Dextroamphetamine
Systematic (IUPAC) name
(2S)-1-phenylpropan-2-amine
Identifiers
CAS number	51-64-9 51-63-8 (sulphate), 1462-73-3 (hydrochloride)
ATC code	N06BA02
PubChem	5826
DrugBank	APRD00480
Chemical data
Formula	C9H13N
Mol. mass	135.206 g/mol
Pharmacokinetic data
Bioavailability	>75%
Metabolism	Hepatic
Half life	10–28 hours (Average ~12 hours)
Excretion	Renal: ~45%
Therapeutic considerations
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Routes	Clinical: Oral, intravenous, sublingual Recreational: Vaporized, insufflated, suppository

Dextroamphetamine is a powerful psychostimulant which produces increased wakefulness, energy and self-confidence in association with decreased fatigue and appetite. It is perhaps the archetypal psychostimulant, and drugs with similar psychoactive properties are often referred to as "amphetamine analogues", or described as having "amphetamine-like", or even "amphetaminergic" effects. Its stimulant properties are similar to those of methylphenidate and methamphetamine, though with a slower onset of action and a duration that lies somewhere between the two.^{[citation needed]} 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. ... A psychostimulant is a substance that enhances locomotor behavior. ... Vitamin R redirects here. ... This article is about the psychostimulant, d-methamphetamine. ...

Dextroamphetamine is the dextrorotary stereoisomer of the amphetamine molecule, which can take two different forms. Other common names for dextroamphetamine include d-amphetamine, dexamphetamine, (S)-(+)-amphetamine, and brand names such as Dexedrine and Dextrostat. It is combined with levo-amphetamine in Adderall and other racemic amphetamines. In chemistry, enantiomers (from the Greek ἐνάντιος, opposite, and μέρος, part or portion) are stereoisomers that are nonsuperimposable complete mirror images of each other, much as ones left and right hands are the same but opposite. ... Amphetamine or Amfetamine (Alpha-Methyl-PHenEThylAMINE), also known as, beta-phenyl-isopropylamine, and benzedrine, is a prescription stimulant commonly used to treat Attention-deficit hyperactivity disorder (ADHD) in adults and children. ... Adderall 25 mg XR Capsules Adderall is a pharmaceutical stimulant amphetamine used to treat attention-deficit disorder/attention-deficit hyperactivity disorder and narcolepsy. ...

History

Amphetamine was first synthesized under the chemical name "phenylisopropylamine" in Berlin, 1887 by the Romanian chemist Lazar Edeleanu. It was not widely marketed until 1932, when the pharmaceutical company Smith, Kline, and French (currently known as GlaxoSmithKline) introduced it in the form of the Benzedrine Inhaler, for combating cold symptoms. Notably, the chemical form of Benzedrine in the inhaler was the liquid-free base, not a chloride or sulfate salt. In free-base form, amphetamine is a volatile oil, hence the efficacy of the inhalers. In chemistry, chemical synthesis is purposeful execution of chemical reactions in order to get a product, or several products. ... This article is about the capital of Germany. ... Lazar Edeleanu (1861-1941) was a famous Romanian chemist. ... GlaxoSmithKline plc (LSE: GSK NYSE: GSK) is a British based pharmaceutical, biologicals, and healthcare company. ... This article does not cite any references or sources. ...

Three years later, in 1935, the medical community became aware of the stimulant properties of amphetamine, specifically dextroamphetamine, and in 1937 Smith, Kline, and French introduced Dexedrine tablets, under the tradename Dexedrine. In the United States, Dexedrine tablets were approved to treat narcolepsy, attention disorders, depression, and obesity. Dextroamphetamine was marketed in various other forms in the following decades, primarily by Smith, Kline, and French, such as several combination medications including a mixture of dextroamphetamine and amobarbital (a barbiturate) sold under the tradename Dexamyl and, in the 1950s, an extended release capsule (the "Spansule"). Narcolepsy is a neurological condition most characterized by Excessive Daytime Sleepiness (EDS). ... DISCLAIMER Please remember that Wikipedia is offered for informational use only. ... Amobarbital (formerly known as amylobarbitone) is a drug that is a barbiturate derivative. ... Barbiturates are drugs that act as central nervous system depressants, and by virtue of this they produce a wide spectrum of effects, from mild sedation to anesthesia. ... Dexamyl is the brand name of a combination drug composed of dextroamphetamine and amylbarbitone (amobarbital). ...

It quickly became apparent that Dexedrine and other amphetamines had a high potential for abuse, although they were not heavily controlled until 1970, when the Comprehensive Drug Abuse Prevention and Control Act was passed by the United States Congress. Dexedrine, along with other sympathomimetics, was eventually classified as schedule II, the most restrictive category possible for a drug with recognized medical uses. Substance abuse refers to the overindulgence in and dependence on a psychoactive leading to effects that are detrimental to the individuals physical health or mental health, or the welfare of others. ... Wikipedia does not yet have an article with this exact name. ... The Controlled Substances Act (CSA), Title II of the Comprehensive Drug Abuse Prevention and Control Act of 1970, is the legal foundation of the United States governments fight against the abuse of drugs and other substances. ...

Chemistry

Dextroamphetamine is a slightly polar, weak base and is lipophilic. This article or section does not cite its references or sources. ...

Formulations

Dextroamphetamine sulfate

5mg dexamphetamine sulfate tablets

A tablet preparation of the salt dextroamphetamine sulfate (pharmaceutical names: Dexedrine or Dextrostat) is available in two strengths: 5 mg and 10 mg. A pharmaceutical with a strength of 30mg dextroamphetamine sulfate is 22.0 mg dextroamphetamine. Image File history File links Metadata Size of this preview: 800 × 533 pixelsFull resolution (3072 × 2048 pixel, file size: 5. ... Image File history File links Metadata Size of this preview: 800 × 533 pixelsFull resolution (3072 × 2048 pixel, file size: 5. ... For other uses, see Salt (disambiguation). ...

Sustained-Release 15mg Dexedrine Spansules

Dextroamphetamine sulfate is also available in a controlled release version (pharmaceutical name: Dexedrine SR or Dexedrine Spansule), capsulated in the strengths: 5 mg, 10 mg, and 15 mg. Image File history File linksMetadata Dexedrine_Spansules. ... Image File history File linksMetadata Dexedrine_Spansules. ...

Lisdexamfetamine

Main article: Lisdexamfetamine

Dextroamphetamine is also the metabolite of the prodrug lisdexamfetamine dimesylate (pharmaceutical name: Vyvanse). Vyvanse is meant to provide once-a-day dosing because it regulates a slow release of dextroamphetamine into the brain. Vyvanse is available as capsules, in three strengths: 30 mg, 50 mg, and 70 mg. A 30mg-strength Vyvanse capsule is molecularly equivalent to 8.88mg dextroamphetamine. However, this molecular equivalence would only hold true as a bioequivalence ratio if: the dimesylate salt instantly dissolved resulting in the complete dissociation of lisdexamfetamine ions, and then the covalent amide bond of every lisdexamfetamine molecule immediately underwent hydrolysis. In fact, being a prodrug, lisdexamfetamine has different properties than dextroamphetamine; for instance, lisdexamfetamine is metabolised in the gastrointestinal tract, while dextroamphetamine's metabolism is hepatic.^[1] Lisdexamfetamine (L-lysine-d-amphetamine) is a prodrug of the psychostimulant d-amphetamine coupled with the essential amino acid L-lysine. ... A metabolite is the product of metabolism. ... A prodrug is a pharmacological substance (drug) which is administered in an inactive (or significantly less active) form. ... Lisdexamfetamine (L-lysine-d-amphetamine) is a prodrug of the psychostimulant d-amphetamine coupled with the essential amino acid L-lysine. ... Look up capsule in Wiktionary, the free dictionary. ... Bioequivalence is a term in pharmacokinetics used to assess the expected in vivo biological equivalence of two proprietary preparations of a drug. ...

Mixed amphetamine salts

Instant Release 30mg Adderall Tablets

Another pharmaceutical that contains "active ingredients" in addition to dextroamphetamine is Adderall. The drug formulation of Adderall (both controlled and instant release forms) is: Image File history File links No higher resolution available. ... Image File history File links No higher resolution available. ... Adderall 25 mg XR Capsules Adderall is a pharmaceutical stimulant amphetamine used to treat attention-deficit disorder/attention-deficit hyperactivity disorder and narcolepsy. ...

One-quarter racemic (d,l-)amphetamine aspartate monohydrate

One-quarter dextroamphetamine saccharate

One-quarter dextroamphetamine sulfate

One-quarter racemic (d,l-)amphetamine sulfate

Aspartate, saccharate, and sulfate salts differ pharmacokinetically in the rate at which they are metabolized by the body. For this and other reasons, Adderall's effects are different from pharmaceuticals with dextroamphetamine as an exclusive active ingredient. Contrary to the beliefs that Adderall is three-quarters dextroamphetamine, dextroamphetamine accounts for 72.7% of the amphetamine base in Adderall (the remaining percentage is levoamphetamine). Adderall’s inclusion of levoamphetamine provides the pharmaceutical with a quicker onset and longer clinical effect compared to pharmaceuticals exclusively formulated of dextroamphetamine.^[2] Although it seems that where the human brain has a preference for dextroamphetamine over levoamphetamine, it has been reported that certain children have a better clinical response to levoamphetamine.^[3] Aspartic acid, also known as aspartate, the name of its anion, is one of the 20 natural proteinogenic amino acids which are the building blocks of proteins. ... Hydrates are compounds formed by the union of water with some other substance, generally forming a neutral body, as certain crystallized salts. ... In inorganic chemistry, a sulfate (IUPAC-recommended spelling; also sulphate in British English) is a salt of sulfuric acid. ... Pharmacokinetics (in Greek: pharmacon meaning drug, and kinetikos meaning putting in motion) is a branch of pharmacology dedicated to the determination of the fate of substances administered externally to a living organism. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... Amphetamine or Amfetamine (Alpha-Methyl-PHenEThylAMINE), also known as, beta-phenyl-isopropylamine, and benzedrine, is a prescription stimulant commonly used to treat Attention-deficit hyperactivity disorder (ADHD) in adults and children. ...

Uses

Clinical

• Primarily used to treat attention deficit hyperactivity disorder (ADHD). In some localities it has replaced methylphenidate as the first-choice medication for ADHD, a role in which it is considered highly effective.
• Treatment of Narcolepsy, generally where non-pharmacological measures have proved insufficient.
• Occasionally prescribed for weight-loss in cases of extreme obesity.

DISCLAIMER Please remember that Wikipedia is offered for informational use only. ... Vitamin R redirects here. ... Narcolepsy is a neurological condition most characterized by Excessive Daytime Sleepiness (EDS). ...

Experimental

Though such use remains out of the mainstream, dextroamphetamine has been successfully applied in the treatment of certain categories of depression as well as other psychiatric syndromes.^[4] Such alternate uses include reduction of fatigue in cancer patients, antidepressant treatment for HIV patients with depression and debilitating fatigue,^[5] early stage physiotherapy for severe stroke victims,^[6] If physical therapy patients take dextroamphetamine while they practice their movements for rehabilitation, they learn to move much faster than without dextroamphetamine, and in practice sessions with shorter lengths.^[7] Species Human immunodeficiency virus 1 Human immunodeficiency virus 2 Human immunodeficiency virus (HIV) is a retrovirus that causes acquired immunodeficiency syndrome (AIDS, a condition in humans in which the immune system begins to fail, leading to life-threatening opportunistic infections). ... Physical therapy (or physiotherapy[1]) is the provision of services to people and populations to develop, maintain and restore maximum movement and functional ability throughout the lifespan. ...

Military

The U.S. Air Force uses dextroamphetamine as its "go-pill,", given to pilots on long missions to help them remain focused and alert.^[8][9] Other branches of the U.S. military (as well as the armed forces of other nations^{[citation needed]}) commonly use or have dispensed dextroamphetamine to troops to prevent or treat fatigue in combat situations^{[citation needed]}. Because of the propensity of dextroamphetamine to cause behavioral side effects, this use is viewed as controversial; (Friendly Fire incidents are linked sometimes to the use of this drug and its effects on long term fatigued pilots; e.g. Tarnak Farm incident) newer stimulant medications with fewer side effects, like modafinil are being investigated for this reason. NASA has also used dextroamphetamine to combat fatigue in astronauts near the end of a mission.^{[citation needed]} 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. ... Modafinil is a eugeroic drug generally prescribed to treat narcolepsy, made by the pharmaceutical company Cephalon Inc. ... The National Aeronautics and Space Administration (NASA) is an agency of the United States government, responsible for the nations public space program. ...

Illicit

Along with Ritalin, illicit use of dextroamphetamine has been reported among students, both as a study aid, social aid, and for purely recreational purposes. According to the National Institute on Drug Abuse, 4% of American college students reported non-prescription stimulant use in 2004.^[10] Cover of a NIDA educational booklet. ...

Overdose

The Physician's 1991 Drug Handbook reports: "Symptoms of overdose include restlessness, tremor, hyperreflexia, tachypnea, confusion, aggressiveness, hallucinations, and panic." Dilated pupils are common with high doses. Image File history File links No higher resolution available. ... Hyperreflexia is defined as overactive or overresponsive reflexes. ... Tachypnea is a medical term for breathing which is more rapid than normal. ... A hallucination is a false sensory perception in the absence of an external stimulus, as distinct from an illusion, which is a misperception of an external stimulus. ... // Mydriasis is an excessive dilation of the pupil due to disease or drugs. ...

The fatal dose in humans is not precisely known, but in various species of rat generally ranges between 50 and 100 mg/kg, or a factor of 100 over what is required to produce noticeable psychological effects.^[11][12] This suggests a wide therapeutic range, in contrast to such drugs as morphine and heroin, where effective doses may be as much as 50% of a fatal dose. Although the symptoms seen in a fatal overdose are similar to those of methamphetamine, their mechanisms are not identical, as some substances which inhibit d-amphetamine toxicity do not do so for methamphetamine.^[13][14] Morphine (INN) (IPA: ) is a highly potent opiate analgesic drug and is the principal active agent in opium and the prototypical opiate. ... Heroin (INN: diacetylmorphine, BAN: diamorphine) is an opioid synthesized directly from the extracts of the opium poppy, Papaver somniferum. ...

An extreme symptom of overdose is amphetamine psychosis, characterized by vivid visual, auditory, and sometimes tactile hallucinations. Many of its symptoms are identical to the psychosis-like state which follows long-term sleep deprivation, so it remains unclear whether these are solely the effect of the drug, or due to the long periods of sleep deprivation which are often undergone by the chronic user or abuser. "In apparently sensitive individuals, psychosis may be produced by 55 to 75 mg of dextroamphetamine. With high enough doses, psychosis can probably be induced in anyone."^[15] Amphetamine psychosis is a form of psychosis which can result from amphetamine or methamphetamine use. ... Psychosis is a generic psychiatric term for a mental state often described as involving a loss of contact with reality. Stedmans Medical Dictionary defines psychosis as a severe mental disorder, with or without organic damage, characterized by derangement of personality and loss of contact with reality and causing deterioration...

Pharmacology

Subjective effects

Dextroamphetamine makes people declare that they are in a friendlier than average mood.^[16] Dextroamphetamine improves self-control for people who have a hard time naturally controlling themselves.^[17] Dextroamphetamine aids a person learning and memory of words, and perhaps makes the brain stronger.^[7] When a person given dextroamphetamine is tested, their brain is extremely active in the brain parts required for the test and radically less active in other parts.^[16] Short practice sessions with dextroamphetamine have a greater effect on learning than sessions without dextroamphetamine.^[7][16] Dextroamphetamine raises decision-making scores, improves choices, and changes beliefs about rewards; at the same time, dextroamphetamine barely—if at all—affects guesses of time.^[17] Those who feel lower amounts of joy from dextroamphetamine have greater impulsivity improvements compared to those who feel extreme happiness.^[17] Clinically signifigant side effects of dextroamphetamine include sleeplessness, reduced appetite, dryness of mouth, and headaches. The Physician's 1991 Drug Handbook reports: "Symptoms of overdose include restlessness, tremor, hyperreflexia, tachypnea, confusion, aggressiveness, hallucinations, and panic." Note that many of the symptoms of Amphetamine psychosis are identical to the psychosis-like state which follows long-term sleep deprivation, so it remains unclear pending further studies whether or not these are solely the effect of the drug(s) themselves, or due to the long periods of sleep deprivation which is often undergone by the use of amphetamines Hyperreflexia is defined as overactive or overresponsive reflexes. ... Tachypnea is a medical term for breathing which is more rapid than normal. ... A hallucination is a sensory perception experienced in the absence of an external stimulus, as distinct from an illusion, which is a misperception of an external stimulus. ... Panic is the primal urge to run and hide in the face of imminent danger. ... Amphetamine psychosis is a form of psychosis which can result from amphetamine or methamphetamine use. ...

Effect on neurochemistry

Dextroamphetamine affects the dynamics neurotransmitter systems, and its mechanisms of action are continously being investigated and discovered. Chemical structure of D-aspartic acid, a common amino acid neurotransmitter. ...

Monoamines

Dextroamphetamine affects dopamine and serotonin levels in the caudate, and norepinephrine in the hippocampus. Because dextroamphetamine is a substrate analog at monoamine transports, at all doses, dextroamphetamine prevents the reuptake of these neurotransmitters,^[18] causing them to remain in the synaptic cleft for a prolonged period (inhibiting monoamine reuptake in rats with ratios of about: NE:DA = 1:1, NE:5HT = 1:10^[19]). At some point, when doses are high, and the concentration of dextroamphetamine is high enough,^[18] dextroamphetamine will enter nerve cells and cause release of monoamines from the cytoplasmic dopamine pool (as opposed to 'protected' vesicular stores).^[20] In such high concentrations, dextroamphetamine will cause the norepinephrine, dopamine and, serotonin(5HT) transporters to reverse their direction of flow. This inversion leads to a release of these transmitters from the vesicles to the cytoplasm and from the cytoplasm to the synapse (releasing monoamines in rats with ratios of about NE:DA = 1:3.5, NE:5HT= 1:250), causing increased stimulation of post-synaptic receptors. Grays Fig. ... The hippocampus is structurally located inside the medial temporal lobe of the brain. ... Norepinephrine (INN)(abbr. ... Dopamine is a phenethylamine naturally produced by the human body. ... Serotonin (pronounced ) (5-hydroxytryptamine, or 5-HT) is a monoamine neurotransmitter synthesized in serotonergic neurons in the central nervous system (CNS) and enterochromaffin cells in the gastrointestinal tract of animals including humans. ... Norepinephrine (INN)(abbr. ... Dopamine is a phenethylamine naturally produced by the human body. ... Serotonin (5-hydroxytryptamine, or 5-HT) is a monoamine neurotransmitter synthesized in serotonergic neurons in the central nervous system (CNS) and enterochromaffin cells in the gastrointestinal tract. ...

Glutamate

Dextroamphetamine does not alter glutamate levels in the prefrontal cortex. This may be because dextroamphetamine increases dopamine release in the prefrontal cortex; activation of the dopamine-2 receptors in the prefrontal cortex inhibits glutamate release in the prefrontal cortex. However activation of the dopamine-1 receptors in the prefrontal cortex, increases glutamate leves in the in the nucleus accumbens. An increase of the glutamate levels in the nucleus accumbens may be part of the reason that dextroamphetamine has the an ability to increase locomotor activity in rats. Serotonin may also play a role in dextroamphetamines affect on glutamate levels.^[21]

Time course and elimination

On average, about one half of a given dose is eliminated unchanged in the urine, while the other half is broken down into various metabolites (mostly benzoic acid).^[22] However, the drug's half-life is highly variable because the rate of excretion is very sensitive to urinary pH. Under alkaline conditions, direct excretion is negligible and 95%+ of the dose is metabolized. The main metabolic pathway is d-amphetamine phenylacetone benzoic acid hippuric acid. Another pathway, mediated by enzyme CYP2D6, is d-amphetamine p-hydroxyamphetamine p-hydroxynorephedrine. Although p-hydroxyamphetamine is a minor metabolite (~5% of the dose), it may may have significant physiological effects as a norepinephrine analogue.^[23] Benzoic acid, C7H6O2 (or C6H5COOH), is a colorless crystalline solid and the simplest aromatic carboxylic acid. ... Phenylacetone (known as 1-phenylpropan-2-one in IUPAC nomenclature, often abbreviated as P2P other synonyms include benzyl methyl ketone; methyl benzyl ketone; phenyl-2-propanone; phenyl acetone) is an organic compound. ... Hippuric acid (Gr. ... 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. ... Norepinephrine (INN)(abbr. ...

Subjective effects are increased by larger doses, however, over the course of a given dose there is a noticeable divergence between such effects and drug concentration in the blood.^[24] In particular, mental effects peak before maximal blood levels are reached, and decline as blood levels remain stable or even continue to increase.^[25][26][27] This indicates a mechanism for development of acute tolerance, perhaps distinct from that seen in chronic use. Its slower onset of action as compared to methamphetamine and methylphenidate is presumably due to a somewhat lower effectiveness in crossing the blood-brain barrier.^[28] Freeze-fracture morphology of the blood-brain barrier of a rat The blood-brain barrier (abbreviated BBB) is a membranic structure that acts primarily to protect the brain from chemicals in the blood, while still allowing essential metabolic function. ...

Chronic use

This section is undergoing active discussion on its talk page. Please feel free to join in. This doesn't mean that you may not be bold in editing this section, but it can't hurt to check the discussion first.

While continuous dosing with amphetamine causes tolerance, intermittent use produces "reverse tolerance" or sensitization to its psychological effects.^{[29][30][31][32][33]} As a result, regular use commonly results in a quick decrease of unwanted side effects, but without an equivalent loss of its stimulant properties. Notably, the sensitization is induced more quickly, and persists far longer than withdrawal-related effects, suggesting a phenomenon more complex than a simple tolerance-induced withdrawal syndrome. Image File history File links No higher resolution available. ...

References

• Poison Information Monograph (PIM 178: Dexamphetamine Sulphate)
• Physician's 1991 Drug Handbook
• Dexamphetamine 1845887055 at GPnotebook
• Package inserts: New Zealand. Canada.
• Yamada H, Baba T, Hirata Y, Oguri K, Yoshimura H (1984). "Studies on N-demethylation of methamphetamine by liver microsomes of guinea-pigs and rats: the role of flavin-containing mono-oxygenase and cytochrome P-450 systems.". Xenobiotica 14 (11): 861-6. PMID 6506758. 

GPnotebook is a British medical database for general practitioners (GPs. ...

Footnotes