U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C10H15N
Molecular Weight 149.2328
Optical Activity ( + )
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHAMPHETAMINE

SMILES

CN[C@@H](C)CC1=CC=CC=C1

InChI

InChIKey=MYWUZJCMWCOHBA-VIFPVBQESA-N
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

HIDE SMILES / InChI

Molecular Formula C10H15N
Molecular Weight 149.2328
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Methamphetamine is a strong central nervous system (CNS) stimulant and is a sympathomimetic drug. It is approved under the brand name DESOXYN for the treatment of attention deficit disorder with hyperactivity (ADHD) and exogenous obesity. It is a scheduled drug in most countries due to its high potential for addiction and abuse. Methamphetamine 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. Methamphetamine has been identified as a potent full agonist of trace amine-associated receptor 1, and also, as an agonist of the alpha-2 adrenergic receptors. Methamphetamine increases extracellular dopamine in reward-relevant pathways by interacting at vesicular monoamine transporter-2 (VMAT2) to inhibit dopamine uptake and promote dopamine release from synaptic vesicles, increasing cytosolic dopamine available for reverse transport by the dopamine transporter (DAT).

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q05940
Gene ID: 6571.0
Gene Symbol: SLC18A2
Target Organism: Homo sapiens (Human)
Target ID: Q96RJ0
Gene ID: 134864.0
Gene Symbol: TAAR1
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
DESOXYN

Approved Use

Attention Deficit Disorder with Hyperactivity: DESOXYN tablets are indicated as an integral part of a total treatment program which typically includes other remedial measures (psychological, educational, social) for a stabilizing effect in children over 6 years of age with a behavioral syndrome characterized by the following group of developmentally inappropriate symptoms: moderate to severe distractibility, short attention span, hyperactivity, emotional lability, and impulsivity. The diagnosis of this syndrome should not be made with finality when these symptoms are only of comparatively recent origin. Nonlocalizing (soft) neurological signs, learning disability, and abnormal EEG may or may not be present, and a diagnosis of central nervous system dysfunction may or may not be warranted. Exogenous Obesity: as a short-term (i.e., a few weeks) adjunct in a regimen of weight reduction based on caloric restriction, for patients in whom obesity is refractory to alternative therapy, e.g., repeated diets, group programs, and other drugs.

Launch Date

-8.2062718E11
Palliative
DESOXYN

Approved Use

Attention Deficit Disorder with Hyperactivity Methamphetamine hydrochloride tablets are indicated as an integral part of a total treatment program which typically includes other remedial measures (psychological, educational, social) for a stabilizing effect in children over 6 years of age with a behavioral syndrome characterized by the following group of developmentally inappropriate symptoms: moderate to severe distractibility, short attention span, hyperactivity, emotional lability, and impulsivity. The diagnosis of this syndrome should not be made with finality when these symptoms are only of comparatively recent origin. Nonlocalizing (soft) neurological signs, learning disability, and abnormal EEG may or may not be present, and a diagnosis of central nervous system dysfunction may or may not be warranted. Exogenous Obesity As a short-term (i.e., a few weeks) adjunct in a regimen of weight reduction based on caloric restriction, for patients in whom obesity is refractory to alternative therapy, e.g., repeated diets, group programs, and other drugs. The limited usefulness of methamphetamine hydrochloride tablets (see CLINICAL PHARMACOLOGY) should be weighed against possible risks inherent in use of the drug, such as those described below.

Launch Date

-8.2062718E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
19.8 ng/mL
0.125 mg/kg single, oral
dose: 0.125 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
METHAMPHETAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
330 ng × h/mL
0.125 mg/kg single, oral
dose: 0.125 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
METHAMPHETAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
8.46 h
0.125 mg/kg single, oral
dose: 0.125 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
METHAMPHETAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
2 g single, oral (max)
Overdose
Dose: 2 g
Route: oral
Route: single
Dose: 2 g
Sources:
healthy, adult
n = 25
Health Status: healthy
Condition: methamphetamine dependence
Age Group: adult
Sex: unknown
Population Size: 25
Sources:
Disc. AE: Intoxication...
AEs leading to
discontinuation/dose reduction:
Intoxication (25 patients)
Sources:
40 mg single, oral
Dose: 40 mg
Route: oral
Route: single
Dose: 40 mg
Sources:
healthy, adult
n = 19
Health Status: healthy
Age Group: adult
Sex: unknown
Population Size: 19
Sources:
AEs

AEs

AESignificanceDosePopulation
Intoxication 25 patients
Disc. AE
2 g single, oral (max)
Overdose
Dose: 2 g
Route: oral
Route: single
Dose: 2 g
Sources:
healthy, adult
n = 25
Health Status: healthy
Condition: methamphetamine dependence
Age Group: adult
Sex: unknown
Population Size: 25
Sources:
PubMed

PubMed

TitleDatePubMed
Methamphetamine--properties and analytical methods of enantiomer determination.
1998 Aug 31
A selective dopamine D4 receptor antagonist, NRA0160: a preclinical neuropharmacological profile.
1999
Enantiomer-specific high-performance liquid chromatography with fluorescence detection of methamphetamines in abusers' hair and urine.
1999 Dec
Methamphetamine administration causes overexpression of nNOS in the mouse striatum.
1999 Dec 18
Selenium, an antioxidant, protects against methamphetamine-induced dopaminergic neurotoxicity.
1999 Feb 13
Brain choline acetyltransferase activity in chronic, human users of cocaine, methamphetamine, and heroin.
1999 Jan
The role of gamma-aminobutyric acid (GABA)-benzodiazepine neurotransmission in an animal model of methamphetamine-induced psychosis.
1999 Mar
Null mutation of c-fos causes exacerbation of methamphetamine-induced neurotoxicity.
1999 Nov 15
Estrogen and progesterone distinctively modulate methamphetamine-induced dopamine and serotonin depletions in C57BL/6J mice.
2000
Cocaine and methamphetamine: differential addiction rates.
2000 Dec
Adult learning deficits after neonatal exposure to D-methamphetamine: selective effects on spatial navigation and memory.
2000 Jun 15
Effects of isradipine, a dihydropyridine-class calcium channel antagonist, on D-methamphetamine-induced cognitive and physiological changes in humans.
2000 May
Methamphetamine-induced striatal dopamine release, behavior changes and neurotoxicity in BALB/c mice.
2000 Oct
Comparison between the role of the neuronal and inducible nitric oxide synthase in methamphetamine-induced neurotoxicity and sensitization.
2000 Sep
The effects of single dose of methamphetamine on lipid peroxidation levels in the rat striatum and prefrontal cortex.
2000 Sep
nNOS inhibitors attenuate methamphetamine-induced dopaminergic neurotoxicity but not hyperthermia in mice.
2000 Sep 11
Direct effects of methamphetamine on hypertrophy and microtubules in cultured adult rat ventricular myocytes.
2000 Sep 11
The association study of DRD2, ACE and AGT gene polymorphisms and metamphetamine dependence.
2001
Anti-apoptotic and apoptotic action of (-)-deprenyl and its metabolites.
2001
Differential effects of cocaine and methamphetamine on neurotensin/neuromedin N and preprotachykinin messenger RNA expression in unique regions of the striatum.
2001
Decision-making deficits, linked to a dysfunctional ventromedial prefrontal cortex, revealed in alcohol and stimulant abusers.
2001
Sensitized increase of period gene expression in the mouse caudate/putamen caused by repeated injection of methamphetamine.
2001 Apr
Neonatal phencyclidine treatment selectively attenuates mesolimbic dopamine function in adult rats as revealed by methamphetamine-induced behavior and c-fos mRNA expression in the brain.
2001 Apr
Dose-dependent protective effects of apomorphine against methamphetamine-induced nigrostriatal damage.
2001 Apr 13
Increased expression of synaptophysin and stathmin mRNAs after methamphetamine administration in rat brain.
2001 Apr 17
Peroxynitrite plays a role in methamphetamine-induced dopaminergic neurotoxicity: evidence from mice lacking neuronal nitric oxide synthase gene or overexpressing copper-zinc superoxide dismutase.
2001 Feb
Contrasting responses by basal ganglia met-enkephalin systems to low and high doses of methamphetamine in a rat model.
2001 Feb
Highly sensitive analysis of methamphetamine and amphetamine in human whole blood using headspace solid-phase microextraction and gas chromatography-mass spectrometry.
2001 Feb 1
Methamphetamine-induced rapid and reversible changes in dopamine transporter function: an in vitro model.
2001 Feb 15
Long-term effects of a high-dose methamphetamine regimen on subsequent methamphetamine-induced dopamine release in vivo.
2001 Feb 16
[Amotivational syndrome in organic solvent abusers].
2001 Jan
Delta opioid peptide augments functional effects and intrastriatal graft survival of rat fetal ventral mesencephalic cells.
2001 Jan-Feb
Plasma and brain methamphetamine concentrations in neonatal rats.
2001 Jan-Feb
Elevations in plasmatic titers of corticosterone and aldosterone, in the absence of changes in ACTH, testosterone, or glial fibrillary acidic protein, 72 h following D,L-fenfluramine or D-fenfluramine administration to rats.
2001 Jan-Feb
Methamphetamine potentiates ischemia/reperfusion insults after transient middle cerebral artery ligation.
2001 Mar
Comparison of ELISAs for opiates, methamphetamine, cocaine metabolite, benzodiazepines, phencyclidine, and cannabinoids in whole blood and urine.
2001 Mar
Higher cortical and lower subcortical metabolism in detoxified methamphetamine abusers.
2001 Mar
Association of dopamine transporter reduction with psychomotor impairment in methamphetamine abusers.
2001 Mar
Airway effects of marijuana, cocaine, and other inhaled illicit agents.
2001 Mar
Lobeline inhibits the neurochemical and behavioral effects of amphetamine.
2001 Mar
Dopaminergic role in stimulant-induced wakefulness.
2001 Mar 1
Differences between methamphetamine users and cocaine users in treatment.
2001 Mar 1
Protective effect of the antioxidant 6-ethoxy-2,2-pentamethylen-1,2-dihydroquinoline (S 33113) in models of cerebral neurodegeneration.
2001 Mar 23
Patents

Sample Use Guides

in rats: 10mg/kg i.p
Route of Administration: Intraperitoneal
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Thu Jul 06 22:59:32 UTC 2023
Edited
by admin
on Thu Jul 06 22:59:32 UTC 2023
Record UNII
44RAL3456C
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METHAMPHETAMINE
HSDB   MI   VANDF  
Common Name English
METAMFETAMINE
INN   WHO-DD  
INN  
Official Name English
J6.362B
Code English
METHYLAMPHETAMINE
Systematic Name English
Metamfetamine [WHO-DD]
Common Name English
metamfetamine [INN]
Common Name English
NSC-25115
Code English
METHAMPHETAMINE [VANDF]
Common Name English
METHAMPHETAMINE [MI]
Common Name English
(S)-PHENYLMETHYLAMINOPROPANE
Common Name English
METHAMPHETAMINE [HSDB]
Common Name English
Classification Tree Code System Code
NDF-RT N0000007883
Created by admin on Thu Jul 06 22:59:35 UTC 2023 , Edited by admin on Thu Jul 06 22:59:35 UTC 2023
WHO-VATC QN06BA03
Created by admin on Thu Jul 06 22:59:35 UTC 2023 , Edited by admin on Thu Jul 06 22:59:35 UTC 2023
NDF-RT N0000175425
Created by admin on Thu Jul 06 22:59:35 UTC 2023 , Edited by admin on Thu Jul 06 22:59:35 UTC 2023
CFR 21 CFR 862.3610
Created by admin on Thu Jul 06 22:59:35 UTC 2023 , Edited by admin on Thu Jul 06 22:59:35 UTC 2023
DEA NO. 1105
Created by admin on Thu Jul 06 22:59:35 UTC 2023 , Edited by admin on Thu Jul 06 22:59:35 UTC 2023
NDF-RT N0000175372
Created by admin on Thu Jul 06 22:59:35 UTC 2023 , Edited by admin on Thu Jul 06 22:59:35 UTC 2023
NDF-RT N0000175729
Created by admin on Thu Jul 06 22:59:35 UTC 2023 , Edited by admin on Thu Jul 06 22:59:35 UTC 2023
WHO-ATC N06BA03
Created by admin on Thu Jul 06 22:59:35 UTC 2023 , Edited by admin on Thu Jul 06 22:59:35 UTC 2023
LIVERTOX 612
Created by admin on Thu Jul 06 22:59:35 UTC 2023 , Edited by admin on Thu Jul 06 22:59:35 UTC 2023
NDF-RT N0000175651
Created by admin on Thu Jul 06 22:59:35 UTC 2023 , Edited by admin on Thu Jul 06 22:59:35 UTC 2023
CFR 21 CFR 250.101
Created by admin on Thu Jul 06 22:59:35 UTC 2023 , Edited by admin on Thu Jul 06 22:59:35 UTC 2023
NDF-RT N0000175739
Created by admin on Thu Jul 06 22:59:35 UTC 2023 , Edited by admin on Thu Jul 06 22:59:35 UTC 2023
NCI_THESAURUS C47795
Created by admin on Thu Jul 06 22:59:35 UTC 2023 , Edited by admin on Thu Jul 06 22:59:35 UTC 2023
NDF-RT N0000175372
Created by admin on Thu Jul 06 22:59:35 UTC 2023 , Edited by admin on Thu Jul 06 22:59:35 UTC 2023
Code System Code Type Description
DRUG CENTRAL
1732
Created by admin on Thu Jul 06 22:59:35 UTC 2023 , Edited by admin on Thu Jul 06 22:59:35 UTC 2023
PRIMARY
ECHA (EC/EINECS)
208-668-7
Created by admin on Thu Jul 06 22:59:35 UTC 2023 , Edited by admin on Thu Jul 06 22:59:35 UTC 2023
PRIMARY
RXCUI
6816
Created by admin on Thu Jul 06 22:59:35 UTC 2023 , Edited by admin on Thu Jul 06 22:59:35 UTC 2023
PRIMARY RxNorm
NCI_THESAURUS
C61840
Created by admin on Thu Jul 06 22:59:35 UTC 2023 , Edited by admin on Thu Jul 06 22:59:35 UTC 2023
PRIMARY
SMS_ID
100000081196
Created by admin on Thu Jul 06 22:59:35 UTC 2023 , Edited by admin on Thu Jul 06 22:59:35 UTC 2023
PRIMARY
CHEBI
6809
Created by admin on Thu Jul 06 22:59:35 UTC 2023 , Edited by admin on Thu Jul 06 22:59:35 UTC 2023
PRIMARY
MERCK INDEX
M7290
Created by admin on Thu Jul 06 22:59:35 UTC 2023 , Edited by admin on Thu Jul 06 22:59:35 UTC 2023
PRIMARY Merck Index
DAILYMED
44RAL3456C
Created by admin on Thu Jul 06 22:59:35 UTC 2023 , Edited by admin on Thu Jul 06 22:59:35 UTC 2023
PRIMARY
CAS
537-46-2
Created by admin on Thu Jul 06 22:59:35 UTC 2023 , Edited by admin on Thu Jul 06 22:59:35 UTC 2023
PRIMARY
INN
1879
Created by admin on Thu Jul 06 22:59:35 UTC 2023 , Edited by admin on Thu Jul 06 22:59:35 UTC 2023
PRIMARY
HSDB
3359
Created by admin on Thu Jul 06 22:59:35 UTC 2023 , Edited by admin on Thu Jul 06 22:59:35 UTC 2023
PRIMARY
NSC
25115
Created by admin on Thu Jul 06 22:59:35 UTC 2023 , Edited by admin on Thu Jul 06 22:59:35 UTC 2023
PRIMARY
DRUG BANK
DB01577
Created by admin on Thu Jul 06 22:59:35 UTC 2023 , Edited by admin on Thu Jul 06 22:59:35 UTC 2023
PRIMARY
PUBCHEM
10836
Created by admin on Thu Jul 06 22:59:35 UTC 2023 , Edited by admin on Thu Jul 06 22:59:35 UTC 2023
PRIMARY
ChEMBL
CHEMBL1201201
Created by admin on Thu Jul 06 22:59:35 UTC 2023 , Edited by admin on Thu Jul 06 22:59:35 UTC 2023
PRIMARY
FDA UNII
44RAL3456C
Created by admin on Thu Jul 06 22:59:35 UTC 2023 , Edited by admin on Thu Jul 06 22:59:35 UTC 2023
PRIMARY
MESH
D008694
Created by admin on Thu Jul 06 22:59:35 UTC 2023 , Edited by admin on Thu Jul 06 22:59:35 UTC 2023
PRIMARY
IUPHAR
4803
Created by admin on Thu Jul 06 22:59:35 UTC 2023 , Edited by admin on Thu Jul 06 22:59:35 UTC 2023
PRIMARY
WIKIPEDIA
METHAMPHETAMINE
Created by admin on Thu Jul 06 22:59:35 UTC 2023 , Edited by admin on Thu Jul 06 22:59:35 UTC 2023
PRIMARY
LACTMED
Methamphetamine
Created by admin on Thu Jul 06 22:59:35 UTC 2023 , Edited by admin on Thu Jul 06 22:59:35 UTC 2023
PRIMARY
EPA CompTox
DTXSID8037128
Created by admin on Thu Jul 06 22:59:35 UTC 2023 , Edited by admin on Thu Jul 06 22:59:35 UTC 2023
PRIMARY
EVMPD
SUB08809MIG
Created by admin on Thu Jul 06 22:59:35 UTC 2023 , Edited by admin on Thu Jul 06 22:59:35 UTC 2023
PRIMARY
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PRECURSOR->PARENT
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