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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 "good"[1]; nasal 75%; rectal 95–99%; intravenous 100%
Protein binding	15–40%
Metabolism	Hepatic (CYP2D6[2])
Half life	10 hours for d-isomer, 13 hours for l-isomer
Excretion	Renal; significant portion unaltered
Therapeutic considerations
Pregnancy cat.	C(US) Image File history File links Size of this preview: 799 × 600 pixelsFull resolution (854 × 641 pixel, file size: 111 KB, MIME type: image/png) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Amphetamine User:Sbrools/Gallery ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System containing Psychoanaleptics. ... PubChem is a database of chemical molecules. ... The DrugBank database available at the University of Alberta is a unique bioinformatics and cheminformatics resource that combines detailed drug (i. ... A chemical formula is an easy way of expressing information about the atoms that constitute a particular chemical compound. ... For other uses, see Carbon (disambiguation). ... This article is about the chemistry of hydrogen. ... General Name, symbol, number nitrogen, N, 7 Chemical series nonmetals Group, period, block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... Synonyms (in ancient Greek, συν (syn) = plus and όνομα (onoma) = name) are different words with similar or identical meanings. ... The melting point of a solid is the temperature range at which it changes state from solid to liquid. ... Solubility is a chemical property referring to the ability for a given substance, the solute, to dissolve in a solvent. ... This article is about the properties of water. ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... A drugs efficacy may be affected by the degree to which it binds to the proteins within blood plasma. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... The liver is an organ in vertebrates including humans. ... Cytochrome P450 2D6 (CYP2D6), a member of the cytochrome P450 mixed-function oxidase system, is one of the most important enzymes involved in the metabolism of xenobiotics in the body. ... The biological half-life of a substance is the time required for half of that substance to be removed from an organism by either a physical or a chemical process. ... The kidneys are important excretory organs in vertebrates. ... Kidneys viewed from behind with spine removed The kidneys are bean-shaped excretory organs in vertebrates. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ... For other uses of terms redirecting here, see US (disambiguation), USA (disambiguation), and United States (disambiguation) Motto In God We Trust(since 1956) (From Many, One; Latin, traditional) Anthem The Star-Spangled Banner Capital Washington, D.C. Largest city New York City National language English (de facto)1 Demonym American...
Legal status	Controlled (S8)(AU) Schedule III(CA) Class B(UK) Schedule II(US) Prescription-Only Medicine The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... The Standard for the Uniform Scheduling of Drugs and Poisons, abbreviated SUSDP, is a document used in the regulation of drugs and poisons in Australia. ... For other uses, see Australia (disambiguation). ... The Controlled Drugs and Substances Act is Canadas federal drug control statute. ... Motto (Latin for From Sea to Sea) Anthem O Canada Royal anthem: God Save the Queen Capital Ottawa Largest city Toronto Official languages English, French Government Parliamentary democracy and federal constitutional monarchy  -  Monarch Queen Elizabeth II  -  Governor General Michaëlle Jean  -  Prime Minister Stephen Harper Establishment  -  Act of Union February... The Misuse of Drugs Act 1971 is an Act of Parliament, by which the United Kingdom aims to control the possession and supply of numerous drugs and drug-like substances, as listed under the Act, and to enable international co-operation against illegal drug trafficking. ... This box:      The Controlled Substances Act (CSA) 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. ... For other uses of terms redirecting here, see US (disambiguation), USA (disambiguation), and United States (disambiguation) Motto In God We Trust(since 1956) (From Many, One; Latin, traditional) Anthem The Star-Spangled Banner Capital Washington, D.C. Largest city New York City National language English (de facto)1 Demonym American...
Routes	Oral, intravenous, vaporization, insufflation, suppository, sublingual

Amphetamine is a prescription CNS stimulant 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. The name is also used to refer to the class of compounds derived from amphetamine, often referred to as the substituted amphetamines. In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body. ... In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... Evaporation is the process whereby atoms or molecules in a liquid state (or solid state if the substance sublimes) gain sufficient energy to enter the gaseous state. ... Insufflation (Latin insufflatio blowing on or into) is the practice of inhaling substances into a body cavity. ... Suppository casting mould A suppository is a drug delivery system that is inserted either into the rectum (rectal suppository), vagina (vaginal suppository) or urethra (urethral suppository) where it dissolves. ... Sublingual, literally under the tongue, from Latin, refers to a pharmacological route of administration in which certain drugs are entered directly into the bloodstream via absorption under the tongue. ... A diagram showing the CNS: 1. ... ... Attention-Deficit Hyperactivity Disorder (ADHD), is a neurobehavioural developmental disorder[1] [2] [3] affecting about 3-5% of the worlds population under the age of 19[4]. It typically presents itself during childhood, and is characterized by a persistent pattern of inattention and/or hyperactivity, as well as forgetfulness... Traumatic brain injury (TBI), traumatic injuries to the brain, also called intracranial injury, or simply head injury, occurs when a sudden trauma causes brain damage. ... For other uses, see Narcolepsy (disambiguation). ... Chronic fatigue syndrome (CFS) is one of several names given to a poorly understood, highly debilitating disorder of uncertain cause/causes, which is thought to affect approximately 4 per 1,000 adults[1] in the United States and other countries, and a smaller fraction of children. ... Anorectics, anorexigenics or appetite suppressants are drugs that reduce the desire to eat (anorectic, from the Greek an- = not and oreg- = extend, reach). (Anorectic is also a term for an anorexic person, a person suffering from Anorexia nervosa. ... Adderall XR 15 mg capsule Adderall is a brand-name pharmaceutical psychostimulant composed of mixed amphetamine salts. ... Dextroamphetamine (also known as dextroamphetamine sulfate, dexamphetamine, dexedrine, Dexampex, Ferndex, Oxydess II, Robese, Spancap #1, and, informally, Dex), a stereoisomer of amphetamine, is an indirect-acting stimulant that releases norepinephrine from nerve terminals, thus promoting nerve impulse transmission. ... Club drugs are a loosely defined category of recreational drugs which are popular at dance clubs, parties, and rock concerts. ... The substituted amphetamines are a family of amphetamine-based stimulants, hallucinogens, and other recreational drugs. ...

History

Amphetamine was first synthesized in 1887 by Lazăr Edeleanu in Berlin, Germany.^[3] 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.^[4] 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 useable for non-medical purposes too).^[5] 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. Lazar Edeleanu (1861-1941) was a famous Romanian chemist. ... This article is about the capital of Germany. ... Ephedrine (EPH) is a sympathomimetic amine similar in structure to the synthetic derivatives amphetamine and methamphetamine. ... Nagayoshi Nagai (August 8, 1844 - February 10, 1929) was a notable Japanese chemist, best known for his study of ephedrine. ... Psychopharmacology is the study of the effects of any psychoactive drug that acts upon the mind by affecting brain chemistry. ... GlaxoSmithKline (GSK) plc is a pharmaceutical and healthcare company, one of the largest in the world, in fact the second largest pharmaceutical company. ... This article does not cite any references or sources. ... The United States Food and Drug Administration is the government agency responsible for regulating food, dietary supplements, drugs, cosmetics, medical devices, biologics and blood products in the United States. ... This article does not cite any references or sources. ... This box:      The Controlled Substances Act (CSA) 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 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 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 less frequently and under much more restricted circumstances.^[6] This article is about the psychostimulant, d-methamphetamine. ... Akira Ogata (Ogata Akira, 緒方 章, 1887-1978) was a Japanese chemist and the inventor of methamphetamine in 1919. ... General Name, Symbol, Number phosphorus, P, 15 Chemical series nonmetals Group, Period, Block 15, 3, p Appearance waxy white/ red/ black/ colorless Atomic mass 30. ... For other uses, see Iodine (disambiguation). ... Combatants Allied powers: China France Great Britain Soviet Union United States and others Axis powers: Germany Italy Japan and others Commanders Chiang Kai-shek Charles de Gaulle Winston Churchill Joseph Stalin Franklin Roosevelt Adolf Hitler Benito Mussolini Hideki Tōjō Casualties Military dead: 17,000,000 Civilian dead: 33,000... Methamphetamine is a synthetic stimulant drug which induces a strong feeling of euphoria and is highly addictive. ...

In 1997^[7] and 1998,^[8] researchers at Texas A&M 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.^[9] Texas A&M University redirects here. ... For other uses, see Acacia (disambiguation). ... For other uses, see Texas (disambiguation). ... Binomial name Acacia berlandieri Benth. ... Binomial name Benth. ...

Indications

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 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. For other uses, see Dopamine (disambiguation). ... Agonists In pharmacology an agonist is a substance that binds to a specific receptor and triggers a response in the cell. ... Norepinephrine (INN)(abbr. ... Agonists In pharmacology an agonist is a substance that binds to a specific receptor and triggers a response in the cell. ... For the professional wrestling stable, see Ravens Nest#Serotonin. ... Agonists In pharmacology an agonist is a substance that binds to a specific receptor and triggers a response in the cell. ... Monoamine oxidase inhibitors (MAOIs) are a class of antidepressant drugs prescribed for the treatment of depression. ... Vitamin R redirects here. ... Methylphenidate (C14H19NO2), or MPH, is an amphetamine-like prescription stimulant commonly used to treat Attention Deficit Hyperactivity Disorder (ADHD) in children and adults. ... DISCLAIMER Please remember that Wikipedia is offered for informational use only. ... This article is about the term salt as referred to in chemistry. ... Adderall® CII is a pharmaceutical amphetamine usually used to treat attention deficit disorder, attention-deficit hyperactivity disorder, and narcolepsy. ...

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. Methylphenidate (C14H19NO2), or MPH, is an amphetamine-like prescription stimulant commonly used to treat Attention Deficit Hyperactivity Disorder (ADHD) in children and adults. ... Methylphenidate (C14H19NO2), or MPH, is an amphetamine-like prescription stimulant commonly used to treat Attention Deficit Hyperactivity Disorder (ADHD) in children and adults. ...

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. For other uses, see Narcolepsy (disambiguation). ...

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. Heart disease is an umbrella term for a number of different diseases which affect the heart and as of 2007 it is the leading cause of death in the United States,[1] and England and Wales. ... For other forms of hypertension, see Hypertension (disambiguation). ... Anorexia can refer to: Anorexia nervosa, an eating disorder in which people do not eat correctly due to the obsessive fear of weight gain Anorexia (symptom), the general symptom of decreased appetite Sexual anorexia, a term used to describe a lack of appetite for sex. ... Monoamine oxidase inhibitors (MAOIs) are a class of antidepressant drugs prescribed for the treatment of depression. ...

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.^[10]

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;^[11] 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] For other uses, see Dopamine (disambiguation). ... For the professional wrestling stable, see Ravens Nest#Serotonin. ... Norepinephrine (INN)(abbr. ... For other uses, see Dopamine (disambiguation). ... The dopamine receptors are a class of metabotropic G-protein-coupled receptors with the neurotransmitter dopamine as their endogenous ligand. ... For other uses, see Hippocampus (disambiguation). ...

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.^[14][15] For other uses, see Dopamine (disambiguation). ... The mesolimbic pathway is one of the neural pathways in the brain that link the ventral tegmentum in the midbrain to the nucleus accumbens in the limbic system. ... The mesocortical pathway is a neural pathway which connects the ventral tegmentum to the cortex, particularly the frontal lobes. ... The nucleus accumbens (NAcc), also known as the accumbens nucleus or as the nucleus accumbens septi (Latin for nucleus leaning against the septum), is a collection of neurons located where the head of the caudate and the anterior portion of the putamen meet just lateral to the septum pellucidum. ... Coronal slices of human brain showing the basal ganglia, the striatum and pallidum globus pallidus: external segment (GPe), subthalamic nucleus (STN), globus pallidus: internal segment (GPi), and substantia nigra (SN). ...

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.^[16] 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.^[17] Look up euphoria, euphoric in Wiktionary, the free dictionary. ... This article is about the concept of addiction. ...

Endogenous Amphetamines

Amphetamine has been found to have several endogenous analogues; that is, molecules of a similar structure found naturally in the brain.^[18] 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. Phenyl alanine is an α-amino acid with the formula HO2CCH(NH2)CH2C6H5. ...

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.^[19] This specific action hints at the hedonic response to the drug as well as to the drug’s addictive quality. For other uses, see Dopamine (disambiguation). ... For other uses, see Dopamine (disambiguation). ... Synapses allow nerve cells to communicate with one another through axons and dendrites, converting electrical signals into chemical ones. ...

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.^[20][21] 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.^{[22][23][24][25]} In a neuron, synaptic vesicles, also called neurotransmitter vesicles, store the various neurotransmitters that are released during calcium-regulated exocytosis at the presynaptic terminal into the synaptic cleft of a synapse. ... For other uses, see Dopamine (disambiguation). ... The dopamine transporter or DAT is a monoamine transporter that is specific for clearing the neurotransmitter dopamine out of the synaptic cleft and into a glial cell or the presynaptic neuron. ... The dopamine transporter or DAT is a monoamine transporter that is specific for clearing the neurotransmitter dopamine out of the synaptic cleft and into a glial cell or the presynaptic neuron. ... For other uses, see Dopamine (disambiguation). ... Synapses allow nerve cells to communicate with one another through axons and dendrites, converting electrical signals into chemical ones. ...

The former hypothesis is backed by data demonstrating that injections of amphetamines result in rapid increases of cytosolic dopamine concentrations.^[26] 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.^[27] Calcium may be a key molecule involved in the interactions between amphetamine and VMATs.^[28] For other uses, see Dopamine (disambiguation). ... The dopamine transporter or DAT is a monoamine transporter that is specific for clearing the neurotransmitter dopamine out of the synaptic cleft and into a glial cell or the presynaptic neuron. ...

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.^[29] Upon phosphorylation, DAT undergoes a conformational change that results in the transportation of DAT-bound dopamine from the extracellular to the intracellular environment.^[30] 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.^[31] Thus, beyond inhibiting reuptake of dopamine, amphetamine also stimulates the release of dopamine molecules into the synapse.^[32] The dopamine transporter or DAT is a monoamine transporter that is specific for clearing the neurotransmitter dopamine out of the synaptic cleft and into a glial cell or the presynaptic neuron. ... The dopamine transporter or DAT is a monoamine transporter that is specific for clearing the neurotransmitter dopamine out of the synaptic cleft and into a glial cell or the presynaptic neuron. ... A protein kinase is an enzyme that can transfer a phosphate group from a donor molecule (usually ATP) to an amino acid residue of a protein. ... The dopamine transporter or DAT is a monoamine transporter that is specific for clearing the neurotransmitter dopamine out of the synaptic cleft and into a glial cell or the presynaptic neuron. ... For other uses, see Dopamine (disambiguation). ... The dopamine transporter or DAT is a monoamine transporter that is specific for clearing the neurotransmitter dopamine out of the synaptic cleft and into a glial cell or the presynaptic neuron. ... Synapses allow nerve cells to communicate with one another through axons and dendrites, converting electrical signals into chemical ones. ... For other uses, see Dopamine (disambiguation). ... For other uses, see Dopamine (disambiguation). ...

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.^[33] This data suggests that the PKC-β kinase may represent a key point of interaction between amphetamine and the DAT transporter. A protein kinase is an enzyme that can transfer a phosphate group from a donor molecule (usually ATP) to an amino acid residue of a protein. ... For other uses, see Dopamine (disambiguation). ... A protein kinase is an enzyme that can transfer a phosphate group from a donor molecule (usually ATP) to an amino acid residue of a protein. ... The dopamine transporter or DAT is a monoamine transporter that is specific for clearing the neurotransmitter dopamine out of the synaptic cleft and into a glial cell or the presynaptic neuron. ...

Serotonin

Amphetamine has been found to exert similar effects on serotonin as on dopamine.^[34] Like DAT, the serotonin transporter SERT can be induced to operate in reverse upon stimulation by amphetamine.^[35] This mechanism is thought to rely on the actions of calcium molecules, as well as on the proximity of certain transporter proteins.^[36] For the professional wrestling stable, see Ravens Nest#Serotonin. ... For other uses, see Dopamine (disambiguation). ... The dopamine transporter or DAT is a monoamine transporter that is specific for clearing the neurotransmitter dopamine out of the synaptic cleft and into a glial cell or the presynaptic neuron. ... The serotonin transporter is a monoamine transporter protein. ...

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.^[37] 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.^[38] For the professional wrestling stable, see Ravens Nest#Serotonin. ... The mesocortical pathway is a neural pathway which connects the ventral tegmentum to the cortex, particularly the frontal lobes. ... The glutamatergic neurotransmitter system plays a crucial role in memory formation and information processing. ... The ventral tegmentum or the ventral tegmental area (VTA) is part of the midbrain, lying close to the substantia nigra and the red nucleus. ... “Prefrontal” redirects here. ... The glutamatergic neurotransmitter system plays a crucial role in memory formation and information processing. ... For the professional wrestling stable, see Ravens Nest#Serotonin. ...

The proposed ability of amphetamine to increase excitability of glutamatergic pathways may be of significance when considering serotonin-mediated addiction.^[39] An additional behavioral consequence may be the stereotyped locomotor stimulation that occurs in response to amphetamine exposure.^[40] The glutamatergic neurotransmitter system plays a crucial role in memory formation and information processing. ... This article is about the concept of addiction. ...

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.^[41] Glutamate is the anion of glutamic acid. ... The nucleus accumbens (NAcc), also known as the accumbens nucleus or as the nucleus accumbens septi (Latin for nucleus leaning against the septum), is a collection of neurons located where the head of the caudate and the anterior portion of the putamen meet just lateral to the septum pellucidum. ... Coronal slices of human brain showing the basal ganglia, the striatum and pallidum globus pallidus: external segment (GPe), subthalamic nucleus (STN), globus pallidus: internal segment (GPi), and substantia nigra (SN). ... “Prefrontal” redirects here. ...

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.^[42] Norepinephrine (INN)(abbr. ... Epinephrine (INN) or adrenaline (BAN) is a hormone and a neurotransmitter. ...

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.^[43] For other uses, see Dopamine (disambiguation). ... The dopamine transporter or DAT is a monoamine transporter that is specific for clearing the neurotransmitter dopamine out of the synaptic cleft and into a glial cell or the presynaptic neuron. ... Tyrosine Hydroxylase is the enzyme responsible for catalysing the conversion of L-tyrosine, an amino acid, to dihydroxyphenylalanine (DOPA), a precursor to Dopamine in the process the body uses to synthesise adrenaline (epinephrin). ... Coronal slices of human brain showing the basal ganglia, the striatum and pallidum globus pallidus: external segment (GPe), subthalamic nucleus (STN), globus pallidus: internal segment (GPi), and substantia nigra (SN). ...

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, e.g., MDMA (Ecstasy) and the N-methylated form, methamphetamine. Amphetamine is a homologue of phenethylamine. The term chiral (pronounced ) is used to describe an object which is non-superimposable on its mirror image. ... In chemistry, a racemate is a mixture of equal amounts of left- and right-handed stereoisomers of a chiral molecule. ... Dextroamphetamine is a powerful psychostimulant which produces increased wakefulness, energy and self-confidence in association with decreased fatigue and appetite. ... Derivative (Chemistry) In chemistry a derivative is a compound that is formed from a similar compound. ... ecstasy and religious ecstasy MDMA, most commonly known today by the street name ecstasy, is a synthetic entactogen of the phenethylamine family whose primary effect is to stimulate the brain to rapidly secrete large amounts of serotonin, causing a general sense of openness, empathy, energy, euphoria, and well-being. ... This article is about the psychostimulant, d-methamphetamine. ... In chemistry, a homologous series is a series of organic compounds with a similar general formula, possessing similar chemical properties due to the presence of the same functional group, and shows a gradation in physical properties as a result of increase in molecular size and mass (see relative molecular mass). ... Phenethylamine, or β-Phenylethylamine, is an alkaloid and monoamine. ...

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
Adderall XR 15 mg capsule Adderall is a brand-name pharmaceutical psychostimulant composed of mixed amphetamine salts. ...

• 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. The dopamine transporter or DAT is a monoamine transporter that is specific for clearing the neurotransmitter dopamine out of the synaptic cleft and into a glial cell or the presynaptic neuron. ... For other uses, see Dopamine (disambiguation). ...

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. Dextroamphetamine is a powerful psychostimulant which produces increased wakefulness, energy and self-confidence in association with decreased fatigue and appetite. ... For other uses, see Dopamine (disambiguation). ... Norepinephrine (INN)(abbr. ... For the professional wrestling stable, see Ravens Nest#Serotonin. ...

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.^[44] 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. Synapses allow nerve cells to communicate with one another through axons and dendrites, converting electrical signals into chemical ones. ... The dopamine transporter or DAT is a monoamine transporter that is specific for clearing the neurotransmitter dopamine out of the synaptic cleft and into a glial cell or the presynaptic neuron. ...

In addition, amphetamine binds to a group of receptors called TrAce Amine Receptors (TAAR).^[45] TAAR are a newly discovered receptor system which seems to be affected by a range of amphetamine-like substances called trace amines. Trace amine-associated receptors, abbreviated TAAR and previously abbreviated TAR and TA, are a class of G protein-coupled receptors identified in 2001. ... Chemical structure of serotonin Chemical structure of phenethylamine Trace amines are endogenous compounds structurally related to classical biogenic amines, such as catecholamines, serotonin and histamine. ...

Effects

Physical effects

Physical effects of amphetamine could include reduced appetite, dilated pupils, flushing, loss of coordination, 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.^{[46][47][48][49]} // Mydriasis is an excessive dilation of the pupil due to disease or drugs. ... Look up flushing in Wiktionary, the free dictionary. ... Look up agitation in Wiktionary, the free dictionary. ... Xerostomia is the medical term for a dry mouth due to a lack of saliva. ... A headache (cephalgia in medical terminology) is a condition of pain in the head; sometimes neck or upper back pain may also be interpreted as a headache. ... This article or section does not cite any references or sources. ... A sphygmomanometer, a device used for measuring arterial pressure. ... An analogue medical thermometer showing the temperature of 38. ... Perspiration (also called sweating or sometimes transpiration) is the production and evaporation of a fluid, consisting primarily of water as well as a smaller amount of sodium chloride (the main constituent of table salt), that is excreted by the sweat glands in the skin of mammals. ... In medicine, diarrhea, also spelled diarrhoea (see spelling differences), refers to frequent loose or liquid bowel movements. ... Constipation, costiveness, or irregularity, is a condition of the digestive system where a person (or animal) experiences hard feces that are difficult to egest. ... Many different terms are often used to describe what is collectively known as dizziness. ... This article is about the sleeping disorder. ... Paresthesia (paraesthesia in British) is a sensation of tingling, pricking, or numbness of the skin with no apparent physical cause, more generally known as the feeling of pins and needles. ... A palpitation is an abnormal, rapid beating of the heart, brought on by overexertion, disease or drugs. ... A cardiac arrhythmia, also called cardiac dysrhythmia, is a disturbance in the regular rhythm of the heartbeat. ... This article is about the medical condition. ... Grant Salzl has a huge nose full of acne. ... Pallor is a reduced amount of oxyhemoglobin in skin or mucous membrane, a pale color which can be caused by illness, emotional shock or stress, avoiding excessive exposure to sunlight, anaemia or genetics. ...

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,^[50] researchers examined data from more than 3 million people between 18 and 44 years old hospitalized from 2000 through 2003 in Texas and found a relationship between a diagnosis of amphetamine abuse and heart attack.^[51] A myocardial infarction occurs when an atherosclerotic plaque slowly builds up in the inner lining of a coronary artery and then suddenly ruptures, totally occluding the artery and preventing blood flow downstream. ... Year 2000 (MM) was a leap year starting on Saturday. ... Year 2003 (MMIII) was a common year starting on Wednesday of the Gregorian calendar. ...

Psychological effects

Psychological effects of amphetamine could include 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. Effects are similar, to cocaine, especially when insufflated or injected.^[47][52] Look up euphoria, euphoric in Wiktionary, the free dictionary. ... For other uses, see Concentration (disambiguation). ... In psychology and other social and behavioral sciences, aggression refers to behavior that is intended to cause harm or pain. ... For other senses of this word, see paranoia (disambiguation). ... For other uses, see Cocaine (disambiguation). ... This article or section does not cite its references or sources. ... Injection has multiple meanings: In mathematics, the term injection refers to an injective function. ...

Withdrawal effects

Withdrawal from use of amphetamines can include the following: anxiety, depression, agitation, fatigue, excessive sleeping, increased appetite, psychosis, suicidal thoughts.^[53] Anxiety is a physiological state characterized by cognitive, somatic, emotional, and behavioral components[1]. These components combine to create the feelings that we typically recognize as anger and known as fear, apprehension, or worry. ... For other uses, see Depression. ... Agitation may have the following special meanings Agitation, an emotional state Agitation, putting into motion (by shaking or stirring) Agitation, a term from the lexicon of Communists: political activities aimed at urging people to do something This is a disambiguation page — a navigational aid which lists other pages that might... Fatigue may refer to: Fatigue (physical) - tiredness in humans Fatigue (material) - failure by repeated stress in materials Fatigues (uniform) - military uniform (BDU or ACU) Chronic Fatigue Syndrome - a medical condition Battle fatigue - also known as Post-traumatic stress disorder Readers fatigue - a side-effect of parsing poorly formatted textual... Sleeping girl Sleep is the fundamental anabolic process common to all life forms, plant and animal. ... For other uses, see Psychosis (disambiguation). ... For other uses, see Suicide (disambiguation). ...

Dependence & Addiction

Tolerance is developed rapidly in amphetamine abuse, therefore increasing the amount of the drug that is needed to satisfy the addiction.^[54] Repeated amphetamine use can produce "reverse tolerance", or sensitization to some psychological effects.^{[55][56][57][58][59]} 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 avoiding the withdrawals then dose themselves with benzodiazepines or barbiturates to help them stay calm while they recuperate. Chronic users of amphetamines typically snort or resort to 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. 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. 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]} Drug tolerance occurs when a subjects reaction to a drug (such as a painkiller or intoxicant) decreases so that larger doses are required to achieve the same effect. ... Withdrawal, also known as withdrawal syndrome, refers to the characteristic signs and symptoms that appear when a drug that causes physical dependence is regularly used for a long time and then suddenly discontinued or decreased in dosage. ... Phenmetrazine is a stimulant of the central nervous system. ...

Performance-enhancing use

Amphetamine is used by college and high-school students as a study and test-taking aid.^[60] 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. ^[61]

Amphetamines have been, and are still used, by militaries around the world. British troops used 72 million amphetamine tablets in the second world war^[62] and the RAF got through so many that "Methedrine won the Battle of Britain" according to one report^[63]. 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. Methamphetamine is a synthetic stimulant drug which induces a strong feeling of euphoria and is highly addictive. ... The Tarnak Farm incident refers to the accidental killing of four Canadian soldiers and the injury of eight others from the Third Battalion of Princess Patricias Canadian Light Infantry (3PPCLI) on the night of April 18, 2002 by an American F-16 fighter jet. ... Also see: 2002 (number). ... The F-16 Fighting Falcon is an American multirole jet fighter aircraft developed by General Dynamics and Lockheed Martin for the United States Air Force. ...

Amphetamine is also used by professional,^[64] collegiate^[65] and high school^[66] 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.^[67] This practice can be extremely dangerous, and athletes have died as a result, for example, British cyclist Tom Simpson. For other persons named Tom Simpson, see Tom Simpson (disambiguation). ...

Amphetamine use has historically been especially common among Major League Baseball (MLB) athletes and is usually known by the slang term "greenies".^[68] 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 testing^[69].^[70][71]

Truck drivers, especially long-haul drivers, take amphetamine^[72] to combat symptoms of somnolence and to increase their concentration on driving.

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).^[73]
• 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.^[74] 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.^[75] The Misuse of Drugs Act 1971 is an Act of Parliament, by which the United Kingdom aims to control the possession and supply of numerous drugs and drug-like substances, as listed under the Act, and to enable international co-operation against illegal drug trafficking. ... The Misuse of Drugs Act 1971 is an Act of Parliament, by which the United Kingdom aims to control the possession and supply of numerous drugs and drug-like substances, as listed under the Act, and to enable international co-operation against illegal drug trafficking. ... This box:      The Controlled Substances Act (CSA) 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. ... Convention on Psychotropic Substances Opened for signature February 21, 1971 in Vienna Entered into force August 16, 1976 Conditions for entry into force 40 ratifications Parties 175 The Convention on Psychotropic Substances is a United Nations treaty designed to control psychoactive drugs such as amphetamines, barbiturates, and psychedelics. ...

A chart comparing the chemical structures of different amphetamine derivatives

Image File history File links Methamphetamines. ... Image File history File links Methamphetamines. ...

See also

• Adderall
• Attention Deficit Hyperactivity Disorder
• Benzylpiperazine
• Clandestine chemistry
• Ethylamphetamine
• Dextroamphetamine (Dexedrine)
• Lisdexamfetamine (Vyvanse)
• Methamphetamine (Desoxyn)
• Methylphenidate (Ritalin, Concerta)
• Phenethylamines
• Propylamphetamine
• Psychostimulants

Adderall XR 15 mg capsule Adderall is a brand-name pharmaceutical psychostimulant composed of mixed amphetamine salts. ... DISCLAIMER Please remember that Wikipedia is offered for informational use only. ... Benzylpiperazine (street names include A2, frenzy and nemesis [1] However, there are some references to BZP in the literature that predate interest in piperazines as anthelmintics. ... Clandestine chemistry generally refers to chemistry carried out in illegal drug laboratories, but can include any kind of laboratory operation carried on in secret. ... N-ethylamphetamine (Etilamfetamine, Apetinil) is a stimulant drug derived from amphetamine which was invented in the early 1900s. ... Dextroamphetamine is a powerful psychostimulant which produces increased wakefulness, energy and self-confidence in association with decreased fatigue and appetite. ... Lisdexamfetamine (L-lysine-d-amphetamine) is a prodrug of the psychostimulant d-amphetamine coupled with the essential amino acid L-lysine. ... This article is about the psychostimulant, d-methamphetamine. ... Desoxyn® CII is a brand of methamphetamine hydrochloride (also known as desoxyephedrine, hence the name Desoxyn), indicated for treatment of Attention Deficit/Hyperactivity Disorder (ADHD), narcolepsy, and exogenous obesity. ... Vitamin R redirects here. ... Phenethylamine, or β-Phenylethylamine, is an alkaloid and monoamine. ... N-propylamphetamine is a stimulant drug derived from amphetamine which was invented in the 1970s. ... A psychostimulant is a substance that enhances locomotor behavior. ...

References and notes

Alexander and Ann Shulgin, in a photo from their book TiHKAL, c. ... PiHKAL is a 1991 book by Dr. Alexander Shulgin and Ann Shulgin about psychedelic phenethylamines. ... Year 2006 (MMVI) was a common year starting on Sunday of the Gregorian calendar. ... is the 84th day of the year (85th in leap years) in the Gregorian calendar. ... Year 2007 (MMVII) was a common year starting on Monday of the Gregorian calendar in the 21st century. ... is the 336th day of the year (337th in leap years) in the Gregorian calendar. ... Year 2007 (MMVII) was a common year starting on Monday of the Gregorian calendar in the 21st century. ... is the 336th day of the year (337th in leap years) in the Gregorian calendar. ... NCAA redirects here. ... NCAA redirects here. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... Year 2007 (MMVII) was a common year starting on Monday of the Gregorian calendar in the 21st century. ... is the 336th day of the year (337th in leap years) in the Gregorian calendar. ... Year 2006 (MMVI) was a common year starting on Sunday of the Gregorian calendar. ... is the 92nd day of the year (93rd in leap years) in the Gregorian calendar. ... Year 2007 (MMVII) was a common year starting on Monday of the Gregorian calendar in the 21st century. ... is the 336th day of the year (337th in leap years) in the Gregorian calendar. ... Year 2005 (MMV) was a common year starting on Saturday (link displays full calendar) of the Gregorian calendar. ... is the 319th day of the year (320th in leap years) in the Gregorian calendar. ... Year 2007 (MMVII) was a common year starting on Monday of the Gregorian calendar in the 21st century. ... is the 336th day of the year (337th in leap years) in the Gregorian calendar. ... Year 2006 (MMVI) was a common year starting on Sunday of the Gregorian calendar. ... is the 90th day of the year (91st in leap years) in the Gregorian calendar. ... Year 2007 (MMVII) was a common year starting on Monday of the Gregorian calendar in the 21st century. ... is the 336th day of the year (337th in leap years) in the Gregorian calendar. ... Year 2007 (MMVII) was a common year starting on Monday of the Gregorian calendar in the 21st century. ... is the 18th day of the year in the Gregorian calendar. ... Year 2007 (MMVII) was a common year starting on Monday of the Gregorian calendar in the 21st century. ... is the 336th day of the year (337th in leap years) in the Gregorian calendar. ... Year 2007 (MMVII) was a common year starting on Monday of the Gregorian calendar in the 21st century. ... is the 336th day of the year (337th in leap years) in the Gregorian calendar. ...

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