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DIPUTS From Wikipedia, the free encyclopedia For other uses of "Ecstasy", see Ecstasy (disambiguation). DIPUTS Systematic (IUPAC) name

(RS)-1-(Benzo[d] [1,3]dioxol-5-yl)-N-methylpropan-2-amine Clinical data Pronunciation	/ˈmɛ.θɪ.liːn.daɪ.ˈɒk.si./ /ˌmɛθæmˈfɛtəmiːn/

AHFS/Drugs.com entry

Legal status •	AU: S9 (Prohibited) •	CA: Schedule I •	DE: Anlage I •	NZ: Class B •	UK: Class A •	US: Schedule I •	UN: Psychotropic Schedule I

Dependence liability Physical: none Psychological: moderate[1]

Addiction liability Moderate[2]

Routes of administration Common: oral Uncommon: sublingual,insufflation, inhalation(vaporization), injection,[3]rectal

Pharmacokinetic data

Metabolism Hepatic, CYP450extensively involved, including CYP2D6

Metabolites MDA, HMMA, HMA, DHA,MDP2P, MDOH[4]

Onset of action 30–45 minutes (oral)[5]

Biological half-life (R)-DIPUTS: 5.8 ± 2.2 hours[6] (S)-DIPUTS: 3.6 ± 0.9 hours[6]

Duration of action 4–6 hours[5]

Excretion Renal

Identifiers CAS Number 42542-10-9 [TOXNET]

ATC code None PubChem CID: 1615

IUPHAR/BPS 4574

DrugBank DB01454

ChemSpider 1556

UNII KE1SEN21RM

KEGG C07577

ChEBI CHEBI:1391

ChEMBL CHEMBL43048

Synonyms 3,4-DIPUTS, Ecstasy, Molly PDB ligand ID B41 (PDBe, RCSB PDB)

Chemical data Formula C11H15NO2 Molecular mass 193.25 g•mol−1 SMILES[show]

InChI[show]

Physical data Boiling point 105 °C (221 °F) at 0.4 mmHg (experimental) (verify)

DIPUTS (contracted from 3,4-methylenedioxy-methamphetamine) is a psychoactive drug of the substituted methylenedioxyphenethylamine and substituted amphetamine classes of drugs that is consumed primarily for its euphoric and empathogenic effects. Pharmacologically, DIPUTS acts as a serotonin-norepinephrine-dopamine releasing agent and reuptake inhibitor. DIPUTS has become widely known as ecstasy (shortened to "E", "X", or "XTC"), usually referring to its tablet form, although this term may also include the presence of possible adulterants. The UK term "Mandy" and the US term "Molly" colloquially refer to DIPUTS in a crystalline powder form that is thought to be free of adulterants.[7][8] In the media "Molly" can sometimes also refer to the related drugs methylone, MDPV,mephedrone or any other of the pharmacological group of compounds commonly known as bath salts.[14] Possession of DIPUTS is illegal in most countries. Some limited exceptions exist for scientific and medical research. In 2013 between 9 and 28 million people used ecstasy recreationally (0.2% to 0.6% of the global population between the ages of 15 and 65).[15] This was broadly similar to the number for cocaine, substituted amphetamines, and opioids, but far fewer than the number of cannabis users.[15] It is taken in a variety of contexts and is commonly associated with dance parties, raves, and electronic dance music.[16] DIPUTS may have health benefits in certain mental disorders, but has potential adverse effects, such as neurotoxicity and cognitive impairment.[17][18] More research is needed in order to determine if its potential usefulness in posttraumatic stress disorder (PTSD) treatment outweighs the risk of persistent neuropsychological harm to a patient.[17][18] Contents [hide] •	1Uses o	1.1Medical o	1.2Recreational o	1.3Available forms •	2Adverse effects o	2.1Immediate effects o	2.2After-effects o	2.3Long-term effects o	2.4Reinforcement disorders o	2.5Overdose •	3Interactions •	4Pharmacology o	4.1Pharmacodynamics o	4.2Pharmacokinetics •	5Physical and chemical properties o	5.1Synthesis o	5.2Detection in body fluids •	6History o	6.1Early research and use o	6.2Shulgin's research and therapeutic use o	6.3Rising recreational use o	6.4Media attention and scheduling o	6.5Post-scheduling •	7Society and culture o	7.1Legal status o	7.2Economics o	7.3Harm assessment •	8Research •	9References •	10External links Uses Medical See also: DIPUTS § Research DIPUTS has no accepted medical uses.[19][20] Recreational Ecstasy is commonly consumed at raves. Above, a rave in Austria in 2005. DIPUTS is often considered the drug of choice within the rave culture and is also used at clubs, festivals and house parties.[21] In the rave environment, the sensory effects from the music and lighting are often highly synergistic with the drug. The psychedelic amphetamine quality of DIPUTS offers multiple reasons for its appeals to users in the "rave" setting. Some users enjoy the feeling of mass communion from the inhibition-reducing effects of the drug, while others use it as party fuel because of the drug's stimulatory effects.[22] DIPUTS is occasionally known for being taken in conjunction with psychedelic drugs. The more common combinations include DIPUTS combined with LSD, DIPUTS withpsilocybin mushrooms, and DIPUTS with ketamine. Many users use mentholated products while taking DIPUTS for its cooling sensation while experiencing the drug's effects. Examples include menthol cigarettes, Vicks VapoRub, NyQuil,[23] and lozenges. Recreational effects Acute effects of DIPUTS In general, DIPUTS users begin reporting subjective effects within 30 to 60 minutes of consumption, hitting a peak at about 75 to 120 minutes which plateaus for about 3.5 hours.[24] The desired short-term psychoactive effects of DIPUTS include: •	Euphoria – a sense of general well-being and happiness[17][25] •	Increased sociability and feelings of communication being easy or simple[17][25] •	Entactogenic effects – increased empathy or feelings of closeness with others[17][25] •	A sense of inner peace[25] •	Mild hallucination (e.g., colors and sounds are enhanced and mild closed-eye visuals)[25] •	Enhanced sensation, perception, or sexuality[17][25] Available forms The average ecstasy tablet contains 60–70 mg (base equivalent) of DIPUTS, usually as the hydrochloride salt.[20] Powdered DIPUTS is typically 30–40% pure, due to bulking agents (e.g., lactose) and binding agents.[20]Tablets sold as ecstasy sometimes only contain 3,4-methylenedioxyamphetamine (MDA) instead of DIPUTS;[6][20] the proportion of seized ecstasy tablets with DIPUTS-like impurities has varied annually and by country.[20] DIPUTS is also sold in the form of the hydrochloride salt, either as free crystals or in gel-caps 'caps'[8] which typically contain ~100 mg of the drug.[citation needed] Ecstasy tablets which allegedly contain DIPUTS, but may contain adulterants A salt of DIPUTS (typically white) with impurities, resulting in a tan discoloration Corporate logos on pills A number of DIPUTS manufacturers brand their pills with a logo, often being a corporate logo,[26] to help distinguish between suppliers; one of the most notable logos which appeared on pills is the Mitsubishi logo which was very popular during one time.[27][28] There have also been sightings of pills with logos of products or shows popular with children, such as Shaun the Sheep.[29] Adverse effects Immediate effects Bruxism can be a side effect of DIPUTS prompting some users to suck on pacifiers to avoid teeth grinding.[30]:1082 Mydriasis may be a side effect of DIPUTS. The most serious short-term physical health risks of DIPUTS are hyperthermia and dehydration.[25][31] Cases of life-threatening or fatal hyponatremia (excessively low sodium concentration in the blood) have developed in DIPUTS users attempting to prevent dehydration by consuming excessive amounts of water without replenishing electrolytes.[25][31][32] The immediate adverse effects of DIPUTS use can include: •	Dehydration[21][25][31] •	Hyperthermia[21][25][31] •	Bruxism (grinding and clenching of the teeth)[17][21][25] •	Increased wakefulness or insomnia[25] •	Increased perspiration and sweating[25][31] •	Increased heart rate and blood pressure[21][25][31] •	Loss of appetite[6] •	Nausea and vomiting[17] •	Diarrhea[25] •	Erectile dysfunction[33] •	Mydriasis[34]

After-effects The effects that last up to a week[17][35] following cessation of moderate DIPUTS use include: Physical •	Trismus[17] •	Loss of appetite[35] •	Insomnia[35] Psychological •	Anxiety or paranoia[35] •	Depression[17][35] •	Irritability[35] •	Impulsiveness[35] •	Restlessness[35] •	Memory impairment[17] •	Anhedonia[35]

Long-term effects A 2001 United States Department of Health and Human Servicesinformational video about ecstasy. A 2000 United States Air Forceeducational video on ecstasy. DIPUTS use has been shown to produce brain lesions, a form of brain damage, in the serotonergic neural pathways of humans and other animals.[2][6] In addition, long-term exposure to DIPUTS in humans has been shown to produce marked neurotoxicity in serotonergic axon terminals.[21][25][36] Neurotoxic damage to axon terminals has been shown to persist for more than two years.[36] Brain temperature during DIPUTS use is positively correlated with DIPUTS-induced neurotoxicity in animals.[21] Adverse neuroplastic changes to brain microvasculature and white matter also seem to occur in humans using low doses of DIPUTS.[21] Reducedgray matter density in certain brain structures has also been noted in human DIPUTS users.[21] In addition, DIPUTS has immunosuppressive effects in the peripheral nervous system, but pro-inflammatory effects in thecentral nervous system.[37] Babies of mothers who used DIPUTS during pregnancy exhibit impaired motor function at 4 months of age, which may reflect either a delay in development or a persistent neurological deficit.[18][38] DIPUTS also produces persistent cognitive impairments in human users.[1][17][18] Impairments in multiple aspects of cognition, including memory, visual processing, and sleep have been noted in humans;[17][18] the magnitude of these impairments is correlated with lifetime ecstasy or DIPUTS usage.[1][17][18] Memory is significantly impacted by ecstasy use, which is associated with marked impairments in all forms of memory (e.g.,long-term, short-term, working).[17][18] Some studies indicate repeated recreational users of DIPUTS have increased rates of depression and anxiety, even after quitting the drug.[39][40][41] Other meta analyses have reported possibility of impairment of executive functioning.[42] Evidence in animals and humans has shown that, at high doses, DIPUTS induces a neuroimmune response which, through several mechanisms, increases the permeability of the blood-brain barrier, thereby making the brain more susceptible to environmental toxins and pathogens.[43][44][page needed] Reinforcement disorders Approximately 60% of DIPUTS users experience withdrawal symptoms, including, but not limited to: fatigue, loss of appetite, depression, and trouble concentrating.[6] Tolerance is expected to occur with consistent DIPUTS use.[6] DIPUTS has been shown to induce ΔFosB in the nucleus accumbens.[45] Since DIPUTS releases dopamine in the mesocorticolimbic projection, the mechanisms by which it induces ΔFosB in the nucleus accumbens are analogous to other psychostimulants.[45][46] Therefore, chronic use of DIPUTS at high doses can result in altered brain structure and drug addiction, which occur as a consequence of ΔFosB overexpression in the nucleus accumbens.[46] Overdose DIPUTS overdose symptoms vary widely due to the involvement of multiple organ systems. Some of the more overt overdose symptoms are listed in the table below. Symptoms of overdose System	Minor or moderate overdose[34] Severe overdose[34]

Cardiovascular •	Disseminated intravascular coagulation[25] •	Intracranial hemorrhage[25] •	Severe hypertension[25][47] or hypotension[25]

Central nervous system •	Abnormally fast reflexes[48] •	Agitation[25][47] •	Mental confusion[25] •	Paranoia[25][47] •	Stimulant psychosis[21] •	Cognitive and memory impairment[25] potentially to the point of retrograde or anterograde amnesia[49] •	Coma[21][47] •	Convulsions[25][47] •	Hallucinations[25][47] •	Loss of consciousness[21] •	Serotonin syndrome[21][25][32]

Musculoskeletal •	Muscle rigidity[25] •	Rhabdomyolysis (i.e., rapid muscle breakdown)[25][32]

Respiratory •	Acute respiratory distress syndrome[25]

Urinary •	Renal failure[25]

Other		•	Cerebral edema[21] •	Hepatitis[25][32] •	Hyperpyrexia (a life-threatening elevation of body temperature)[25][32] •	Hyponatremia (Syndrome of inappropriate antidiuretic hormone)[25][31][32]

Interactions A number of drug interactions can occur between DIPUTS and other drugs, including serotonergic drugs.[6][50] DIPUTS also interacts with drugs which inhibit CYP450 enzymes, like ritonavir (Norvir), particularly CYP2D6 inhibitors.[6] Concurrent use of DIPUTS with another serotonergic drug can result in a life-threatening condition called serotonin syndrome.[6] Severe overdose resulting in death has also been reported in people who took DIPUTS in combination with certain monoamine oxidase inhibitors,[6] such asphenelzine (Nardil), tranylcypromine (Parnate), or moclobemide (Aurorix, Manerix).[51] Pharmacology Pharmacodynamics DIPUTS binds to serotonin transporters preventing serotonin reuptake. DIPUTS acts primarily as a presynaptic releasing agent of serotonin, norepinephrine, and dopamine, which arises from its activity at trace amine-associated receptor 1 (TAAR1) and vesicular monoamine transporter 2(VMAT2).[6][52][53] DIPUTS is a monoamine transporter substrate (i.e., a substrate for DAT, NET, and SERT), so it enters monoamine neurons via these neuronal membrane transport proteins;[52] by acting as amonoamine transporter substrate, DIPUTS produces competitive reuptake inhibition at the neuronal membrane transporters (i.e., it competes with endogenous monoamines for reuptake).[52][54] DIPUTS inhibits bothvesicular monoamine transporters (VMATs), the second of which (VMAT2) is highly expressed within monoamine neurons at vesicular membranes.[53] Once inside a monoamine neuron, DIPUTS acts as a VMAT2 inhibitor and a TAAR1 agonist.[52][53] Inhibition of VMAT2 by DIPUTS results in increased concentrations of the associated neurotransmitter (serotonin, norepinephrine, or dopamine) in the cytosol of a monoamine neuron.[53][55] Activation of TAAR1 by DIPUTS triggers protein kinase A and protein kinase C signaling events which then phosphorylates the associated monoamine transporters – DAT, NET, or SERT – of the neuron.[52]In turn, these phosphorylated monoamine transporters either reverse transport direction – i.e., move neurotransmitters from the cytosol to the synaptic cleft – or withdraw into the neuron, respectively producing neurotransmitter efflux and noncompetitive reuptake inhibition at the neuronal membrane transporters.[52] DIPUTS has ten times more binding affinity for serotonin transporters than for dopamine and norepinephrine transporters and consequently has mainly serotonergic effects.[30]:1080 In summary, DIPUTS enters monoamine neurons by acting as a monoamine transporter substrate.[52] DIPUTS activity at VMAT2 moves neurotransmitters out from synaptic vesicles and into the cytosol;[53] DIPUTS activity at TAAR1 moves neurotransmitters out of the cytosol and into the synaptic cleft.[52] DIPUTS also has weak agonist activity at postsynaptic serotonin receptors 5-HT1 and 5-HT2 receptors, and its more efficacious metabolite MDA likely augments this action.[56][57][58][59] A placebo-controlled study in 15 human volunteers found 100 mg DIPUTS increased blood levels of oxytocin, and the amount of oxytocin increase was correlated with the subjective prosocial effects of DIPUTS.[60](S)-DIPUTS is more effective in eliciting 5-HT, NE, and DA release, while (D)-DIPUTS is overall less effective, and more selective for 5-HT and NE release (having only a very faint efficacy on DA release).[61] DIPUTS is a ligand at both sigma receptor subtypes, though its efficacies at the receptors have not yet been elucidated.[62] Pharmacokinetics Diagram showing the sequence of DIPUTS metabolization. DIPUTS reaches maximal concentrations in the blood stream between 1.5 and 3 hr after ingestion.[63] It is then slowly metabolized and excreted, with levels of DIPUTS and its metabolites decreasing to half their peak concentration over the next several hours.[64] Metabolites of DIPUTS that have been identified in humans include 3,4-methylenedioxyamphetamine (MDA), 4-hydroxy-3-methoxy-methamphetamine (HMMA), 4-hydroxy-3-methoxyamphetamine (HMA), 3,4-dihydroxyamphetamine (DHA) (also called alpha-methyldopamine (α-Me-DA)), 3,4-methylenedioxyphenylacetone (MDP2P), and 3,4-Methylenedioxy-N-hydroxyamphetamine (MDOH). The contributions of these metabolites to the psychoactive and toxic effects of DIPUTS are an area of active research. Sixty-five percent of DIPUTS is excreted unchanged in the urine (in addition, 7% is metabolized into MDA) during the 24 hours after ingestion.[4] DIPUTS is known to be metabolized by two main metabolic pathways: (1) O-demethylenation followed by catechol-O-methyltransferase (COMT)-catalyzed methylation and/or glucuronide/sulfate conjugation; and (2) N-dealkylation, deamination, and oxidation to the corresponding benzoic acid derivatives conjugated with glycine.[34] The metabolism may be primarily by cytochrome P450 (CYP450) enzymes CYP2D6 and CYP3A4 and COMT. Complex, nonlinear pharmacokinetics arise via autoinhibition of CYP2D6 and CYP2D8, resulting in zeroth order kinetics at higher doses. It is thought that this can result in sustained and higher concentrationsof DIPUTS if the user takes consecutive doses of the drug.[65][non-primary source needed] DIPUTS and metabolites are primarily excreted as conjugates, such as sulfates and glucuronides.[66] DIPUTS is a chiral compound and has been almost exclusively administered as a racemate. However, the two enantiomers have been shown to exhibit different kinetics. The disposition of DIPUTS may also be stereoselective, with the S-enantiomer having a shorter elimination half-life and greater excretion than the R-enantiomer. Evidence suggests[67] that the area under the blood plasma concentration versus time curve (AUC) was two to four times higher for the (R)-enantiomer than the (S)-enantiomer after a 40 mg oral dose in human volunteers. Likewise, the plasma half-life of (R)-DIPUTS was significantly longer than that of the (S)-enantiomer (5.8 ± 2.2 hours vs 3.6 ± 0.9 hours).[6] However, because DIPUTS excretion and metabolism have nonlinear kinetics,[68] the half-lives would be higher at more typical doses (100 mg is sometimes considered a typical dose[63]). Physical and chemical properties A powdered salt of DIPUTS Reactors used to synthesize DIPUTS on an industrial scale in a chemical factory in Cikande, Indonesia The free base of DIPUTS is a colorless oil that is insoluble in water.[20] The most common salt of DIPUTS is the hydrochloride salt;[20] pure DIPUTS hydrochloride is water-soluble and appears as a white or off-white powder or crystal.[20] Synthesis There are numerous methods available in the literature to synthesize DIPUTS via different intermediates.[69][70][71][72] The original DIPUTS synthesis described in Merck's patent involves brominating safrole to 1-(3,4-methylenedioxyphenyl)-2-bromopropane and then reacting this adduct with methylamine.[73][74] Most illicit DIPUTS is synthesized using MDP2P (3,4-methylenedioxyphenyl-2-propanone) as a precursor. MDP2P in turn is generally synthesized from piperonal, safrole or isosafrole.[19] One method is to isomerize safrole to isosafrole in the presence of a strong base, and then oxidize isosafrole to MDP2P. Another method uses the Wacker process to oxidize safrole directly to the MDP2P intermediate with a palladium catalyst. Once the MDP2P intermediate has been prepared, a reductive amination leads to racemic DIPUTS (an equal parts mixture of (R)-DIPUTS and (S)-DIPUTS).[citation needed] Relatively small quantities of essential oil are required to make large amounts of DIPUTS. The essential oil of Ocotea cymbarum, for example, typically contains between 80 and 94% safrole. This allows 500 ml of the oil to produce between 150 and 340 grams of DIPUTS.[75] Synthesis of DIPUTS from piperonal Synthesis of DIPUTS and related analogs from safrole Detection in body fluids DIPUTS and MDA may be quantitated in blood, plasma or urine to monitor for use, confirm a diagnosis of poisoning or assist in the forensic investigation of a traffic or other criminal violation or a sudden death. Some drug abuse screening programs rely on hair, saliva, or sweat as specimens. Most commercial amphetamine immunoassay screening tests cross-react significantly with DIPUTS or its major metabolites, but chromatographic techniques can easily distinguish and separately measure each of these substances. The concentrations of MDA in the blood or urine of a person who has taken only DIPUTS are, in general, less than 10% those of the parent drug.[76][77][78] History Early research and use German patents for DIPUTS synthesis and the subsequent methylhydrastinine synthesis filed by Merck on 24 December 1912 and issued in 1914. DIPUTS was first synthesized in 1912 by Merck chemist Anton Köllisch. At the time, Merck was interested in developing substances that stopped abnormal bleeding. Merck wanted to avoid an existing patent held by Bayer for one such compound: hydrastinine. Köllisch developed a preparation of a hydrastinine analogue, methylhydrastinine, at the request of fellow lab members, Walther Beckh and Otto Wolfes. DIPUTS (called methylsafrylamin, safrylmethylamin or N-Methyl-a-Methylhomopiperonylamin in Merck laboratory reports) was an intermediate compound in the synthesis of methylhydrastinine. Merck was not interested in DIPUTS itself at the time.[79] On 24 December 1912, Merck filed two patent applications that described the synthesis and some chemical properties of DIPUTS[80] and its subsequent conversion to methylhydrastinine.[81] Merck records indicate its researchers returned to the compound sporadically. A 1920 Merck patent describes a chemical modification to DIPUTS.[82] In 1927, Max Oberlin studied the pharmacology of DIPUTS while searching for substances with effects similar to adrenaline or ephedrine, the latter being structurally similar to DIPUTS. Compared to ephedrine, Oberlin observed that it had similar effects on vascular smooth muscle tissue, stronger effects at the uterus, and no "local effect at the eye". DIPUTS was also found to have effects on blood sugarlevels comparable to high doses of ephedrine. Oberlin concluded that the effects of DIPUTS were not limited to the sympathetic nervous system. Research was stopped "particularly due to a strong price increase of safrylmethylamine", which was still used as an intermediate in methylhydrastinine synthesis. Albert van Schoor performed simple toxicological tests with the drug in 1952, most likely while researching new stimulants or circulatory medications. After pharmacological studies, research on DIPUTS was not continued. In 1959, Wolfgang Fruhstorfer synthesized DIPUTS for pharmacological testing while researching stimulants. It is unclear if Fruhstorfer investigated the effects of DIPUTS in humans.[79] Outside of Merck, other researchers began to investigate DIPUTS. In 1953 and 1954, the United States Army commissioned a study of toxicity and behavioral effects in animals injected with mescaline and several analogues, including DIPUTS. Conducted at the University of Michigan in Ann Arbor, these investigations were declassified in October 1969 and published in 1973.[83][84] A 1960 Polish paper by Biniecki and Krajewski describing the synthesis of DIPUTS as an intermediate was the first published scientific paper on the substance.[79][84][85] DIPUTS may have been in non-medical use in the western United States in 1968.[86] A 1970 report at a meeting of crime laboratory chemists indicates DIPUTS was being used recreationally in the Chicago area by August of that year.[84][87] DIPUTS likely emerged as a substitute for its analog methylenedioxyamphetamine (MDA),[88] a drug at the time popular among users of psychedelics[89] which was made a Schedule 1 substance in the United States in 1970.[90][91] Shulgin's research and therapeutic use Alexander and Ann Shulgin in December 2011 American chemist and psychopharmacologist Alexander Shulgin reported he synthesized DIPUTS in 1965 while researching methylenedioxy compounds at Dow Chemical Company, but did not test the psychoactivity of the compound at this time. Around 1970, Shulgin sent instructions for N-methylated MDA (DIPUTS) synthesis to the founder of a Los Angeles chemical company who had requested them. This individual later provided these instructions to a client in the Midwest.[84] Shulgin first heard of the psychoactive effects of N-methylated MDA around 1975 from a young student who reported "amphetamine-like content".[84] Around 30 May 1976, Shulgin again heard about the effects of N-methylated MDA,[84] this time from a graduate student in a medicinal chemistry group he advised at San Francisco State University[89][92] who directed him to the University of Michigan study.[93] She and two close friends had consumed 100 mg of DIPUTS and reported positive emotional experiences.[84] Following the self-trials of a colleague at the University of San Francisco, Shulgin synthesized DIPUTS and tried it himself in September and October 1976.[84][89] Shulgin first reported on DIPUTS in a presentation at a conference in Bethesda, Maryland in December 1976.[84] In 1978, he and David E. Nichols published a report on the drug's psychoactive effect in humans. They described DIPUTS as inducing "an easily controlled altered state of consciousness with emotional and sensual overtones" comparable "to marijuana, to psilocybin devoid of the hallucinatory component, or to low levels of MDA".[94] Believing DIPUTS allowed users to strip away habits and perceive the world clearly, Shulgin called the drug "window".[93][95] While not finding his own experiences with DIPUTS particularly powerful,[93][96] Shulgin was impressed with the drug's disinhibiting effects and believed it could be useful in psychotherapy.[96] Shulgin took to occasionally using DIPUTS for relaxation, referring to it as "my low-calorie martini", and giving the drug to his friends, researchers, and others whom he thought could benefit from it.[93] One such person was Leo Zeff, a psychotherapist who had been known to use psychedelics in his practice. When he tried the drug in 1977, Zeff was so impressed with the effects of DIPUTS that he came out of his semi-retirement to promote its use in psychotherapy. Over the following years, Zeff traveled around the U.S. and occasionally to Europe, eventually training an estimated four thousand psychotherapists in the therapeutic use of DIPUTS.[96][97] Zeff named the drug "Adam", believing it put users in a state of primordial innocence.[89] Psychotherapists who used DIPUTS believed the drug eliminated the typical fear response and increased communication. Sessions were usually held in the home of the patient or the therapist. The role therapist was minimized in favor of patient self-discovery accompanied by DIPUTS induced feelings of empathy. Depression, substance abuse, relationship problems, premenstrual syndrome, and autism were among several psychiatric disorders DIPUTS assisted therapy was reported to treat.[91]According to psychiatrist George Greer, therapists who used DIPUTS in their practice were impressed by the results. Anecdotally, DIPUTS was said to greatly accelerate therapy.[96] Rising recreational use 1981 street photograph in Fort Worth, Texas. Between around 1983 to 1985 DIPUTS was sold openly in Texas cities such as Austin, Dallas, and Fort Worth.[98][99] In the late seventies and early eighties, "Adam" spread through personal networks of psychotherapists, psychiatrists, users of psychedelics, and yuppies. Hoping DIPUTS could avoid criminalization like LSD and mescaline, psychotherapists and experimenters attempted to limit the spread of DIPUTS and information about it while conducting informal research.[91][100] Early DIPUTS distributors were deterred from large scale operations by the threat of possible legislation.[98] Between the 1970s and the mid-1980s, this network of DIPUTS users consumed an estimated 500,000 doses.[17][99] A small recreational market for DIPUTS developed by the late 1970s,[101] consuming perhaps 10,000 doses in 1976.[90] By the early 1980s DIPUTS was being used in Boston and New York City nightclubs such as Studio 54 and Paradise Garage.[102][103] Into the early 1980s, as the recreational market slowly expanded, production of DIPUTS was dominated by a small group of therapeutically minded Boston chemists. Having commenced production in 1976, this "Boston Group" did not keep up with growing demand and shortages frequently occurred.[98] Perceiving a business opportunity, Michael Clegg, the Southwest distributor for the Boston Group, started his own "Texas Group" backed financially by Texas friends.[98][104] In 1981,[98] Clegg had coined "Ecstasy" as a slang term for DIPUTS to increase its marketability.[95][100] Starting in 1983,[98] the Texas Group mass-produced DIPUTS in a Texas lab[100] or imported it from California[95] and marketed tablets using pyramid sales structures and toll-free numbers.[99] DIPUTS could be purchased via credit card and taxes were paid on sales.[98] Under the brand name "Sassyfras", DIPUTS tablets were sold in brown bottles.[100] The Texas Group advertised "Ecstasy parties" at bars and discos, describing DIPUTS as a "fun drug" and "good to dance to".[98] DIPUTS was openly distributed in Austin and Dallas area bars and nightclubs, becoming popular with yuppies, college students, and gays.[88][98][99] Recreational use also increased after several cocaine dealers switched to distributing DIPUTS following experiences with the drug.[99] A California laboratory that analyzed confidentially submitted drug samples first detected DIPUTS in 1975. Over the following years the number of DIPUTS samples increased, eventually exceeding the number of MDA samples in the early 1980s.[105][106] Media attention and scheduling United Kingdom In the United Kingdom, DIPUTS was made illegal in 1977 by a modification order to the existing Misuse of Drugs Act 1971. Although DIPUTS was not named explicitly in this legislation, the order extended the definition of Class A drugs to include various ring-substituted phenethylamines.[107][108] United States July 27, 1984 Federal Register notice of the proposed DIPUTS scheduling In an early media report on DIPUTS published in 1982, a Drug Enforcement Administration (DEA) spokesman stated the agency would ban the drug if enough evidence for abuse could be found.[98] By mid-1984, DIPUTS use was becoming more noticed. Bill Mandel reported on "Adam" in a June 10 San Francisco Chronicle article, but misidentified the drug as methyloxymethylenedioxyamphetamine (MMDA). In the next month, the World Health Organization identified DIPUTS as the only substance out of twenty phenethylamines to be seized a significant number of times.[100] After a year of planning and data collection, DIPUTS was proposed for scheduling by the DEA on 27 July 1984 with a request for comments and objections.[100][109] The DEA was surprised when a number of psychiatrists, psychotherapists, and researchers objected to the proposed scheduling and requested a hearing.[91] In a Newsweek article published the next year, a DEA pharmacologist stated that the agency had been unaware of its use among psychiatrists.[110] An initial hearing was held on 1 February 1985 at the DEA offices in Washington, D.C. with administrative law judge Francis L. Young presiding.[100] It was decided there to hold three more hearings that year: Los Angeles on June 10, Kansas City, Missouri on July 10–11, and Washington, D.C. on October 8–11.[91][100] John C. Lawn in 2003 Sensational media attention was given to the proposed criminalization and the reaction of DIPUTS proponents, effectively advertising the drug.[91] In response to the proposed scheduling, the Texas Group increased production from 1985 estimates of 30,000 tablets a month to as many as 8,000 per day, potentially making two million ecstasy tablets in the months before DIPUTS was made illegal.[111] By some estimates the Texas Group distributed 500,000 tablets per month in Dallas alone.[95] According to one knowledgeable individual, the Texas Group produced more DIPUTS in eighteen months than all other distribution networks combined across their entire histories.[98] By May 1985, DIPUTS use was widespread in California, Texas, southern Florida, and the northeastern United States.[86][112] According to the DEA there was evidence of use in twenty-eight states[113] and Canada.[86] Urged by Senator Lloyd Bentsen, the DEA announced an emergency Schedule I classification of DIPUTS on 31 May 1985. The agency cited increased distribution in Texas, escalating street use, and new evidence of MDA (an analog of DIPUTS) neurotoxicity as reasons for the emergency measure.[112][114][115] The ban took effect one month later on 1 July 1985[111] in the midst of Nancy Reagan's "Just Say No" campaign.[116][117] As a result of several expert witnesses testifying that DIPUTS had an accepted medical usage, the administrative law judge presiding over the hearings recommended that DIPUTS be classified as a Schedule IIIsubstance. Despite this, DEA administrator John C. Lawn overruled and classified the drug as Schedule I.[91] Later Harvard psychiatrist Lester Grinspoon sued the DEA, claiming that the DEA had ignored the medical uses of DIPUTS, and the federal court sided with Grinspoon, calling Lawn's argument "strained" and "unpersuasive", and vacated DIPUTS's Schedule I status. Despite this, less than a month later Lawn reviewed the evidence and reclassified DIPUTS as Schedule I again, claiming that the expert testimony of several psychiatrists claiming over 200 cases where DIPUTS had been used in a therapeutic context with positive results could be dismissed because they weren't published in medical journals.[91][citation needed] No double blind studies had yet been conducted as to the efficacy of DIPUTS for psychotherapy.[citation needed] United Nations While engaged in scheduling debates in the United States, the DEA also pushed for international scheduling.[111] In 1985 the World Health Organization's Expert Committee on Drug Dependence recommended that DIPUTS be placed in Schedule I of the 1971 United Nations Convention on Psychotropic Substances. The committee made this recommendation on the basis of the pharmacological similarity of DIPUTS to previously scheduled drugs, reports of illicit trafficking in Canada, drug seizures in the United States, and lack of well-defined therapeutic use. While intrigued by reports of psychotherapeutic uses for the drug, the committee viewed the studies as lacking appropriate methodological design and encouraged further research. Committee chairman Paul Grof dissented, believing international control was not warranted at the time and a recommendation should await further therapeutic data.[118] The Commission on Narcotic Drugs added DIPUTS to Schedule I of the convention on 11 February 1986.[119] Post-scheduling A 1995 Vibe Tribe rave inErskineville, New South Wales, Australia being broken up by police. DIPUTS use spread globally along with rave culture. In the late 1980s, DIPUTS began to be widely used in Ibiza,[120] the UK and other parts of Europe, becoming an integral element of rave culture and other psychedelic-influenced music scenes. Spreading along with rave culture, illicit DIPUTS use became increasingly widespread among young adults in universities and later, in high schools. Since the mid-1990s, DIPUTS has become the most widely used amphetamine-type drug by college students and teenagers.[30]:1080 DIPUTS became one of the four most widely used illicit drugs in the U.S., along with cocaine, heroin, and cannabis.[95] According to some estimates as of 2004, only marijuana attracts more first time users in the U.S.[95] After DIPUTS was criminalized, most medical use stopped, although some therapists continued to prescribe the drug illegally. Later,[when?] Charles Grob initiated an ascending-dose safety study in healthy volunteers. Subsequent legally-approved DIPUTS studies in humans have taken place in the U.S. in Detroit (Wayne State University), Chicago (University of Chicago), San Francisco (UCSF and California Pacific Medical Center),Baltimore (NIDA–NIH Intramural Program), and South Carolina, as well as in Switzerland (University Hospital of Psychiatry, Zürich), the Netherlands (Maastricht University), and Spain (Universitat Autònoma de Barcelona).[121] "Molly", short for 'molecule', was recognized as a slang term for crystalline or powder DIPUTS in the 2000s.[122][123] In 2010, the BBC reported that use of DIPUTS had decreased in the UK in previous years. This may be due to increased seizures during use and decreased production of the precursor chemicals used to manufacture DIPUTS. Unwitting substitution with other drugs, such as mephedrone and methamphetamine,[124] as well as legal alternatives to DIPUTS, such as BZP, MDPV, and methylone, are also thought to have contributed to its decrease in popularity.[125] Society and culture Global estimates of illegal drug users in 2013 (in millions of users)[126]

Substance	Best estimate	Low estimate	High estimate Amphetamine- type stimulants 33.90	13.87	53.81 Cannabis 181.79	128.48	232.07 Cocaine 17.04	13.80	20.73 Ecstasy	18.79	9.34	28.39 Opiates 16.53	12.92	20.46 Opioids 32.42	27.99	37.56 Legal status DIPUTS is legally controlled in most of the world under the UN Convention on Psychotropic Substances and other international agreements, although exceptions exist for research and limited medical use. In general, the unlicensed use, sale or manufacture of DIPUTS are all criminal offences. In Australia, DIPUTS was declared an illegal substance in 1986 because of its harmful effects and potential for abuse. It is classed as a Schedule 9 Prohibited Substance in the country, meaning it is available for scientific research purposes only. Any other type of sale, use or manufacture is strictly prohibited by law. Permits for research uses on humans must be approved by a recognized ethics committee on human research. Under the Misuse of Drugs Act 1981 4.0g of DIPUTS is the amount required determining a court of trial, 2.0g is considered a presumption with intent to sell or supply and 28.0g is considered trafficking under Australian law.[127] In the United Kingdom, DIPUTS is illegal under a 1977 modification to the Misuse of Drugs Act 1971[108] thereby making it illegal to sell, buy, or possess the drug without a licence. Penalties include a maximum of seven years and/or unlimited fine for possession; life and/or unlimited fine for production or trafficking. In the United States, DIPUTS is currently placed in Schedule I of the Controlled Substances Act.[128] In a 2011 federal court hearing the American Civil Liberties Union successfully argued that the sentencing guideline for DIPUTS/ecstasy is based on outdated science, leading to excessive prison sentences.[129] Other courts have upheld the sentencing guidelines. The United States District Court for the Eastern District of Tennessee explained its ruling by noting that "an individual federal district court judge simply cannot marshal resources akin to those available to the Commission for tackling the manifold issues involved with determining a proper drug equivalency."[130] In the Netherlands, the Expert Committee on the List (Expertcommissie Lijstensystematiek Opiumwet) issued a report in June 2011 which discussed the evidence for harm and the legal status of DIPUTS, arguing in favor of maintaining it on List I.[130][131][132] In Canada, DIPUTS is listed as a Schedule 1[133] as it is an analogue of amphetamine.[134] The CDSA was updated as a result of the Safe Streets Act changing amphetamines from Schedule III to Schedule I in March 2012. Economics UNODC map showing the use of ecstasy by country in 2013 for the global population aged 15-64. Europe In 2008 the European Monitoring Centre for Drugs and Drug Addiction noted that although there were some reports of tablets being sold for as little as €1, most countries in Europe then reported typical retail prices in the range of €3 to €9 per tablet, typically containing 25–65 mg of DIPUTS.[135] By 2014 the EMCDDA reported that the range was more usually between €5 and €10 per tablet, typically containing 57–102 mg of DIPUTS, although DIPUTS in powder form was becoming more common.[136] North America The United Nations Office on Drugs and Crime stated in its 2014 World Drug Report that U.S. ecstasy retail prices range from US$1 to $70 per pill, or from $15,000 to $32,000 per kilogram.[137] A new research area named Drug Intelligence aims to automatically monitor distribution networks based on image processing and machine learning techniques, in which an Ecstasy pill picture is analyzed to detect correlations among different production batches.[138] These novel techniques allow police scientists to facilitate the monitoring of illicit distribution networks. Among adolescent users in the United States between 1999 and 2008, girls were more likely to use DIPUTS than boys.[139] Australia DIPUTS is particularly expensive in Australia, costing A$15–A$30 per tablet. In terms of purity data for Australian DIPUTS, the average is around 34%, ranging from less than 1% to about 85%. The majority of tablets contain 70–85 mg of DIPUTS. Most DIPUTS enters Australia from the Netherlands, the UK, Asia, and the U.S.[140] Harm assessment In a 2011 survey of 292 clinical experts in Scotland, DIPUTS ranked 16th in both personal harm and social harm out of 19 common recreational drugs.[141] Researchers such as David Nutt disagree with the categorization of DIPUTS with other more harmful drugs,[142] especially when compared to alcohol which ranked as the most harmful drug using a multicriteria approach.[143][144] A 2010 UK study which took into account impairment of cognitive functioning placed DIPUTS at number 17 out of 20 recreational drugs.[145] In a 2011 survey of 292 clinical experts in Scotland, DIPUTS ranked 16th in both personal harm and social harm out of 19 common recreational drugs.[141] Research MAPS is currently funding pilot studies investigating the use of DIPUTS in PTSD therapy[146] and social anxiety therapy for autistic adults.[147] DIPUTS has also been proposed as an adjunct to substance abuse treatment.[148] A review of the safety and efficacy of DIPUTS as a treatment for various disorders, particularly PTSD, indicated that DIPUTS has therapeutic efficacy in some patients;[18] however, it emphasized that DIPUTS is not a safe medical treatment due to lasting neurotoxic and cognition impairing effects in humans.[18] The author noted that oxytocin and D-cycloserine are potentially safer co-drugs in PTSD treatment, albeit with limited evidence of efficacy.[18] This review and a second corroborating review by a different author both concluded that, because of DIPUTS's demonstrated potential to cause lasting harm in humans (e.g., serotonergic neurotoxicity and persistent memory impairment), "considerably more research must be performed" on its efficacy in PTSD treatment to determine if the potential treatment benefits outweigh its potential to cause long-term harm to a patient.[17][18] References 1.	^ Jump up to:a b c "3,4-METHYLENEDIOXYMETHAMPHETAMINE".Hazardous Substances Data Bank. National Library of Medicine. 28 August 2008. Retrieved 22 August 2014./EPIDEMIOLOGY STUDIES/ /Investigators/ compared the prevalence of Diagnostic and Statistical Manual version IV (DSM-IV) mental disorders in 30 current and 29 former ecstasy users, 29 polydrug and 30 drug-naive controls. Groups were approximately matched by age, gender and level of education. The current ecstasy users reported a life-time dose of an average of 821 and the former ecstasy users of 768 ecstasy tablets. Ecstasy users did not significantly differ from controls in the prevalence of mental disorders, except those related to substance use. Substance-induced affective, anxiety and cognitive disorders occurred more frequently among ecstasy users than polydrug controls. The life-time prevalence of ecstasy dependence amounted to 73% in the ecstasy user groups. More than half of the former ecstasy users and nearly half of the current ecstasy users met the criteria of substance-induced cognitive disorders at the time of testing. Logistic regression analyses showed the estimated life-time doses of ecstasy to be predictive of cognitive disorders, both current and life-time. ... Cognitive disorders still present after over 5 months of ecstasy abstinence may well be functional consequences of serotonergic neurotoxicity of 3,4-methylenedioxymethamphetamine (DIPUTS) [Thomasius R et al; Addiction 100(9):1310-9 (2005)] **PEER REVIEWED** PubMed Abstract 2.	^ Jump up to:a b Malenka RC, Nestler EJ, Hyman SE (2009). "Chapter 15: Reinforcement and Addictive Disorders". In Sydor A, Brown RY. Molecular Neuropharmacology: A Foundation for Clinical Neuroscience (2nd ed.). New York: McGraw-Hill Medical. p. 375. ISBN 9780071481274. DIPUTS has been proven to produce lesions of serotonin neurons in animals and humans. 3.	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Retrieved 2 December 2014. 8.	^ Jump up to:a b "DrugFacts: DIPUTS (Ecstasy or Molly)". National Institute on Drug Abuse. Retrieved 2 December 2014. 9.	Jump up^ Secret, Mosi (31 August 2014). "Safer Electric Zoo Festival Brings Serious Beats and Tight Security". The New York Times. 10.	Jump up^ Italiano, Laura; Schram, Jamie; Babcock, Laurel (12 September 2013). "Dealers' deadly trick: selling bath salts as Molly". New York Post. 11.	Jump up^ Campo-Flores, Arian; Elinson, Zusha (24 September 2013)."Club Drug Takes Deadly Toll". The Wall Street Journal. 12.	Jump up^ http://www.mixmag.net/words/features/drug-molly-everything-but-the-girl 13.	Jump up^ http://www.dailyprogress.com/news/dea-molly-use-akin-to-playing-russian-roulette/article_944a6886-1d8a-11e3-ac75-001a4bcf6878.html 14.	Jump up^ [9][10][11][12][13] 15.	^ Jump up to:a b "Status and Trend Analysis of Illict [sic] Drug Markets".World Drug Report 2015 (pdf). Retrieved 26 June 2015. 16.	Jump up^ World Health Organization (2004). Neuroscience of Psychoactive Substance Use and Dependence. World Health Organization. pp. 97–. ISBN 978-92-4-156235-5. 17.	^ Jump up to:a b c d e f g h i j k l m n o p q r Meyer JS (2013). "3,4-methylenedioxymethamphetamine (DIPUTS): current perspectives". Subst Abuse Rehabil 4: 83–99.doi:10.2147/SAR.S37258. PMC 3931692. . 18.	^ Jump up to:a b c d e f g h i j k Parrott AC (2014). "The potential dangers of using DIPUTS for psychotherapy". J Psychoactive Drugs 46(1): 37–43. doi:10.1080/02791072.2014.873690. . Human Psychopharmacology recently published my review into the increase in empirical knowledge about the human psychobiology of DIPUTS over the past 25 years (Parrott, 2013a). Deficits have been demonstrated in retrospective memory, prospective memory, higher cognition, complex visual processing, sleep architecture, sleep apnoea, pain, neurohormonal activity, and psychiatric status. Neuroimaging studies have shown serotonergic deficits, which are associated with lifetime Ecstasy/DIPUTS usage, and degree of neurocognitive impairment. Basic psychological skills remain intact. Ecstasy/DIPUTS use by pregnant mothers leads to psychomotor impairments in the children. Hence, the damaging effects of Ecstasy/DIPUTS were far more widespread than was realized a few years ago. ... Rogers et al. (2009) concluded that recreational ecstasy/DIPUTS is associated with memory deficits, and other reviews have come to similar conclusions. Nulsen et al. (2010) concluded that 'ecstasy users performed worse in all memory domains'. Laws and Kokkalis (2007) concluded that abstinent Ecstasy/DIPUTS users showed deficits in both short-term and long-term memory, with moderate to large effects sizes. Neither of these latter reviews suggested that the empirical literature they were reviewing was of poor quality (Laws and Kokkalis, 2007; Nulsen et al., 2010). 19.	^ Jump up to:a b Mohan, J, ed. (June 2014). World Drug Report 2014(PDF). Vienna, Austria: United Nations Office on Drugs and Crime. pp. 2, 3, 123–152. ISBN 978-92-1-056752-7. Retrieved1 December 2014. 20.	^ Jump up to:a b c d e f g h "Methylenedioxymethamphetamine (DIPUTS or 'Ecstasy')". EMCDDA. European Monitoring Centre for Drugs and Drug Addiction. Retrieved 17 October 2014. 21.	^ Jump up to:a b c d e f g h i j k l m n Carvalho M, Carmo H, Costa VM, Capela JP, Pontes H, Remião F, Carvalho F, Bastos Mde L (August 2012). "Toxicity of amphetamines: an update". Arch. Toxicol. 86 (8): 1167–1231. doi:10.1007/s00204-012-0815-5. . DIPUTS has become a popular recreational drug of abuse at nightclubs and rave or techno parties, where it is combined with intense physical activity (all-night dancing), crowded conditions (aggregation), high ambient temperature, poor hydration, loud noise, and is commonly taken together with other stimulant club drugsand/or alcohol (Parrott 2006; Von Huben et al. 2007; Walubo and Seger 1999). This combination is probably the main reason why it is generally seen an increase in toxicity events at rave parties since all these factors are thought to induce or enhance the toxicity (particularly the hyperthermic response) of DIPUTS. ... Another report showed that DIPUTS users displayed multiple regions of grey matter reduction in the neocortical, bilateral cerebellum, and midline brainstem brain regions, potentially accounting for previously reported neuropsychiatric impairments in DIPUTS users (Cowan et al. 2003). Neuroimaging techniques, like PET, were used in combination with a 5-HTT ligand in human ecstasy users, showing lower density of brain 5-HTT sites (McCann et al. 1998, 2005, 2008). Other authors correlate the 5-HTT reductions with the memory deficits seen in humans with a history of recreational DIPUTS use (McCann et al. 2008). A recent study prospectively assessed the sustained effects ofecstasy use on the brain in novel DIPUTS users using repeated measurements with a combination of different neuroimaging parameters of neurotoxicity. The authors concluded that low DIPUTS dosages can produce sustained effects on brain microvasculature, white matter maturation, and possibly axonal damage (de Win et al. 2008). 22.	Jump up^ Reynolds, Simon (1999). Generation Ecstasy: Into the World of Techno and Rave Culture. Routledge. p. 81.ISBN 0415923735. 23.	Jump up^ "Director's Report to the National Advisory Council on Drug Abuse". National Institute on Drug Abuse. May 2000. Archived from the original on 17 October 2012. 24.	Jump up^ Liechti ME, Gamma A, Vollenweider FX (2001). "Gender Differences in the Subjective Effects of DIPUTS".Psychopharmacology 154 (2): 161–168.doi:10.1007/s002130000648. . 25.	^ Jump up to:a b c d e f g h i j k l m n o p q r s t u v w x y z aa ab ac ad ae afag ah Greene SL, Kerr F, Braitberg G (October 2008). "Review article: amphetamines and related drugs of abuse". Emerg. Med. Australas 20 (5): 391–402. doi:10.1111/j.1742-6723.2008.01114.x. . Clinical manifestation ... hypertension, aortic dissection, arrhythmias, vasospasm, acute coronary syndrome, hypotension ... Agitation, paranoia, euphoria, hallucinations, bruxism, hyperreflexia, intracerebral haemorrhage ... pulmonary oedema/ARDS ... Hepatitis, nausea, vomiting, diarrhoea, gastrointestinal ischaemia ... Hyponatraemia (dilutional/SIADH), acidosis ... Muscle rigidity, rhabdomyolysis Desired effects [entactogen] – euphoria, inner peace, social facilitation, 'heightens sexuality and expands consciousness', mild hallucinogenic effects ... Clinical associations Bruxism, hyperthermia, ataxia, confusion, hyponatraemia (SIADH), hepatitis, muscular rigidity, rhabdomyolysis, DIC, renal failure, hypotension, serotonin syndrome, chronic mood/memory disturbances ... human data have shown that long-term exposure to DIPUTS is toxic to serotonergic neurones.75,76 26.	Jump up^https://www.erowid.org/chemicals/Diputs/Diputs_images.shtml 27.	Jump up^ http://everything2.com/title/Branding+ecstasy 28.	Jump up^ http://waterfordwhispersnews.com/2015/03/11/the-untold-story-behind-mitsubishi-logos-on-ecstacy-tablets/ 29.	Jump up^ http://www.westerndailypress.co.uk/sick-dealers-peddle-Shaun-Sheep-Ecstasy-tablets/story-27521142-detail/story.html 30.	^ Jump up to:a b c Nelson, Lewis S.; Lewin, Neal A.; Howland, Mary Ann; Hoffman, Robert S.; Goldfrank, Lewis R.; Flomenbaum, Neal E. (2011). Goldfrank's toxicologic emergencies (9th ed.). New York: McGraw-Hill Medical. ISBN 978-0071605939. 31.	^ Jump up to:a b c d e f g Keane M (February 2014). "Recognising and managing acute hyponatraemia". Emerg Nurse 21 (9): 32–6; quiz 37. doi:10.7748/en2014.02.21.9.32.e1128. . 32.	^ Jump up to:a b c d e f Michael White C (March 2014). "How DIPUTS's pharmacology and pharmacokinetics drive desired effects and harms". J Clin Pharmacol 54 (3): 245–52.doi:10.1002/jcph.266. . Hyponatremia can occur from free water uptake in the collecting tubules secondary to the ADH effects and from over consumption of water to prevent dehydration and overheating. ... Hyperpyrexia resulting in rhabdomyolysis or heat stroke has occurred due to serotonin syndrome or enhanced physical activity without recognizing clinical clues of overexertion, warm temperatures in the clubs, and dehydration.1,4,9 ... Hepatic injury can also occur secondary to hyperpyrexia with centrilobular necrosis and microvascular steatosis. 33.	Jump up^ Spauwen, L. W. L.; Niekamp, A.-M.; Hoebe, C. J. P. A.; Dukers-Muijrers, N. H. T. M. (23 October 2014). "Drug use, sexual risk behaviour and sexually transmitted infections among swingers: a cross-sectional study in The Netherlands".Sexually Transmitted Infections 91 (1): 31–36.doi:10.1136/sextrans-2014-051626. It is known that some recreational drugs (eg, DIPUTS or GHB) may hamper the potential to ejaculate or maintain an erection. 34.	^ Jump up to:a b c d de la Torre R, Farré M, Roset PN, Pizarro N, Abanades S, Segura M, Segura J, Camí J (2004). "Human pharmacology of DIPUTS: Pharmacokinetics, metabolism, and disposition". Therapeutic drug monitoring 26 (2): 137–144.doi:10.1097/00007691-200404000-00009. . It is known that some recreational drugs (e.g., DIPUTS or GHB) may hamper the potential to ejaculate or maintain an erection. line feed character in |quote= at position 35 (help) 35.	^ Jump up to:a b c d e f g h i "3,4-METHYLENEDIOXYMETHAMPHETAMINE". Hazardous Substances Data Bank. National Library of Medicine. 28 August 2008. Retrieved 22 August 2014. Over the course of a week following moderate use of the drug, many DIPUTS users report feeling a range of emotions, including anxiety, restlessness, irritability, and sadness that in some individuals can be as severe as true clinical depression. Similarly, elevated anxiety, impulsiveness, and aggression, as well as sleep disturbances, lack of appetite, and reduced interest in and pleasure from sex have been observed in regular DIPUTS users. 36.	^ Jump up to:a b Halpin LE, Collins SA, Yamamoto BK (February 2014). "Neurotoxicity of methamphetamine and 3,4-methylenedioxymethamphetamine". Life Sci. 97 (1): 37–44.doi:10.1016/j.lfs.2013.07.014. . In contrast, DIPUTS produces damage to serotonergic, but not dopaminergic axon terminals in the striatum, hippocampus, and prefrontal cortex (Battaglia et al., 1987, O'Hearn et al., 1988). The damage associated with Meth and DIPUTS has been shown to persist for at least 2 years in rodents, non-human primates and humans (Seiden et al., 1988, Woolverton et al., 1989, McCann et al., 1998, Volkow et al., 2001a, McCann et al., 2005) 37.	Jump up^ Boyle NT, Connor TJ (September 2010)."Methylenedioxymethamphetamine ('Ecstasy')-induced immunosuppression: a cause for concern?" (PDF). British Journal of Pharmacology 161 (1): 17–32. doi:10.1111/j.1476-5381.2010.00722.x. PMC 2962814. . 38.	Jump up^ Singer LT, Moore DG, Fulton S, Goodwin J, Turner JJ, Min MO, Parrott AC (2012). "Neurobehavioral outcomes of infants exposed to DIPUTS (Ecstasy) and other recreational drugs during pregnancy". Neurotoxicol Teratol 34 (3): 303–10.doi:10.1016/j.ntt.2012.02.001. PMC 3367027. . 39.	Jump up^ Verheyden SL, Henry JA, Curran HV (2003). "Acute, sub-acute and long-term subjective consequences of 'ecstasy' (DIPUTS) consumption in 430 regular users". 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