From Wikipedia, the free encyclopedia
|CAS number||300-62-9 405-41-4|
|SMILES||eMolecules & PubChem|
|Synonyms||(±)-alpha-methylbenzeneethanamine, alpha-methylphenethylamine, beta-phenyl-isopropylamine|
|Melt. point||285–281 °C (545–538 °F)|
||50–100 mg/mL (16C°) mg/mL (20 °C)|
|Bioavailability||Oral 20-25%; nasal 75%; rectal 95–99%; intravenous 100%|
|Half life||12h average for d-isomer, 13h for l-isomer|
Controlled (S8)(AU) Schedule III(CA) Class B(UK) Schedule II(US) Prescription-Only Medicine
|Y(what is this?) (verify)|
Amphetamine (amfetamine (INN)) is a
Recreational users of amphetamine have coined numerous nicknames for amphetamine, some of the more common street names for amphetamine include speed and whizz. The European Monitoring Centre for Drugs and Drug Addiction reports the typical retail price of amphetamine in Europe varied between €10 and €15 a gram in half of the reporting countries.
Amphetamine was first synthesized in 1887 by the Romanian chemist Lazăr Edeleanu in Berlin, Germany. 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
The related compound methamphetamine was first synthesized from ephedrine in Japan in 1918 by chemist Akira Ogata, via reduction of ephedrine using
In 1997 and 1998, researchers at Texas A&M University claimed to have found 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. 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.
Amphetamines were still in use in the
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
 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 appears to be specific; 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.
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. 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
The fact 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. 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.
 Endogenous amphetamines
Amphetamine has been found to have several endogenous analogues; that is, molecules of a similar structure found naturally in the brain. 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.
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
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. 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
The former hypothesis is backed by data demonstrating that injections of amphetamines result in rapid increases of cytosolic dopamine concentrations. 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. Calcium may be a key molecule involved in the interactions between amphetamine and VMATs.
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
In support of the above hypothesis, it has been found that
Amphetamine has been found to exert similar effects on serotonin as on dopamine. Like DAT, the serotonin transporter SERT can be induced to operate in reverse upon stimulation by amphetamine. This mechanism is thought to rely on the actions of calcium molecules, as well as on the proximity of certain transporter proteins.
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
The proposed ability of amphetamine to increase excitability of
 Other relevant neurotransmitters
Several other neurotransmitters have been linked to amphetamine activity. For instance, extracellular levels of
Additionally, several studies demonstrate increased levels of norepinephrine, a neurotransmitter related to
 Chemical properties
Amphetamine is a chiral compound. The
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
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
Amphetamine and other amphetamine-type stimulants principally act to release dopamine into the
In addition, amphetamine binds to a group of receptors called TrAce Amine Receptors (
 Physical effects
Physical effects of amphetamine can include reduced appetite, increased/distorted sensations, hyperactivity,
Occasionally amphetamine use in males can cause an odd and sometimes startling effect to occur in which the penis when flaccid appears to have shrunk. The reason this occurs is because amphetamine is a potent
Young adults who abuse amphetamines may be at greater risk of suffering a
 Psychological effects
Psychological effects of amphetamine can include anxiety and/or general nervousness (by increased norepinephrine), euphoria, metacognition, creative or philosophical thinking, increased confidence, perception of increased energy, increased sense of well being, increase of goal-orientated thoughts or organized behavior, repetitive behavior, increased concentration/mental sharpness, increased alertness, feeling of power or superiority, Increased aggression,
 Withdrawal effects
Withdrawal from chronic recreational use of amphetamines can include anxiety, depression, agitation, fatigue, excessive
An amphetamine overdose is rarely fatal but can lead to a number of different symptoms, including psychosis, chest pain, and hypertension.
 Dependence and addiction
Tolerance is developed rapidly in amphetamine abuse, therefore increasing the amount of the drug that is needed to satisfy the addiction. Repeated amphetamine use can produce “reverse tolerance”, or sensitization to some psychological effects. Amphetamine does not have the potential to cause physical dependence, though withdrawal can still be hard for a user. Many users will repeat the amphetamine cycle by taking more of the drug during the withdrawal. This leads to a very dangerous cycle and may involve the use of other drugs to get over the withdrawal process. Users will commonly stay up for 2 or 3 days to avoid the withdrawals then dose themselves with benzodiazepines, barbiturate, and in some cases heroin, to help them stay calm while they recuperate or simply to extend the positive effects of the drug. Chronic users of amphetamines sometimes snort or use drug injection to experience the full effects of the drug in a faster and more intense way, with the added risks of infection, vein damage, and higher risk of overdose with drug injection.
 Performance-enhancing use
Amphetamine is used by some college and high-school students as a study and test-taking aid. Amphetamine works by increasing energy levels, concentration, and motivation, thus allowing students to study for an extended period of time. This drug is often acquired through ADHD prescriptions to students and peers, rather than illicitly produced drugs.
Amphetamine has been, and is still, used by militaries around the world. British troops used 72 million amphetamine tablets in the second world war and the RAF used so many that “
Amphetamine is also used by some professional, collegiate and high school 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. 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”. In 2006, the MLB banned the use of amphetamine. The ban is enforced through periodic drug-testing. If a player tests positive for amphetamine, the consequences are significant. 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.
Amphetamine was formerly in widespread use by truck drivers to combat symptoms of somnolence and to increase their concentration during driving, especially in the decades prior to the signing by former
 Cultural impact of amphetamine
The social and cultural impact of amphetamine has been, and continues to be, quite extensive.
From the 1960s onward, amphetamine has been popular with many
The hippie counterculture was very critical of amphetamines due to the behaviors they cause; beat writer Allen Ginsberg wrote that users ran the risk of becoming a “Frankenstein speed freak”. The mods, being working class, were often opposed to the slower, more
 In literature
The writers of the Beat Generation used amphetamine extensively, mainly under the Benzedrine
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.
Amphetamines are frequently mentioned in the work of American journalist Hunter S. Thompson. Speed appears not only amongst the astoundingly diverse and voluminous 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, such as in his “Author’s Note” in Fear and Loathing on the Campaign Trail ’72:
“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 science
Famous mathematician Paul Erdős took amphetamines, 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. 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 “
The Who’s 1965 iconic Mod/youth anthem My Generation, famously re-creates in Roger Daltrey‘s vocals, the effect of amphetamine on the ability to speak. The pills accelerate the brain’s processes to the degree that ideas flow faster than the ability to communicate them by speech, resulting in the characteristic stuttering of words. At various times, in the period 1965-66, either to avoid controversy or to keep the true drug-related reason a secret among “those in the know”, Pete Townshend stated the stuttering was a protest at the government’s poor record of national education opportunities. However, several years later he later spilled the beans that it mimicked someone under the effect of amphetamine.
Many rock’n’roll bands have named themselves after amphetamine and drug slang surrounding it. For example Mod revivalists,
” first got into speed because it was a utilitarian drug and kept you awake when you needed to be awake, when otherwise you’d just be flat out on your back. If you drive to Glasgow for nine hours in the back of a sweaty truck you don’t really feel like going onstage feeling all bright and breezy… It’s the only drug I’ve found that I can get on with, and I’ve tried them all — except smack and morphine: I’ve never fixed anything.”
The amphetamine use and experience or perception of high energy and electronic dance music, particularly the more rapid-tempo genres like gabber and drum and bass, has long been associated with consumption of amphetamine.
 In film
Many films have been created that are either visually or aesthetically influenced by the perceived effects of amphetamine, or that portray amphetamine use in their plotlines.
In MASH (film), an announcement is made over the intercom stating that “Corporal Judson has informed the colonel’s office that three cases of amphetamine sulfate are unaccounted for again. This is the third occurrence of this type in the last month. It must stop by order of Colonel Blake’s office, 4077th M*A*S*H unit.”
Producer David O. Selznick was an amphetamine user, and would often dictate long and rambling memos under the influence of amphetamine to his directors. The documentary Shadowing The Third Man relates that Selznick introduced
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.
In the movie Requiem for a Dream, Sara Goldfarb begins taking a regimen of prescription amphetamine pills to lose weight. She steadily increases her dosage throughout the movie, inducing nightmarish hallucinations.
The movie Ciao! Manhattan was riddled with amphetamine usage and is based on the life of Edie Sedgwick who was a socialite, Andy Warhol’s superstar, model, actress, and ‘It’ girl of 1965. She died before the movie’s release on November 16, 1971.
In the movie Empire Records Liv Tyler‘s character, Corey, ingests amphetamine in several scenes, using the drug to both be alert so she’ll do well in school to please her father and to calm herself in stressful situations.
 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).
- 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. 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.
 See also
- Attention-deficit hyperactivity disorder
- Clandestine chemistry
- Dextroamphetamine (Dexedrine)
- Lisdexamfetamine (Vyvanse)
- Methamphetamine (
- Methylphenidate (Ritalin, Concerta)
- Releasing Agents
 References and notes
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