6-APB

From PsychonautWiki
(Redirected from 6-ABP)
Jump to navigation Jump to search
Summary sheet: 6-APB
6-APB
6-APB.svg
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

WARNING: Always start with lower doses due to differences between individual body weight, tolerance, metabolism, and personal sensitivity. See responsible use section.



Oral
Dosage
Threshold 15 mg
Light 30 - 60 mg
Common 60 - 90 mg
Strong 90 - 120 mg
Heavy 120 mg +
Duration
Total 7 - 10 hours
Onset 30 - 60 minutes
Come up 60 - 120 minutes
Peak 3 - 4 hours
Offset 2 - 3 hours
After effects 6 - 48 hours









DISCLAIMER: PW's dosage information is gathered from users and resources for educational purposes only. It is not a recommendation and should be verified with other sources for accuracy.

Interactions
Alcohol
MXE
Dissociatives
DXM
MDMA
Stimulants
25x-NBOMe
25x-NBOH
Tramadol
MAOIs
SNRIs
Serotonin releasers
SSRIs
5-HTP

6-(2-Aminopropyl)benzofuran (also known as 6-APB and "Benzofury") is a novel entactogen substance of the benzofuran class. It is structurally related to entactogens like MDA, MDMA, 5-APB, and 5-MAPB.

6-APB was first synthesized in 1993 by 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]

Subjective effects include anxiety suppression, disinhibition, muscle relaxation, and euphoria. 6-APB's effects are commonly compared to those of MDA and other entactogens.

Very little data exists about the pharmacological properties, metabolism, and toxicity of 6-APB, and it has only a brief history of human usage. It has been marketed alongside research chemical entactogens like 5-MAPB and 5-APB as a legal, grey-market alternative to MDMA, and is typically commercially distributed by online research chemical vendors. It is highly advised to use harm reduction practices if using this substance.

History and culture

History icon.svg

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 6-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 6-APB and a number of analogues were classified as Temporary Class Drugs in the UK following an ACMD recommendation.[2] On November 28, 2013 the ACMD recommended that 6-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.[3]

Chemistry

6-APB, also known as 6-(2-aminopropyl)benzofuran, is a synthetic molecule of the benzofuran class. The benzofuran class of substances are members of the amphetamine and phenylethylamine classes. Molecules of this class contain a phenethylamine core 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. It is composed of an an oxygen-substituted benzofuran ring fused at R3 and R4 of the phenyl ring.

Notably, 6-APB shares this benzofuran ring with related compounds such as 5-APB, 5-MAPB, and 6-MAPB.

Three distinct batches have been in circulation since its initial release to markets. Originally, only hydrochloride was available, and its dosage range shared characteristics most similar to that of MDA in terms of dose-response. However, succinate and fumarate batches both entered the market, and have very different effects by weight, and vastly different loose bulk densities.[citation needed]

Pharmacology

6-APB is a serotoninnorepinephrinedopamine reuptake inhibitor (SNDRI) with Ki values of 117, 150, and 2698 nM for the norepinephrine transporter (NET), dopamine transporter (DAT), and serotonin transporter (SERT), respectively.[4] 6-APB also possesses additional activity as a releasing agent of these monoamine neurotransmitters.[5]

6-APB is a potent full agonist of the serotonin 5-HT2B receptor (Ki = 3.7 nM)[4], with higher affinity for this target than any other site.[6] Moreover, unlike MDMA, 6-APB shows 100-fold selectivity for the 5-HT2B receptor over the 5-HT2A and 5-HT2C receptors.[6][7]

Aside from the 5-HT2B receptor, 6-APB has also been found to bind with high affinity to the α2C-adrenergic receptor subtype (Ki = 45 nM), although the clinical significance of this action is unknown.[4]

The potent agonism of the 5-HT2B receptor makes it likely that 6-APB would be cardiotoxic with chronic or long-term use, as seen with other 5-HT2B receptor agonists such as the withdrawn serotonergic anorectic fenfluramine.[4][8]

The monoamine neurotransmitters known as serotonin, dopamine and noradrenaline are the global neurotransmitters that modulate the brain's ability to feel pleasure, motivation, reward, planning, attention, and focus. When their reuptake is inhibited or their release is promoted, these neurotransmitters accumulate in the synaptic cleft (gaps between neurons) to non-ordinary levels, which makes them able to be reused. The result is neuronal activation at a multitude of brain regions which has the net result of producing a combination of stimulating, relaxing, disinhibiting and euphoric effects.[9]

Subjective effects

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
Child.svg

Visual effects
Eye.svg

Cognitive effects
User.svg

Transpersonal effects
Infinity4.svg

After effects
Aftereffects (3).svg

Experience reports

Anecdotal reports which describe the effects of this compound within our experience index include:

Additional experience reports can be found here:

Reagent results

Exposing compounds to the reagents gives a colour change which is indicative of the compound under test.

Compound Marquis Mecke Mandelin Liebermann Froehde Gallic Ehrlich Hofmann Simon’s Folin
6-APB Purple Purple - black Purple - black Black Purple Brown Orange Light orange No reaction Light orange
6-APB succinate Purple Purple - black Purple - black Black Purple Brown Faint orange No reaction No reaction Light orange

Toxicity and harm potential

Due to only having a short history of human use, the toxicity and harm potential is not exactly known. Due to its similarity to MDMA, it is likely that the administration of repeated or high dosages of 6-APB may be both neurotoxic and cardiotoxic[10][11] in some form.

The exact toxic dosage is unknown. It is strongly recommended that one use harm reduction practices when using this substance.

Short-term physical health risks of 6-APB consumption include dehydration, insomnia, and hyperthermia (overheating).[12] Continuous activity without sufficient rest or rehydration may cause body temperature to rise to dangerous levels, and loss of fluid via excessive sweating puts the body at further risk as the stimulating and euphoric properties of the substance may render the user oblivious to their energy expenditure for quite some time. Diuretics such as alcohol may exacerbate these risks further.

Although it has not been formally studied, small changes in ambient temperature may cause large changes in 6-APB-induced serotonergic neurotoxicity as is the case with MDMA.[13][14]

The neurotoxicity of 6-APB is subject to ongoing debate. It was specifically designed to be less neurotoxic than MDA or MDMA by circumventing the production of certain metabolic byproducts thought to underlie their toxicity (specifically alpha-methyl-dopamine).[citation needed] Although it is likely to be physically safe to try in a responsible context, it is completely possible that the administration of repeated or high dosages of 6-APB could result in neurotoxicity in some form, presenting as deficits in cognitive, affective and psychomotor function.

As with MDMA, the long-term, heavy usage of 6-APB (i.e. regular daily or weekly usage) is likely cardiotoxic and may lead to valvulopathy (heart valve issues) via its significant affinity for the 5-HT2B receptor.[10][11]

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.

As a potent releaser of serotonin, tolerance builds quickly with prolonged and repeated use to the point that the substance eventually loses any positive effects and instead leaves the user in an uncomfortable state of anxious, dysphoric stimulation. This results in users having to administer increasingly large doses to achieve the same effects. After that, it takes about 3-4 weeks for the tolerance to be reduced to half and 6-8 weeks to be back at baseline (in the absence of further consumption). 6-APB presents cross-tolerance with 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.

  • 25x-NBOMe & 25x-NBOH - 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.
  • 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 - 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.
  • Tramadol - Tramadol is known to lower the seizure threshold[15] and combinations with stimulants may further increase this risk.

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.

There is an increased risk of serotonin syndrome when 6-APB is taken with many antidepressants, particularly monoamine oxidase inhibitors (MAOIs).[citation needed] Additionally, if 6-APB is taken with SSRIs and SNRIs, it is likely to be significantly less effective if it produces any discernible effects at all.

Legal status

  • Australia and New Zealand: 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.[citation needed]
  • 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.[citation needed]
  • Germany: 6-APB is controlled under Anlage II BtMG (Narcotics Act, Schedule II)[18] as of July 17, 2013.[19] It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.[20]
  • Italy: 6-APB is illegal in Italy.[21]
  • Japan: 6-APB is a controlled substance in Japan effective December 17th, 2012.[22]
  • Luxembourg: 6-APB is not cited in the list of prohibited substances[23]. Therefore, it is still a legal substance.
  • Sweden: 6-APB is prohibited in Sweden as a "health hazard" as of 2009.[citation needed]
  • Switzerland: 6-APB is a controlled substance specifically named under Verzeichnis E.[24]
  • Turkey: 6-APB is a classed as drug and is illegal to possess, produce, supply, or import.[25] [26]
  • United Kingdom: On June 10, 2013, 6-APB and some analogues were classified as Temporary Class Drugs in the U.K. following an ACMD recommendation. On March 5, 2014, the U.K. 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.[3]
  • United States: 6-APB is unscheduled in the United States, but not currently approved by the Food and Drug Administration for human consumption.

See also

External links

Discussion

Literature

References

  1. 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. 
  2. 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.
  3. 3.0 3.1 The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014 
  4. 4.0 4.1 4.2 4.3 Iversen, L., Gibbons, S., Treble, R., Setola, V., Huang, X.-P., Roth, B. L. (January 2013). "Neurochemical profiles of some novel psychoactive substances". European Journal of Pharmacology. 700 (1–3): 147–151. doi:10.1016/j.ejphar.2012.12.006. ISSN 0014-2999. 
  5. Rickli, A., Kopf, S., Hoener, M. C., Liechti, M. E. (July 2015). "Pharmacological profile of novel psychoactive benzofurans: Novel psychoactive benzofurans". British Journal of Pharmacology. 172 (13): 3412–3425. doi:10.1111/bph.13128. ISSN 0007-1188. 
  6. 6.0 6.1 Canal, C. E., Murnane, K. S. (January 2017). "The serotonin 5-HT 2C receptor and the non-addictive nature of classic hallucinogens". Journal of Psychopharmacology. 31 (1): 127–143. doi:10.1177/0269881116677104. ISSN 0269-8811. 
  7. Analytics for US Patent No. 7045545, Aminoalkylbenzofurans as serotonin (5-HT(2c)) agonists 
  8. 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.
  9. Fleckenstein, A. E., Volz, T. J., Riddle, E. L., Gibb, J. W., Hanson, G. R. (1 February 2007). "New Insights into the Mechanism of Action of Amphetamines". Annual Review of Pharmacology and Toxicology. 47 (1): 681–698. doi:10.1146/annurev.pharmtox.47.120505.105140. ISSN 0362-1642. 
  10. 10.0 10.1 Elangbam, C. S. (October 2010). "Drug-induced Valvulopathy: An Update". Toxicologic Pathology. 38 (6): 837–848. doi:10.1177/0192623310378027. ISSN 0192-6233. 
  11. 11.0 11.1 Droogmans, S., Cosyns, B., D’haenen, H., Creeten, E., Weytjens, C., Franken, P. R., Scott, B., Schoors, D., Kemdem, A., Close, L., Vandenbossche, J.-L., Bechet, S., Van Camp, G. (1 November 2007). "Possible association between 3,4-methylenedioxymethamphetamine abuse and valvular heart disease". The American Journal of Cardiology. 100 (9): 1442–1445. doi:10.1016/j.amjcard.2007.06.045. ISSN 0002-9149. 
  12. Nimmo, S. M., Kennedy, B. W., Tullett, W. M., Blyth, A. S., Dougall, J. R. (October 1993). "Drug-induced hyperthermia". Anaesthesia. 48 (10): 892–895. doi:10.1111/j.1365-2044.1993.tb07423.x. ISSN 0003-2409. 
  13. Malberg, J. E., Seiden, L. S. (1 July 1998). "Small changes in ambient temperature cause large changes in 3,4-methylenedioxymethamphetamine (MDMA)-induced serotonin neurotoxicity and core body temperature in the rat". The Journal of Neuroscience: The Official Journal of the Society for Neuroscience. 18 (13): 5086–5094. ISSN 0270-6474. 
  14. Wolff, K., Tsapakis, E. M., Winstock, A. R., Hartley, D., Holt, D., Forsling, M. L., Aitchison, K. J. (May 2006). "Vasopressin and oxytocin secretion in response to the consumption of ecstasy in a clubbing population". Journal of Psychopharmacology. 20 (3): 400–410. doi:10.1177/0269881106061514. ISSN 0269-8811. 
  15. 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. 
  16. Gillman, P. K. (2005). "Monoamine oxidase inhibitors, opioid analgesics and serotonin toxicity". British Journal of Anaesthesia. 95 (4): 434–441. doi:10.1093/bja/aei210Freely accessible. eISSN 1471-6771. ISSN 0007-0912. OCLC 01537271. PMID 16051647. 
  17. Gillman, P. K. (2005). "Monoamine oxidase inhibitors, opioid analgesics and serotonin toxicity". British Journal of Anaesthesia. 95 (4): 434–441. doi:10.1093/bja/aei210Freely accessible. eISSN 1471-6771. ISSN 0007-0912. OCLC 01537271. PMID 16051647. 
  18. "Anlage II BtMG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 18, 2019. 
  19. "Siebenundzwanzigste Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften" (in German). Bundesanzeiger Verlag. Retrieved December 18, 2019. 
  20. "§ 29 BtMG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 18, 2019. 
  21. http://www.salute.gov.it/imgs/C_17_pagineAree_3729_listaFile_itemName_0_file.pdf
  22. "平成24年12月17日付けで以下の8物質が指定薬物に指定されました。" (in Japanese). 厚生労働省 [Ministry of Health, Labour and Welfare (MHLW)]. Retrieved May 2, 2022.
  23. 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
  24. "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Bundeskanzlei [Federal Chancellery of Switzerland]. Retrieved January 1, 2020. 
  25. Başbakanlık Mevzuatı Geliştirme ve Yayın Genel Müdürlüğü 
  26. https://resmigazete.gov.tr/eskiler/2014/01/20140125-3-1.pdf