1.
Heterocyclic compound
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A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring. Heterocyclic chemistry is the branch of chemistry dealing with the synthesis, properties. Examples of heterocyclic compounds include all of the acids, the majority of drugs, most biomass. Although heterocyclic compounds may be inorganic, most contain at least one carbon, while atoms that are neither carbon nor hydrogen are normally referred to in organic chemistry as heteroatoms, this is usually in comparison to the all-carbon backbone. But this does not prevent a compound such as borazine from being labelled heterocyclic, IUPAC recommends the Hantzsch-Widman nomenclature for naming heterocyclic compounds. Heterocyclic compounds can be classified based on their electronic structure. The saturated heterocycles behave like the acyclic derivatives, thus, piperidine and tetrahydrofuran are conventional amines and ethers, with modified steric profiles. Therefore, the study of heterocyclic chemistry focuses especially on unsaturated derivatives, included are pyridine, thiophene, pyrrole, and furan. Another large class of heterocycles are fused to rings, which for pyridine, thiophene, pyrrole, and furan are quinoline, benzothiophene, indole. Fusion of two benzene rings gives rise to a large family of compounds, respectively the acridine, dibenzothiophene, carbazole. The unsaturated rings can be classified according to the participation of the heteroatom in the pi system, heterocycles with three atoms in the ring are more reactive because of ring strain. Those containing one heteroatom are, in general, stable and those with two heteroatoms are more likely to occur as reactive intermediates. Five-membered rings with one heteroatom, The 5-membered ring compounds containing two heteroatoms, at least one of which is nitrogen, are called the azoles. Thiazoles and isothiazoles contain a sulfur and an atom in the ring. A large group of 5-membered ring compounds with three heteroatoms also exists, one example is dithiazoles that contain two sulfur and a nitrogen atom. Five-member ring compounds with four heteroatoms, With 5-heteroatoms, the compound may be considered rather than heterocyclic. With 7-membered rings, the heteroatom must be able to provide an empty pi orbital for normal aromatic stabilization to be available, otherwise, for example, with the benzo-fused unsaturated nitrogen heterocycles, pyrrole provides indole or isoindole depending on the orientation. The pyridine analog is quinoline or isoquinoline, for azepine, benzazepine is the preferred name
2.
Benzofuran
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Benzofuran is the heterocyclic compound consisting of fused benzene and furan rings. This colourless liquid is a component of coal tar, benzofuran is the parent of many related compounds with more complex structures. For example, psoralen is a derivative that occurs in several plants. Benzofuran is extracted from coal tar and it is also obtained by dehydrogenation of 2-ethylphenol. Benzofurans can be prepared by various methods in the laboratory, notable examples include, O-alkylation of salicylaldehyde with chloroacetic acid followed by dehydration of the resulting ether. Indole, an analog with a nitrogen instead of the oxygen atom, benzothiophene, an analog with a sulfur instead of the oxygen atom. Isobenzofuran, the isomer with oxygen in the adjacent position
3.
Psychoactive drug
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A psychoactive drug, psychopharmaceutical, or psychotropic is a chemical substance that changes brain function and results in alterations in perception, mood, or consciousness. These substances may be used recreationally, to alter ones consciousness, or, as entheogens, for ritual, spiritual, or shamanic purposes. Some categories of drugs, which have medical therapeutic value, are prescribed by medical doctors. There are also some psychoactive substances used in the detoxification and rehabilitation programs for drug users. Psychoactive substances often bring about changes in consciousness and mood that the user may find rewarding. In addition, sustained use of some substances may produce a physical dependence or psychological dependence syndrome associated with somatic or psychological-emotional withdrawal states respectively, Drug rehabilitation aims to break this cycle of dependency, through a combination of psychotherapy, support groups, maintenance and even other psychoactive substances. However, the reverse is true in some cases, that certain experiences on drugs may be so unfriendly. This is especially true of certain deliriants, powerful dissociatives, and classic psychedelics, in part because of this potential for substance misuse, addiction, or dependence, the ethics of drug use is debated. Restrictions on drug production and sales in an attempt to drug abuse are very common among national and sub-national governments worldwide. Ethical concerns have also raised about over-use of these drugs clinically. Psychoactive drug use can be traced to prehistory, there is archaeological evidence of the use of psychoactive substances dating back at least 10,000 years, and historical evidence of cultural use over the past 5,000 years. The chewing of coca leaves, for example, dates back over 8,000 years ago in Peruvian society, medicinal use is one important facet of psychoactive drug usage. However, some have postulated that the urge to alter ones consciousness is as primary as the drive to satiate thirst, hunger or sexual desire. Supporters of this belief contend that the history of use and even childrens desire for spinning, swinging. It is, however, necessary to precisely what is meant by the use of drugs. We do not mean the purely physical craving, but there are not many drugs which have the power of stilling such craving. This relationship is not limited to humans, a number of animals consume different psychoactive plants, animals, berries and even fermented fruit, becoming intoxicated, such as cats after consuming catnip. Traditional legends of sacred plants often contain references to animals that introduced humankind to their use, animals and psychoactive plants appear to have co-evolved, possibly explaining why these chemicals and their receptors exist within the nervous system
4.
Stimulant
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Stimulants is an overarching term that covers many drugs including those that increase activity of the body, drugs that are pleasurable and invigorating, or drugs that have sympathomimetic effects. Due to their rendering a characteristic up feeling, stimulants are also referred to as uppers. Depressants or downers, which decrease mental and/or physical function, are in stark contrast to stimulants and are considered to be the functionally opposite drug class, Stimulants are widely used throughout the world as prescription medicines as well as without a prescription as performance-enhancing or recreational drugs. The most frequently prescribed stimulants as of 2013 were lisdexamfetamine, methylphenidate and it is estimated that the percent of the population that has abused amphetamines, cocaine and MDMA combined is between. 8% and 2. 1%. Stimulants in therapeutic doses, such as given to patients with ADHD, increases ability to focus, vigor, sociability, libido. However, in higher doses stimulants may actually decrease the ability to focus, in higher doses stimulants may also produce euphoria, vigor, and decrease need for sleep. Many, but not all, stimulants have ergogenic effects, Drugs such as ephedrine, pseudoephedrine, amphetamine and methylphenidate have well documented ergogenic effects, while drugs such as cocaine and methamphetamine have the opposite effect. In some cases psychiatric phenomenon may emerge such as stimulant psychosis, paranoia, acute toxicity has been reportedly associated with a homicide, paranoia, aggressive behavior, motor dysfunction, and punding. The violent and aggressive behavior associated with acute stimulant toxicity may partially be driven by paranoia, most drugs classified as stimulants are sympathomimetics, that is they stimulate the sympathetic branch of the autonomic nervous system. This leads to such as mydriasis, increased heart rate, blood pressure, respiratory rate. When these changes become pathological, they are called arrhythmia, hypertension, and hyperthermia, however given the complexity of the mechanisms that underly these potentially fatal outcomes of acute stimulant toxicity, it is impossible to determine what dose may be lethal. Assessment of the effects of stimulants is relevant given the large population currently taking stimulants. A systematic review of cardiovascular effects of prescription stimulants found no association in children, a review over a four-year period found that there were few negative effects of stimulant treatment, but stressed the need for longer term studies. A review of a long period of prescription stimulate use in those with ADHD found that cardiovascular side effects were limited to transient increases in blood pressure only. Initiation of stimulant treatment in those with ADHD in early childhood appears to carry benefits into adulthood with regard to social and cognitive functioning, Abuse of prescription stimulants or of illicit stimulants carries many negative health risks. Abuse of cocaine, depending upon route of administration, increases risk of disease, stroke. Cocaine may also increase risk for disease, as well as damage nasal cartilage. Abuse of methamphetamine produces similar effects as well as marked degeneration of dopaminergic neurons, Drugs used to treat sleep disorders such as excessive daytime sleepiness are called eugeroics, and include notable stimulants such as modafinil
5.
Psychedelic drug
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A psychedelic drug is a drug whose primary action is to alter cognition and perception, typically by agonising serotonin receptors. The psychedelic experience is often compared to forms of consciousness such as trance, meditation, yoga, religious ecstasy, dreaming. With a few exceptions, most psychedelic drugs fall into one of the three following families of compounds, tryptamines, phenethylamines, and lysergamides. Many psychedelic drugs are illegal worldwide under the UN conventions unless used in a medical or religious context, despite these regulations, recreational use of psychedelics is common. The word was coined in 1956 by British psychiatrist, Humphry Osmond, the spelling loathed by American ethnobotanist, Richard Schultes, aldous Huxley had suggested to Humphry Osmond in 1956 his own coinage phanerothyme. Recently, the term entheogenic has come into use to denote the use of drugs in a religious/spiritual/mystical context. Psychedelics have a history of traditional use in medicine and religion. In this context, they are known as entheogens. Native American practitioners using mescaline-containing cacti have reported success against alcoholism, ayahuasca, which contains the powerful psychedelic DMT, is used in Peru and other parts of South America for spiritual and physical healing as well as in religious festivals. Classical or serotonergic psychedelics include LSD, psilocin, mescaline, and this class of psychedelics includes the classical hallucinogens, including the lysergamides like LSD and LSA, tryptamines like psilocybin and DMT, and phenethylamines like mescaline and 2C-B. Many of these psychedelics cause remarkably similar effects, despite their different chemical structure, however, many users report that the three families have subjectively different qualities in the feel of the experience, which are difficult to describe. At lower doses, these include sensory alterations, such as the warping of surfaces, shape suggestibility, users often report intense colors that they have not previously experienced, and repetitive geometric shapes are common. Higher doses often cause intense and fundamental alterations of sensory perception, some compounds, such as 2C-B, have extremely tight dose curves, meaning the difference between a non-event and an overwhelming disconnection from reality can be very slight. There can be substantial differences between the drugs, however. The empathogen-entactogens are phenethylamines of the MDxx class such as MDMA, MDEA and their effects are characterized by feelings of openness, euphoria, empathy, love, heightened self-awareness, and by mild audio and visual distortions. Their adoption by the subculture is probably due to the enhancement of the overall social and musical experience. Certain dissociative drugs acting via NMDA antagonism are known to produce what some might consider psychedelic effects, the main differences between dissociative psychedelics and serotonergic hallucinogens are that the dissociatives cause more intense derealization and depersonalization. For example, ketamine produces sensations of being disconnected from ones body, salvia divinorum is a dissociative that is sometimes classified as an atypical psychedelic
6.
Dimemebfe
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Dimemebfe is a recreational drug and research chemical. It acts as an agonist for the 5-HT1A and 5-HT2 family of serotonin receptors and it is related in structure to the psychedelic tryptamine derivative 5-MeO-DMT, but with the indole nitrogen replaced by oxygen, making dimemebfe a benzofuran derivative. It is several times less potent as a serotonin agonist than 5-MeO-DMT and with more activity at 5-HT1A. Dimemebfe is a Schedule I controlled substance in the US state of Alabama
7.
5-APB
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5-APB is an empathogenic psychoactive compound of the substituted benzofuran, substituted amphetamine and substituted phenethylamine classes. 5-APB and other compounds are sometimes informally called Benzofury, 5-APB is commonly found as the succinate and hydrochloride salt. The hydrochloride salt is 10% more potent by mass and doses should be adjusted accordingly, 5-APB has been sold as a designer drug since 2010. 5-APB is a serotonin–norepinephrine–dopamine reuptake inhibitor with Ki=180 nmol/L, Ki=265 nmol/L and it is also a serotonin–norepinephrine–dopamine releasing agent. 5-APB is a potent agonist for the 5-HT2A and 5-HT2B receptors, a forensic standard of 5-APB is available, and the compound has been posted on the Forendex website of potential drugs of abuse. The US Department of Justice and DEA have also conducted studies concerning the detection of 5-APB, largely, effects reported were similar to that of the drug MDA but not as strong. Recreational use of 5-APB has been associated with death in combination with other drugs, 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
8.
5-MAPB
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5-MAPB is an entactogenic designer drug similar to MDMA on its structure and effects. 5-MAPB is not listed itself in the CDSA but since it is related to MDMA it would be considered illegal in Canada. As of October 2015 5-MAPB is a substance in China. 5-MAPB was originally banned in the UK in June 2013 under a Temporary class drug order, on March 5,2014 the UK Home Office announced that 5-MAPB would be made a class B drug on 10 June 2014 alongside every other benzofuran entactogen and many structurally related drugs. Little formal knowledge exists on 5-MAPB and it does not share the neurotoxicity of MDA caused by the alpha-methyldopamine metabolite. A study in rats indicated that the metabolites of 5-MAPB are 5-APB. 5-MAPB binds to the transporter in rat brain cells with a lower potency than cocaine. In silico data suggests that the action on dopamine is through reversal of the transporter to release dopamine. This is consistent with the effects and it is likely that it exerts a similar action on serotonin and norepinephrine transporters
9.
6-APB
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6-APB is an empathogenic psychoactive compound of the substituted benzofuran, substituted amphetamine and substituted phenethylamine classes. 6-APB and other compounds are sometimes informally called Benzofury in newspaper reports and it is similar in structure to MDA, but differs in that the 3, 4-methylenedioxyphenyl ring system has been replaced with a benzofuran ring. 6-APB is also the unsaturated derivative of 6-APDB. It may appear as a tan grainy powder, 6-APB was first synthesized by David Nichols and his team in 1993 while studying non-neurotoxic analogs of MDMA. While the drug never became popular, it briefly entered the rave and underground clubbing scene in the UK before its sale. It falls under the category of chemicals, sometimes called legal highs. Because 6-APB and other substituted benzofurans have not been outlawed in some countries, they are often technically legal. In addition, 6-APB not only blocks the reuptake of these monoamine neurotransmitters but is also an agent of them. In addition to actions at the monoamine transporters, 6-APB is a potent full agonist of the serotonin 5-HT2B receptor, moreover, unlike MDMA, 6-APB shows 100-fold selectivity for the 5-HT2B receptor over the 5-HT2A and 5-HT2C receptors. Aside from the 5-HT2B receptor, 6-APB has also found to bind with high affinity to the α2C-adrenergic receptor subtype. 6-APB showed little other affinity at a selection of other sites. The pharmacokinetics of 6-APB have not been studied, however, some information can be extracted from user reports and these suggest an slow onset of 20–120 minutes. The drugs maximum effects last 3–4 hours, followed by a phase of up to 24 hours. Although limited literature is available, there is data on metabolism of 6-APB in rats. Its Phase I metabolism involves hydroxylation of the ring, then cleavage of the ring. The resulting aldehyde may then takes two paths and it is either oxidized to a carboxylic acid or reduced to an alcohol, and then hydroxylated. Phase II metabolism consists of glucuronidation, the most prevalent metabolites in rats were 3-carboxymethyl-4-hydroxyamphetamine and 4-carboxymethyl-3-hydroxyamphetamine. 6-APB and its structural isomer 5-APB have been tested with a series of agents including, Marquis, Liebermann, Mecke, exposing compounds to the reagents gives a colour change which is indicative of the compound under test
10.
5-APDB
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5--2, 3-dihydrobenzofuran is a putative entactogen drug of the phenethylamine and amphetamine classes. It is an analogue of MDA where the heterocyclic 3-position oxygen from the 3, 6-APDB is an analogue of 5-APDB where the 4-position oxygen has been replaced by a methylene bridge instead. 5-APDB was developed by a led by David E. Nichols at Purdue University as part of their research into non-neurotoxic analogues of MDMA. In animal studies, 5-APDBs effects generalize most closely to non-stimulant MDMA analogues such as MBDB and MMAI, as of October 2015 5-APDB is a controlled substance in China. On June 10,2013 5-APDB and a number of analogues were classified as Temporary Class Drugs in the UK following an ACMD recommendation and this means that sale and import of the named substances are criminal offences and are treated as for class B drugs
11.
6-APDB
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6--2, 3-dihydrobenzofuran is a stimulant and entactogen drug of the phenethylamine and amphetamine classes. It is an analogue of MDA where the heterocyclic 4-position oxygen from the 3, 5-APDB is an analogue of 6-APDB where the 3-position oxygen has been replaced with a methylene instead. 6-APDB, along with 5-APDB, was first synthesized by David E. Nichols in the early 1990s while investigating non-neurotoxic MDMA analogues, in animal studies, 6-APDB fully substitutes for MBDB and MMAI but not for amphetamine or LSD. In vitro, 6-APDB has been shown to inhibit the reuptake of serotonin, dopamine, and norepinephrine with IC50 values of 322 nM,1,997 nM, and 980 nM, respectively. These values are similar to those of MDA, but with those for the catecholamines slightly lower in comparison. In contrast, 5-APDB is highly selective for serotonin, the unsaturated benzofuran derivative 6-APB, or 6-benzofuran is also known, but the difference in pharmacological effects between 6-APB and 6-APDB is unclear. 6-APDB is a class B drug in the UK since June 10,2013 and it is banned by a blanket law on benzofurans and related compounds
12.
F-2 (drug)
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F-2, or 6--5-methoxy-2-methyl-2, 3-dihydrobenzofuran, is a lesser-known psychedelic drug. F-2 was first synthesized by Alexander Shulgin, in his book PiHKAL, the minimum dosage is listed as 15 mg, and the duration unknown. F-2 produces few to no effects, very little data exists about the pharmacological properties, metabolism, and toxicity of F-2. F-2 Entry in PiHKAL F-2 Entry in PiHKAL • info
13.
F-22 (psychedelic)
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F-22 is a lesser-known psychedelic drug. F-22 was first synthesized by Alexander Shulgin, in his book PiHKAL, the minimum dosage is listed as 15 mg, and the duration unknown. F-22 produces few to no effects, very little data exists about the pharmacological properties, metabolism, and toxicity of F-22. F-22 Entry in PiHKAL F-22 Entry in PiHKAL • info
14.
2C-B-FLY
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2C-B-FLY is a psychedelic phenethylamine of the 2C family. It was first synthesized by Aaron P. Monte, the full name of the chemical is 2-ethanamine. It has been subject to formal study, but its appearance as a designer drug has led the DEA to release analytical results for 2C-B-FLY. In theory, dihydrodifuran analogues of any of the 2Cx / DOx family of drugs could be made, the larger saturated hexahydrobenzodipyran ring derivatives have been referred to as butterfly compounds. The 8-bromo group can also be replaced by groups to give compounds such as TFMFly. A large number of symmetrical and unsymmetrical derivatives can be produced by using different combinations of ring systems, because the 2- and 5- positions are not equivalent, all unsymmetrical combinations also have two possible positional isomers, with different potencies at the various 5-HT2 subtypes. A large number of possible combinations have been synthesised and tested for activity, alexander Shulgin lists a dosage of 2C-B-FLY at 10 mg orally. 2C-B-FLY produces psychedelic effects that last 6–8 hours, or up to 12 hours in larger doses, the toxicity of 2C-B-FLY in humans is unknown. As of October 31st,2016, 2C-B-FLY is a substance in Canada. Http, //gazette. gc. ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng. php 2C-B-FLY is unscheduled and uncontrolled in the United States, however, it may fall under the scope of the Federal Analog Act if it is intended for human consumption given its similarity to 2C-B. 2C-B-FLY Entry at Erowid 2C-B-FLY Entry at Isomerdesign
15.
Bromo-DragonFLY
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Bromo-DragonFLY is a psychedelic drug related to the phenethylamine family. Bromo-DragonFLY has a stereocenter and --bromo-DragonFLY is the active stereoisomer. Bromo-DragonFLY was first synthesized by Matthew Parker in the laboratory of David E. Nichols in 1998, as with the earlier and less potent dihydrofuran series of compounds nicknamed FLY, Bromo-DragonFLY was named after its superficial structural resemblance to a dragonfly. The hallucinogenic effect of bromo-DragonFLY is mediated by its agonist activity at the 5-HT2A serotonin receptor, the typical dose of Bromo-DragonFLY is not known, however it has varied from 500 μg to 1 mg. It has about 300 times the potency of mescaline, or 1/5 the potency of LSD and it has been sold in the form of blotters, similar to the distribution method of LSD, which has led to confusion, and reports of mistakenly consuming Bromo-DragonFly. It has a longer duration of action than LSD and can last for up to 2–3 days following a single large dose. Laboratory testing has confirmed that in October 2009, a batch of Bromo-Dragonfly was distributed, mislabeled as the related compound 2C-B-FLY and this mistake is believed to have contributed to several lethal overdoses and additional hospitalizations. The batch implicated in these deaths also contained significant synthesis impurities, vasoconstrictive action resulting from severe overdose of Bromo-DragonFLY is known to have caused tissue necrosis of the extremities in at least one case. Treatment was of limited efficacy in this case, although tolazoline is reportedly an effective treatment where available, overdose-associated disturbing experiences and health problems have been described. One case in 2008 in England involved inhalation of vomit, causing nearly fatal asphyxia, on October 3,2009, a 22-year-old male from Copenhagen died after ingesting Bromo-dragonfly. His friend described the trip saying, It was like being dragged to hell and it is the most evil Ive ever tried. On May 7,2011, in the United States, two adults died after overdosing on Bromo-DragonFLY, which they thought was 2C-E, and several others were hospitalized during the same incident. Because they took a dosage appropriate for 2C-E, those who took the drug received, in some cases, both deaths followed seizures, vomiting blood, and terrifying hallucinations. Several surviving victims are still suffering from its physical effects. Bromo-DragonFLY is listed as a Schedule I in Oklahoma, Schedule III as of Oct 122016. 2C-phenethylamines and their salts, derivatives, isomers and salts of derivatives and isomers that correspond to a definition that includes anything with a 2. This includes most 2C-s, DOx, TMA, Aleph, NBOMes, NBOHs, NBF, bk-2-C-B, 2C-B-Fly, Bromo-DragonFLY, Bromo-DragonFLY is widely reported by the media as being a class A drug. If the prosecution could demonstrate structural similarity in court, it would be considered a Class A substance and it is not explicitly named in the misuse of drugs act
16.
Recreational drug use
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Recreational drug use is the use of a psychoactive drug to alter ones mental state in a way that modifies emotions, perceptions, and feelings for recreational purposes. When a substance enters the body, it brings on an intoxicating effect. Generally, people use drugs that fall into three categories, depressants, stimulants, and psychedelic drugs. In popular usage, it is considered to be a tolerated social behaviour rather than a serious medical condition such as self-medication. The substances classified as controlled and illegal drugs vary by country, in 2009 it was estimated that about 3% to 6% of people aged 15 to 65 had used illegal drugs at least once. International and domestic law enforcement agencies are perpetually occupied with interdiction efforts against illegal use, manufacture. Many researchers have explored the etiology of recreational drug use, there has not been agreement around any one single cause. Instead, experts tend to apply the biopsychosocial model, any number of these factors are likely to influence an individual’s drug use as they are not mutually exclusive. Regardless of genetics, mental health or traumatic experiences, social factors play a role in exposure to and availability of certain types of drugs. According to addiction researcher Martin A. Plant, many go through a period of self-redefinition before initiating recreational drug use. They tend to view using drugs as part of a lifestyle that involves belonging to a subculture that they associate with heightened status. Plant says, “From the users point of there are many positive reasons to become part of the milieu of drug taking. The reasons for drug use appear to have as much to do with needs for friendship, pleasure, becoming a drug taker, to many people, is a positive affirmation rather than a negative experience. ”Anthropological research has suggested that humansmay have evolved to counter-exploit plant neurotoxins. The ability to use chemicals to serve the function of endogenous neurotransmitters may have improved survival rates. A typically restrictive prehistoric diet may have emphasised the apparent benefit of consuming psychoactive drugs, severity and type of risks that come with recreational drug use vary widely with the drug in question and the amount being used. There are many factors in the environment and within the user interact with each drug differently. Overall, some studies suggest that alcohol is one of the most dangerous of all drugs, only heroin, crack cocaine. Researcher David Nutt stated that studies showing benefits for moderate alcohol consumption lacked control for the variable of what the subjects were drinking
17.
5-IT
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5-indole is an indole and phenethylamine derivative with empathogenic effects. Its preparation was first reported by Albert Hofmann in 1962 and it is a designer drug that has been openly sold as a recreational drug by online vendors since 2011. Although 5-IT is an isomer of the tryptamine drug αMT. The compound is closer chemically to phenethylamine derivatives such as 5-APB and this is reflected in the compounds effects when used as a drug, which are reportedly stimulating rather than psychedelic. 5-IT acts as a monoamine releasing agent with EC50 values of 12.9 nM for dopamine,13.3 nM for norepinephrine and 104.8 nM for serotonin. As 5-IT is not a tryptamine and thus not within the scope of the book and it is an MAOI, and when combined with a contraindicated substance, it can lead to death. 5-IT has been attributed to 14 deaths of people in Sweden since its discovery, 5-IT was listed as the sole intoxicant in two cases but other drugs were also found in the twelve other post mortem examinations. The 14 deaths occurred between April and July 2012, but a definitive identification of 5-IT in the samples was not made until July. All of the dead were men aged between 20-30. Eleven non-fatal poisonings due to 5-IT also reportedly occurred during the time period. 5-IT is an isomer of αMT, and as such is considered legally the same as αMT under the Controlled Substance Act in the USA. 5-IT is illegal in the UK, as it was banned as a temporary class drug in June 2013, along with 9 other related compounds. On March 5,2014 the UK Home Office announced that 5-API would be made a class B drug on 10 June 2014 alongside every other benzofuran entactogen and many structurally related drugs. A formal application for 5-IT to be illegal in Sweden was made on July 26,2012. 5-IT was made illegal in Denmark on 30 September 2012, 5-IT is a Anlage I controlled drug in Germany. The European Commission published a proposal for a decision calling upon its member states to take measures to control 5-indole and it asked member states to introduce control measures and criminal penalties as provided under their national legislation covering psychotropic substances
18.
Substituted amphetamine
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The compounds in this class span a variety of pharmacological subclasses, including stimulants, empathogens, and hallucinogens, among others. Some of amphetamines substituted derivatives occur in nature, for example in the leaves of Ephedra and these have been used since antiquity for their pharmacological effects. Amphetamine was first produced at the end of the 19th century, by the 1930s, amphetamine and some of its derivative compounds found use as decongestants in the symptomatic treatment of colds and also occasionally as psychoactive agents. Their effects on the nervous system are diverse, but can be summarized by three overlapping types of activity, psychoanaleptic, hallucinogenic and empathogenic. Various substituted amphetamines may cause these actions either separately or in combination, amphetamines are a subgroup of the substituted phenethylamine class of compounds. Substitution of hydrogen results in a large class of compounds. Natives of Yemen and Ethiopia have a tradition of chewing khat leaves to achieve a stimulating effect. The active substances of khat are cathinone and, to a lesser extent, amphetamine was first synthesized in 1887 by Romanian chemist Lazăr Edeleanu, although its pharmacological effects remained unknown until the 1930s. MDMA was produced in 1912 as an intermediate product, however, this synthesis also went largely unnoticed. In the 1920s, both methamphetamine and the dextrorotatory optical isomer of amphetamine, dextroamphetamine, were synthesized and this synthesis was a by-product of a search for ephedrine, a bronchodilator used to treat asthma extracted exclusively from natural sources. Over-the-counter use of substituted amphetamines was initiated in the early 1930s by the pharmaceutical company Smith, Kline & French, as a medicine for colds and nasal congestion. Subsequently, amphetamine was used in the treatment of narcolepsy, obesity, hay fever, orthostatic hypotension, epilepsy, Parkinsons disease, alcoholism, the reinforcing effects of substituted amphetamines were quickly discovered, and the misuse of substituted amphetamines had been noted as far back as 1936. During World War II, amphetamines were used by the German military to keep their tank crews awake for long periods and it was noticed that extended rest was required after such artificially induced activity. The widespread use of substituted amphetamines began in postwar Japan and quickly spread to other countries, modified designer amphetamines gained popularity since the 1960s, such as MDA and PMA. In 1970, the United States adopted the Controlled Substances Act that limited non-medical use of substituted amphetamines, street use of PMA was noted in 1972. MDMA emerged as a substitute to MDA in the early 1970s, american chemist Alexander Shulgin first synthesized the drug in 1976 and through him the drug was briefly introduced into psychotherapy. Recreational use grew and in 1985 MDMA was banned by the US authorities in an emergency scheduling initiated by the Drug Enforcement Administration, since the mid-1990s, MDMA has become a popular entactogenic drug among the youth and quite often non-MDMA substances were sold as ecstasy. Ongoing trials are investigating its efficacy as an adjunct to psychotherapy in the management of treatment-resistant post-traumatic stress disorder
19.
Substituted cathinone
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Substituted cathinones, which include some stimulants and entactogens, are derivatives of cathinone. They feature a core with an alkyl group attached to the alpha carbon. Cathinone occurs naturally in the plant khat whose leaves are chewed as a recreational drug and this ban covers compounds with the aforementioned general structure, with 28 compounds specifically named. This text was added as an amendment to the Misuse of Drugs Act 1971, note that four of the above compounds were already illegal in the UK at the time the ACMD report was issued. Naphyrone analogues were subsequently banned in July 2010 following a review by the ACMD. In the United States, substituted cathinones are the ingredients in bath salts which as of July 2011 were banned by at least 28 states. Markush structure Substituted amphetamines Substituted methylenedioxyphenethylamines Substituted phenethylamines Substituted phenylmorpholines Arylcyclohexylamines
20.
Substituted methylenedioxyphenethylamine
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These agents are used as research chemicals, designer drugs and as recreational substances. When referring to MDMA and its counterparts, the term MDxx is often used with the exception of MDPV, the base compound of the MDxx class is 3, 4-methylenedioxyphenethylamine, and the prototypical agent of this class is 3, 4-methylenedioxy-N-methylamphetamine. Other mentionables include 3, 4-methylenedioxyamphetamine,3, 4-methylenedioxy-N-ethylamphetamine, N-methyl-1, 3-benzodioxolylbutanamine and this makes them useful for comparison
21.
Substituted phenethylamine
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The structural formula of any substituted phenethylamine contains a phenyl ring that is joined to an amino group via an ethyl sidechain. Hence, any substituted phenethylamine can be classified according to the substitution of hydrogen atoms on phenethylamines phenyl ring, sidechain, numerous endogenous compounds – including hormones, monoamine neurotransmitters, and many trace amines – are substituted phenethylamines. Several notable recreational drugs, such as MDMA, methamphetamine, all of the substituted amphetamines and substituted methylenedioxyphenethylamines are substituted phenethylamines as well. Substituted amphetamines Substituted methylenedioxyphenethylamines Substituted cathinones Substituted phenylmorpholines 2Cs and DOx Substituted tryptamines
22.
PubMed Identifier
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PubMed is a free search engine accessing primarily the MEDLINE database of references and abstracts on life sciences and biomedical topics. The United States National Library of Medicine at the National Institutes of Health maintains the database as part of the Entrez system of information retrieval, from 1971 to 1997, MEDLINE online access to the MEDLARS Online computerized database primarily had been through institutional facilities, such as university libraries. PubMed, first released in January 1996, ushered in the era of private, free, home-, the PubMed system was offered free to the public in June 1997, when MEDLINE searches via the Web were demonstrated, in a ceremony, by Vice President Al Gore. Information about the journals indexed in MEDLINE, and available through PubMed, is found in the NLM Catalog. As of 5 January 2017, PubMed has more than 26.8 million records going back to 1966, selectively to the year 1865, and very selectively to 1809, about 500,000 new records are added each year. As of the date,13.1 million of PubMeds records are listed with their abstracts. In 2016, NLM changed the system so that publishers will be able to directly correct typos. Simple searches on PubMed can be carried out by entering key aspects of a subject into PubMeds search window, when a journal article is indexed, numerous article parameters are extracted and stored as structured information. Such parameters are, Article Type, Secondary identifiers, Language, publication type parameter enables many special features. As these clinical girish can generate small sets of robust studies with considerable precision, since July 2005, the MEDLINE article indexing process extracts important identifiers from the article abstract and puts those in a field called Secondary Identifier. The secondary identifier field is to store numbers to various databases of molecular sequence data, gene expression or chemical compounds. For clinical trials, PubMed extracts trial IDs for the two largest trial registries, ClinicalTrials. gov and the International Standard Randomized Controlled Trial Number Register, a reference which is judged particularly relevant can be marked and related articles can be identified. If relevant, several studies can be selected and related articles to all of them can be generated using the Find related data option, the related articles are then listed in order of relatedness. To create these lists of related articles, PubMed compares words from the title and abstract of each citation, as well as the MeSH headings assigned, using a powerful word-weighted algorithm. The related articles function has been judged to be so precise that some researchers suggest it can be used instead of a full search, a strong feature of PubMed is its ability to automatically link to MeSH terms and subheadings. Examples would be, bad breath links to halitosis, heart attack to myocardial infarction, where appropriate, these MeSH terms are automatically expanded, that is, include more specific terms. Terms like nursing are automatically linked to Nursing or Nursing and this important feature makes PubMed searches automatically more sensitive and avoids false-negative hits by compensating for the diversity of medical terminology. The My NCBI area can be accessed from any computer with web-access, an earlier version of My NCBI was called PubMed Cubby
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4-Chlorophenylisobutylamine
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4-Chlorophenylisobutylamine, also known as 4-chloro-α-ethylphenethylamine, is an entactogen and stimulant drug of the phenethylamine class. It is an analogue of para-chloroamphetamine where the alpha position methyl has been replaced with an ethyl group, though its dopaminergic activity is significantly attenuated compared to PCA, unlike the case of MBDB, it is not abolished, and is actually similar to that of MDMA. Relative to PCA, 4-CAB is also substantially less effective as a serotonergic neurotoxin, a single 10 mg/kg administration of PCA to rats produces an approximate 80% decrease in serotonin markers as observed 1 week later. In contrast,11 mg/kg and 22 mg/kg doses of 4-CAB result in only 20% and 50% decreases and this is once again similar to MDMA which causes a 40-60% reduction with a single 20 mg/kg dose
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4-Fluoroamphetamine
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4-Fluoroamphetamine, also known as para-fluoroamphetamine is a psychoactive research chemical of the phenethylamine and substituted amphetamine chemical classes. It produces stimulant and entactogenic effects, and is described subjectively as being between amphetamine and MDMA, as a recreational drug, 4-FA is sometimes sold along with related compounds such as 2-fluoroamphetamine and 4-fluoromethamphetamine. 4-FA is popular in the Netherlands where it is used for its specific effects rather than its legal status. The general course of effects involves primarily empathogenic effects for the first few hours, the dopamine reuptake inhibition produced by 4-FA is stronger than that of either 4-CA or 4-IA. 4-FA also produces less hyperthermia than similar compounds such as PMA, 3-MTA, common acute side effects are nausea, headaches, increased heart rate and insomnia. 4-FA reacts with reagent tests to give an array of colors which can be used to aid its identification. 4-Fluoroamphetamine is an agent and reuptake inhibitor of dopamine, serotonin. The respective EC50 values are 2.0 x 10−7 M,7.3 x 10−7 M, and 0.37 x 10−7 M, while the IC50 values are 7.7 x 10−7 M,68 x 10−7 M, and 4.2 x 10−7 M. Regarding the metabolic fate of 4-FA, the C-F bond at the 4-position on the phenyl ring likely resists deactivation in the liver by cytochrome P450 oxidase, 4-FA does not cause long-lasting depletion of brain serotonin, unlike its analogs 4-CA and 4-BA. This is thought to reflect the inability of the fluoro-compound to be metabolized in the way as the other haloamphetamines. Neurotoxicity does not increase down the series of para-halogenated amphetamine derivatives, for example, 4-iodoamphetamine is less toxic than is 4-chloroamphetamine. Hence, this property is not related to serotonin releasing potency as such and it is unclear where 4-methylamphetamine fits in on the neurotoxicity scale. Exceptions include 4-MTA, a para-substituted, non-neurotoxic amphetamine, the LD50 of 4-FA is 46 mg/kg. 4-FA has only involved in one death worldwide, where it was combined with amphetamine, methadone. As of October 2015, 4-FA is a substance in China. 4-FA is banned in the Czech Republic, as of April 1,2017 4-FA is a controlled substance in the Netherlands. 4-FA is also controlled in Belgium, UK, Germany, Israel, Slovakia, Chile, Brazil, Canada, Croatia, Sweden, USA, New Zealand, 2-Fluoroamphetamine 3-Fluoroamphetamine 4-Fluoromethamphetamine 4-Fluoromethcathinone para-Bromoamphetamine Erowid, 4-Fluoroamphetamine
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4-Fluoromethamphetamine
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4-Fluoromethamphetamine is a stimulant drug related to methamphetamine and 4-fluoroamphetamine. It has been reported to be sold on the market as a controlled substance analogue. It was first detected from legal highs sold in Japan in 2006 and it reduces the metabolism of methamphetamine, which has the effect of increasing its potency, duration and systemic toxicity while also reducing its cellular toxicity. As of October 2015 4-FMA is a substance in China. 4-FMA is considered a Schedule 9 substance in Australia under the Poisons Standard
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4-Methylthioamphetamine
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4-Methylthioamphetamine is a designer drug developed in the 1990s by a team led by David E. Nichols at Purdue University. It acts as a highly selective serotonin releasing agent in animals. It is distantly related to several other SSRAs, including MMAI, MDAI, 4-MTA is a strong serotonin releaser similar to paramethoxyamphetamine, which can cause pronounced hyperthermia potentially resulting in organ failure and death. The subjective effects of 4-MTA include prolonged stimulation, which, in contrast to other amphetamines, is accompanied by little sense of euphoria. 4-MTA is also an MAO-A inhibitor, which may explain its tendency to cause adverse effects. It was also sold on the black market as MDMA during the late 1990s, mainly in the USA. 4-MTA is currently a Class A drug in the United Kingdom although it has suggested it be rescheduled as a Class B drug. It is also a controlled substance in Argentina
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4,4'-Dimethylaminorex
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4, 4-Dimethylaminorex, sometimes referred to by the street name Serotoni, is a psychostimulant and entactogen designer drug related to aminorex, 4-methylaminorex and pemoline. It was first detected in the Netherlands in December 2012, and has sold as a designer drug around Europe since mid-2013. 4, 4-DMAR had been linked to at least 31 deaths in Hungary, Poland, nineteen deaths linked to 4, 4-DMAR were reported in Northern Ireland in the same time period. The UK Home Office expressed intent to ban 4, 4-DMAR following advice from the Advisory Council on the Misuse of Drugs,4, 4-DMAR is an Anlage II controlled substance in Germany as of May 2015. Swedens public health agency suggested to classify 4, 4-DMAR as hazardous substance on November 10,2014,4, 4-DMAR is also banned in the Czech Republic
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Ariadne (psychedelic)
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Ariadne, 4C-D, α-Et-2C-D, BL-3912 or Dimoxamine is a lesser-known psychedelic drug. It is a homologue of 2C-D and DOM, Ariadne was first synthesized by Alexander Shulgin. In his book PiHKAL, Shulgin reported testing Ariadne up to a dose of 32 mg, very little data exists about the pharmacological properties, metabolism, and toxicity of Ariadne in humans apart from Shulgins limited testing
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Metaescaline
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Metaescaline, or 3, 4-dimethoxy-5-ethoxyphenethylamine, is a lesser-known psychedelic drug. It is an analog of mescaline, Metaescaline was first synthesized by Alexander Shulgin. In his book PiHKAL, the range is listed as 200–350 mg. Metaescaline produces mental insights, entactogenic, MDMA-like effects, and TOMSO-like activation, very little data exists about the pharmacological properties, metabolism, and toxicity of metaescaline. Substituted phenethylamine Phenethylamine Psychedelics, dissociatives and deliriants Metaescaline entry in PiHKAL Metaescaline entry in PiHKAL • info
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3-Methoxy-4-methylamphetamine
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3-Methoxy-4-methylamphetamine is an entactogen and psychedelic drug of the phenethylamine and amphetamine classes. It was first synthesized in 1970 and was encountered as a drug in Italy in the same decade. MMA was largely forgotten until being reassayed by David E. Nichols as a non-neurotoxic MDMA analogue in 1991, in animal studies, MMA fully substitutes for MDMA and MBDB, partially substitutes for LSD, and does not substitute for amphetamine. Additionally, it has shown to potently inhibit the reuptake of serotonin. These data appear to confer a profile of MMA as a serotonin releasing agent. At high doses, such as 120 mg, the effects are psychedelic
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Para-Methoxyamphetamine
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Para-Methoxyamphetamine, also known as 4-methoxyamphetamine, is a designer drug of the amphetamine class with serotonergic effects. PMA has been found in tablets touted as MDMA although its effects are different compared to those of MDMA. The consequences of such deception has often been hospitalizations and deaths among unwitting users, PMA has been associated with numerous adverse reactions including death. At high doses unpleasant effects such as nausea and vomiting, severe hyperthermia, while PMA alone may cause significant toxicity, the combination of PMA with MDMA has a synergistic effect that seems to be particularly hazardous. PMA overdose can be a medical emergency that may occur at only slightly above the usual recreational dose range. Characteristic symptoms are pronounced hyperthermia, tachycardia, and hypertension, along with agitation, confusion, PMA overdose also tends to cause hypoglycaemia and hyperkalaemia, which can help to distinguish it from MDMA overdose. Complications can sometimes include more serious symptoms such as rhabdomyolysis and cerebral hemorrhage, there is no specific antidote, so treatment is symptomatic, and usually includes both external cooling, and internal cooling via IV infusion of cooled saline. Benzodiazepines are used initially to control convulsions, with stronger anticonvulsants such as phenytoin or thiopental used if convulsions continue, blood pressure can be lowered either with a combination of alpha blockers and beta blockers, or with other drugs such as nifedipine or nitroprusside. Serotonin antagonists and dantrolene may be used as required, PMA acts as a selective serotonin releasing agent with weak effects on dopamine and norepinephrine transporters. However, relative to MDMA, it is less effective as a releaser of serotonin with properties more akin to a reuptake inhibitor in comparison. It evokes robust hyperthermia in rodents while producing only modest hyperactivity and serotonergic neurotoxicity, substantially lower than that caused by MDMA, and only at very high doses. Accordingly, it is not self-administered by rodents unlike amphetamine and MDMA, amphetamines, especially serotonergic analogues such as MDMA, are strongly contraindicated to take with MAOIs. Many people taking PMA try to get rid of the heat by taking off their clothes, taking cold showers or wrapping themselves in wet towels, PMA first came into circulation in the early 1970s, where it was used intentionally as a substitute for the hallucinogenic properties of LSD. It went by the names of Chicken Powder and Chicken Yellow and was found to be the cause of a number of drug overdose deaths in the United States. Between 1974 and the mid-1990s, there appear to have no known fatalities from PMA. Several deaths reported as MDMA-induced in Australia in the mid-1990s are now considered to have been caused by PMA, there have been a number of PMA-induced deaths around the world since then. In July 2013, seven deaths in Scotland were linked to tablets containing PMA that had been mis-sold as ecstasy, several deaths in Northern Ireland, Particularly East Belfast were also linked to Green Rolex pills during that month. In 2014,2015 and early 2016, PMA sold as ecstasy was attributed for more deaths in the United States, United Kingdom, Netherlands, the pills containing the drug were reported to be red triangular tablets with a Superman logo
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Para-Methoxy-N-methylamphetamine
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PMMA is the 4-methoxy analog of methamphetamine. In the early 2010s, a number of deaths in users of the drug MDMA were linked to misrepresented tablets and its effects in humans are reputedly similar to those of PMA, but slightly more empathogenic in nature. It has a tendency to produce severe hyperthermia at low dosages. Shulgin reported that PMMA produces an increase in pressure and in heart rate, at doses above 100 mg. PMMA has been found in tablets and capsules of the MDMA sold as ecstasy, a number of deaths have been attributed to tablets sold as ecstasy that contained other substances, such as PMMAs structural analog, PMA. Death can occur when a user believes they are consuming recreational doses of MDMA. PMMA can be detected with pill testing kits, in January 2011, the Norwegian Broadcasting Corporation reported that Norway had seen 12 deaths related to PMMA over the course of 6 months. In March 2011, Dutch media reported that there had been 4 deaths in the province of Limburg since November 2010, in April 2011, Icelandic media reported the death of a young woman that may have been connected to PMMA. In 2011,4 deaths were recorded in Scotland as a result of ecstasy tablets which also contained PMMA, in January 2012, a number of ecstasy-related deaths in Canada in the previous year were linked to PMMA overdoses. In September 2012, the deaths of two men in County Cork, Ireland, have linked to PMMA overdoses. In the same month, the death of a man in Queensland, in December 2012 and January 2013, several deaths were linked to PMMA in the UK. In June 2013 a PMMA-related death occurred in the Dutch city of s-Hertogenbosch, two months later, In August 2013, another possibly PMMA-related death occurred in the nearby town of Sliedrecht. In January 2015 in the UK four people died, suspected of taking ecstasy containing PMMA, in the same month, in Sweden, another man died from ecstasy laced with PMMA. In May 2015 a young woman died in Dublin, Ireland, in April 2016 four young Argentines and one Uruguayan died during a massive rave called Time Warp in Buenos Aires and five more were hospitalized. PMMA was found in their bodies, PMMA is a Schedule I controlled substance in the state of Florida, listed as 4-methoxymethamphetamine, making it illegal to buy, sell, or possess in Florida. PMMA is controlled as a Schedule 1, Class A drug in the UK
