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Identification
NameMethamphetamine
Accession NumberDB01577
TypeSmall Molecule
GroupsApproved, Illicit
Description

Methamphetamine is a psychostimulant and sympathomimetic drug. It is a member of the amphetamine group of sympathomimetic amines. Methamphetamine can induce effects such as euphoria, increased alertness and energy, and enhanced self-esteem. It is a scheduled drug in most countries due to its high potential for addiction and abuse.

Structure
Thumb
Synonyms
(+)-(S)-N-alpha-Dimethylphenethylamine
(+)-(S)-N-α-dimethylphenethylamine
(AlphaS)-N,alpha-dimethylbenzeneethanamine
(S)-N,alpha-Dimethylbenzeneethanamine
(S)-N,α-dimethylbenzeneethanamine
(αS)-N,α-dimethylbenzeneethanamine
d-1-phenyl-2-methylaminopropane
d-deoxyephedrine
d-desoxyephedrine
d-N-methylamphetamine
d-phenylisopropylmethylamine
Dextromethamphetamine
Métamfétamine
Metamfetamine
Metamfetaminum
Metanfetamina
Methamphetamine
Methamphetaminum
Methyl-beta-phenylisopropylamine
methyl-β-phenylisopropylamine
External Identifiers Not Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Desoxyntablet5 mg/1oralRECORDATI RARE DISEASES, INC.1943-12-312016-04-05Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Methamphetamine Hydrochloridetablet5 mg/1oralMylan Pharmaceuticals Inc.2010-04-262018-10-31Us
Methamphetamine Hydrochloridetablet5 mg/1oralMayne Pharma Inc.2010-04-262016-04-05Us
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Methamphetamine hydrochloride
Thumb
  • InChI Key: MYWUZJCMWCOHBA-VIFPVBQESA-N
  • Monoisotopic Mass: 149.120449485
  • Average Mass: 149.2328
DBSALT000734
Categories
UNII44RAL3456C
CAS number537-46-2
WeightAverage: 149.2328
Monoisotopic: 149.120449485
Chemical FormulaC10H15N
InChI KeyInChIKey=MYWUZJCMWCOHBA-VIFPVBQESA-N
InChI
InChI=1S/C10H15N/c1-9(11-2)8-10-6-4-3-5-7-10/h3-7,9,11H,8H2,1-2H3/t9-/m0/s1
IUPAC Name
methyl[(2S)-1-phenylpropan-2-yl]amine
SMILES
CN[C@@H](C)CC1=CC=CC=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenethylamines
Direct ParentAmphetamines and derivatives
Alternative Parents
Substituents
  • Amphetamine or derivatives
  • Phenylpropane
  • Aralkylamine
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of Attention Deficit Disorder with Hyperactivity (ADHD) and exogenous obesity.
PharmacodynamicsMethamphetamine is a potent central nervous system stimulant which affects neurochemical mechanisms responsible for regulating heart rate, body temperature, blood pressure, appetite, attention, mood and responses associated with alertness or alarm conditions. The acute effects of the drug closely resemble the physiological and psychological effects of an epinephrine-provoked fight-or-flight response, including increased heart rate and blood pressure, vasoconstriction (constriction of the arterial walls), bronchodilation, and hyperglycemia (increased blood sugar). Users experience an increase in focus, increased mental alertness, and the elimination of fatigue, as well as a decrease in appetite.
Mechanism of actionMethamphetamine enters the brain and triggers a cascading release of norepinephrine, dopamine and serotonin. To a lesser extent methamphetamine acts as a dopaminergic and adrenergic reuptake inhibitor and in high concentrations as a monamine oxidase inhibitor (MAOI). The mechanism of action involved in producing the beneficial behavioral changes seen in hyperkinetic children receiving methamphetamine is unknown.
Related Articles
AbsorptionMethamphetamine is rapidly absorbed from the gastrointestinal tract with peak methamphetamine concentrations occurring in 3.13 to 6.3 hours post ingestion. Methamphetamine is also well absorbed following inhalation and following intranasal administration. It is distributed to most parts of the body. Because methamphetamine has a high lipophilicity it is distributed across the blood brain barrier and crosses the placenta.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic. The primary site of metabolism is in the liver by aromatic hydroxylation, N-dealkylation and deamination. At least seven metabolites have been identified in the urine, with the main metabolites being amphetamine (active) and 4-hydroxymethamphetamine. Other minor metabolites include 4-hydroxyamphetamine, norephedrine, and 4-hydroxynorephedrine.

SubstrateEnzymesProduct
Methamphetamine
Not Available
NorephedrineDetails
Methamphetamine
Not Available
4-hydroxyamphetamineDetails
Methamphetamine
Not Available
4-hydroxymethamphetamineDetails
Methamphetamine
Not Available
4-HydroxynorephedrineDetails
Route of eliminationExcretion occurs primarily in the urine, the rate of which is dependent on urine pH. Between 30-54% of an oral dose is excreted in urine as unchanged methamphetamine and 10-23% as unchanged amphetamine. Following an intravenous dose, 45% is excreted as unchanged parent drug and 7% amphetamine.
Half lifeThe biological half-life has been reported in the range of 4 to 5 hours.
ClearanceNot Available
ToxicityManifestations of acute overdosage with methamphetamine include restlessness, tremor, hyperreflexia, rapid respiration, confusion, assaultiveness, hallucinations, panic states, hyperpyrexia, and rhabdomyolysis. Fatigue and depression usually follow the central stimulation. Cardiovascular effects include arrhythmias, hypertension or hypotension, and circulatory collapse. Gastrointestinal symptoms include nausea, vomiting, diarrhea, and abdominal cramps. Fatal poisoning usually terminates in convulsions and coma.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug Reactions
Interacting Gene/EnzymeSNP RS IDAllele nameDefining changeAdverse ReactionReference(s)
PRKCA-binding protein
Gene symbol: PICK1
UniProt: Q9NRD5
rs713729 Not AvailableT alleleMethamphetamine psychosis and addiction17606663
PRKCA-binding protein
Gene symbol: PICK1
UniProt: Q9NRD5
rs2076369 Not AvailableG alleleMethamphetamine psychosis and addiction17606663
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.993
Blood Brain Barrier+0.9695
Caco-2 permeable+0.8675
P-glycoprotein substrateNon-substrate0.6682
P-glycoprotein inhibitor INon-inhibitor0.9338
P-glycoprotein inhibitor IINon-inhibitor0.9816
Renal organic cation transporterNon-inhibitor0.736
CYP450 2C9 substrateNon-substrate0.7898
CYP450 2D6 substrateSubstrate0.8919
CYP450 3A4 substrateNon-substrate0.7
CYP450 1A2 substrateNon-inhibitor0.6771
CYP450 2C9 inhibitorNon-inhibitor0.957
CYP450 2D6 inhibitorInhibitor0.8695
CYP450 2C19 inhibitorNon-inhibitor0.7754
CYP450 3A4 inhibitorNon-inhibitor0.9536
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9095
Ames testNon AMES toxic0.9306
CarcinogenicityNon-carcinogens0.8161
BiodegradationNot ready biodegradable0.7508
Rat acute toxicity3.1862 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9443
hERG inhibition (predictor II)Non-inhibitor0.9118
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Tabletoral5 mg/1
Prices
Unit descriptionCostUnit
Desoxyn 5 mg tablet5.1USD tablet
Methamphetamine 5 mg tablet3.6USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP2.07HANSCH,C ET AL. (1995)
pKa9.87 (at 25 °C)PERRIN,DD (1965)
Predicted Properties
PropertyValueSource
Water Solubility0.928 mg/mLALOGPS
logP2.23ALOGPS
logP2.24ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)10.21ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity48.48 m3·mol-1ChemAxon
Polarizability18.04 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (2.96 KB)
Spectra
Spectrum TypeDescriptionSplash Key
MSMass Spectrum (Electron Ionization)splash10-z300000000-fd0454cafd58d60de713View in MoNA
References
Synthesis Reference

Nobuyuki Shigetoh, Hiroshi Nakayama, Jinsei Miyazaki, Tadayasu Mitsumata, “Labelling colors for detecting cocaine or methamphetamine, method of preparing the same and detector for cocaine or methamphetamine.” U.S. Patent US5571727, issued October, 1981.

US5571727
General References
  1. Schepers RJ, Oyler JM, Joseph RE Jr, Cone EJ, Moolchan ET, Huestis MA: Methamphetamine and amphetamine pharmacokinetics in oral fluid and plasma after controlled oral methamphetamine administration to human volunteers. Clin Chem. 2003 Jan;49(1):121-32. [PubMed:12507968 ]
  2. McGregor C, Srisurapanont M, Jittiwutikarn J, Laobhripatr S, Wongtan T, White JM: The nature, time course and severity of methamphetamine withdrawal. Addiction. 2005 Sep;100(9):1320-9. [PubMed:16128721 ]
  3. Bennett BA, Hollingsworth CK, Martin RS, Harp JJ: Methamphetamine-induced alterations in dopamine transporter function. Brain Res. 1998 Jan 26;782(1-2):219-27. [PubMed:9519266 ]
  4. Hasan AA, Ciancio S: Relationship between amphetamine ingestion and gingival enlargement. Pediatr Dent. 2004 Sep-Oct;26(5):396-400. [PubMed:15460293 ]
  5. Shaner JW: Caries associated with methamphetamine abuse. J Mich Dent Assoc. 2002 Sep;84(9):42-7. [PubMed:12271905 ]
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (55.2 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AbirateroneThe serum concentration of Methamphetamine can be increased when it is combined with Abiraterone.
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Methamphetamine.
AcepromazineAcepromazine may decrease the stimulatory activities of Methamphetamine.
AcetaminophenThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Acetaminophen.
AcetazolamideAcetazolamide may decrease the excretion rate of Methamphetamine which could result in a lower serum level and potentially a reduction in efficacy.
AcetophenazineAcetophenazine may decrease the stimulatory activities of Methamphetamine.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Acetylsalicylic acid.
Aluminum hydroxideAluminum hydroxide may decrease the excretion rate of Methamphetamine which could result in a lower serum level and potentially a reduction in efficacy.
AminophyllineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Aminophylline.
AmisulprideAmisulpride may decrease the stimulatory activities of Methamphetamine.
AmitriptylineAmitriptyline may increase the stimulatory activities of Methamphetamine.
Ammonium chlorideThe serum concentration of Methamphetamine can be decreased when it is combined with Ammonium chloride.
AmphetamineThe risk or severity of adverse effects can be increased when MethAmphetamine is combined with Amphetamine.
ArformoterolThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Arformoterol.
AripiprazoleAripiprazole may decrease the stimulatory activities of Methamphetamine.
ArmodafinilThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Armodafinil.
ArticaineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Articaine.
AtomoxetineAtomoxetine may increase the hypertensive activities of Methamphetamine.
BenzphetamineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Benzphetamine.
BenzquinamideBenzquinamide may decrease the stimulatory activities of Methamphetamine.
BrompheniramineMethamphetamine may decrease the sedative activities of Brompheniramine.
ButalbitalThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Butalbital.
CaffeineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Caffeine.
Calcium AcetateCalcium Acetate may decrease the excretion rate of Methamphetamine which could result in a lower serum level and potentially a reduction in efficacy.
Calcium carbonateCalcium carbonate may decrease the excretion rate of Methamphetamine which could result in a lower serum level and potentially a reduction in efficacy.
CarphenazineCarphenazine may decrease the stimulatory activities of Methamphetamine.
ChlormezanoneChlormezanone may decrease the stimulatory activities of Methamphetamine.
ChlorphentermineThe risk or severity of adverse effects can be increased when Chlorphentermine is combined with Methamphetamine.
ChlorpromazineChlorpromazine may decrease the stimulatory activities of Methamphetamine.
ChlorprothixeneChlorprothixene may decrease the stimulatory activities of Methamphetamine.
ClenbuterolThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Methamphetamine.
ClozapineClozapine may decrease the stimulatory activities of Methamphetamine.
CobicistatThe serum concentration of Methamphetamine can be increased when it is combined with Cobicistat.
CocaineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Cocaine.
DarunavirThe serum concentration of Methamphetamine can be increased when it is combined with Darunavir.
DexmethylphenidateThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Dexmethylphenidate.
DextroamphetamineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Dextroamphetamine.
DiclofenamideDiclofenamide may decrease the excretion rate of Methamphetamine which could result in a lower serum level and potentially a reduction in efficacy.
DiethylpropionThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Diethylpropion.
DihydrocodeineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Dihydrocodeine.
DipivefrinThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Dipivefrin.
DobutamineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Dobutamine.
DopamineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Dopamine.
DoxapramThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Doxapram.
DoxofyllineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Doxofylline.
DronabinolDronabinol may increase the tachycardic activities of Methamphetamine.
DroperidolDroperidol may decrease the stimulatory activities of Methamphetamine.
DyphyllineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Dyphylline.
EphedrineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Ephedrine.
EpinephrineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Epinephrine.
EthosuximideThe therapeutic efficacy of Ethosuximide can be decreased when used in combination with Methamphetamine.
EthoxzolamideEthoxzolamide may decrease the excretion rate of Methamphetamine which could result in a lower serum level and potentially a reduction in efficacy.
FencamfamineFencamfamine may decrease the stimulatory activities of Methamphetamine.
FenoterolThe risk or severity of adverse effects can be increased when Fenoterol is combined with Methamphetamine.
FluoxetineThe metabolism of Methamphetamine can be decreased when combined with Fluoxetine.
FlupentixolFlupentixol may decrease the stimulatory activities of Methamphetamine.
FluphenazineFluphenazine may decrease the stimulatory activities of Methamphetamine.
FluspirileneFluspirilene may decrease the stimulatory activities of Methamphetamine.
Fluticasone PropionateThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Fluticasone Propionate.
FormoterolThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Formoterol.
HaloperidolHaloperidol may decrease the stimulatory activities of Methamphetamine.
HexamethylenetetramineThe serum concentration of Methamphetamine can be decreased when it is combined with Hexamethylenetetramine.
IndacaterolThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Indacaterol.
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Methamphetamine.
Ioflupane I 123Methamphetamine may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
Ipratropium bromideThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Ipratropium bromide.
IsomethepteneThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Isometheptene.
IsoprenalineThe risk or severity of adverse effects can be increased when Isoprenaline is combined with Methamphetamine.
LabetalolThe risk or severity of adverse effects can be increased when Labetalol is combined with Methamphetamine.
LevonordefrinThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Levonordefrin.
LinezolidLinezolid may increase the hypertensive activities of Methamphetamine.
LisdexamfetamineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Lisdexamfetamine.
LithiumLithium may decrease the stimulatory activities of Methamphetamine.
LoxapineLoxapine may decrease the stimulatory activities of Methamphetamine.
Magnesium oxideMagnesium oxide may decrease the excretion rate of Methamphetamine which could result in a lower serum level and potentially a reduction in efficacy.
MephentermineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Methamphetamine.
MepivacaineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Mepivacaine.
MesoridazineMesoridazine may decrease the stimulatory activities of Methamphetamine.
MetaraminolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Methamphetamine.
MethotrimeprazineMethotrimeprazine may decrease the stimulatory activities of Methamphetamine.
MethoxamineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Methamphetamine.
MethylphenidateThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Methylphenidate.
MidodrineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Midodrine.
ModafinilThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Modafinil.
MolindoneMolindone may decrease the stimulatory activities of Methamphetamine.
MorphineMethamphetamine may increase the analgesic activities of Morphine.
NabiloneNabilone may increase the tachycardic activities of Methamphetamine.
NaphazolineThe risk or severity of adverse effects can be increased when Naphazoline is combined with Methamphetamine.
NorepinephrineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Norepinephrine.
OlanzapineOlanzapine may decrease the stimulatory activities of Methamphetamine.
OlodaterolThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Olodaterol.
OndansetronOndansetron may decrease the stimulatory activities of Methamphetamine.
OrciprenalineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Methamphetamine.
OxymetazolineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Oxymetazoline.
PaliperidonePaliperidone may decrease the stimulatory activities of Methamphetamine.
PanobinostatThe serum concentration of Methamphetamine can be increased when it is combined with Panobinostat.
Peginterferon alfa-2bThe serum concentration of Methamphetamine can be decreased when it is combined with Peginterferon alfa-2b.
PerphenazinePerphenazine may decrease the stimulatory activities of Methamphetamine.
PhendimetrazineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Phendimetrazine.
PhenelzinePhenelzine may increase the hypertensive activities of Methamphetamine.
PheniramineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Pheniramine.
PhenmetrazineThe risk or severity of adverse effects can be increased when Phenmetrazine is combined with Methamphetamine.
PhenobarbitalThe serum concentration of Phenobarbital can be decreased when it is combined with Methamphetamine.
PhentermineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Phentermine.
PhenylephrineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Phenylephrine.
PhenylpropanolamineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Methamphetamine.
PhenytoinThe serum concentration of Phenytoin can be decreased when it is combined with Methamphetamine.
PimozidePimozide may decrease the stimulatory activities of Methamphetamine.
PiperacetazinePiperacetazine may decrease the stimulatory activities of Methamphetamine.
PirbuterolThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Pirbuterol.
ProchlorperazineProchlorperazine may decrease the stimulatory activities of Methamphetamine.
PromazinePromazine may decrease the stimulatory activities of Methamphetamine.
PropylhexedrineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Propylhexedrine.
PseudoephedrineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Pseudoephedrine.
QuetiapineQuetiapine may decrease the stimulatory activities of Methamphetamine.
RacepinephrineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Racepinephrine.
RemoxiprideRemoxipride may decrease the stimulatory activities of Methamphetamine.
ReserpineReserpine may decrease the stimulatory activities of Methamphetamine.
RisperidoneRisperidone may decrease the stimulatory activities of Methamphetamine.
RitodrineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Methamphetamine.
RitonavirThe metabolism of Methamphetamine can be decreased when combined with Ritonavir.
SalbutamolThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Salbutamol.
SalmeterolThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Salmeterol.
SertindoleSertindole may decrease the stimulatory activities of Methamphetamine.
SulpirideSulpiride may decrease the stimulatory activities of Methamphetamine.
Tedizolid PhosphateTedizolid Phosphate may increase the hypertensive activities of Methamphetamine.
TerbutalineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Terbutaline.
TheophyllineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Theophylline.
ThioridazineThioridazine may decrease the stimulatory activities of Methamphetamine.
ThiothixeneThiothixene may decrease the stimulatory activities of Methamphetamine.
TiclopidineThe metabolism of Methamphetamine can be decreased when combined with Ticlopidine.
TranylcypromineTranylcypromine may increase the hypertensive activities of Methamphetamine.
TrifluoperazineTrifluoperazine may decrease the stimulatory activities of Methamphetamine.
TriflupromazineTriflupromazine may decrease the stimulatory activities of Methamphetamine.
TriprolidineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Triprolidine.
VilanterolThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Vilanterol.
Vitamin CThe serum concentration of Methamphetamine can be decreased when it is combined with Vitamin C.
ZiprasidoneZiprasidone may decrease the stimulatory activities of Methamphetamine.
ZuclopenthixolZuclopenthixol may decrease the stimulatory activities of Methamphetamine.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
negative modulator
General Function:
Monoamine transmembrane transporter activity
Specific Function:
Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:
SLC6A3
Uniprot ID:
Q01959
Molecular Weight:
68494.255 Da
References
  1. Escubedo E, Camarasa J, Chipana C, Garcia-Rates S, Pubill D: Involvement of nicotinic receptors in methamphetamine- and MDMA-induced neurotoxicity: pharmacological implications. Int Rev Neurobiol. 2009;88:121-66. doi: 10.1016/S0074-7742(09)88006-9. [PubMed:19897077 ]
  2. 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:15602501 ]
  3. 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:15661631 ]
  4. 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:15764732 ]
  5. 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:15795321 ]
  6. 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:15950014 ]
  7. 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:15728379 ]
  8. Fleckenstein AE, Volz TJ, Riddle EL, Gibb JW, Hanson GR: New insights into the mechanism of action of amphetamines. Annu Rev Pharmacol Toxicol. 2007;47:681-98. [PubMed:17209801 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
negative modulator
General Function:
Serotonin:sodium symporter activity
Specific Function:
Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into the pre-synaptic terminal for re-utilization. Plays a key role in mediating regulation of the availability of serotonin to other receptors of serotonergic systems. Terminates the action of serotonin an...
Gene Name:
SLC6A4
Uniprot ID:
P31645
Molecular Weight:
70324.165 Da
References
  1. Numachi Y, Ohara A, Yamashita M, Fukushima S, Kobayashi H, Hata H, Watanabe H, Hall FS, Lesch KP, Murphy DL, Uhl GR, Sora I: Methamphetamine-induced hyperthermia and lethal toxicity: role of the dopamine and serotonin transporters. Eur J Pharmacol. 2007 Oct 31;572(2-3):120-8. Epub 2007 Jun 27. [PubMed:17673199 ]
  2. Tellez R, Rocha L, Castillo C, Meneses A: Autoradiographic study of serotonin transporter during memory formation. Behav Brain Res. 2010 Sep 1;212(1):12-26. doi: 10.1016/j.bbr.2010.03.015. Epub 2010 Mar 11. [PubMed:20226815 ]
  3. Sora I, Li B, Fumushima S, Fukui A, Arime Y, Kasahara Y, Tomita H, Ikeda K: Monoamine transporter as a target molecule for psychostimulants. Int Rev Neurobiol. 2009;85:29-33. doi: 10.1016/S0074-7742(09)85003-4. [PubMed:19607959 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
negative modulator
General Function:
Norepinephrine:sodium symporter activity
Specific Function:
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:
SLC6A2
Uniprot ID:
P23975
Molecular Weight:
69331.42 Da
References
  1. Fleckenstein AE, Volz TJ, Riddle EL, Gibb JW, Hanson GR: New insights into the mechanism of action of amphetamines. Annu Rev Pharmacol Toxicol. 2007;47:681-98. [PubMed:17209801 ]
  2. 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:15955613 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Monoamine transmembrane transporter activity
Specific Function:
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.
Gene Name:
SLC18A2
Uniprot ID:
Q05940
Molecular Weight:
55712.075 Da
References
  1. Horton DB, Siripurapu KB, Norrholm SD, Culver JP, Hojahmat M, Beckmann JS, Harrod SB, Deaciuc AG, Bardo MT, Crooks PA, Dwoskin LP: meso-Transdiene analogs inhibit vesicular monoamine transporter-2 function and methamphetamine-evoked dopamine release. J Pharmacol Exp Ther. 2011 Mar;336(3):940-51. doi: 10.1124/jpet.110.175117. Epub 2010 Dec 21. [PubMed:21177475 ]
  2. 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:15955613 ]
  3. 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:7751968 ]
  4. Yasumoto S, Tamura K, Karasawa J, Hasegawa R, Ikeda K, Yamamoto T, Yamamoto H: Inhibitory effect of selective serotonin reuptake inhibitors on the vesicular monoamine transporter 2. Neurosci Lett. 2009 May 1;454(3):229-32. doi: 10.1016/j.neulet.2009.03.049. Epub 2009 Mar 18. [PubMed:19429089 ]
  5. Fleckenstein AE, Volz TJ, Riddle EL, Gibb JW, Hanson GR: New insights into the mechanism of action of amphetamines. Annu Rev Pharmacol Toxicol. 2007;47:681-98. [PubMed:17209801 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Serotonin transmembrane transporter activity
Specific Function:
Involved in the transport of biogenic monoamines, such as serotonin, from the cytoplasm into the secretory vesicles of neuroendocrine and endocrine cells.
Gene Name:
SLC18A1
Uniprot ID:
P54219
Molecular Weight:
56256.71 Da
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:15955613 ]
  2. Henry JP, Sagne C, Bedet C, Gasnier B: The vesicular monoamine transporter: from chromaffin granule to brain. Neurochem Int. 1998 Mar;32(3):227-46. [PubMed:9587917 ]
  3. Fleckenstein AE, Volz TJ, Riddle EL, Gibb JW, Hanson GR: New insights into the mechanism of action of amphetamines. Annu Rev Pharmacol Toxicol. 2007;47:681-98. [PubMed:17209801 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Trace-amine receptor activity
Specific Function:
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 ami...
Gene Name:
TAAR1
Uniprot ID:
Q96RJ0
Molecular Weight:
39091.34 Da
References
  1. Grandy DK: Trace amine-associated receptor 1-Family archetype or iconoclast? Pharmacol Ther. 2007 Dec;116(3):355-90. Epub 2007 Jul 17. [PubMed:17888514 ]
  2. Borowsky B, Adham N, Jones KA, Raddatz R, Artymyshyn R, Ogozalek KL, Durkin MM, Lakhlani PP, Bonini JA, Pathirana S, Boyle N, Pu X, Kouranova E, Lichtblau H, Ochoa FY, Branchek TA, Gerald C: Trace amines: identification of a family of mammalian G protein-coupled receptors. Proc Natl Acad Sci U S A. 2001 Jul 31;98(16):8966-71. Epub 2001 Jul 17. [PubMed:11459929 ]
  3. 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:17218486 ]
  4. 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:17234900 ]
  5. 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:17212650 ]
  6. 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:17234899 ]
  7. 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:15764732 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Thioesterase binding
Specific Function:
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianser...
Gene Name:
ADRA2A
Uniprot ID:
P08913
Molecular Weight:
48956.275 Da
References
  1. Jeng CH, Wang Y: Methamphetamine modulates GABA-induced electrophysiological depression by alternating noradrenergic actions in cerebellar Purkinje neurons. Psychopharmacology (Berl). 1998 Mar;136(2):132-8. [PubMed:9551769 ]
  2. 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:15955613 ]
  3. Nishio M, Kanda Y, Mizuno K, Watanabe Y: Methamphetamine increases the hippocampal alpha(2A)-adrenergic receptor and Galpha(o) in mice. Neurosci Lett. 2002 Dec 16;334(3):145-8. [PubMed:12453616 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Epinephrine binding
Specific Function:
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phent...
Gene Name:
ADRA2B
Uniprot ID:
P18089
Molecular Weight:
49565.8 Da
References
  1. Jeng CH, Wang Y: Methamphetamine modulates GABA-induced electrophysiological depression by alternating noradrenergic actions in cerebellar Purkinje neurons. Psychopharmacology (Berl). 1998 Mar;136(2):132-8. [PubMed:9551769 ]
  2. 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:15955613 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Protein homodimerization activity
Specific Function:
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins.
Gene Name:
ADRA2C
Uniprot ID:
P18825
Molecular Weight:
49521.585 Da
References
  1. Jeng CH, Wang Y: Methamphetamine modulates GABA-induced electrophysiological depression by alternating noradrenergic actions in cerebellar Purkinje neurons. Psychopharmacology (Berl). 1998 Mar;136(2):132-8. [PubMed:9551769 ]
  2. 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:15955613 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Serotonin binding
Specific Function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular Weight:
59681.27 Da
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:15955613 ]
  2. Ulus IH, Maher TJ, Wurtman RJ: Characterization of phentermine and related compounds as monoamine oxidase (MAO) inhibitors. Biochem Pharmacol. 2000 Jun 15;59(12):1611-21. [PubMed:10799660 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Primary amine oxidase activity
Specific Function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular Weight:
58762.475 Da
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:15955613 ]
  2. Ulus IH, Maher TJ, Wurtman RJ: Characterization of phentermine and related compounds as monoamine oxidase (MAO) inhibitors. Biochem Pharmacol. 2000 Jun 15;59(12):1611-21. [PubMed:10799660 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
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.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Toxin transporter activity
Specific Function:
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.
Gene Name:
SLC22A3
Uniprot ID:
O75751
Molecular Weight:
61279.485 Da
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:9830022 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Symporter activity
Specific Function:
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.
Gene Name:
SLC22A5
Uniprot ID:
O76082
Molecular Weight:
62751.08 Da
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:9618255 ]
  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:10454528 ]
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Drug created on August 29, 2007 08:51 / Updated on November 16, 2015 12:32