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Identification
Name Amphetamine
Accession Number DB00182 (APRD00480)
Type small molecule
Groups illicit, approved
Description

Amphetamine is a chiral compound. The racemic mixture can be divided into its optical antipodes: 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.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
(+/-)-Benzedrine
(+/-)-beta-Phenylisopropylamine
(+/-)-Desoxynorephedrine
[1-(3-Methoxyphenyl)-2-propyl]amine
1-Methyl-2-phenylethylamine
1-Phenyl-2-aminopropane
3-Methoxyamphetamine
alpha-Methylbenzeneethaneamine
Amfetamine
Amphetamine Sulfate
beta-Aminopropylbenzene
beta-phenyl-isopropylamine
dl-1-Phenyl-2-aminopropane
DL-alpha-Methylphenethylamine
dl-Amphetamine
dl-Benzedrine
Fenylo-izopropylaminyl
m-Methoxyamphetamine
Methamphetamine HCL
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Salts Not Available
Brand names
Name Company
Actedron
Adipan
Allodene
Anorexide
Anorexine
Benzebar
Benzedrine
Benzolone
Dexampex
Elastonon
Fenamin
Ferndex
Finam
Isoamycin
Isoamyne
Isomyn
Mecodrin
Methampex
Norephedrane
Novydrine
Oktedrin
Ortedrine
Paredrine
Percomon
Phenamine
Phenedrine
Profamina
Propisamine
Psychedrine
Raphetamine
Rhinalator
Simpatedrin
Simpatina
Sympamin
Sympamine
Sympatedrine
Weckamine
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Brand mixtures
Brand Name Ingredients
Adderall amphetamine + dextroamphetamine
Adderall XR 10mg Amphetamine Aspartate + Amphetamine Sulfate + Dextroamphetamine Saccharate + Dextroamphetamine Sulfate
Adderall XR 15mg Amphetamine Aspartate + Amphetamine Sulfate + Dextroamphetamine Saccharate + Dextroamphetamine Sulfate
Adderall XR 20mg Amphetamine Aspartate + Amphetamine Sulfate + Dextroamphetamine Saccharate + Dextroamphetamine Sulfate
Adderall XR 25mg Amphetamine Aspartate + Amphetamine Sulfate + Dextroamphetamine Saccharate + Dextroamphetamine Sulfate
Adderall XR 30mg Amphetamine Aspartate + Amphetamine Sulfate + Dextroamphetamine Saccharate + Dextroamphetamine Sulfate
Adderall XR 5mg Amphetamine Aspartate + Amphetamine Sulfate + Dextroamphetamine Saccharate + Dextroamphetamine Sulfate
Categories
  • Adrenergic Agents
  • Dopamine Agents
  • Dopamine Uptake Inhibitors
  • Adrenergic Uptake Inhibitors
  • Central Nervous System Stimulants
  • Amphetamines
  • Sympathomimetics
CAS number 300-62-9
Weight Average: 135.2062
Monoisotopic: 135.104799421
Chemical Formula C9H13N
InChI Key InChIKey=KWTSXDURSIMDCE-UHFFFAOYSA-N
InChI
InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3
Plain Text
IUPAC Name
1-phenylpropan-2-amine
SMILES
CC(N)CC1=CC=CC=C1
Plain Text
Mass Spec show (7.59 KB)
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication For treatment of Attention Deficit Disorder with Hyperactivity (ADDH) and narcolepsy in children.
Pharmacodynamics Amphetamine and dextroamphetamine, non-catechloamine sypathomimetic agents, are used in combination to treat attention-deficit hyperactivity disorder (ADHD) or narcolepsy. Adderall consists of equivalent amounts of amphetamine aspartate, amphetamine sulfate, dextroamphetamine saccharate, and dextroamphetamine sulfate.
Mechanism of action Amphetamines stimulate the release of norepinephrine from central adrenergic receptors. At higher dosages, they cause release of dopamine from the mesocorticolimbic system and the nigrostriatal dopamine systems. Amphetamine may also act as a direct agonist on central 5-HT receptors and may inhibit monoamine oxidase (MAO). In the periphery, amphetamines are believed to cause the release of noradrenaline by acting on the adrenergic nerve terminals and alpha- and beta-receptors. Modulation of serotonergic pathways may contribute to the calming affect. The drug interacts with VMAT enzymes to enhance release of DA and 5-HT from vesicles. It may also directly cause the reversal of DAT and SERT.
Absorption Amphetamine forms easily absorbed molecules that are highly lipid soluble
Volume of distribution Not Available
Protein binding 15-40%
Metabolism Hepatic
Route of elimination Not Available
Half life 10 hours
Clearance Not Available
Toxicity LD50=180 mg/kg(subcutaneous injection in rat). The most common presenting symptoms seen are agitation, hallucinations, suicidal behaviour, and chest pain.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Lannett co inc
  • Akorn inc
  • Teva pharmaceuticals usa inc
Packagers
Dosage forms
Form Route Strength
Capsule, extended release Oral
Tablet Oral
Prices
Unit description Cost Unit
Desoxyn 5 mg tablet 5.1 USD tablet
Dexedrine 15 mg 24 Hour Capsule 4.22 USD capsule
Dexedrine 10 mg 24 Hour Capsule 3.23 USD capsule
Dexedrine 5 mg 24 Hour Capsule 3.0 USD capsule
Dexedrine spansule 15 mg 2.45 USD each
Dexedrine spansule 10 mg 1.91 USD each
Dexedrine spansule 5 mg 1.91 USD each
Amphetamine salts 12.5 mg tablet 1.43 USD tablet
Amphetamine salts 15 mg tablet 1.43 USD tablet
Amphetamine salts 7.5 mg tablet 1.43 USD tablet
Amphetamine salts 10 mg tablet 1.37 USD tablet
Amphetamine salts 20 mg tablet 1.37 USD tablet
Amphetamine salts 30 mg tablet 1.37 USD tablet
Amphetamine salts 5 mg tablet 1.37 USD tablet
Amphetamine Salt Combo 7.5 mg tablet 1.3 USD tablet
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DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point Volatizes slowly at room temperature Not Available
water solubility Slightly Not Available
logP 1.76 HANSCH,C ET AL. (1995)
pKa 10.1 (at 20 °C) PERRIN,DD (1965)
Predicted Properties
Property Value Source
water solubility 1.74e+00 g/l ALOGPS
logP 1.85 ALOGPS
logP 1.8 ChemAxon
logS -1.9 ALOGPS
pKa (strongest basic) 10.01 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 1 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 26.02 ChemAxon
rotatable bond count 2 ChemAxon
refractivity 43.71 ChemAxon
polarizability 16.17 ChemAxon
References
Synthesis Reference Not Available
General Reference
  1. Leith NJ, Kuczenski R: Chronic amphetamine: tolerance and reverse tolerance reflect different behavioral actions of the drug. Pharmacol Biochem Behav. 1981 Sep;15(3):399-404. Pubmed
  2. Chaudhry IA, Turkanis SA, Karler R: Characteristics of “reverse tolerance” to amphetamine-induced locomotor stimulation in mice. Neuropharmacology. 1988 Aug;27(8):777-81. Pubmed
  3. Sax KW, Strakowski SM: Behavioral sensitization in humans. J Addict Dis. 2001;20(3):55-65. Pubmed
  4. Sulzer D, Sonders MS, Poulsen NW, Galli A: Mechanisms of neurotransmitter release by amphetamines: a review. Prog Neurobiol. 2005 Apr;75(6):406-33. Pubmed
External Links
Resource Link
KEGG Compound C07514 Link_out
ChEBI 2679 Link_out
ChEMBL 2679 Link_out
Therapeutic Targets Database DAP001146 Link_out
PharmGKB PA448408 Link_out
IUPHAR 2147 Link_out
Guide to Pharmacology 2147 Link_out
Drug Product Database 2248813 Link_out
RxList http://www.rxlist.com/cgi/generic/adderallxr.htm Link_out
Drugs.com http://www.drugs.com/amphetamine.html Link_out
PDRhealth http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/add1008.shtml Link_out
Wikipedia http://en.wikipedia.org/wiki/Amphetamine Link_out
ATC Codes
  • N06BA01
  • N06BA02
AHFS Codes
  • 28:20.04
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions
Drug Interaction
Chlorpromazine Decreased anorexic effect, may increase psychotic symptoms
Fluoxetine Risk of serotoninergic syndrome
Fluphenazine Decreased anorexic effect, may increase psychotic symptoms
Fluvoxamine Risk of serotoninergic syndrome
Guanethidine Amphetamine may decrease the effect of guanethidine.
Isocarboxazid Possible hypertensive crisis
Mesoridazine Decreased anorexic effect, may increase psychotic symptoms
Methotrimeprazine Decreased anorexic effect, may increase psychotic symptoms
Paroxetine Risk of serotoninergic syndrome
Perphenazine Decreased anorexic effect, may increase psychotic symptoms
Phenelzine Possible hypertensive crisis
Prochlorperazine Decreased anorexic effect, may increase pyschotic symptoms
Promethazine Decreased anorexic effect, may increase pyschotic symptoms
Propericiazine Decreased anorexic effect, may increase pyschotic symptoms
Rasagiline Possible hypertensive crisis
Thioridazine Decreased anorexic effect, may increase psychotic symptoms
Trifluoperazine Decreased anorexic effect, may increase psychotic symptoms
Food Interactions Not Available
Targets

1. Synaptic vesicular amine transporter

Pharmacological action: yes
Actions: inhibitor

Involved in the ATP-dependent vesicular transport of biogenic amine neurotransmitters. Pumps cytosolic monoamines including dopamine, norepinephrine, serotonin, and histamine into synaptic vesicles. Requisite for vesicular amine storage prior to secretion via exocytosis

Organism class: human
UniProt ID: Q05940 Link_out
Gene: SLC18A2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Sulzer D, Sonders MS, Poulsen NW, Galli A: Mechanisms of neurotransmitter release by amphetamines: a review. Prog Neurobiol. 2005 Apr;75(6):406-33. Pubmed
  2. Sulzer D, Chen TK, Lau YY, Kristensen H, Rayport S, Ewing A: Amphetamine redistributes dopamine from synaptic vesicles to the cytosol and promotes reverse transport. J Neurosci. 1995 May;15(5 Pt 2):4102-8. Pubmed

2. Sodium-dependent dopamine transporter

Pharmacological action: yes
Actions: negative modulator

Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals

Organism class: human
UniProt ID: Q01959 Link_out
Gene: SLC6A3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Lott DC, Kim SJ, Cook EH Jr, de Wit H: Dopamine transporter gene associated with diminished subjective response to amphetamine. Neuropsychopharmacology. 2005 Mar;30(3):602-9. Pubmed
  2. Fone KC, Nutt DJ: Stimulants: use and abuse in the treatment of attention deficit hyperactivity disorder. Curr Opin Pharmacol. 2005 Feb;5(1):87-93. Pubmed
  3. Miller GM, Verrico CD, Jassen A, Konar M, Yang H, Panas H, Bahn M, Johnson R, Madras BK: Primate trace amine receptor 1 modulation by the dopamine transporter. J Pharmacol Exp Ther. 2005 Jun;313(3):983-94. Epub 2005 Mar 11. Pubmed
  4. Garcia BG, Wei Y, Moron JA, Lin RZ, Javitch JA, Galli A: Akt is essential for insulin modulation of amphetamine-induced human dopamine transporter cell-surface redistribution. Mol Pharmacol. 2005 Jul;68(1):102-9. Epub 2005 Mar 28. Pubmed
  5. Madras BK, Miller GM, Fischman AJ: The dopamine transporter and attention-deficit/hyperactivity disorder. Biol Psychiatry. 2005 Jun 1;57(11):1397-409. Epub 2005 Jan 5. Pubmed
  6. Kahlig KM, Binda F, Khoshbouei H, Blakely RD, McMahon DG, Javitch JA, Galli A: Amphetamine induces dopamine efflux through a dopamine transporter channel. Proc Natl Acad Sci U S A. 2005 Mar 1;102(9):3495-500. Epub 2005 Feb 22. Pubmed

3. Cocaine- and amphetamine-regulated transcript protein

Pharmacological action: yes
Actions: agonist

Satiety factor closely associated with the actions of leptin and neuropeptide y; this anorectic peptide inhibits both normal and starvation-induced feeding and completely blocks the feeding response induced by neuropeptide Y and regulated by leptin in the hypothalamus. It promotes neuronal development and survival in vitro

Organism class: human
UniProt ID: Q16568 Link_out
Gene: CARTPT Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Loos RJ, Rankinen T, Tremblay A, Perusse L, Chagnon Y, Bouchard C: Melanocortin-4 receptor gene and physical activity in the Quebec Family Study. Int J Obes (Lond). 2005 Apr;29(4):420-8. Pubmed
  2. McAlister ED, Van Vugt DA: Effect of leptin administration versus re-feeding on hypothalamic neuropeptide gene expression in fasted male rats. Can J Physiol Pharmacol. 2004 Dec;82(12):1128-34. Pubmed
  3. Muhlhausler BS, Adam CL, Marrocco EM, Findlay PA, Roberts CT, McFarlane JR, Kauter KG, McMillen IC: Impact of glucose infusion on the structural and functional characteristics of adipose tissue and on hypothalamic gene expression for appetite regulatory neuropeptides in the sheep fetus during late gestation. J Physiol. 2005 May 15;565(Pt 1):185-95. Epub 2005 Jan 20. Pubmed
  4. Scruggs P, Lai CC, Scruggs JE, Dun NJ: Cocaine- and amphetamine-regulated transcript peptide potentiates spinal glutamatergic sympathoexcitation in anesthetized rats. Regul Pept. 2005 Apr 15;127(1-3):79-85. Pubmed
  5. Oliveira VX Jr, Fazio MA, Miranda MT, da Silva JM, Bittencourt JC, Elias CF, Miranda A: Leptin fragments induce Fos immunoreactivity in rat hypothalamus. Regul Pept. 2005 Apr 15;127(1-3):123-32. Pubmed
  6. Vicentic A, Lakatos A, Jones D: The CART receptors: background and recent advances. Peptides. 2006 Aug;27(8):1934-7. Epub 2006 May 19. Pubmed

4. Trace amine-associated receptor 1

Pharmacological action: yes
Actions: agonist

Receptor for trace amines, including beta- phenylethylamine (b-PEA), p-tyramine (p-TYR), octopamine and tryptamine, with highest affinity for b-PEA and p-TYR. Unresponsive to classical biogenic amines, such as epinephrine and histamine and only partially activated by dopamine and serotonine. Trace amines are biogenic amines present in very low levels in mammalian tissues. Although some trace amines have clearly defined roles as neurotransmitters in invertebrates, the extent to which they function as true neurotransmitters in vertebrates has remained speculative. Trace amines are likely to be involved in a variety of physiological functions that have yet to be fully understood. The signal transduced by this receptor is mediated by the G(s)-class of G-proteins which activate adenylate cyclase

Organism class: human
UniProt ID: Q96RJ0 Link_out
Gene: TAAR1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Reese EA, Bunzow JR, Arttamangkul S, Sonders MS, Grandy DK: Trace amine-associated receptor 1 displays species-dependent stereoselectivity for isomers of methamphetamine, amphetamine, and para-hydroxyamphetamine. J Pharmacol Exp Ther. 2007 Apr;321(1):178-86. Epub 2007 Jan 11. Pubmed
  2. Xie Z, Westmoreland SV, Bahn ME, Chen GL, Yang H, Vallender EJ, Yao WD, Madras BK, Miller GM: Rhesus monkey trace amine-associated receptor 1 signaling: enhancement by monoamine transporters and attenuation by the D2 autoreceptor in vitro. J Pharmacol Exp Ther. 2007 Apr;321(1):116-27. Epub 2007 Jan 18. Pubmed
  3. Wolinsky TD, Swanson CJ, Smith KE, Zhong H, Borowsky B, Seeman P, Branchek T, Gerald CP: The Trace Amine 1 receptor knockout mouse: an animal model with relevance to schizophrenia. Genes Brain Behav. 2007 Oct;6(7):628-39. Epub 2006 Dec 21. Pubmed
  4. Xie Z, Miller GM: Trace amine-associated receptor 1 is a modulator of the dopamine transporter. J Pharmacol Exp Ther. 2007 Apr;321(1):128-36. Epub 2007 Jan 18. Pubmed
  5. Miller GM, Verrico CD, Jassen A, Konar M, Yang H, Panas H, Bahn M, Johnson R, Madras BK: Primate trace amine receptor 1 modulation by the dopamine transporter. J Pharmacol Exp Ther. 2005 Jun;313(3):983-94. Epub 2005 Mar 11. Pubmed
Enzymes

1. Cytochrome P450 2D6

Actions: substrate, inhibitor

Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants

UniProt ID: P10635 Link_out
Gene: CYP2D6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 2A6

Actions: inhibitor

Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase

UniProt ID: P11509 Link_out
Gene: CYP2A6
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
Transporters

1. Solute carrier family 22 member 3

Actions: inhibitor

Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain

UniProt ID: O75751 Link_out
Gene: SLC22A3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Wu X, Kekuda R, Huang W, Fei YJ, Leibach FH, Chen J, Conway SJ, Ganapathy V: Identity of the organic cation transporter OCT3 as the extraneuronal monoamine transporter (uptake2) and evidence for the expression of the transporter in the brain. J Biol Chem. 1998 Dec 4;273(49):32776-86. Pubmed

2. Organic cation/carnitine transporter 2

Actions: inhibitor

Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also Relative uptake activity ratio of carnitine to TEA is 11.3

UniProt ID: O76082 Link_out
Gene: SLC22A5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Wu X, Prasad PD, Leibach FH, Ganapathy V: cDNA sequence, transport function, and genomic organization of human OCTN2, a new member of the organic cation transporter family. Biochem Biophys Res Commun. 1998 May 29;246(3):589-95. Pubmed
  2. Wu X, Huang W, Prasad PD, Seth P, Rajan DP, Leibach FH, Chen J, Conway SJ, Ganapathy V: Functional characteristics and tissue distribution pattern of organic cation transporter 2 (OCTN2), an organic cation/carnitine transporter. J Pharmacol Exp Ther. 1999 Sep;290(3):1482-92. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19