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20-September-2008 09:55:55 - Dextroamphetamine Dextroamphetamine Systematic IUPAC name 2S-1-phenylpropan-2-amine Identifiers CAS number 51-64-9 51-63-8 sulfate, 1462-73-3 hydrochloride ATC code N06BA02 PubChem 5826 DrugBank APRD00480 Chemical data Formula C9H13N Mol. mass 135.206 g/mol SMILES eMolecules PubChem Pharmacokinetic data Bioavailability 75% Metabolism Hepatic Half life 10-28 hours Average ~12 hours Excretion Renal: ~45% Therapeutic considerations Pregnancy cat. B3AU CUS Legal status Controlled S8AU Schedule IIICA Class BUK Schedule IIUS Routes Clinical: Oral, intravenous, sublingual Recreational: Vaporized, insufflated, suppository Dextroamphetamine is a psychostimulant which produces increased wakefulness, energy and self-confidence in association with decreased fatigue and appetite. It is perhaps the archetypal psycho-stimulant, and drugs with similar psychoactive properties are often referred to as amphetamine analogues, or described as having amphetamine-like, or even amphetaminergic effects. As a CNS stimulant, enantiopure dextroamphetamine is more powerful than racemic amphetamine and has stimulant properties that are similar to those of methamphetamine, but is slightly less potent. 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 racemic-amphetamine in the ADHD drug Adderall. It is the active metabolite of the recently introduced prodrug lisdexamfetamine, known by its brand name Vyvanse. In addition, it is an active metabolite of several older N-substituted amphetamine prodrugs used as anorectics, such as clobenzorex Asenlix, benzphetamine Didrex and amphetaminil Aponeuron. Contents 1 History 2 Contraindications 3 Effects 3.1 Physical effects 3.2 Psychological effects 3.3 Withdrawal effects 4 Overdose 5 Chemistry 6 Formulations 6.1 Dextroamphetamine sulfate 6.2 Lisdexamfetamine 6.3 Mixed amphetamine salts 7 Uses 7.1 Clinical 7.1.1 Experimental 7.2 Military 7.3 Illicit 8 Pharmacology 8.1 Effect on neurochemistry 8.1.1 Monoamines 8.1.2 Glutamate 8.2 Time course and elimination 9 Dextroamphetamine in popular culture 10 References 11 Footnotes 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. 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 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. 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. Internationally, it has been available under the names AmfeDyn Italy, Curban US, Obetrol Switzerland, Simpamina Italy, Dexedrine US, and Stild Spain. 1 Contraindications The drug should be avoided for those who have: hypersensitivity to amphetamines, a history of drug abuse, cardiovascular diseases, hypertensive disease, hyperthyroidism, or in those with glaucoma. Effects Dextroamphetamine use, either for recreational or medical use can induce many different effects as shown below. In general negative effects are increased with increasing dosage amounts, and at medical dosages rarely causes serious adverse effects. Physical effects Physical effects of dextroamphetamine can include reduced or absent appetite, hyperactivity, dilated pupils, flushing, restlessness, dry mouth, headache, tachycardia, increased breathing rate, increased blood pressure, fever, sweating, diarrhea, constipation, blurred vision, impaired speech, dizziness, uncontrollable movements, insomnia, numbness, palpitations, arrhythmia. In high doses or chronic use convulsions, dry or itchy skin, acne, pallor can occur. With high chronic dosages a myocardial infarction can occur.234567 Psychological effects Psychological effects of dextroamphetamine can include anxiety and/or general nervousness by increased norepinephrine8, euphoria, dysphoria, a sense of well being, increased alertness, increased concentration, increased talkativeness, increased energy, excitability, feeling of power or superiority, repetitive behaviors, psychomotor agitation, increased aggression, and in rare cases paranoia and amphetamine psychosis.2910 Withdrawal effects Withdrawal from use of dextroamphetamine; either used for recreational or medical use, can include anxiety, depression, agitation, fatigue, excessive sleeping, vivid or lucid dreams deep REM sleep, increased appetite, psychosis and suicidal thoughts.111213 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. 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.1415 This suggests a wide therapeutic rangecitation needed, in contrast to such drugs as morphine and heroin, where effective doses may be as much as 50% of a fatal dosecitation needed. 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.1617 Methamphetamine is often considered to be significantly more neurotoxic than d-amphetamine in cases of overdose, particularly to serotonergic and dopaminergic neurons in the CNS.citation needed 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 extraordinarily sensitive individuals--such as those with a pre-existing neuropsychiatric disorder--psychosis may be produced by 55 to 75 mg of dextroamphetamine. With high enough doses, psychosis can probably be induced in anyone. Amphetamine psychosis, however, is extremely rare in individuals taking oral amphetamines at therapeutic doses; it is usually seen in cases of prolonged or high-dose intravenous IV abuse.18 Chemistry Dextroamphetamine is a slightly polar, weak base and is lipophilic. Formulations Dextroamphetamine sulfate 5mg dexamphetamine sulfate tablets 5mg dexamphetamine sulfate tablets A tablet preparation of the salt dextroamphetamine sulfate pharmaceutical names: Dexedrine or Dextrostat is available in 5mg and 10mg strengths in the United States. A pharmaceutical with a strength of 10 mg dextroamphetamine sulfate is 7.33mg dextroamphetamine. Sustained-Release 15 mg Dexedrine Spansules Sustained-Release 15 mg 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. Lisdexamfetamine Main article: Lisdexamfetamine Dextroamphetamine is also the active metabolite of the prodrug lisdexamfetamine dimesylate pharmaceutical trade 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 30 mg-strength Vyvanse capsule is molecularly equivalent to 8.88 mg 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.19 Vyvanse is also being marketed for its lower abuse and misuse potential than when compared to similar drugs such as Adderall, Dexedrine, and the methylphenidate preparations, though it is still rated as a Schedule II drug by the U.S. Drug Enforcement Administration. Vyvanse significantly slower onset and its route of administration is limited to being taken orally, unlike many similar drugs which are commonly nasally insufflated to achieve a much faster onset and higher bioavailability. Since Vyvanse is a prodrug and thus not psychoactive it must be metabolized into dextroamphetamine first before having psychoactive effects. Insufflation of Vyvanse is expected to produce no stimulant property, though this is disputed by the DEA. Mixed amphetamine salts Instant Release 30 mg Adderall Tablets Instant Release 30 mg Adderall Tablets Another pharmaceutical that contains dextroamphetamine is Adderall. The drug formulation of Adderall both controlled and instant release forms is: 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. Adderall is roughly three-quarters dextroamphetamine, with it accounting 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.20 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.21 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 treatment-resistant obesity. 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.22 Such alternate uses include reduction of fatigue in cancer patients, antidepressant treatment for HIV patients with depression and debilitating fatigue,23 early stage physiotherapy for severe stroke victims,24 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.25 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.262728 Friendly fire incidents have been linked 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 and sometimes issued for this reason.26 Illicit Along with Ritalin and Adderall, 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 2004.29 Pharmacology Effect on neurochemistry Dextroamphetamine affects the dynamics neurotransmitter systems, and its mechanisms of action are continuously being investigated and discovered. 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,30 causing them to remain in the synaptic cleft for a prolonged period inhibiting monoamine reuptake in rats with a norepinephrine to dopamine ratio NE:DA of about 1:1 and a norepinephrine to 5-hydroxytryptamine ratio NE:5HT of about 1:1031. At some point, when doses are high, and the concentration of dextroamphetamine is high enough,30 dextroamphetamine will enter nerve cells and cause release of monoamines from the cytoplasmic dopamine pool as opposed to 'protected' vesicular stores.32 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 and NE:5HT = 1:250, causing increased stimulation of post-synaptic receptors. 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 inhibits glutamate release in the prefrontal cortex. However, activation of the dopamine-1 receptors in the prefrontal cortex, increases glutamate leves in the nucleus accumbens. An increase of the glutamate levels in the nucleus accumbens may be part of the reason that dextroamphetamine has an ability to increase locomotor activity in rats. Serotonin may also play a role in dextroamphetamine's affect on glutamate levels; however, at therapeutic doses, dextroamphetamine would likely have little if any effect on the serotonin transporter SERT.33 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.34 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. Having an alkaline stomach will cause the drug to be absorbed faster through the stomach resulting in a higher blood level concentration of amphetamine. Having an alkaline bladder causes the drug to be excreted very slowly. It is possible with acute doses of sodium bicarbonate dissolved in water during amphetamine's course in the body for the half-life of the drug to last about 24 hours, with after effects lasting another 10 hours. The main metabolic pathway is d-amphetamine \rightarrow \; phenylacetone \rightarrow \; benzoic acid \rightarrow \; hippuric acid. Another pathway, mediated by enzyme CYP2D6, is d-amphetamine \rightarrow \; p-hydroxyamphetamine \rightarrow \; p-hydroxynorephedrine. Although p-hydroxyamphetamine is a minor metabolite ~5% of the dose, it may have significant physiological effects as a norepinephrine analogue.35 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.36 In particular, mental effects peak before maximal blood levels are reached, and decline as blood levels remain stable or even continue to increase.373839 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.40 Dextroamphetamine in popular culture In the Left Behind series of Christian novels, dextroamphetamine as Benzedrine or Dexedrine is mentioned as a drug used to aid characters in regaining consciousness or staying awake after injury or fatigue. The English pop group Dexys Midnight Runners were named after Dexedrine,which was popularly used as a recreational drug among Northern Soul fans at the time. The main character, Case, in the William Gibson novel Neuromancer takes Brazilian dex in the form of octagon shaped pills. In the American television program Boston Legal, Denny Crane, a character with Alzheimer's disease, says he is taking dextroamphetamine. Johnny Cash is known for having abused Dextroamphetamine for the majority of his career. Cash frequently mentions this abuse in his 1997 autobiography. Dextroamphetamine is used by members of the United States military as a go-pill, to promote alertness during stressful missions and demanding exercises. This has often generated controversy. 41 Waylon Jennings is known to have used Dextroamphetamine during his early career, before switching to cocaine. He describes its use and his addiction in depth in his 1996 autobiography. 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. Footnotes ^ PHARMACEUTICAL MANUFACTURING ENCYCLOPEDIA Second ion, Marshall Sittig, Volume 1, NOYES PUBLICATIONS ^ a b Erowid Amphetamines Vault : Effects ^ Amphetamine; Facts ^ Amphetamines - Better Health Channel ^ adderall xr, adderall medication, adderall side effects, adderall abuse ^ Side Effects of Dexedrine amphetamines; Biphetamine, Desoxyn dextroamphetamine sulfate ^ Dextroamphetamine Oral Route - MayoClinic.com ^ http://www.drugs.com/sfx/amphetamine-side-effects.html Side Effects drugs.com ^ Dexedrine | ADD ADHD Information Library ^ Dextroamphetamine ^ Symptoms of Amphetamine withdrawal - WrongDiagnosis.com ^ Dextroamphetamine Withdrawals ^ Drug Abuse Help: Dexedrine Information ^ Miczek K 1979. A new test for aggression in rats without aversive stimulation: differential effects of d-amphetamine and cocaine Abstract. Psychopharmacology Berl 60 3: 253-9. doi:10.1007/BF00426664. PMID 108702. ^ Grilly D, Loveland A 2001. What is a low dose of d-amphetamine for inducing behavioral effects in laboratory rats?. Psychopharmacology Berl 153 2: 155-69. doi:10.1007/s002130000580. PMID 11205415. ^ Derlet R, Albertson T, Rice P 1990. Antagonism of cocaine, amphetamine, and methamphetamine toxicity. Pharmacol Biochem Behav 36 4: 745-9. doi:10.1016/0091-30579090071-O. PMID 2217500. ^ Derlet R, Albertson T, Rice P 1990. The effect of SCH 23390 against toxic doses of cocaine, d-amphetamine and methamphetamine. Life Sci 47 9: 821-7. doi:10.1016/0024-32059090555-6. PMID 2215083. ^ LS Goodman, A Gilman 1970. The Pharmacological Basis of Therapeutics, 7th Ed., New York: Macmillan Co.. ^ FDA Approval of Vyvanse Pharmacological Reviews Pages 18 and 19 ^ Glaser, et al. 2005. Differential Effects of Amphetamine Isomers on Dopamine in the Rat Striatum and Nucleus Accumbens Core. Psychopharmacology 178: 250-258 Pages: 255,256. doi:10.1007/s00213-004-2012-6. ^ Arnold 2000. Methylphenidate vs Amphetamine: Comparative Review. Journal of Attention Disorders 3 4: 200-211. doi:10.1177/108705470000300403. ^ Warneke L 1990. Psychostimulants in psychiatry. Can J Psychiatry 35 1: 3-10. PMID 2180548. ^ Wagner G, Rabkin R 2000. Effects of dextroamphetamine on depression and fatigue in men with HIV: a double-blind, placebo-controlled trial. J Clin Psychiatry 61 6: 436-40. PMID 10901342. ^ Martinsson L, Yang X, Beck O, Wahlgren N, Eksborg S Sep-Oct 2003. Pharmacokinetics of dexamphetamine in acute stroke. Clin Neuropharmacol 26 5: 270-6. doi:10.1097/00002826-200309000-00012. PMID 14520168. ^ Butefisch CM et al. 2002. Modulation of Use-Dependent Plasticity by D-Amphetamine. Annals of Neurology 51 1: 59-68. doi:10.1002/ana.10056. PMID 11782985. ^ a b Air Force scientists battle aviator fatigue ^ U.S. Pilots Stay Up Taking 'Uppers' ^ Emonson DL, Vanderbeek RD. 1995 The use of amphetamines in U.S. Air Force tactical operations during Desert Shield and Storm. 668:802 ^ NIDA Notes Volume 20, Number 4 March 2006 ^ a b Kuczenski R et al. 1995. Hippocampus Norepinephrine, Caudate Dopamine and Serotonin, and Behavioral Responses to the Stereoisomers of Amphetamine and Methamphetamine. The Journal of Neuroscience 15 2: 1308-1317. PMID 7869099. Free full text PDF ^ Rothman, et al. Amphetamine-Type Central Nervous System Stimulants Release Norepinephrine more Potently than they Release Dopamine and Serotonin. 2001: Synapse 39, 32-41 Table V. on page 37 ^ Patrick, and Markowitz 1997. Pharmacology of Methylphenidate, Amphetamine Enantiomers and Pemoline in Attention-Deificit Hyperacitivty Disorder. Human Psychopharmacology 12: 527-546 Page:530. doi:10.1002/SICI1099-1077199711/1212:6527::AID-HUP9323.0.CO;2-U. ^ Shoblock J, Sullivan E, Maisonneuve I, Glick S 2003. Neurochemical and behavioral differences between d-methamphetamine and d-amphetamine in rats. Psychopharmacology Berl 165 4: 359-69. doi:10.1007/s00213-002-1288-7. PMID 12491026. ^ Mofenson H, Greensher J 1975. Letter: Physostigmine as an antidote: use with caution. J Pediatr 87 6 Pt 1: 1011-2. doi:10.1016/S0022-34767580946-2. PMID 1185381. ^ Rangno R, Kaufmann J, Cavanaugh J, Island D, Watson J, Oates J 1973. Effects of a false neurotransmitter, p-hydroxynorephedrine, on the function of adrenergic neurons in hypertensive patients Scanned copy. J Clin Invest 52 4: 952-60. doi:10.1172/JCI107260. PMID 4348345. ^ Asghar S, Tanay V, Baker G, Greenshaw A, Silverstone P 2003. Relationship of plasma amphetamine levels to physiological, subjective, cognitive and biochemical measures in healthy volunteers. Hum Psychopharmacol 18 4: 291-9. doi:10.1002/hup.480. PMID 12766934. ^ Angrist B, Corwin J, Bartlik B, Cooper T 1987. Early pharmacokinetics and clinical effects of oral D-amphetamine in normal subjects. Biol Psychiatry 22 11: 1357-68. doi:10.1016/0006-32238790070-9. PMID 3663788. ^ Brown G, Hunt R, Ebert M, Bunney W, Kopin I 1979. Plasma levels of d-amphetamine in hyperactive children. Serial behavior and motor responses Abstract. Psychopharmacology Berl 62 2: 133-40. doi:10.1007/BF00427126. PMID 111276. ^ Brauer L, Ambre J, De Wit H 1996. Acute tolerance to subjective but not cardiovascular effects of d-amphetamine in normal, healthy men. J Clin Psychopharmacol 16 1: 72-6. doi:10.1097/00004714-199602000-00012. PMID 8834422. ^ MacKenzie R, Heischober B 1997. Methamphetamine. Pediatr Rev 18 9: 305-9. doi:10.1542/pir.18-9-305. PMID 9286149. ^ Amphetamine Go-Pills dextroamphetamine friendly fire v d e Stimulants Alkylamines Cyclopentamine Geranamine Isometheptene Octodrine Propylhexedrine Tuamine Alphapyrrolidinylalkiophenones α-PPP MDPPP MDPV MPBP MPHP MPPP MOPPP Pyrovalerone Cholinergics ABT-089 ABT-418 Anabasine Arecoline Cotinine Cytisine Dianicline Epibatidine Epiboxidine GTS-21 Ispronicline Nicotine Rivanicline Tebanicline Varenicline Convulsants Bicuculline DMCM Gabazine Pentetrazol Picrotoxin Strychnine Thujone Eugeroics Adrafinil Armodafinil Carphedon Modafinil Phenethylamines 4-Bromomethcathinone 4-Fluoroamphetamine 4-Fluoromethamphetamine 4-Fluoromethcathinone 4-Methylmethcathinone 4-MTA Aletamine Amfepentorex Amphechloral Amphetamine Dextroamphetamine, Adderall Amphetaminil Benzphetamine Bupropion Cathinone Chlorphentermine Clenbuterol Clobenzorex Clortermine Diethylpropion Dimethoxyamphetamine Dimethylamphetamine Dimethylcathinone Ephedrine Epinephrine Ethcathinone Ethylamphetamine Fenethylline Fenfluramine Fenproporex Fludorex Furfenorex Levomethamphetamine Lisdexamfetamine MDMA Mefenorex Methamphetamine Methcathinone Methoxyphedrine Methylone Octopamine Ortetamine Parahydroxyamphetamine PCA PIA PMA PMEA PMMA PPAP Phendimetrazine Phenmetrazine Phentermine Phenylephrine Phenylpropanolamine Propylamphetamine Pseudoephedrine Selegiline Synephrine Tiflorex Xylopropamine Phenylaminooxazoles 4-Methyl-aminorex Aminorex Clominorex Fenozolone Fluminorex Pemoline Thozalinone Piperazines 2C-B-BZP BZP GBR-12783 GBR-12935 GBR-13069 GBR-13098 GBR-13119 MeOPP MBZP Vanoxerine Piperidines 2-Benzylpiperidine Desoxypipradrol Diphemethoxidine Ethylphenidate HDMP-28 --Methyl-1-methyl-4β-2-naphthylpiperidine-3β-carboxylate Methylphenidate Dexmethylphenidate Nocaine Phacetoperane Pipradrol Tropanes 3α-Bis-4-fluorophenylmethoxytropane 3α-4-Chlorophenylphenylmethoxytropane 3-Pseudotropyl-4-fluorobenzoate Altropane IACFT Brasofensine CFT WIN 35,428 β-CIT RTI-55 Cocaethylene Cocaine β-CPPIT Dichloropane RTI-111 Difluoropine FE-β-CPPIT FP-β-CPPIT PIT PTT RTI-31 RTI-32 RTI-51 RTI-112 RTI-113 RTI-121 IPCIT RTI-126 RTI-150 RTI-171 RTI-177 RTI-336 Tesofensine Troparil β-CPT, WIN 35,065-2 WF-23 WF-33 WF-60 Xanthines Aminophylline Caffeine Dimethazan Paraxanthine Theobromine Theophylline Others Amineptine Bemegride Benzydamine BPAP Bromantane BTQ Clofenciclan Cypenamine Cyprodenate Diclofensine Dimethocaine Diphenyl prolinol Ethamivan Fencamfamine Feprosidnine Gilutensin GYKI-52895 Hexacyclonate Indanorex Indatraline LR-5182 Mazindol Mesocarb Naphthylisopropylamine Nikethamide Nomifensine Phthalimidopropiophenone Prolintane Sibutramine Yohimbine Zylofuramine See also Sympathomimetic amines v d e Psychoanaleptics: psychostimulants, agents used for ADHD and nootropics N06B Centrally acting sympathomimetics Amphetamine - Amphetaminil - Atomoxetine - Dextroamphetamine - Dextromethamphetamine - Fencamfamin - Fenozolone - Fenetylline - Methylphenidate - Mesocarb - Pemoline - Pipradrol - Prolintane Xanthine derivatives Caffeine - Propentofylline Glutamate receptor Racetams Aniracetam - Nefiracetam - Oxiracetam - Phenylpiracetam - Piracetam - Pramiracetam Ampakines CX-516 - CX-546 - CX-614 - CX-691 - CX-717 - IDRA-21 - LY-503,430 - PEPA Eugeroics / Benzhydryl compounds Adrafinil - Armodafinil - Modafinil Histamine H3 receptor antagonists ABT-239 - Ciproxifan Other psychostimulants and nootropics Acetylcarnitine - Citicoline - Cyprodenate - Idebenone - Ispronicline - Deanol - Dimebon - Fipexide - Linopirdine - Meclofenoxate - Nizofenone - Pirisudanol - Pyritinol - Sulbutiamine - Taltirelin - Tricyanoaminopropene - Vinpocetine Retrieved from http://en..org/wiki/Dextroamphetamine Categories: AmphetaminesHidden categories: All articles with statements | Articles with statements since September 2007 | Articles with statements since July 2008 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages БългарÑ?ки Galego Nederlands Polski Português Suomi This page was last modified on 21 August 2008, at 05:05
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