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6-(2-Aminopropyl)benzofuran (6-APB): A Novel Entactogen
6-(2-Aminopropyl)benzofuran, commonly referred to as 6-APB or "Benzofury," is an emerging entactogen belonging to the benzofuran class. It shares structural affinities with well-known entactogens like MDA, MDMA, 5-APB, and 5-MAPB.
History and Culture
Origin and Emergence
In 1993, David E. Nichols, a distinguished medicinal chemist and psychedelic researcher at Purdue University, pioneered the synthesis of 6-APB. His primary objectives were twofold: to explore alternative substances to MDMA, which exhibited neurotoxic tendencies, and to investigate the interaction of the MDA dioxle ring structure with serotonergic neurons. Remarkably, it took over a decade before this novel compound surfaced within recreational circles and the global research chemical market. During its initial appearance, it was prominently marketed alongside other benzofuran entactogens under the "Benzofury" alias.
Global Recognition and Legal Status
Notably, human usage data did not emerge until 2010 when 6-APB became commercially available within the research chemical market. Its presence was especially conspicuous in the United Kingdom's "legal highs" market, where it was distributed as "Benzofury." Regulatory changes swiftly followed, with the UK classifying 6-APB and analogous compounds as Temporary Class Drugs in June 2013, later elevating their status to Class B, Schedule 1 substances in November 2013. Consequently, on June 10, 2014, the UK Home Office officially designated 6-APB as a class B drug, along with other benzofuran entactogens and structurally related substances.
Chemistry
The Molecule
6-APB, scientifically recognized as 6-(2-aminopropyl)benzofuran, is a synthetic compound within the benzofuran class. This class is distinguished by its membership in the amphetamine and phenylethylamine categories. The fundamental structure consists of a phenethylamine core, connected to an amino (NH2) group through an ethyl chain, featuring an additional methyl substitution at Rα. Unlike its counterparts, 6-APB lacks a methyl substitution on RN. It is characterized by an oxygen-substituted benzofuran ring fused at R3 and R4 of the phenyl ring.
Notably, the benzofuran ring is a shared feature with related compounds such as 5-APB, 5-MAPB, and 6-MAPB. Multiple batches of 6-APB have been in circulation since its introduction to the market. Initially, only the hydrochloride variant was available, exhibiting a dosage range akin to MDA. Subsequently, succinate and fumarate batches entered the market, offering contrasting effects in terms of weight and bulk density.
Pharmacology
Biological Activity
6-APB operates as a serotonin–norepinephrine–dopamine 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. Beyond reuptake inhibition, it also functions as a releasing agent for these monoamine neurotransmitters.
Notably, 6-APB is a potent full agonist of the serotonin 5-HT2B receptor, exhibiting a high affinity (Ki = 3.7 nM). It displays a remarkable selectivity for the 5-HT2B receptor over the 5-HT2A and 5-HT2C receptors, distinguishing it from MDMA. Additionally, 6-APB has shown binding affinity to the α2C-adrenergic receptor subtype (Ki = 45 nM), although the clinical significance of this interaction remains unclear.
The pronounced agonism of the 5-HT2B receptor raises concerns about potential cardiotoxicity with chronic or long-term usage, a phenomenon observed with other 5-HT2B receptor agonists like the withdrawn serotonergic anorectic fenfluramine.
Neurotransmitter Modulation
6-APB's mechanism of action revolves around modulating global neurotransmitters such as serotonin, dopamine, and noradrenaline. Inhibition of reuptake and promotion of release lead to the accumulation of these neurotransmitters in synaptic clefts, resulting in diverse effects including stimulation, relaxation, disinhibition, and euphoria across various brain regions. These effects collectively influence pleasure, motivation, reward, planning, attention, and focus.
Subjective Effects
Physical Effects
Stimulation & Sedation 6-APB exhibits a paradoxical quality of stimulating and sedating effects on the user's physical energy levels. Compared to MDMA and MDA, it's notably less energetic, often inducing a pronounced "stoning" or "couch-locking" sensation. The stimulation it provides is gentler, akin to psychedelics like mescaline.
Spontaneous Physical Sensations Users commonly experience a warm, euphoric tingling sensation throughout the body, described as moderate to powerful. At higher doses, this sensation can become overwhelmingly pleasurable, even immobilizing the user, with its intensity rising steadily from onset to peak.
Tactile Enhancement 6-APB enhances tactile sensations, making touch more pleasurable and sensory.
Bodily Control Enhancement Users often report improved control over their physical movements, which can enhance dance and physical activities.
Stamina Enhancement Increased stamina is observed, allowing users to engage in physical activities for extended periods.
Temperature Regulation Suppression 6-APB can disrupt the body's ability to regulate core temperature, leading to elevated body and brain temperature. This effect is comparable to MDA and MDMA but tends to be slightly warmer.
Increased Bodily Temperature The substance induces a consistent increase in core body temperature, similar to MDA and MDMA. However, excessively high doses can pose a risk of serotonin syndrome, a potentially life-threatening condition.
Vibrating Vision At common to high doses, eyeballs may rapidly wiggle, causing blurred and unfocused vision—a condition known as nystagmus.
Abnormal Heartbeat An irregular heartbeat can occur, though this effect is relatively rare.
Increased Heart Rate Users may experience an elevated heart rate, leading to increased blood pressure and perspiration.
Dehydration Increased heart rate and bodily metabolism can result in dry mouth and dehydration. Users should be cautious not to overhydrate, which can lead to water intoxication.
Dry Mouth A dry mouth is a common effect due to increased metabolic activity.
Difficulty Urinating Higher doses may temporarily hinder urination due to 6-APB's influence on anti-diuretic hormone (ADH) release. Warming the genital area with a hot flannel can alleviate this effect.
Appetite Suppression Users may experience reduced appetite during the experience.
Pupil Dilation 6-APB causes pupil dilation, a common effect with many psychoactive substances.
Excessive Yawning Frequent yawning is often observed.
Temporary Erectile Dysfunction Some users may experience difficulty achieving or maintaining an erection.
Teeth Grinding Teeth grinding, similar to MDMA or MDA, is typically present at moderate to higher doses.
Seizure While rare, seizures are possible, particularly in those predisposed or under physically taxing conditions such as dehydration, fatigue, undernourishment, or overheating.
Visual Effects
Enhancements 6-APB produces mild visual enhancements compared to traditional psychedelics:
- Color Enhancement: Colors appear bright and synthetic, remaining consistent throughout the experience.
- Pattern Recognition Enhancement: Users may notice improved recognition of patterns.
Distortions Visual distortions include:
- Tracers: Tracers are similar to those associated with MDA, with longer sections of continuity before slight discontinuity.
- Symmetrical Texture Repetition
Geometry The visual geometry during a 6-APB experience is more akin to mescaline than LSD or psilocin. It's characterized by intricate, abstract, organic, structured, dimly lit patterns in predominantly monotone colors, with a glossy shading and sharp edges. These patterns are small, fast-moving, smooth, with both round and angular corners, offering a non-immersive depth and consistent intensity. Higher doses are more likely to lead to level 8A visual geometry over level 8B.
Hallucinatory States At high to heavy doses, 6-APB can induce various hallucinatory states, but these are less consistent and reproducible than those of other psychedelics. They often occur during the experience's offset and can include:
- Transformations
- External Hallucination: This effect is similar to deliriants but happens mainly at high doses, presenting memory replays and semi-realistic or expected events.
- Internal Hallucination: Spontaneous breakthroughs occur at extremely high doses, often manifesting as hypnagogic scenarios.
- Peripheral Information Misinterpretation
What is Benzo Fury (6-APB)?
Benzo Fury, also known as 6-APB (6-(2-aminopropyl)benzofuran), is a synthetic compound that belongs to the substituted benzofuran class. It is often used as a research chemical and is chemically related to amphetamines and phenethylamines.
Is Benzo Fury legal?
The legal status of Benzo Fury varies by country and region. It may be considered a controlled substance in some places, while in others, it may exist in a legal gray area or be unregulated. It's essential to check your local laws and regulations regarding its possession and use.
What are the effects of Benzo Fury?
Benzo Fury is known to produce effects similar to amphetamines and MDMA (ecstasy). Users may experience increased energy, enhanced mood, and heightened sensory perception. It can also lead to side effects such as increased heart rate, dilated pupils, and potential risks like anxiety and nausea.
Is Benzo Fury safe to use?
The safety of Benzo Fury has not been extensively studied in humans. Using research chemicals like Benzo Fury carries risks, including potential health hazards and legal consequences. It's essential to exercise caution and consider the potential risks and uncertainties associated with its use.
How is Benzo Fury typically consumed?
Benzo Fury is often consumed orally in the form of a pill or capsule. It can also be found as a powder, which users may insufflate (snort) or dissolve in liquid. The dosage and route of administration can vary, but it is crucial to be aware of potential risks and dosage guidelines.
Are there any known side effects of Benzo Fury?
Side effects of Benzo Fury may include increased heart rate, dilated pupils, dehydration, anxiety, nausea, and potential cognitive and emotional disturbances. The severity of side effects can vary depending on the individual and the dosage used.
Can Benzo Fury be addictive?
Research chemicals like Benzo Fury have the potential for psychological dependence. Repeated use can lead to tolerance and a desire for more significant effects, which may increase the risk of abuse and addiction.