Amphetamine (USAN United States Adopted Names are unique nonproprietary names assigned to pharmaceuticals marketed in the United States. Each name is assigned by the USAN Council, which is co-sponsored by the American Medical Association , the United States Pharmacopeial Convention (USP), and the American Pharmacists Association (APhA)) or amfetamine (INN An International Nonproprietary Name is the official non-proprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization (WHO)[citation needed]. The plethora of named proprietary preparations containing a given substance can lead to confusion about the identity of the active ingredient. INNs) is a psychostimulant Stimulants are psychoactive drugs which induce temporary improvements in either mental or physical function or both. Examples of these kinds of effects may include enhanced alertness, wakefulness, and locomotion, among others. Due to their effects typically having an "up" quality to them, stimulants are also occasionally referred to as & drug A drug, broadly speaking, is any substance that, when absorbed into the body of a living organism, alters normal bodily function. There is no single, precise definition, as there are different meanings in drug control law, government regulations, medicine, and colloquial usage that is known to produce increased wakefulness Wakefulness is a daily recurring brain state in which an individual is conscious and engages in coherent cognitive and behavior responses to the external world such as communication, ambulation, nutritional ingestion and procreation. Being awake is the opposite of being asleep in which most external inputs to the brain are excluded from neural and focus in association with decreased fatigue Fatigue is a state of awareness. It can describe a range of afflictions, varying from a general state of lethargy to a specific work-induced burning sensation within one's muscles. It can be both physical and mental. Physical fatigue is the inability to continue functioning at the level of one's normal abilities. It is ubiquitous in everyday life, and appetite The appetite is the desire to eat food, felt as hunger. Appetite exists in all higher life-forms, and serves to regulate adequate energy intake to maintain metabolic needs. It is regulated by a close interplay between the digestive tract, adipose tissue and the brain. Decreased desire to eat is termed anorexia, while polyphagia is increased eating. Amphetamine is chemically related to methamphetamine Methamphetamine , also known as metamfetamine (INN), dextromethamphetamine, methylamphetamine, N-methylamphetamine, desoxyephedrine, and colloquially as meth (not to be confused with methadone, sometimes referred to as "meth" by opioid users) or crystal meth, is a psychoactive stimulant (psychostimulant or psychoanaleptic) drug. It and lisdexamfetamine Lisdexamfetamine is a psychoactive drug and stimulant prodrug of the phenethylamine and amphetamine chemical classes. Its molecular structure consists of dextroamphetamine coupled with the essential amino acid L-lysine, a class of potent drugs that act by increasing levels of dopamine Dopamine is a catecholamine neurotransmitter that occurs in a wide variety of animals, including both vertebrates and invertebrates. In the brain, this phenethylamine functions as a neurotransmitter, activating the five types of dopamine receptors—D1, D2, D3, D4, and D5—and their variants. Dopamine is produced in several areas of the brain, and norepinephrine Norepinephrine (abbreviated norepi or NE) or noradrenaline (BAN) (abbreviated NA or NAd) is a catecholamine with multiple roles including as a hormone and a neurotransmitter in the brain, inducing euphoria Euphoria is medically recognized as a mental/emotional state defined as a profound sense of well-being. Some do not wish to admit that concepts such as 'euphoria' are essentially metaphysical. Technically, euphoria is an affect, but the term is often colloquially used to define emotion as an intense state of transcendent happiness combined with an.^[2][3] The class includes prescription CNS The central nervous system is the part of the nervous system that coordinates the activity of all parts of the bodies of bilaterian animals—that is, all multicellular animals except sponges and radially symmetric animals such as jellyfish. It contains the majority of the nervous system and consists of the brain and the spinal cord, as well as drugs commonly used to treat attention-deficit hyperactivity disorder Attention-Deficit Hyperactivity Disorder is a neurobehavioral developmental disorder. It is primarily characterized by "the co-existence of attentional problems and hyperactivity, with each behavior occurring infrequently alone" and symptoms starting before seven years of age (ADHD). It is also used to treat symptoms of traumatic brain injury Traumatic brain injury occurs when an external force traumatically injures the brain. TBI can be classified based on severity, mechanism (closed or penetrating head injury), or other features (e.g. occurring in a specific location or over a widespread area). Head injury usually refers to TBI, but is a broader category because it can involve damage (TBI) and the daytime drowsiness symptoms of narcolepsy Narcolepsy is a chronic sleep disorder, or dyssomnia, characterized by excessive daytime sleepiness in which a person experiences extreme fatigue and possibly falls asleep at inappropriate times, such as while at work or at school. Narcoleptics usually experience disturbed nocturnal sleep and an abnormal daytime sleep pattern, which is often, postural orthostatic tachycardia syndrome Postural orthostatic tachycardia syndrome is a condition of dysautonomia, more specifically orthostatic intolerance, in which a change from the supine position to an upright position causes an abnormally large increase in heart rate, called tachycardia. By the definition of POTS used of at the Mayo Clinic, this is not accompanied by a fall in (POTS) and chronic fatigue syndrome Сhronic fatigue syndrome is the most common name given to a variably debilitating disorder or disorders generally defined by persistent fatigue unrelated to exertion and not substantially relieved by rest, and accompanied by the presence of other specific symptoms for a minimum of six months. The disorder may also be referred to as post-viral (CFS). Initially, amphetamine was more popularly used to diminish the appetite An anorectic or anorexic , also known as anorexigenic or appetite suppressant, is a dietary supplements and/or drug which reduces appetite, food consumption, and as a result, causes weight loss to occur and to control weight. Brand names of the drugs that contain, or metabolize into, amphetamine include Adderall Adderall is a brand-name psychostimulant medication composed of racemic amphetamine aspartate monohydrate, racemic amphetamine sulfate, dextroamphetamine saccharide and dextroamphetamine sulfate, which is thought to work by increasing the amount of dopamine and norepinephrine in the brain. Adderall is widely reported to increase alertness, libido,, Vyvanse Lisdexamfetamine is a psychoactive drug and stimulant prodrug of the phenethylamine and amphetamine chemical classes. Its molecular structure consists of dextroamphetamine coupled with the essential amino acid L-lysine, and Dexedrine Dextroamphetamine is a psychostimulant drug which is known to produce increased wakefulness and focus in association with decreased fatigue and decreased appetite. Drugs with similar psychoactive properties can be referred to or described as "amphetamine analogues", "amphetamine-like", or having "amphetaminergic", as well as Benzedrine Benzedrine is the trade name of the racemic mixture of amphetamine . It was marketed under this brandname in the USA by Smith, Kline & French in the form of inhalers, starting in 1928. Benzedrine was used to enlarge nasal and bronchial passages and it is closely related to other stimulants produced later, such as dextroamphetamine (d- in the past.

The drug is also used recreationally Recreational drug use is the use of a psychoactive substance with the intention of creating or enhancing recreational experience. Such use is controversial, however, often being considered to be also drug abuse, and it is often illegal. Also, it may overlap with other uses, such as medicinal , performance enhancement, and entheogenic (spiritual) and as a performance enhancer As they have become more widely used and sophisticated, various organizations have banned their use for doping in sport, developed testing and enforcement procedures to prevent athletes from using these drugs, and penalized athletes caught using these drugs. Recreational users of amphetamine have coined numerous street names for amphetamine, such as speed and crank. The European Monitoring Centre for Drugs and Drug Addiction The European Monitoring Centre for Drugs and Drug Addiction is an agency of the European Union. Established in 1993, the EMCDDA is located in Lisbon, Portugal reports the typical retail price of amphetamine in Europe Europe is one of the world's seven continents. Comprising the westernmost peninsula of Eurasia, Europe is generally divided from Asia to its east by the water divide of the Ural Mountains, the Ural River, the Caspian Sea, the Caucasus region (Specification of borders) and the Black Sea to the southeast. Europe is bordered by the Arctic Ocean and varied between €10 and €15 ($14.38 to $21.55 USD The United States dollar is the official currency of the United States. The U.S. dollar is normally abbreviated as the dollar sign, $, or as USD or US$ to distinguish it from other dollar-denominated currencies and from others that use the $ symbol. It is divided into 100 cents) a gram in half of the reporting countries.^[4] The name amphetamine is derived from its chemical name: alpha-methyl In chemistry, a methyl group is a hydrophobic alkyl functional group named after methane (C phenethylamine Phenethylamine is a natural monoamine alkaloid, trace amine, and psychoactive drug with stimulant effects. In the mammalian central nervous system, phenethylamine is believed to function as a neuromodulator or neurotransmitter. It is biosynthesized from the amino acid phenylalanine by enzymatic decarboxylation. Besides mammals, phenethylamine is.

History

Amphetamine was first synthesized in 1887 by the Romanian Romania (pronounced /roʊˈmeɪniə/ roe-MAY-nee-ə; dated: Rumania, Lolmania; Romanian: România [romɨˈni.a] ( listen)) is a country located at the crossroads of Central and Southeastern Europe, north of the Balkan Peninsula, on the Lower Danube, within and outside the Carpathian arch, bordering on the Black Sea. Almost all of the Danube Delta chemist Lazăr Edeleanu in Berlin, Germany Berlin (English pronunciation: /bɜrˈlɪn/; German pronunciation: [bɛɐ̯ˈliːn] ) is the capital city and one of 16 states of Germany. With a population of 3.4 million people, Berlin is Germany's largest city. It is the second most populous city proper and the eighth most populous urban area in the European Union. Located in northeastern.^[5] He named the compound phenylisopropylamine. It was one of a series of compounds related to the plant derivative ephedrine Ephedrine is a sympathomimetic amine commonly used as a stimulant, appetite suppressant, concentration aid, decongestant, and to treat hypotension associated with anaesthesia, which had been isolated from Ma-Huang that same year by Nagayoshi Nagai Nagai Nagayoshi was a notable Japanese organic chemist and pharmacologist, best known for his study of ephedrine.^[6] No pharmacological use was found for amphetamine until 1927, when pioneer psychopharmacologist Psychopharmacology is the study of drug-induced changes in mood, sensation, thinking, and behavior Gordon Alles resynthesized and tested it on himself, in search of an artificial replacement for ephedrine. From 1933 or 1934 Smith, Kline and French GlaxoSmithKline plc is a United Kingdom-based pharmaceutical, biological, and healthcare company. GSK is the world's second largest pharmaceutical company and a research-based company with a wide portfolio of pharmaceutical products covering anti-infectives, central nervous system, respiratory, gastro-intestinal/metabolic, oncology, and vaccines began selling the volatile base form of the drug as an inhaler An inhaler or puffer is a medical device used for delivering medication into the body via the lungs. It is mainly used in the treatment of asthma and Chronic Obstructive Pulmonary Disease . Zanamivir (Relenza), used to treat influenza, must be administered via inhaler under the trade name A trade name, also known as a trading name or a business name, is the name which a business trades under for commercial purposes, although its registered, legal name, used for contracts and other formal situations, may be another Benzedrine Benzedrine is the trade name of the racemic mixture of amphetamine . It was marketed under this brandname in the USA by Smith, Kline & French in the form of inhalers, starting in 1928. Benzedrine was used to enlarge nasal and bronchial passages and it is closely related to other stimulants produced later, such as dextroamphetamine (d-, useful as a decongestant but readily usable for non-medical purposes.^[7] One of the first attempts at using amphetamine as a scientific study was done by M. H. Nathanson, a Los Angeles physician, in 1935. He studied the subjective effects of amphetamine in 55 hospital workers who were each given 20 mg of Benzedrine. The two most commonly reported drug effects were "a sense of well being and a feeling of exhilaration" and "lessened fatigue in reaction to work".^[8] During World War II amphetamine was extensively used to combat fatigue and increase alertness in soldiers. After decades of reported abuse, the FDA The Food and Drug Administration is a Government agency of the United States Department of Health and Human Services and is responsible for regulating and supervising the safety of foods, tobacco products, dietary supplements, Medication drugs, vaccines, Biopharmaceutical, blood transfusion, medical devices, Electromagnetic radiation emitting banned Benzedrine inhalers, and limited amphetamine to prescription use in 1965, but non-medical use remained common. Amphetamine became a schedule II drug under the Controlled Substances Act The Controlled Substances Act was enacted into law by the Congress of the United States as Title II of the Comprehensive Drug Abuse Prevention and Control Act of 1970. The CSA is the federal U.S. drug policy under which the manufacture, importation, possession, use and distribution of certain substances is regulated. The Act also served as the in 1971.

The related compound methamphetamine Methamphetamine , also known as metamfetamine (INN), dextromethamphetamine, methylamphetamine, N-methylamphetamine, desoxyephedrine, and colloquially as meth (not to be confused with methadone, sometimes referred to as "meth" by opioid users) or crystal meth, is a psychoactive stimulant (psychostimulant or psychoanaleptic) drug. It was first synthesized from ephedrine Ephedrine is a sympathomimetic amine commonly used as a stimulant, appetite suppressant, concentration aid, decongestant, and to treat hypotension associated with anaesthesia in Japan Japan is an island state in East Asia. Located in the Pacific Ocean, it lies to the east of the Sea of Japan, China, North Korea, South Korea and Russia, stretching from the Sea of Okhotsk in the north to the East China Sea and Taiwan in the south. The characters that make up Japan's name mean "sun-origin", which is why Japan is in 1918 by chemist Akira Ogata Akira Ogata was a Japanese chemist and the first to synthesize methamphetamine in crystalline form in 1919, via reduction of ephedrine using red phosphorus Elemental phosphorus can exist in several allotropes; the most common of which are white and red solids. There are also violet and black phosphorus solids, and gaseous diphosphorus and iodine Iodine , from Greek: ιώδης iodes, meaning violet or purple, is a chemical element that has the symbol I and the atomic number 53. The pharmaceutical Pervitin was a tablet of 3 mg methamphetamine which was available in Germany from 1938 and widely used in the Wehrmacht The Wehrmacht (German pronunciation: [ˈveːɐ̯maxt] Defence Force) was the unified armed forces of Germany from 1935 to 1945. It consisted of the Heer (army), the Kriegsmarine (navy) and the Luftwaffe (air force), 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 less frequently and with increasing discrimination.^[9]

In 1997 and 1998,^[10][11] researchers at Texas A&M University Texas A&M University, often referred to as A&M or TAMU, is a coeducational public research university located in College Station, Texas. It is the flagship institution of the Texas A&M University System. The seventh-largest university in the United States, A&M enrolls over 48,000 students in ten academic colleges. Texas A&M's claimed to have found amphetamine and methamphetamine in the foliage of two Acacia Acacia is a genus of shrubs and trees belonging to the subfamily Mimosoideae of the family Fabaceae, first described in Africa by the Swedish botanist Carl Linnaeus in 1773. Many non-Australian species tend to be thorny, whereas the majority of Australian Acacias are not. They are pod-bearing, with sap and leaves typically bearing large amounts of species native to Texas, A. berlandieri and A. rigidula. Previously, both of these compounds had been thought to be human inventions. These findings have never been duplicated, and the analyses are believed by many biochemists to be the result of experimental error, and as such the validity of the report has come into question. Alexander Shulgin, one of the most experienced biochemical investigators and the discoverer of many new psychotropic substances, has tried to contact the Texas A&M researchers and verify their findings. The authors of the paper have not responded; natural amphetamine remains most likely a false discovery.^[12]

Contraindications

Amphetamine elevates cardiac output and blood pressure making it dangerous for use by patients with a history of heart disease or hypertension. Amphetamine can cause a life-threatening complication in patients taking MAOI antidepressants. The use of amphetamine and amphetamine-like drugs is contraindicated in patients with narrow-angle glaucoma or anatomically narrow angles. Like other sympathomimetic amines, amphetamine can induce transient mydriasis. In patients with narrow angles, pupillary dilation can provoke an acute attack of angle-closure glaucoma. These agents should also be avoided in patients with other forms of glaucoma, as mydriasis may occasionally increase intraocular pressure.^[13]

Amphetamine has been shown to pass through into breast milk. Because of this, mothers taking amphetamine are advised to avoid breastfeeding during their course of treatment.^[14]

Major neurobiological mechanisms

Primary sites of action

Amphetamine exerts its behavioral effects by modulating several key neurotransmitters in the brain, including dopamine, serotonin, and norepinephrine. However, the activity of amphetamine throughout the brain appears to be specific;^[15] 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.^[15]

The major neural systems affected by amphetamine are largely implicated in the brain’s reward circuitry. Moreover, neurotransmitters involved in various reward pathways of the brain appear to be the primary targets of amphetamine.^[16] 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 striatum, the nucleus accumbens, and the ventral striatum—have been found to be primary sites of amphetamine action.^[17][18]

The fact that amphetamine influences neurotransmitter activity specifically in regions implicated in reward provides insight into the behavioral consequences of the drug, such as the stereotyped onset of euphoria.^[18] A better understanding of the specific mechanisms by which amphetamine operates may increase our ability to treat amphetamine addiction, as the brain’s reward circuitry has been widely implicated in addictions of many types.^[19]

Endogenous amphetamines

Amphetamine has been found to have several endogenous analogues; that is, molecules of a similar structure found naturally in the brain.^[20] l-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.^[21] 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 amphetamine affects 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.^[20][22] 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.^{[16][23][24][25]}

The former hypothesis is backed by data demonstrating that injections of amphetamine result in rapid increases of cytosolic dopamine concentrations.^[25] Amphetamine is believed to interact with dopamine-containing synaptic vesicles in the axon terminal. Amphetamine is a substrate for a specific neuronal synaptic vesicle uptake transporter called VMAT2. When amphetamine is taken up by VMAT2, the vesicle releases dopamine molecules into the cytosol in exchange. The redistributed dopamine is then believed to interact with DAT to promote reverse transport.^[20] Calcium may be a key molecule involved in the interactions between amphetamine and VMATs.^[22]

The latter hypothesis postulates a direct interaction between amphetamine and the DAT. The activity of DAT is believed to depend on specific phosphorylating kinases, such as protein kinase c, specifically PKC-β.^[25] Upon phosphorylation, DAT undergoes a conformational change that results in the transportation of DAT-bound dopamine from the extracellular to the intracellular environment.^[24] 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.^[23] Thus, beyond inhibiting reuptake of dopamine, amphetamine also stimulates the release of dopamine molecules into the synapse.^[16]

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.^[25] 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.^[26] Like DAT, the serotonin transporter SERT can be induced to operate in reverse upon stimulation by amphetamine.^[27] This mechanism is thought to rely on the actions of calcium ions, as well as on the proximity of certain transporter proteins.^[27]

The interaction between amphetamine and serotonin is only apparent in particular regions of the brain, such as the mesocorticolimbic 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.^[26] 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.^[26]

The proposed ability of amphetamine to increase excitability of glutamatergic pathways may be of significance when considering serotonin-mediated addiction.^[26] An additional behavioral consequence may be the stereotyped locomotor stimulation that occurs in response to amphetamine exposure.^[21]

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.

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.^[28]

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 ecstasy, 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 dextro-amphetamine saccharate
• 1/4 dextro-amphetamine sulfate
• 1/4 (racemic amphetamine) aspartate monohydrate
• 1/4 (racemic 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. Amphetamine, unlike similar dopamine acting stimulant cocaine, does not act as a ligand but does slow reuptake by a secondary acting mechanism through the phosphorylation of dopamine transporters.^[29] The primary action is through the increased amphetamine concentration which 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 Associated 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, increased/distorted sensations, hyperactivity, dilated pupils, flushing, restlessness, dry mouth, erectile dysfunction, headache, tachycardia, increased breathing rate, increased blood pressure, fever, sweating, diarrhea, constipation, blurred vision, impaired speech, dizziness, uncontrollable movements or shaking, insomnia, numbness, palpitations, and arrhythmia. In high doses or chronic use convulsions, dry or itchy skin, acne, pallor can occur.^{[32][33][34][35]}

Occasionally amphetamine use in males can cause an odd and sometimes startling effect in which the penis when flaccid appears to have shrunk due to vasoconstriction. Upon erection the penis returns to normal size.^[36] However, this may simply be an urban myth. "There are no published scientific reports which provide objective evidence that penile shrinkage occurs as an effect of amphetamine use."^[37]

Young adults who abuse amphetamine may be at greater risk of suffering a heart attack. In a study published in the journal Drug and Alcohol Dependence,^[38] 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.^[39]

Psychological effects

Psychological effects can include euphoria, anxiety, increased libido, alertness, concentration, energy, self-esteem, self-confidence, sociability, irritability, aggression, psychosomatic disorders, psychomotor agitation, hubris, excessive feelings of power and superiority, repetitive and obsessive behaviors, paranoia, and with chronic and/or high doses, amphetamine psychosis can occur.^[32]

Based on a study in rats, amphetamine use during adolescence may impair adult working memory.^[40]

Withdrawal effects

Withdrawal from chronic use of amphetamine can include anxiety, depression, agitation, fatigue, excessive sleeping, increased appetite, short temper, psychosis and suicidal thoughts.^[41]

Overdose

An amphetamine overdose is rarely fatal but can lead to a number of different symptoms, including psychosis, chest pain, and hypertension.

Psychosis

Abuse of amphetamines can result in a stimulant psychosis that can present as a number of psychotic disorders (ie. paranoia, hallucinations, delusions). The intensity and duration of symptoms may vary, but unlike true psychotic disorders (ie. schizophrenia), stimulant psychoses are not considered to be permanent and will eventually resolve upon discontinuation of the drug's use.^{[citation needed]}

Dependence and addiction

Tolerance is developed rapidly in amphetamine abuse, therefore periods of extended use require increasing amounts of the drug in order to achieve the same effect.^[42]

Performance-enhancing use

Amphetamine is used by some college and high-school students as a study and test-taking aid.^[43] Amphetamine works by increasing energy levels, concentration, and motivation, thus allowing students to study for an extended period of time.

Amphetamine has been, and is still, used by militaries around the world. British troops used 72 million amphetamine tablets in the second world war^[44] and the RAF used so many that "Methedrine won the Battle of Britain" according to one report.^[45] American bomber pilots use amphetamine ("go pills") to stay awake during long missions. The Tarnak Farm incident, in which an American F-16 pilot killed several friendly Canadian soldiers on the ground, was blamed by the pilot on his use of amphetamine.^[46] A nonjudicial hearing rejected the pilot's claim.^{[citation needed]}

Amphetamine is also used by some professional,^[47] collegiate^[48] and high school^[48] athletes for its strong stimulant effect. Energy levels are perceived to be dramatically increased and sustained, which is believed to allow for more vigorous and longer play. However, at least one study has found that this effect is not measurable.^[49] The use of amphetamine during strenuous physical activity can be extremely dangerous, especially when combined with alcohol, 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".^[50] In 2006, the MLB banned the use of amphetamine. The ban is enforced through periodic drug-testing. However, the MLB has received some criticism because the consequences for amphetamine use are dramatically less severe than for anabolic steroid use, with the first offense bringing only a warning and further testing.^[51][52][53]

Amphetamine was formerly in widespread use by truck drivers^[54] to combat symptoms of somnolence and to increase their concentration during driving, especially in the decades prior to the signing by former president Ronald Reagan of Executive Order 12564, which initiated mandatory random drug testing of all truck drivers and employees of other DOT-regulated industries. Although implementation of the order on the trucking industry was kept to a gradual rate in consideration of its projected effects on the national economy, in the decades following the order, amphetamine and other drug abuse by truck drivers has since dropped drastically. (See also Truck driver—Implementation of drug detection).

Detection in body fluids

Amphetamine is frequently measured in urine as part of a drug abuse testing program, in plasma or serum to confirm a diagnosis of poisoning in hospitalized victims, or in whole blood to assist in the forensic investigation of a traffic or other criminal violation or a case of sudden death. Techniques such as immunoassay may cross-react with a number of sympathomimetics drugs, so chromatographic methods specific for amphetamine should be employed to prevent false positive results. Chiral techniques may be employed to help distinguish the source of the drug, whether obtained legally (via prescription) or illicitly, or possibly as a result of formation from a prodrug such as lisdexamfetamine or selegiline. Chiral separation is needed to assess the possible contribution of l-methamphetamine (Vicks Inhaler) toward a positive test result.^[55][56][57]

Cultural impact of amphetamine

From the 1960s onward, amphetamine has been popular with many youth subcultures in Britain (and other parts of the world) as a recreational drug. It has been commonly used by mods, skinheads, punks, goths, gangstas, and casuals in all night soul and ska dances, punk concerts, basement shows and fighting on the terraces by casuals.^{[citation needed]}

The hippie counterculture was very critical of amphetamines due to the behaviors they cause; in an interview with the Los Angeles Free Press in 1965, beat writer Allen Ginsberg commented that "Speed is antisocial, paranoid making, it's a drag... all the nice gentle dope fiends are getting screwed up by the real horror monster Frankenstein speed freaks who are going round stealing and bad-mouthing everybody".^[58]

In literature

The writers of the Beat Generation used amphetamine extensively, mainly under the Benzedrine brand name. Jack Kerouac was a particularly avid user of amphetamine, which was said to provide him with the stamina needed to work on his novels for extended periods of time.^[59]

Scottish author Irvine Welsh often portrays drug use in his novels, though in one of his journalism works he comments on how drugs (including amphetamine) 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.^[60]

Amphetamine is frequently mentioned in the work of American journalist Hunter S. Thompson. Speed appears not only amongst the inventory of drugs Thompson consumed for what could broadly be defined as recreational purposes, but also receives frequent, explicit mention as an essential component of his writing toolkit,^[61] such as in his "Author's Note" in Fear and Loathing on the Campaign Trail '72.^[62]

"One afternoon about three days ago [the publishers] showed up at my door with no warning, and loaded about forty pounds of supplies into the room: two cases of Mexican beer, four quarts of gin, a dozen grapefruits, and enough speed to alter the outcome of six Super Bowls. ... Meanwhile, [...] with the final chapter still unwritten and the presses scheduled to start rolling in twenty-four hours . . . . unless somebody shows up pretty soon with extremely powerful speed, there might not be a final chapter. About four fingers of king-hell Crank would do the trick, but I am not optimistic."

In mathematics

Famous mathematician Paul Erdős took amphetamine, and once won a bet from his friend Ron Graham, who bet him $500 that he could not stop taking the drug for a month.^[63] Erdős won the bet, but complained during his abstinence that mathematics had been set back by a month: "Before, when I looked at a piece of blank paper my mind was filled with ideas. Now all I see is a blank piece of paper." After he won the bet, he promptly resumed his amphetamine habit.

In music

Many songs have been written about amphetamine, for example in the track entitled "St. Ides Heaven" from singer/songwriter, Elliott Smith's self-titled album. Semi Charmed Life by Third Eye Blind also references amphetamine. It has also influenced the aesthetics of many rock'n'roll bands (especially in the garage rock, mod R&B, death rock, punk/hardcore, gothic rock and extreme heavy metal genres). Hüsker Dü, Jesus and Mary Chain's and The Who were keen amphetamine users early in their existence. Land Speed Record is an allusion to Hüsker Dü's amphetamine use.^{[citation needed]}

Many rock'n'roll bands have named themselves after amphetamine and drug slang surrounding it. For example Mod revivalists, The Purple Hearts named themselves after the amphetamine tablets popular with mods during the 1960s, as did the Australian band of the same name during the mid 1960's.^{[citation needed]} The Amphetameanies, a ska-punk band, are also named after amphetamine, but also imitate its effects. Dexy's Midnight Runners, of number one hit "Come On Eileen" are named after Dexedrine. Motorhead named themselves after the slang for an amphetamine addict.^{[citation needed]}

In film

Producer David O. Selznick was an amphetamine user, and would often dictate long and rambling memos under the influence of amphetamine to his directors.^[64] The documentary Shadowing The Third Man relates that Selznick introduced Third Man director Carol Reed to the use of amphetamine, which allowed Reed to bring the picture in below budget and on schedule by filming nearly 22 hours at a time.^[65]

Garrett Scott's documentary Cul-de-Sac: A Suburban War Story has a brief history of the manufacture and spread of amphetamine, and of its effects.^[66]

In the film Requiem for a Dream, Ellen Burstyn portrays Sara Goldfarb, an elderly widow who becomes addicted to weight-loss amphetamine pills. After suffering from amphetamine psychosis, she is hospitalized against her will, undergoes electro-convulsive therapy, and later on was confined at a mental asylum.^[67]

The title of the 2009 movie Amphetamine plays on the double meaning of the word in Chinese - besides the name for the drug it also means 'isn't this his fate?' which figuratively ties to the movie's plot. The word is transliterated as 安 非 他 命 - "ān fēi tā mìng" - and as commonly happens with transliteration of non-Chinese terms each character has independent meaning as an individual unrelated word.

Legal issues

• In the United Kingdom, amphetamines are regarded as Class B drugs. The maximum penalty for unauthorized 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).^[68]
• 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 gel capsules.
• In the United States, amphetamine and methamphetamine are Schedule II drugs, classified as CNS (central nervous system) stimulants.^[69] 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.^[70]

Prodrugs

A number of substances have been shown to produce amphetamine and/or methamphetamine as metabolites, including amphetaminil, benzphetamine, clobenzorex, dimethylamphetamine, ethylamphetamine, famprofazone, fencamine, fenethylline, fenproporex, furfenorex, lisdexamfetamine, mefenorex, mesocarb, prenylamine, propylamphetamine, and selegiline, among others.^[71][72] These compounds may produce false positives for amphetamine on drug tests.^[71][72]

See also

• Psychostimulant
• Methamphetamine
• Dextroamphetamine
• Adderall
• Lisdexamfetamine
• Amphetamine psychosis
• Attention-deficit hyperactivity disorder
• Methylphenidate
• Benzylpiperazine
• Clandestine chemistry
• Ethylamphetamine
• Phenethylamine
• Propylamphetamine
• Releasing agent

References and notes

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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
• U.S. National Library of Medicine: Drug Information Portal - Amphetamine

Categories: Stimulants | Amphetamines | Sympathomimetic amines | Anorectics | German inventions | Monoamine oxidase inhibitors | Dopamine agonists | Norepinephrine reuptake inhibitors | Serotonin receptor agonists | Drugs acting on the nervous system | Drugs acting on the cardiovascular system | Euphoriants

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• Methamphetamine: Encyclopedia
• Methamphetamine Precursor Control Act: Encyclopedia

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