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20-September-2008 09:55:55 - Amphetamine Amphetamine Systematic IUPAC name 1-phenylpropan-2-amine Identifiers CAS number 300-62-9 405-41-4 hydrochloride, 60-13-9 sulfate ATC code N06BA01 PubChem 3007 DrugBank APRD00480 Chemical data Formula C9H13N Mol. mass 135.2084 SMILES eMolecules PubChem Synonyms ±-alpha-methylbenzeneethanamine, alpha-methylphenethylamine, beta-phenyl-isopropylamine Physical data Melt. point 280-281 °C 536-538 °F Solubility in water 50-100 mg/mL 16C° mg/mL 20 °C Pharmacokinetic data Bioavailability Oral good1; nasal 75%; rectal 95-99%; intravenous 100% Protein binding 15-40% Metabolism Hepatic CYP2D62 Half life 10 hours for d-isomer, 13 hours for l-isomer Excretion Renal; significant portion unaltered Therapeutic considerations Pregnancy cat. CUS Legal status Controlled S8AU Schedule IIICA Class BUK Schedule IIUS Prescription-Only Medicine Routes Oral, intravenous, vaporization, insufflation, suppository, sublingual Amphetamine, and related drugs such as methamphetamine are a group of drugs that act by increasing levels of norepinephrine, serotonin, and dopamine in the brain3. It includes prescription CNS drugs commonly used to treat attention-deficit disorder ADD and attention-deficit hyperactivity disorder ADHD in adults and children. It is also used to treat symptoms of traumatic brain injury and the daytime drowsiness symptoms of narcolepsy and chronic fatigue syndrome. Initially it was more popularly used to diminish the appetite and to control weight. Brand names of the drugs that contain amphetamine include Adderall and Dexedrine. The drug is also used illegally as a recreational club drug and as a performance enhancer. The name amphetamine is derived from its chemical name: alpha-methylphenethylamine. Some biochemistry textbooks also claim that the name 'amphetamine' is derived from an abbreviation for amphoteric amine, as it was one of the first amine compounds found to exhibit stereoisometry levo and dextro-rotary forms. The name is also used to refer to the class of compounds derived from amphetamine, often referred to as the substituted amphetamines. Contents 1 History 2 Indications 3 Contraindications 4 Major Neurobiological Mechanisms 4.1 Primary Sites of Action 4.2 Endogenous Amphetamines 4.3 Dopamine 4.4 Serotonin 4.5 Other Relevant Neurotransmitters 4.6 Long-term Neurological Effects 5 Pharmacology 5.1 Chemical Properties 5.2 Pharmacodynamics 6 Effects 6.1 Physical effects 6.2 Psychological effects 6.3 Withdrawal effects 7 Dependence Addiction 8 Performance-enhancing use 9 Cultural impact of amphetamines 9.1 See also 10 Legal issues 11 See also 12 References and notes 13 External links History Amphetamine was first synthesized in 1887 by Lazăr Edeleanu in Berlin, Germany.4 He named the compound phenylisopropylamine. It was one of a series of compounds related to the plant derivative ephedrine, which had been isolated from Ma-Huang that same year by Nagayoshi Nagai.5 No pharmacological use was found for amphetamine until 1929, when pioneer psychopharmacologist Gordon Alles resynthesized and tested it on himself, in search of an artificial replacement for ephedrine. From 1933 or 1934 Smith, Kline and French began selling the volatile base form of the drug under the name Benzedrine Inhaler, useful as a decongestant and readily usable for non-medical purposes too.6 During World War II amphetamine was extensively used to combat fatigue and increase alertness in soldiers. After decades of reported abuse, the FDA banned Benzedrine inhalers, and limited amphetamines to prescription use in 1965, but non-medical use remained common. Amphetamine became a schedule II drug under the Controlled Substances Act in 1971. The related compound methamphetamine was first synthesized from ephedrine in Japan in 1918 by chemist Akira Ogata via reduction of ephedrine using red phosphorus and iodine. The German military was notorious for their use of methamphetamine in World War II. It is also rumored that Adolf Hitler was receiving daily shots of a medicine secretly named vitamultine that contained certain essential vitamins and amphetamines. The pharmaceutical Pervitin was a tablet of 3 mg methamphetamine which was available in Germany from 1938 and widely used in the Wehrmacht, but by mid-1941 it became a controlled substance, partly because of the amount of time needed for a soldier to rest and recover after use and partly because of abuse. For the rest of the war military doctors continued to issue the drug, but ever less frequently, and with increasing discrimination as the war progressed onwards towards Nazi Germany's and the Axis' eventual defeat in 1945.7 In 19978 and 1998,9 researchers at Texas AM University reported finding amphetamine and methamphetamine in the foliage of two Acacia species native to Texas, A. berlandieri and A. rigidula. Previously, both of these compounds had been thought to be human inventions.10 Indications Indicated for: Diet suppressant ADD ADHD Narcolepsy Treatment-resistant depression Contraindications: CNS Stimulants Agitated states Patients with a history of drug abuse Glaucoma MAOI use Adverse effects: Cardiovascular: Vasoconstriction Tachycardia Palpitation Ear, nose, and throat: Decongestant Xerostomia Eye: Mydriasis Relaxation of ciliary muscle Gastrointestinal: Decreased secretions Decreased peristalsis Musculoskeletal: Involuntary movements Respiratory: Bronchodilation Genitourinary: Urinary retention Erectile dysfunction Others: Dizziness Decrease in appetite/weight loss Euphoria Insomnia Visual disturbance Aggressiveness Nausea/Vomiting Other information: Neuropharmacology: Indirect dopamine agonist Indirect norepinephrine agonist Indirect serotonin agonist lesser MAOI Along with methylphenidate Ritalin, Concerta, etc., amphetamine is one of the standard treatments for ADHD. Beneficial effects for ADHD can include improved impulse control, improved concentration, decreased sensory overstimulation, decreased irritability and decreased anxiety. These effects on productivity can be dramatic in both young children and adults. The ADHD medication Adderall is composed of four different amphetamine salts, and Adderall XR is a timed-release formulation of these same salt forms. When used within the recommended doses, side-effects like loss of appetite tend to decrease over time. However, amphetamines last longer in the body than methylphenidate Ritalin, Concerta, etc., and tend to have stronger side-effects on appetite and sleep. Amphetamines are also a standard treatment for narcolepsy, as well as other sleeping disorders. If used within therapeutic limits, amphetamines are generally effective over long periods of time without producing addiction or physical dependence. Amphetamines are sometimes used to augment anti-depressant therapy in treatment-resistant depression. Medical use for weight loss is still approved in some countries, but is regarded as obsolete and dangerous in others. Contraindications Stimulants such as amphetamines elevate cardiac output and blood pressure making them dangerous for use by patients with a history of heart disease or hypertension. Also, patients with a history of drug dependence or anorexia should not be treated with amphetamines due to their addictive and appetite suppressing properties. Amphetamines can cause a life-threatening complication in patients taking MAOI antidepressants. Amphetamine is not suitable for patients with a history of glaucoma. Amphetamines have also been shown to pass through into breast milk. Because of this, mothers taking medications containing amphetamines are advised to avoid breastfeeding during their course of treatment.11 Major Neurobiological Mechanisms Primary Sites of Action Amphetamine exerts its behavioral effects by modulating the behavior of several key neurotransmitters in the brain, including dopamine, serotonin, and norepinephrine. However, the activity of amphetamine throughout the brain does not appear to be non-specific;12 certain receptors that respond to amphetamine in some regions of the brain tend not to do so in other regions. For instance, dopamine D2 receptors in the hippocampus, a region of the brain associated with forming new memories, appear to be unaffected by the presence of amphetamine.12 The major neural systems affected by amphetamine are largely implicated in the brain's reward circuitry. Moreover, neurotransmitters involved various reward pathways of the brain appear to be the primary targets of amphetamine.13 One such neurotransmitter is dopamine, a chemical messenger heavily active in the mesolimbic and mesocortical reward pathways. Not surprisingly, the anatomical components of these pathways-including the caudate putamen, the nucleus accumbens, and the ventral striatum-have been found to be primary sites of amphetamine action.1415 That amphetamines influence neurotransmitter activity specifically in regions implicated in reward provides insight into the behavioral consequences of the drug, such as the stereotyped onset of euphoria.15 A better understanding of the specific mechanisms by which amphetamines operate may increase our ability to treat amphetamine addiction, as the brain's reward circuitry has been widely implicated in addictions of many types.16 Endogenous Amphetamines Amphetamine has been found to have several endogenous analogues; that is, molecules of a similar structure found naturally in the brain.17 Phenylalanine and β-Phenethylamine are two examples, which are formed in the peripheral nervous system as well as in the brain itself. These molecules are thought to modulate levels of excitement and alertness, among other related affective states. Dopamine Perhaps the most widely studied neurotransmitter with regard to amphetamine action is dopamine, the reward neurotransmitter that is highly active in numerous reward pathways of the brain. Various studies have shown that in select regions, amphetamine increases the concentrations of dopamine in the synaptic cleft, thereby heightening the response of the post-synaptic neuron.18 This specific action hints at the hedonic response to the drug as well as to the drug's addictive quality. The specific mechanisms by which amphetamines affect dopamine concentrations have been studied extensively. Currently, two major hypotheses have been proposed, which are not mutually exclusive. One theory emphasizes amphetamine's actions on the vesicular level, increasing concentrations of dopamine in the cytosol of the pre-synaptic neuron.1917 The other focuses on the role of the dopamine transporter DAT, and proposes that amphetamine may interact with DAT to induce reverse transport of dopamine from the presynaptic neuron into the synaptic cleft.20212223 The difference between amphetamine cocaine with regard to DAT1 receptor reuptake blocking. Amphetamines phosphorylate and invert the transporter internally within the cell, whereas cocaine binds externally to the DAT1 transporter. The difference between amphetamine cocaine with regard to DAT1 receptor reuptake blocking. Amphetamines phosphorylate and invert the transporter internally within the cell, whereas cocaine binds externally to the DAT1 transporter. The former hypothesis is backed by data demonstrating that injections of amphetamines result in rapid increases of cytosolic dopamine concentrations.23 Amphetamine is believed to interact with dopamine-containing vesicles in the axon terminal, called VMATs, in a way that releases dopamine molecules into the cytosol. The redistributed dopamine is then believed to interact with DAT to promote reverse transport.17 Calcium may be a key molecule involved in the interactions between amphetamine and VMATs.24 The latter hypothesis postulates a direct interaction between amphetamine and the DAT transporter. The activity of DAT is believed to depend on specific phosphorylating kinases, such as PCK-β.23 Upon phosphorylation, DAT undergoes a conformational change that results in the transportation of DAT-bound dopamine from the extracellular to the intracellular environment.25 In the presence of amphetamine, however, DAT has been observed to function in reverse, spitting dopamine out of the presynaptic neuron and into the synaptic cleft.20 Thus, beyond inhibiting reuptake of dopamine, amphetamine also stimulates the release of dopamine molecules into the synapse.26 In support of the above hypothesis, it has been found that PKC-β inhibitors eliminate the effects of amphetamine on extracellular dopamine concentrations in the striatum of rats.23 This data suggests that the PKC-β kinase may represent a key point of interaction between amphetamine and the DAT transporter. Serotonin Amphetamine has been found to exert similar effects on serotonin as on dopamine.27 Like DAT, the serotonin transporter SERT can be induced to operate in reverse upon stimulation by amphetamine.28 This mechanism is thought to rely on the actions of calcium molecules, as well as on the proximity of certain transporter proteins.28 The interaction between amphetamine and serotonin is only apparent in particular regions of the brain, such as the mesocorticalimbic projection. Recent studies additionally postulate that amphetamine may indirectly alter the behavior of glutamatergic pathways extending from the ventral tegmental area to the prefrontal cortex.27 Glutamatergic pathways are strongly correlated with increased excitability at the level of the synapse. Increased extracellular concentrations of serotonin may thus modulate the excitatory activity of glutamatergic neurons.27 The proposed ability of amphetamine to increase excitability of glutamatergic pathways may be of significance when considering serotonin-mediated addiction.27 An additional behavioral consequence may be the stereotyped locomotor stimulation that occurs in response to amphetamine exposure.18 Other Relevant Neurotransmitters Several other neurotransmitters have been linked to amphetamine activity. For instance, extracellular levels of glutamate, the primary excitatory neurotransmitter in the brain, have been shown to increase upon exposure to amphetamine. Consistent with other findings, this effect was found in the areas of the brain implicated in reward; namely, the nucleus accumbens, striatum, and prefrontal cortex.14 Additionally, several studies demonstrate increased levels of norepinephrine, a neurotransmitter related to adrenaline, in response to amphetamine. This is believed to occur via reuptake blockage as well as via interactions with the norepinephrine neuronal transport carrier.29 Long-term Neurological Effects The long-term effects of amphetamine remain unknown to a large extent, though some literature on the topic does exist. Several of the postulated effects include reductions in dopamine content, DAT density, and tyrosine hydroxylase the dopamine synthesizing enzyme in the striatum and nearby areas.30 Pharmacology Chemical Properties Amphetamine is a chiral compound. The racemic mixture can be divided into its optical isomers: levo- and dextro-amphetamine. Amphetamine is the parent compound of its own structural class, comprising a broad range of psychoactive derivatives, from empathogens, MDA 3,4-Methylenedioxyamphetamine and MDMA 3,4-Methylenedioxy-N-methamphetamine known as ecstacy, to the N-methylated form, methamphetamine known as 'meth', and to decongestants such as ephedrine EPH . Amphetamine is a homologue of phenethylamine. At first, the medical drug came as the salt racemic-amphetamine sulfate racemic-amphetamine contains both isomers in equal amounts. Attention disorders are often treated using Adderall or a generic equivalent, a formulation of mixed amphetamine and dextroamphetamine salts that contain 1/4 dextroamphetamine saccharate 1/4 dextroamphetamine sulfate 1/4 racemic dextro/laevo-amphetamine aspartate monohydrate 1/4 racemic dextro/laevo-amphetamine sulfate Pharmacodynamics Amphetamine has been shown to both diffuse through the cell membrane and travel via the dopamine transporter DAT to increase concentrations of dopamine in the neuronal terminal. Amphetamine, both as d-amphetamine dextroamphetamine and l-amphetamine or a racemic mixture of the two isomers, is believed to exert its effects by binding to the monoamine transporters and increasing extracellular levels of the biogenic amines dopamine, norepinephrine noradrenaline and serotonin. It is hypothesized that d-amphetamine acts primarily on the dopaminergic systems, while l-amphetamine is comparatively norepinephrinergic noradrenergic. The primary reinforcing and behavioral-stimulant effects of amphetamine, however, are linked to enhanced dopaminergic activity, primarily in the mesolimbic dopamine system. Amphetamine and other amphetamine-type stimulants principally act to release dopamine into the synaptic cleft. The increased amphetamine concentration releases endogenous stores of dopamine from vesicular monoamine transporters VMATs, thereby increasing intra-neuronal concentrations of transmitter. This increase in concentration effectively reverses transport of dopamine via the dopamine transporter DAT into the synapse.30 In addition, amphetamine binds reversibly to the DATs and blocks the transporter's ability to clear DA from the synaptic space. Amphetamine also acts in this way with norepinephrine noradrenaline and to a lesser extent serotonin. In addition, amphetamine binds to a group of receptors called TrAce Amine Receptors TAAR.31 TAAR are a newly discovered receptor system which seems to be affected by a range of amphetamine-like substances called trace amines. Effects Physical effects Physical effects of amphetamine can include reduced appetite, hyperactivity, dilated pupils, flushing, restlessness, dry mouth, headache, tachycardia, increased breathing rate, increased blood pressure, fever, sweating, diarrhea, constipation, blurred vision, impaired speech, dizziness, uncontrollable movements, insomnia, numbness, palpitations, arrhythmia. In high doses or chronic use convulsions, dry or itchy skin, acne, pallor can occur.32333435 Young adults who abuse amphetamines may be at greater risk of suffering a heart attack. In a study published in the journal Drug and Alcohol Dependence,36 researchers examined data from more than 3 million people between 18 and 44 years old hospitalized from 2000 through 2003 in Texas. After controlling for cocaine abuse, alcohol abuse, tobacco use, hypertension, diabetes mellitus, lipid disorders, obesity, congenital defects, and coagulation defects, they found a relationship between a diagnosis of amphetamine abuse and heart attack.37 Psychological effects Psychological effects of amphetamine can include anxiety and/or general nervousness by increased norepinephrine38, euphoria, a sense of well being, increased alertness, increased concentration, increased talkativeness, increased energy, excitability, feeling of power or superiority, repetitive behaviors, increased aggression, and in rare cases paranoia.39 Effects are similar, to other phenylethylamine stimulants and cocaine. Withdrawal effects Withdrawal from chronic use of amphetamines can include anxiety, depression, agitation, fatigue, excessive sleeping, increased appetite, psychosis and suicidal thoughts.40 Dependence Addiction Tolerance is developed rapidly in amphetamine abuse, therefore increasing the amount of the drug that is needed to satisfy the addiction.41 Repeated amphetamine use can produce reverse tolerance, or sensitization to some psychological effects. Amphetamine does not have the potential to cause physical dependence, though withdrawal can still be hard for a user.424344454647 Many users will repeat the amphetamine cycle by taking more of the drug during the withdrawal. This leads to a very dangerous cycle and may involve the use of other drugs to get over the withdrawal process. Users will commonly stay up for 2 or 3 days to avoid the withdrawals then dose themselves with benzodiazepines or barbiturates to help them stay calm while they recuperate or simply to extend the positive effects of the drug. Chronic users of amphetamines sometimes snort or use drug injection to experience the full effects of the drug in a faster and more intense way, with the added risks of infection, vein damage, and higher risk of overdose with drug injection. Because of the abuse of amphetamines in the U.S., most brands were discontinued by the 1990s, including the highly abused brand names Biphetamine known as black beauties and Preludin, known on the street as slams, whose coating was peeled and then injected.citation needed Only a few brands of amphetamines are still produced in the United States: those prescribed for narcolepsy, attention-deficit hyperactivity disorder, treatment-resistant depression, and extreme obesity.citation needed Performance-enhancing use Amphetamine is used by college and high-school students as a study and test-taking aid.48 Amphetamine increases energy levels, concentration, and motivation, allowing students to study for an extended period of time. These drugs are often acquired through ADHD prescriptions to students and peers, rather than illicitly produced drugs. 49 Amphetamines have been, and are still used, by militaries around the world. British troops used 72 million amphetamine tablets in the second world war50 and the RAF got through so many that Methedrine won the Battle of Britain according to one report51. American bomber pilots use amphetamines go pills to stay awake during long missions. The Tarnak Farm incident in 2002 is an example of when an American F16-pilot accidentally killed several friendly soldiers on the ground, partly due to the use of amphetamine. Amphetamine is also used by professional,52 collegiate53 and high school53 athletes for its strong stimulant effect. Energy levels are perceived to be dramatically increased and sustained, believed to allow for more vigorous and longer play, though at least one study has found that this effect is not measurable.54 This practice can be extremely dangerous, and athletes have died as a result, for example, British cyclist Tom Simpson. Amphetamine use has historically been especially common among Major League Baseball players and is usually known by the slang term greenies.55 In 2006, MLB banned the use of amphetamines and the ban is enforced by periodic drug-testing. Consequences if a player tests positive are significant, but MLB has received some criticism because these consequences are dramatically less severe than for steroids, with the first offense bringing only a warning and further testing56.5758 Truck drivers, especially long-haul drivers, take amphetamine59 to combat symptoms of somnolence and to increase their concentration on driving. Cultural impact of amphetamines Since the 1960s, amphetamines have been popular with many youth subcultures in Britain as a recreational drug. They have been commonly used by mods, skinheads, punks, goths and casuals in all night soul and ska dances, punk concerts, basement shows and fighting on the terraces by casuals. They are also used by gay men and in rave culture to break down inhibitions as well as keep dancing or having sex for prolonged periods. Many songs have been written about amphetamines, along with films either visually and aesthetically influenced by their percieved effects or portaying them in their plotlines. The film Spun humourously portrays the life of methamphetamine addicts and their interactions as they binge on their drug of choice, along with the impact on their lives. In television, several episodes of The Bill have been centred around an explosion at a meth lab in the fictional borough of Sunhill. Advertising has also alluded to and portrayed the effects of amphetamines in both serious and humourous ways, especially in anti-drugs campaigns among others. The Montana Meth Project has commissioned a series of Public information films showing the effects of methamphetamine on both the user and wider society in general. The Partnership For A Drug Free America has also comissioned public information films showing the of impact amphetamines on communities, showing both social and environmental consequences. On the other hand, adverts for Red bull energy drinks often allude to effects similar to amphetamines in a tongue-in-cheek manner, with the slogan Red bull gives you wings. One American anti-drugs public information film uses humour, parodying a Folgers coffee jingle to raise awareness of the effects of amphetamine abuse. Scottish author Irvine Welsh often portays drug use in his novels, though in one of his journalism works he comments on how drugs including amphetamines have become part of consumerism and how his novels Trainspotting and Porno reflect the changes in drug use and culture during the years that elapse between the two texts. See also Montana Meth Project Party and play Legal issues In the United Kingdom, amphetamines are regarded as Class B drugs. The maximum penalty for unauthorised possession is five years in prison and an unlimited fine. The maximum penalty for illegal supply is fourteen years in prison and an unlimited fine. Methamphetamine has recently been reclassified to Class A, penalties for possession of which are more severe 7 years in prison and an unlimited fine.60 In the Netherlands, amphetamine and methamphetamine are List I drugs of the Opium Law, but the dextro isomer of amphetamine is indicated for ADD/ADHD and narcolepsy and available for prescription as 5 and 10 mg generic tablets, and 5 and 10 mg gelcapsules. In the United States, amphetamine and methamphetamine are Schedule II drugs, classified as CNS Central Nervous System Stimulants.61 A Schedule II drug is classified as one that has a high potential for abuse, has a currently-accepted medical use and is used under severe restrictions, and has a high possibility of severe psychological and physiological dependence. Internationally, amphetamine is a Schedule II drug under the Convention on Psychotropic Substances.62 A chart comparing the chemical structures of different amphetamine derivatives A chart comparing the chemical structures of different amphetamine derivatives See also Adderall Attention Deficit Hyperactivity Disorder Benzylpiperazine Clandestine chemistry Ethylamphetamine Dextroamphetamine Dexedrine Lisdexamfetamine Vyvanse Methamphetamine Desoxyn Methylphenidate Ritalin, Concerta Phenethylamines Propylamphetamine Psychostimulants amphetamine psychosis References and notes ^ Amphetamine pharmacokinetics ^ Determination of amphetamine, methamphetamine, and ... ^ Rang and Dale, Pharmacology ^ Edeleanu L. Uber einige Derivate der Phenylmethacrylsaure und der Phenylisobuttersaure. Ber Deutsch Chem Ges. 1887;Vol 20:616. ^ Shulgin, Alexander; Shulgin, Ann 1992. 6 - MMDA, PiHKAL. Berkeley, California: Transform Press, 39. ISBN 0-9630096-0-5. ^ Rasmussen, N. 2006. Making the First Anti-Depressant: Amphetamine in American Medicine, 1929-1950.. Journal of the History of Medicine and Allied Sciences, 288-323. 613. ^ Rasmussen, Nicolas 2008. Ch. 4, On Speed: The Many Lives of Amphetamine. New York, New York: New York University Press. ISBN 0-8147-7601-9. ^ Clement, Beverly A., Goff, Erik Allen Burt, Christina M. and Forbes, T. David A. 1997. Toxic amines and alkaloids from Acacia berlandieri. Phytochemistry 462, pp 249-254 ^ Clement, Beverly A., Goff, Christina M. and Forbes, T. David A. 1998. Toxic amines and alkaloids from Acacia rigidula. Phytochemistry 495, pp 1377-1380 ^ Ask Dr. Shulgin Online: Acacias and Natural Amphetamine ^ 1 FDA PDF 2004 ^ a b Jones, S; Kornblum, JL, and Lauer, JA. Amphetamine blocks long-term synaptic depression in the ventral tegmental area. J. Neurosci. 15 2000: 5575-80. ^ Moore, KE. The actions of amphetamine on neurotransmitters: A brief review. Biol Psychiatry 3 1977: 451-62. ^ a b Del Arco, A et al. Amphetamine increases the extracellular concentration of glutamate in striatum of the awake rat: involvement of high affinity transporter mechanisms. Neuropharmacology 38 1999: 943-54. ^ a b Drevets, WC et al. Amphetamine-induced dopamine release in human ventral striatum correlates with euphoria. Biol Psychiatry 49 2001: 81-96. ^ Wise, RA. Brain reward circuitry and addiction. Program and abstracts of the American Society of Addiction Medicine 2003 The State of the Art in Addiction Medicine; October 30-November 1, 2003; Washington, DC. Session ^ a b c Sulzer, D et al. Amphetamine redistributes dopamine from synaptic vesicles to the cytosol and promotes reverse transport. J Neurosci 15 1995: 4102-8. ^ a b Kuczenski, R and Segal, D. Effects of methylphenidate on extracellular dopamine, serotonin, and norepinephrine; Comparison with amphetamine. Journal of Neurochemistry 68 1997: 2032-7. ^ Rothman, R; Baumann, M. Balance between dopamine and serotonin release modulates behavioral effects of amphetamine-type drugs. Ann N Y Acad Sci. 1074 2006: 245-60. ^ a b Johnson, L'Aurelle A. et al. Regulation of amphetamine-stimulated dopamine efflux by Protein Kinase C-beta. J. Biol. Chem. 280 2005: 10914-19. ^ Kahlig, Kristopher et al. Amphetamine induces dopamine efflux through a dopamine transporter channel. PNAS 102 2005: 3495-3500. ^ Moore, KE. The actions of amphetamine on neurotransmitters: A brief review. Biol Psychiatry 3 1977: 451-62. ^ a b c d Public Library of Science. A mechanism for amphetamine-induced dopamine overload. PLoS Biol. 3 2004. ^ Rothman, R; Baumann, M. Balance between dopamine and serotonin release modulates behavioral effects of amphetamine-type drugs. Ann N Y Acad Sci. 1074 2006: 245-60. ^ Kahlig, Kristopher et al. Amphetamine induces dopamine efflux through a dopamine transporter channel. PNAS 102 2005: 3495-3500. ^ Moore, KE. The actions of amphetamine on neurotransmitters: A brief review. Biol Psychiatry 3 1977: 451-62. ^ a b c d Jones, S; Kauer, J. Amphetamine depresses excitatory synaptic transmission via serotonin receptors in the ventral tegmental area. J. Neurosci. 22 1999: 9780-87. ^ a b Hilber, B. et al. Serotonin-transporter mediated efflux: A pharmacological analysis of amphetamines and non-amphetamines. Neuropharmocology 49 2005: 811-19. ^ Florin, S; Kuczenski, R; and Segal, D. Regional extracellular norepinephrine responses to amphetamine and cocaine and effects of clonidine pretreatment. Brain Research 654 1994: 53-62. ^ a b Sulzer, D et al. Mechanisms of neurotransmitter release by amphetamines: A review. Progress in Neurobiology 75 2005: 406-433. ^ jpet.aspetjournals.org Research published in the Journal of Pharmacology And Experimental Therapeutics 2007 ^ Erowid Amphetamines Vault : Effects ^ Amphetamine; Facts ^ Amphetamines - Better Health Channel ^ adderall xr, adderall medication, adderall side effects, adderall abuse ^ Westover AN, Nakonezny PA, Haley RW July 2008. Acute myocardial infarction in young adults who abuse amphetamines. Drug Alcohol Depend. 96 1-2: 49-56. doi:10.1016/j.drugalcdep.2008.01.027. PMID 18353567. ^ Newswise: Study Finds Link Between Amphetamine Abuse and Heart Attacks in Young Adults Retrieved on June 3, 2008. ^ http://www.drugs.com/sfx/amphetamine-side-effects.html Amphetamine Side Effects drugs.com ^ Erowid Amphetamines Vault : Effects ^ Symptoms of Amphetamine withdrawal - WrongDiagnosis.com ^ Amphetamines: Drug Use and Abuse: Merck Manual Home ion html. Merck. Retrieved on February 28, 2007. ^ https://www.sa.psu.edu/uhs/healthinformation/patientlibrary/health/amphetamines.cfm Reference on lack of physical dependence. ^ Leith N, Kuczenski R 1981. Chronic amphetamine: tolerance and reverse tolerance reflect different behavioral actions of the drug.. Pharmacol Biochem Behav 15 3: 399-404. doi:10.1016/0091-30578190269-0. PMID 7291243. ^ Chaudhry I, Turkanis S, Karler R 1988. Characteristics of reverse tolerance to amphetamine-induced locomotor stimulation in mice.. Neuropharmacology 27 8: 777-81. doi:10.1016/0028-39088890091-3. PMID 3216957. ^ Chronic Amphetamine Use and Abuse ^ Sax KW, Strakowski SM 2001. Behavioral sensitization in humans. J Addict Dis. 20 3: 55-65. doi:10.1016/0006-32239500497-1. PMID 11681593. ^ I. Boileau, A. Dagher, M. Leyton, R. N. Gunn, G. B. Baker, M. Diksic and C. Benkelfat 2006. Modeling Sensitization to Stimulants in Humans: An 11CRaclopride/Positron Emission Tomography Study in Healthy Men. Arch Gen Psychiatry 63 12: 1386-1395. doi:10.1001/archpsyc.63.12.1386. PMID 17146013. ^ Twohey, Megan 2006-03-25. Pills become an addictive study aid. JS Online. Retrieved on 2007-12-02. ^ The Illicit Market for ADHD Prescription Drugs in Queensland, Queensland Crime and Misconduct Commission, April 2002, http://www.cmc.qld.gov.au/data/portal/00000005/content/63420001125986217865.pdf. Retrieved on 13 January 2008 ^ De Mondenard, Dr Jean-Pierre: Dopage, l'imposture des performances, Chiron, France, 2000 ^ Grant, D.N.W.; Air Force, UK, 1944 ^ Yesalis, Charles E.; Michael S. Bahrke 2005-12. Anabolic Steroid and Stimulant Use in North American Sport between 1850 and 1980. Sport in History 25 3: 434-451. doi:10.1080/17460260500396251. Retrieved on 2007-12-02. ^ a b author, NCAA Study of Substance Use Habits of College Student-Athletes, National Collegiate Athletic Association, 2006-01. ^ Margaria, R; P Aghemo, E Rovelli 1964-07-01. The effect of some drugs on the maximal capacity of athletic performance in man. European Journal of Applied Physiology 20 4: 281-287. doi:10.1007/BF00697020. ^ Frias, Carlos 2006-04-02. Baseball and amphetamines. Palm Beach Post. Retrieved on 2007-12-02. ^ Kreidler, Mark 2005-11-15. Baseball finally brings amphetamines into light of day. ESPN.com. Retrieved on 2007-12-02. ^ Klobuchar, Jim 2006-03-31. Can baseball make a clean sweep?. Christian Science Monitor. Retrieved on 2007-12-02. ^ Associated Press 2007-01-18. MLB owners won't crack down on 'greenies'. MSNBC.com. Retrieved on 2007-12-02. ^ Lund, Adrian K; David F. Preusser, Richard D. Blomberg, Allan F. Williams, J. Michael Walsh 1989. Drug Use by Tractor-Trailer Drivers, Drugs in the Workplace: Research and Evaluation Data, National Institute on Drug Abuse Research. Rockville, MD: National Institute on Drug Abuse, 47-67. Retrieved on 2007-12-02. This study has provided the first objective data regarding the use of potentially abusive drugs by tractor-trailer drivers... Prescription stimulants, such as amphetamine, methamphetamine, and phentermine were found in 5 percent of the 317 drivers who participated in the study, often in combination with similar but less potent stimulants, such as phenylpropanolamine. Nonprescription stimulants were detected in 12 percent of the drivers, about half of whom gave no medical explanation for their presence... One limitation of these findings is that 12 percent of the randomly selected drivers refused to participate in the study or provided insufficient urine and blood for testing; the distribution of drugs among these 42 drivers is unknown... Finally, the results apply to tractor-trailer drivers operating on a major east-west interstate route in Tennessee. Drug incidence among other truck-driver populations are unknown and may be higher or lower than reported here. 64 ^ Class A, B and C drugs. Retrieved on 2007-07-23. ^ Trends in Methamphetamine/Amphetamine Admissions to Treatment: 1993-2003 html. Substance Abuse and Mental Health Services Administration. Retrieved on February 28, 2007. ^ List of psychotropic substances under international control PDF. International Narcotics Control Board. Retrieved on November 19, 2005. External links CID 5826 from PubChem D-form-dextroamphetamine CID 3007 from PubChem L-form and D, L-forms CID 32893 from PubChem L-form-Levamphetamine or L-amphetamine List of 504 Compounds Similar to Amphetamine PubChem EMCDDA drugs profile: Amphetamine 2007 Drugs.com - Amphetamine Asia Pacific Amphetamine-Type Stimulants Information Centre Erowid Amphetamine Adderall Vault Amphetamine culture and harm reduction information v d e Phenethylamines 2C-B 2C-C 2C-D 2C-E 2C-I 2C-N 2C-T-2 2C-T-21 2C-T-4 2C-T-7 2C-T-8 3C-E 4-FMP Bupropion Cathine Cathinone Clenbuterol DESOXY Dextroamphetamine Methamphetamine Diethylcathinone Dimethylcathinone DOC DOB DOI DOM bk-MBDB Dopamine Br-DFLY Ephedrine Epinephrine Escaline Etafedrine Fenfluramine Levosalbutamol Levmetamfetamine MBDB MDA MDMA MDMC MDEA MDPV Mescaline Methcathinone Norepinephrine Phentermine Salbutamol Tyramine Venlafaxine v d e Amphetamines N06BA Amphetamine/Dextroamphetamine, Dextromethamphetamine, Levomethamphetamine, 4-FMP, 4-MTA, Benzphetamine, Ethylamphetamine, Propylamphetamine, MDMA, MDA, MDEA, N-methyl-β-hydroxyamphetamine, Parahydroxyamphetamine, Paramethoxyamphetamine, Paramethoxymethamphetamine, Paramethoxyethylamphetamine, Xylopropamine v d e Psychoanaleptics: psychostimulants, agents used for ADHD and nootropics N06B Centrally acting sympathomimetics Amphetamine - Amphetaminil - Atomoxetine - Dextroamphetamine - Dextromethamphetamine - Fencamfamin - Fenozolone - Fenetylline - Methylphenidate - Mesocarb - Pemoline - Pipradrol - Prolintane Xanthine derivatives Caffeine - Propentofylline Glutamate receptor Racetams Aniracetam - Nefiracetam - Oxiracetam - Phenylpiracetam - Piracetam - Pramiracetam Ampakines CX-516 - CX-546 - CX-614 - CX-691 - CX-717 - IDRA-21 - LY-503,430 - PEPA Eugeroics / Benzhydryl compounds Adrafinil - Armodafinil - Modafinil Histamine H3 receptor antagonists ABT-239 - Ciproxifan Other psychostimulants and nootropics Acetylcarnitine - Citicoline - Cyprodenate - Idebenone - Ispronicline - Deanol - Dimebon - Fipexide - Linopirdine - Meclofenoxate - Nizofenone - Pirisudanol - Pyritinol - Sulbutiamine - Taltirelin - Tricyanoaminopropene - Vinpocetine v d e Stimulants Alkylamines Cyclopentamine Geranamine Isometheptene Octodrine Propylhexedrine Tuamine Alphapyrrolidinylalkiophenones α-PPP MDPPP MDPV MPBP MPHP MPPP MOPPP Pyrovalerone Cholinergics ABT-089 ABT-418 Anabasine Arecoline Cotinine Cytisine Dianicline Epibatidine Epiboxidine GTS-21 Ispronicline Nicotine Rivanicline Tebanicline Varenicline Convulsants Bicuculline DMCM Gabazine Pentetrazol Picrotoxin Strychnine Thujone Eugeroics Adrafinil Armodafinil Carphedon Modafinil Phenethylamines 4-Bromomethcathinone 4-Fluoroamphetamine 4-Fluoromethamphetamine 4-Fluoromethcathinone 4-Methylmethcathinone 4-MTA Aletamine Amfepentorex Amphechloral Amphetamine Dextroamphetamine, Adderall Amphetaminil Benzphetamine Bupropion Cathinone Chlorphentermine Clenbuterol Clobenzorex Clortermine Diethylpropion Dimethoxyamphetamine Dimethylamphetamine Dimethylcathinone Ephedrine Epinephrine Ethcathinone Ethylamphetamine Fenethylline Fenfluramine Fenproporex Fludorex Furfenorex Levomethamphetamine Lisdexamfetamine MDMA Mefenorex Methamphetamine Methcathinone Methoxyphedrine Methylone Octopamine Ortetamine Parahydroxyamphetamine PCA PIA PMA PMEA PMMA PPAP Phendimetrazine Phenmetrazine Phentermine Phenylephrine Phenylpropanolamine Propylamphetamine Pseudoephedrine Selegiline Synephrine Tiflorex Xylopropamine Phenylaminooxazoles 4-Methyl-aminorex Aminorex Clominorex Fenozolone Fluminorex Pemoline Thozalinone Piperazines 2C-B-BZP BZP GBR-12783 GBR-12935 GBR-13069 GBR-13098 GBR-13119 MeOPP MBZP Vanoxerine Piperidines 2-Benzylpiperidine Desoxypipradrol Diphemethoxidine Ethylphenidate HDMP-28 --Methyl-1-methyl-4β-2-naphthylpiperidine-3β-carboxylate Methylphenidate Dexmethylphenidate Nocaine Phacetoperane Pipradrol Tropanes 3α-Bis-4-fluorophenylmethoxytropane 3α-4-Chlorophenylphenylmethoxytropane 3-Pseudotropyl-4-fluorobenzoate Altropane IACFT Brasofensine CFT WIN 35,428 β-CIT RTI-55 Cocaethylene Cocaine β-CPPIT Dichloropane RTI-111 Difluoropine FE-β-CPPIT FP-β-CPPIT PIT PTT RTI-31 RTI-32 RTI-51 RTI-112 RTI-113 RTI-121 IPCIT RTI-126 RTI-150 RTI-171 RTI-177 RTI-336 Tesofensine Troparil β-CPT, WIN 35,065-2 WF-23 WF-33 WF-60 Xanthines Aminophylline Caffeine Dimethazan Paraxanthine Theobromine Theophylline Others Amineptine Bemegride Benzydamine BPAP Bromantane BTQ Clofenciclan Cypenamine Cyprodenate Diclofensine Dimethocaine Diphenyl prolinol Ethamivan Fencamfamine Feprosidnine Gilutensin GYKI-52895 Hexacyclonate Indanorex Indatraline LR-5182 Mazindol Mesocarb Naphthylisopropylamine Nikethamide Nomifensine Phthalimidopropiophenone Prolintane Sibutramine Yohimbine Zylofuramine See also Sympathomimetic amines v d e Articles about Methamphetamine Methamphetamine Desoxyn Yaba drug Meth mouth Party and play Montana Meth Project Levomethamphetamine Amphetamine Image Gallery Combat Methamphetamine Epidemic Act of 2005 Illinois Methamphetamine Precursor Control Act Crystal Meth Anonymous Retrieved from http://en..org/wiki/Amphetamine Categories: Methamphetamine | Amphetamine alkaloids | Sympathomimetic amines | Stimulants | AmphetaminesHidden categories: All articles with statements | Articles with statements since August 2008 | Articles with statements since October 2007 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages العربية БългарÑ?ки Dansk Deutsch Eesti Ελληνικά Español Français Galego Hrvatski Bahasa Indonesia Italiano עברית Lietuvių Magyar Bahasa Melayu Nederlands 日本語 ‪Norsk bokmÃ¥l‬ ‪Norsk nynorsk‬ Polski Português Română РуÑ?Ñ?кий SlovenÅ¡Ä?ina СрпÑ?ки / Srpski Suomi Svenska Türkçe УкраїнÑ?ька ä¸æ–‡ This page was last modified on 18 August 2008, at 13:3
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