
6-APB
6-APB | |||||||||||||||||||||||||||||||||
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Chemical Nomenclature | |||||||||||||||||||||||||||||||||
Common names | 6-APB, Benzofury | ||||||||||||||||||||||||||||||||
Substitutive name | 6-(2-Aminopropyl)benzofuran | ||||||||||||||||||||||||||||||||
Systematic name | 1-(1-Benzofuran-6-yl)propan-2-amine | ||||||||||||||||||||||||||||||||
Class Membership | |||||||||||||||||||||||||||||||||
Psychoactive class | Entactogen / Psychedelic | ||||||||||||||||||||||||||||||||
Chemical class | Amphetamine / Benzofuran | ||||||||||||||||||||||||||||||||
Routes of Administration | |||||||||||||||||||||||||||||||||
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Interactions | |||||||||||||||||||||||||||||||||
MAOIs | |||||||||||||||||||||||||||||||||
Serotonin releasers | |||||||||||||||||||||||||||||||||
SSRIs | |||||||||||||||||||||||||||||||||
5-HTP |
Summary sheet: 6-APB |
6-APB (6-(2-aminopropyl)benzofuran) is a stimulant and entactogenic research of the phenethylamine and amphetamine class. It is a close synthetic analogue to MDA and shares the broad characteristic of serotoonergic triple monoamine inhibitors and other entactogenic or empathogenic compounds.
6-APB was first synthesized and studied in 1993 by the chemist David E. Nichols as a potential non-neurotoxic alternative to MDMA. It did not find common use until over a decade later briefly entered the rave and underground clubbing scene in the UK before its sale and import were banned. Because 6-APB and other substituted benzofurans have not been explicitly outlawed in some countries, they are often technically legal, contributing to their popularity.
Chemistry

6-APB, also known as (6-(2-aminopropyl)benzofuran, is a synthetic molecule of the benzofuran family. Molecules of this class contain a phenethylamine core featuring a benzofuran ring bound to an amino (NH2) group through an ethyl chain with an additional methyl substitution at Rα. 6-APB does not contain a methyl substitution on RN, which it shares with MDA. 6APB also contains substitutions at and R4 of the phenyl ring with oxygen groups. These oxygen groups are incorporated into a furan ring. 6-APB shares this furan ring with 5-APB and 5-MAPB and 6-MAPB.
Pharmacology
6-APB acts as a releasing agent and triple reuptake inhibitor of the neurotransmitters known as serotonin, dopamine and noradrenaline[1] which are the global neurotransmitters that modulate the brain's ability to feel pleasure, motivation, reward, planning and focus. This is done by inhibiting the reuptake and reabsorption of the neurotransmitters after they have performed their function of transmitting a neural impulse, essentially allowing them to accumulate and render them liable for immediate reuse/excitation in a manner which causes physically stimulating, relaxing, disinhibiting and euphoric effects.[2]
Subjective effects
The effects listed below are based upon the subjective effects index and personal experiences of PsychonautWiki contributors. The listed effects will rarely (if ever) occur all at once, but heavier dosages will increase the chances and are more likely to induce a full range of effects.
Physical effects
- Spontaneous tactile sensations - The "body high" of 6-APB can be described as a moderate to extreme euphoric tingling sensation that radiates the entire body. It is capable of becoming overwhelmingly pleasurable at higher doses. This sensation maintains a consistent presence that steadily rises with the onset and hits its limit once the peak has been reached.
- Stimulation - In terms of its effects on the user's physical energy levels, 6-APB is commonly considered to be be both stimulating and sedating/relaxing. It is thought to be far less energetic than MDMA and can exert a noticeable sedating couchlocking effect. This does not particularly encourage activities such as running, climbing and dancing in a way that makes MDMA a popular choice for musical events such as festivals and raves. The particular style of stimulation which 6-APB presents is far less forceful, and more like that of mescaline.
- Vibrating vision - At high doses, a person's eyeballs may begin to spontaneously wiggle back and forth in a rapid motion, causing the vision to become blurry and temporarily out of focus. This is a condition known as nystagmus.
- Dehydration - Feelings of dry mouth and dehydration are a universal experience with this class of compounds; this effect is a product of an increased heart rate and metabolism. While it is important to avoid becoming dehydrated (especially when out dancing in a hot environment) there have been a number of users suffering from water intoxication through over-drinking, so it is advised that users simply sip at water and never over-drink.
- Difficulty urinating - Like with other triple releasers, higher doses of 6-APB result in an overall difficulty when it comes to urination. This is an effect that is completely temporary and harmless. It is due to 6-APB’s promotion of the release of anti-diuretic hormone (ADH); ADH is responsible for regulating urination. This effect can be lessened by simply relaxing, but can be significantly relieved by placing a hot flannel over the genitals to warm them up and encourage blood flow.
- Appetite suppression
- Bodily control enhancement
- Brain zaps
- Increased blood pressure
- Increased bodily temperature - As 6-APB is a serotonin releasing agent, rise in core body temperature tends to be high and consistent throughout the experience. Caution must be taken as too high of a dose results in the dysregulating the brain's ability to regulate its internal temperature, which can result in serotonin syndrome (which can be fatal if left untreated).
- Increased heart rate
- Increased perspiration
- Perception of decreased weight
- Physical euphoria
- Pupil dilation
- Stamina enhancement
- Tactile enhancement
- Teeth grinding - This is usually only present in the higher dose range.
- Temporary erectile dysfunction
Cognitive effects
The cognitive effects of 6-APB can be broken down into several components which progressively intensify proportional to dosage. The general head space of 6-APB is described by many as one of moderate mental stimulation, feelings of love or empathy, bodily/mental looseness and powerful euphoria. It contains a large number of typical psychedelic, entactogenic and stimulant cognitive effects.
The most prominent of these cognitive effects generally include:
- Cognitive euphoria - Strong emotional euphoria and feelings of happiness are present within 6-APB and are likely a direct result of serotonin and dopamine release.
- Empathy, love, and sociability enhancement - This particular effect is generally more consistent, pronounced, powerful and therapeutic with 6-APB than any other known substance. It is the most obvious and noticeable effect within any 6-APB experience and dominates the head space. With time, repeated use, and improper spacing, however, this effect becomes severely diminished as the perspective it instills becomes fully grounded and already in place, making people feel merely stimulated and euphoric with no new found urges to communicate with others.
- Time distortion - Strong feelings of time compression are common within 6-APB and alter the experience of time quite noticeably.
- Unity and interconnectedness - Experiences of unity, oneness and interconnectedness between level 2 - 3 are common within 6-APB. This component most consistently manifests itself at high doses within large crowds at raves and musical events in the form of "becoming one with the crowd."
- Effect::Anxiety suppression
- Compulsive redosingDue to its euphoria inducing effects, there is the potential for 6-APB to encourage compulsive redosing, much like with MDMA or MDA. Yet due to the length of the experience, one finds this unnecessary, especially considering how much harder-hitting on the serotonin system that 6-APB is.
- Creativity enhancement
- Dream suppression
- Existential self-realization - Although this effect is present, it is not quite as pronounced or as consistent when compared to other hallucinogens such as mescaline, LSD or MXE. Due to the relative calmness and lack of chaotic energy that 6-APB possesess relative to MDMA, however, this combined with its extended duration may make it a better therapeutic agent and is more in the spectrum of mescaline than MDMA is.
- Focus enhancement - This component is most effective at low to moderate doses as anything higher will usually impair concentration.
- Immersion enhancement
- Increased libido
- Increased music appreciation
- Mindfulness
- Motivation enhancement
- Thought acceleration
- Wakefulness
Visual effects
Similar to MDMA, the visual effects of 6-APB have an occurrence rating that is more selective and less consistent than any of the traditional psychedelics. This is to the point where many people disregard psychedelic experiences within 6-APB as a "myth" or "rumour", but this is simply because they have not experienced it for themselves. The effects can never be guaranteed to manifest themselves, but are more likely to occur with chemically pure, high dose 6-APB experiences, towards the end of the experience and if the user has been smoking cannabis. They are also more likely to occur if the user has prior experience with psychedelics, but also remain entirely possible within those who have never tried one for themselves.
Enhancements
6-APB presents an array of visual enhancements which are mild in comparison to traditional psychedelics, but still distinctively present. These generally include:
Distortions
The visual geometry that is present throughout this trip can be described as more similar in appearance to that of psilocin than LSD. It can be comprehensively described through its variations as primarily intricate in complexity, abstract in form, organic in style, structured in organization, dimly lit in lighting, mostly monotone in colour with blues and greys, glossy in shading, sharp in edges, small in size, fast in speed, smooth in motion, equal in round and angular corners, non-immersive in depth and consistent in intensity. At higher doses, they are significantly more likely to result in states of level 8A visual geometry over level 8B.
Hallucinatory states
6-APB is capable of producing a unique range of low and high level hallucinatory states in a fashion that is significantly less consistent and reproducible than that of many other commonly used psychedelics. These effects are far more common during the offset of the experience and commonly include:
- External hallucinations (autonomous entities; settings, sceneries, and landscapes; alterations in perspective and scenarios and plots) - This effect is very similar to the same experience found within deliriants, but does not manifest itself consistently and usually happens only at high doses. It can be comprehensively described through its variations as delirious in believability, autonomous in controllability and solid in style. They usually follow themes of memory replays and semi-realistic or expected events. For example, people could be casually holding objects or performing actions which one would expect them to be in real life before disappearing and dissolving under further inspection. Common examples of this include seeing people wearing glasses or hats when they are not and mistaking faces of your friends for random people, and objects as human beings or animals.
- Internal hallucinations - The internal hallucinations which 6-APB induces are generally only present as spontaneous breakthroughs at extremely high doses. This effect's variations are delirious in believability, interactive in style, new experiences in content, autonomous in controllability and solid in appearance. The most common way in which they manifest themselves are through hypnagogic scenarios which the user may experience as they are drifting off to sleep after a night of use; these can usually be described as memory replay from the previous several hours. These are short and fleeting, but frequent and completely believable and convincing as they happen. In terms of the theme, they often take the form of conversations with the people who were with you or instead manifest themselves as bizarre and extremely nonsensical plots.
- Peripheral information misinterpretation
Auditory 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:
- Anxiety
- Appetite suppression
- Cognitive fatigue
- Depression
- Dream potentiation - Some users note extremely strange and sometimes rather scary dreams for several nights after taking large doses of 6-APB.
- Irritability
- Motivation suppression
- Thought deceleration
- Wakefulness
Toxicity and harm potential
Due to only having a short-history of human use, the toxicity and harm potential is not known, though it would be reasonable to assume it is very close to that of MDA due to its molecular genealogy. As a potent releaser of serotonin, tolerance builds quickly to the point the drug loses any positive effect and instead leaves the user in an uncomfortable state of anxious stimulation.
Short-term health concerns
Short-term physical health risks of 6-APB consumption include dehydration, insomnia, hyperthermia,[3][4] and hyponatremia.[5] Continuous activity without sufficient rest or rehydration may cause body temperature to rise to dangerous levels, and loss of fluid via excessive perspiration puts the body at further risk as the stimulatory and euphoric qualities of the drug may render the user oblivious to their energy expenditure for quite some time. Diuretics such as alcohol may exacerbate these risks further, though this is more of a problem for MDMA than it is 6-APB.
The exact toxic dosage is unknown, but considered to be far greater than its active dose.
Long-term health concerns
The neurotoxicity of 6-APB is debatable. While designed to be less directly neurotoxic than MDA or MDMA, scientific study has resulted in the general agreement that, although it is physically safe to try in a responsible context, the administration of repeated or high dosages of 6-APB is most certainly neurotoxic.
As with MDMA, long-term heavy use of 6-APB is likely cardiotoxic and leads to valvulopathy through its actions on the 5-HT2B receptor.[6] In one study, 28% of long-term users (2-3 doses per week for a mean of 6 years, mean of age 24.3 years) had developed clinically evident valvular heart disease.[7]
It is strongly recommended that one use harm reduction practices when using this drug.
Tolerance and addiction potential
As with other stimulants, the chronic use of 6-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 6-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 21-30 days for the tolerance to be reduced to half and 2-3 months to be back at baseline (in the absence of further consumption). 6-APB presents cross-tolerance with [[Cross-tolerance::all dopaminergic stimulants]], meaning that after the consumption of 6-APB all stimulants will have a reduced effect.
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.
- "[[DangerousInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] & "[[DangerousInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - 25x compounds are highly stimulating and physically straining. Combinations with 6-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.
- "[[UncertainInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - 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.
- "[[UnsafeInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - 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.
- "[[UnsafeInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - 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).
- "[[UncertainInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - Some reports suggest combinations with MXE may dangerously increase blood pressure and increase the risk of mania and psychosis.
- "[[UncertainInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - Both classes carry a risk of delusions, mania and psychosis, and these risk may be multiplied when combined.
- "[[UnsafeInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - 6-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.
- "[[DangerousInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - Tramadol is known to lower the seizure threshold[8] and combinations with stimulants may further increase this risk.
- "[[DangerousInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - 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.[9]
- Stimulants - The neurotoxic effects of 6-APBmay be increased when combined with other stimulants.
- Cocaine - This combination may increase strain on the heart.
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.[10]
- Serotonin releasers - Such as MDMA, 4-FA, methamphetamine, methylone and αMT.
- SSRIs - Such as citalopram and sertraline
- [[Wikipedia:SNRIs|DangerousInteraction::SNRIs]] - Such as tramadol and venlafaxine
- 5-HTP
There is an increased risk of serotonin syndrome when 6-APB is taken with many antidepressants, particularly selective serotonin reuptake inhibitors (SSRIs) and serotonin-norepinephrine reuptake inhibitors (SNRIs). Additionally, if 6-APB is taken with SSRIs and SNRIs, the 6-APB will be significantly less powerful or may have no distinguishable effects at all.
Legal issues
- Canada: 6-APB is Schedule III in Canada as it is an analogue of MDA. The CDSA was updated as a result of the Safe Streets Act changing amphetamines from Schedule 3 to Schedule 1.
- France: 6-APB is unscheduled in France.
- Netherlands: Possession, production and sale is illegal.
- UK: On June 10, 2013 6-APB and a number of analogues were classified as Temporary Class Drugs in the UK following an ACMD recommendation. 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[11]
- USA: 6-APB is unscheduled in the United States, but not currently approved by the Food and Drug Administration for human consumption.
- Italy: 6-APB is illegal in Italy.[12]
- Sweden: 6-APB is prohibited in Sweden as a "health hazard" as of 2009
- New Zealand and Australia: Certain countries contain a "substantially similar" catch-all clause in their drug law, such as New Zealand and Australia. This includes 6-APB as it is similar in chemical structure to the class A drug MDA, meaning 6-APB may be viewed as a controlled substance analogue in these jurisdictions
- Germany: 6-APB is illegal in Germnany
Experience reports
To be included later.
See also
External links
References
- ↑ Effects of 6-APB on the release of monoamines from rat brain slices https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3582025/
- ↑ New Insights into the Mechanism of Action of Amphetamines | http://www.annualreviews.org/doi/abs/10.1146/annurev.pharmtox.47.120505.105140
- ↑ Drug-induced hyperthermia | http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2044.1993.tb07423.x/abstract;jsessionid=FC30A9B157A2BAFC81048D8595714565.f02t03
- ↑ Though it has not been formally studied, it is reasonable to assume that like with MDMA small changes in ambient temperature may cause large changes in 6-APB-induced serotonin neurotoxicity and core body temperature in the rat (PubMed.gov / NCBI) | http://www.ncbi.nlm.nih.gov/pubmed/9634574
- ↑ Vasopressin and oxytocin secretion in response to the consumption of ecstasy in a clubbing population | http://jop.sagepub.com/content/20/3/400
- ↑ Drug-induced Valvulopathy: An Update | tpx.sagepub.com/content/38/6/837.full
- ↑ Possible association between 3,4-methylenedioxymethamphetamine abuse and valvular heart disease. (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/17950805
- ↑ 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://www.legislation.gov.uk/uksi/2014/1106/contents/made
- ↑ http://www.salute.gov.it/imgs/C_17_pagineAree_3729_listaFile_itemName_0_file.pdf