||||||||||
5-(2-methylaminopropyl)benzofuran (abbreviated 5-MAPB) is a synthetic entactogen of the substituted benzofuran class of chemicals, which are known to produce euphoric, entactogenic, stimulating and mildly hallucinogenic effects. These include such MDA-inspired substances as 5-APB, 6-APB and 5-EAPB, among others. 5-MAPB is the N-methylated form of 5-APB, analogously to how MDMA is the N-methylated form of MDA.
This compound is known for its stimulating, euphoric and entactogenic effects that is capable of acting a quasi-substitute for MDMA proper, which has resulted in its rise in popularity as a research chemical that is easily accessible through the use of online vendors. It has been sold as a designer drug since 2010.[1]
5-MAPB is commonly found as the succinate and hydrochloride salt. The hydrochloride salt is 36% more potent by mass so doses should be adjusted accordingly.[citation needed]
Chemistry
5-(2-methylaminopropyl)benzofuran, or 5-MAPB, is a substituted benzofuran and phenethylamine. It is comprised of an N-methylated ethylamine chain and a furan ring attached to a central benzene ring. It can also be classified as a derivative of methamphetamine because the N-methylated ethylamine chain is alpha methylated in an analagous manner. 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 atom 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 usually renders it more psychedelic in effect.
Pharmacology
5-MAPB is a triple reuptake inhibitor for the monoamines norepinephrine, dopamine and serotonin as well as being an agonist for the 5-HT2A and 5-HT2B receptors.[2][3] It has also been speculated that 5-MAPB acts as a releasing agent for the previously mentioned neurotransmitters.
As a result, releasing agents such as 5-MAPB may exert their activity by effectively boosting the levels of the serotonin, norepinephrine and dopamine neurotransmitters in the brain by binding to and partially blocking the transporter proteins that normally clear and reuptake those monoamines from the synaptic cleft. This allows serotonin, dopamine and norepinephrine to accumulate within various reward and cognition-related areas in 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 
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- Stimulation - In terms of its effects on the user's physical energy levels, 5-MAPB is commonly regarded as significantly less stimulating and energizing than MDMA, while still retaining its core entactogenic effects. Unlike MDMA, which encourages activities such as running, climbing and dancing in a way that makes it a popular choice for musical events such as festivals and raves, the distinct style of stimulation which 5-MAPB presents can be described as mildly to moderately forced, trending more towards sedation and relaxation. This means that at higher doses, it becomes difficult or impossible to keep still as jaw clenching, involuntarily body shakes and vibrations become present, resulting in an extreme unsteadiness of the hands and a general lack of motor control, though to a far lesser degree than with MDMA.
- Increased heart rate
- Dehydration
- Appetite suppression
- Nausea
- Temporary erectile dysfunction
- Increased perspiration
- Nystagmus
Visual effects 
Cognitive effects 
- The cognitive effects of 5-MAPB are mostly comparable to MDMA, but missing the physical and mental stimulation that would be associated. Instead, it focuses mostly on serotonergic activity, leading to more pronounced feelings of empathy, euphoria and a general relaxed state of mind. At higher dosages, this becomes less apparent as physical and cognitive side effects appear which can result in states of confusion and restlessness perhaps more severe than with MDMA. It also shares many of its effects with 5-APB.
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:
- Experience:3-MeO-PCP, LSD, Clonazolam, and Amphetamine - Excessive Amounts and Excessive Confusion
- Experience:A combination of DOC, 5-MAPB, 5-MeO-DMT, ETH-LAD, Cannabis, Pentedrone
Additional experience reports can be found here:
Toxicity and harm potential
The toxicity and long-term health effects of recreational 5-MAPB use do not seem to have been studied in any scientific context and the exact toxic dosage is unknown. This is because 5-MAPB has very little history of human usage. Anecdotal evidence from people who have tried 5-MAPB 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-MAPB's notable agonism at the serotonin-2b (5-HT2b) receptor (which has been associated with cardiovalvulopathy) suggests that it 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 drug.
Tolerance and addiction potential
As with other entactogenic stimulants, the chronic use of 5-MAPB 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-MAPB 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-MAPB presents cross-tolerance with all dopaminergic stimulants, meaning that after the consumption of 5-MAPB 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-MAPB 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-MAPB 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[4] 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.[5]
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.[6]
- 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. |
- France: 5-MAPB is classified as a narcotic since May 9, 2018, alongside other substances derived from benzofuran.[7]
- Germany: 5-MAPB is controlled under the NpSG (New Psychoactive Substances Act)[8] as of November 26, 2016.[9] Production and import with the aim to place it on the market, administration to another person and trading is punishable. Possession is illegal but not penalized.[10]
- Japan: 5-MAPB is a controlled substance in Japan effective August 15th, 2015.[11]
- Luxembourg: 5-MAPB is not cited in the list of prohibited substances[12]. Therefore, it is still a legal substance.
- Switzerland: 5-MAPB is a controlled substance specifically named under Verzeichnis E.[13]
- United Kingdom: 5-MAPB is a Class B drug.
- United States: 5-MAPB could be considered an analogue of MDA and therefore would be covered under the Federal Analogue Act if intended for human consumption.
See also
External links
- 5-MAPB (Wikipedia)
- 5-MAPB (Erowid Vault)
- 5-MAPB (Isomer Design)
- The Big and Dandy 5-MAPB Thread (Bluelight)
References
- ↑ EMCDDA–Europol 2010 Annual Report on the implementation of Council Decision 2005/387/JHA
- ↑ 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.
- ↑ "Article Annexe IV - Arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants" (in French). Légifrance. Retrieved September 23, 2022.
- ↑ "Anlage NpSG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 18, 2019.
- ↑ "Gesetz zur Bekämpfung der Verbreitung neuer psychoaktiver Stoffe" (PDF) (in German). Bundesanzeiger Verlag. Retrieved December 18, 2019.
- ↑ "§ 4 NpSG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 18, 2019.
- ↑ "平成26年8月15日付けで以下の21物質が指定薬物に指定されました。（施行日：平成26年8月25日）" (in Japanese). 厚生労働省 [Ministry of Health, Labour and Welfare (MHLW)]. Retrieved on May 2, 2022.
- ↑ Loi du 19 février 1973 concernant la vente de substances médicamenteuses et la lutte contre la toxicomanie. | http://legilux.public.lu/eli/etat/leg/loi/1973/02/19/n1/jo
- ↑ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Bundeskanzlei [Federal Chancellery of Switzerland]. Retrieved January 1, 2020.