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

Details

Stereochemistry ABSOLUTE
Molecular Formula C10H15N
Molecular Weight 149.2332
Optical Activity ( + )
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHAMPHETAMINE

SMILES

C[C@@]([H])(Cc1ccccc1)NC

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 149.2332
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: https://www.ncbi.nlm.nih.gov/pubmed/22037049 | https://www.drugs.com/uk/vicks-inhaler-leaflet.html | https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=38849 | https://www.ncbi.nlm.nih.gov/pubmed/17015058

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).

Originator

Curator's Comment:: methamphetamine, was developed in Japan in 1919

Approval Year

TargetsConditions

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

-820627200000
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

-820627200000
Primary
LEVMETAMFETAMINE
Primary
LEVMETAMFETAMINE
Primary
LEVMETAMFETAMINE
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
Overdose
Dose: 2 g
Route: oral
Route: single
Dose: 2 g
Sources:
healthy, adult
Health Status: healthy
Age Group: adult
Sex: unknown
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
Health Status: healthy
Age Group: adult
Sex: unknown
Sources:
AEs

AEs

AESignificanceDosePopulation
Intoxication 25 patients
Disc. AE
2 g single, oral
Overdose
Dose: 2 g
Route: oral
Route: single
Dose: 2 g
Sources:
healthy, adult
Health Status: healthy
Age Group: adult
Sex: unknown
Sources:
Sourcing
PubMed

PubMed

TitleDatePubMed
Carbon-monoxide poisoning in young drug addicts due to indoor use of a gasoline-powered generator.
2001 Jun
Parkin-deficient mice are not more sensitive to 6-hydroxydopamine or methamphetamine neurotoxicity.
2005 Dec 24
Potential marker for smoked methamphetamine hydrochloride based on a gas chromatography-mass spectrometry quantification method for trans-phenylpropene.
2005 Sep
The acute effects of d-amphetamine and methamphetamine on attention and psychomotor performance.
2006 Aug
High doses of methamphetamine that cause disruption of the blood-brain barrier in limbic regions produce extensive neuronal degeneration in mouse hippocampus.
2006 Dec 1
NMR regulatory analysis: enantiomeric purity determination for (R)-(-)-desoxyephedrine and antipode methamphetamine.
2006 Mar
Behavioral effects of ketamine and toxic interactions with psychostimulants.
2006 Mar 16
Long-term effects of a single adult methamphetamine challenge: minor impact on dopamine fibre density in limbic brain areas of gerbils.
2006 Mar 28
Comparison of the monoamine transporters from human and mouse in their sensitivities to psychostimulant drugs.
2006 Mar 3
Armodafinil, the R-enantiomer of modafinil: wake-promoting effects and pharmacokinetic profile in the rat.
2006 Nov
Human pharmacology of the methamphetamine stereoisomers.
2006 Oct
Phosphodiesterase 1B differentially modulates the effects of methamphetamine on locomotor activity and spatial learning through DARPP32-dependent pathways: evidence from PDE1B-DARPP32 double-knockout mice.
2006 Oct
Effects of (+/-)3,4-methylenedioxymethamphetamine, (+/-)3,4-methylenedioxyamphetamine and methamphetamine on temperature and activity in rhesus macaques.
2006 Oct 13
[Analysis of active components of evidence materials secured in the cases of drugs abuse associated with amphetamines and cannabis products].
2006 Oct-Dec
Comparison of monoamine and corticosterone levels 24 h following (+)methamphetamine, (+/-)3,4-methylenedioxymethamphetamine, cocaine, (+)fenfluramine or (+/-)methylphenidate administration in the neonatal rat.
2006 Sep
Effects of methamphetamine on single unit activity in rat medial prefrontal cortex in vivo.
2007
Smokable ("ice", "crystal meth") and non smokable amphetamine-type stimulants: clinical pharmacological and epidemiological issues, with special reference to the UK.
2007
Selective inhibition of cyclooxygenase-2 exacerbates methamphetamine-induced dopamine depletion in the striatum in rats.
2007 Dec 19
Application of mixtures of tartaric acid derivatives in resolution via supercritical fluid extraction.
2007 Jun
Oral administration of (+/-)3,4-methylenedioxymethamphetamine and (+)methamphetamine alters temperature and activity in rhesus macaques.
2007 May
PET studies of d-methamphetamine pharmacokinetics in primates: comparison with l-methamphetamine and ( --)-cocaine.
2007 Oct
Methamphetamine body packer: acute poisoning death due to massive leaking of methamphetamine.
2007 Sep
Perinatal asphyxia reduces dentate granule cells and exacerbates methamphetamine-induced hyperlocomotion in adulthood.
2008
Redetermination of (+)-methamphetamine hydro-chloride at 90 K.
2008 Apr 30
Regional differences in HIV prevalence among drug users in China: potential for future spread of HIV?
2008 Aug 4
Myocardial lesions after long-term administration of methamphetamine in rats.
2008 Dec
Histopathological studies of cardiac lesions after an acute high dose administration of methamphetamine.
2008 Jan
Neurochemical consequences of dysphoric state during amphetamine withdrawal in animal models: a review.
2008 Jan
The clinical pharmacology of intranasal l-methamphetamine.
2008 Jul 21
Rapid nondestructive on-site screening of methylamphetamine seizures by attenuated total reflection fourier transform infrared spectroscopy.
2008 Jun
Evaluation of effects of methamphetamine repeated dosing on proliferation and apoptosis of rat germ cells.
2008 Mar-Apr
Environmental enrichment has no effect on the development of dopaminergic and GABAergic fibers during methylphenidate treatment of early traumatized gerbils.
2008 May 16
Identification of impurities and statistical classification of methamphetamine hydrochloride drugs seized in China.
2008 Nov 20
Applications of nanomaterials in electrogenerated chemiluminescence biosensors.
2009
Local hippocampal methamphetamine-induced reinforcement.
2009
Changes in glutamate/NMDA receptor subunit 1 expression in rat brain after acute and subacute exposure to methamphetamine.
2009
Cryogenic terahertz spectrum of (+)-methamphetamine hydrochloride and assignment using solid-state density functional theory.
2009 Apr 30
An electrochemiluminescent sensor for methamphetamine hydrochloride based on multiwall carbon nanotube/ionic liquid composite electrode.
2009 Jan 1
Rapid analysis of methamphetamine in hair by micropulverized extraction and microchip-based competitive ELISA.
2009 Jan 30
"Ice" use and eating disorders: a report of three cases.
2009 Mar
Characterization of route specific impurities found in methamphetamine synthesized by the Leuckart and reductive amination methods.
2009 Sep 1
Effect of an electronic control device exposure on a methamphetamine-intoxicated animal model.
2010 Apr
Enantioselective piezoelectric quartz crystal sensor for d-methamphetamine based on a molecularly imprinted polymer.
2010 Aug
Distribution and pharmacokinetics of methamphetamine in the human body: clinical implications.
2010 Dec 7
Reinforcing effects of methamphetamine in an animal model of attention-deficit/hyperactivity disorder--the spontaneously hypertensive rat.
2010 Dec 9
Regulation of the dopamine transporter: aspects relevant to psychostimulant drugs of abuse.
2010 Feb
Methamphetamine reduces LTP and increases baseline synaptic transmission in the CA1 region of mouse hippocampus.
2010 Jun 30
Toward a Better Understanding of Non-Addicted, Methamphetamine-Using, Men who Have Sex with Men (MSM) in Atlanta.
2010 May 14
A neurotoxic regimen of methamphetamine exacerbates the febrile and neuroinflammatory response to a subsequent peripheral immune stimulus.
2010 Nov 22
Detection of volatile indicators of illicit substances by the olfactory receptors of Drosophila melanogaster.
2010 Sep
Patents

Sample Use Guides

adults and children 12 years of age and over 2 inhalations in each nostril
Route of Administration: Nasal
TA receptor activation was assayed in RD-HGA16cells stably expressing Gα16 and the hTAAR1 receptor. These cells were plated in HAM’s F-12 medium with 10% fetal bovine serum, 400 µg/ml hygromycin, and 400 µg/ml geneticin at 30,000 cells/well in 96-well, black, clear-bottom plates and incubated at 37 °C 5% CO2 overnight. Activation of hTAAR1 via Levomethamphetamine ((R)-10) was assessed the next day using the Calcium 3 Assay Kit (Molecular Devices). On the day of assay, the culture medium was removed and the cells washed once in 100 µl HBSS buffer containing 0.78 mg/ml probenicid, followed by the addition of 100 µl HBSS buffer plus probenicid and 100 µl of Calcium 3 dye (one-third the suggested concentration). The cells were incubated with the dye at 37 °C for 1 h. Levomethamphetamine were evaluated using 10 different concentrations run in duplicate. These were added to cells at 5 times the final concentration in HBSS/probenicid containing 1.25% DMSO (0.25% final concentration). The effect of test compound on internal calcium mobilization was determined with a FlexStation set for bottom read with 485-nm excitation and 525-nm emission wavelengths
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:47:34 UTC 2021
Edited
by admin
on Fri Jun 25 21:47:34 UTC 2021
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 [INN]
Common Name English
NSC-25115
Code English
METAMFETAMINE [WHO-DD]
Common Name 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 Fri Jun 25 21:47:35 UTC 2021 , Edited by admin on Fri Jun 25 21:47:35 UTC 2021
WHO-VATC QN06BA03
Created by admin on Fri Jun 25 21:47:35 UTC 2021 , Edited by admin on Fri Jun 25 21:47:35 UTC 2021
NDF-RT N0000175425
Created by admin on Fri Jun 25 21:47:35 UTC 2021 , Edited by admin on Fri Jun 25 21:47:35 UTC 2021
CFR 21 CFR 862.3610
Created by admin on Fri Jun 25 21:47:35 UTC 2021 , Edited by admin on Fri Jun 25 21:47:35 UTC 2021
DEA NO. 1105
Created by admin on Fri Jun 25 21:47:35 UTC 2021 , Edited by admin on Fri Jun 25 21:47:35 UTC 2021
NDF-RT N0000175372
Created by admin on Fri Jun 25 21:47:35 UTC 2021 , Edited by admin on Fri Jun 25 21:47:35 UTC 2021
NDF-RT N0000175729
Created by admin on Fri Jun 25 21:47:35 UTC 2021 , Edited by admin on Fri Jun 25 21:47:35 UTC 2021
WHO-ATC N06BA03
Created by admin on Fri Jun 25 21:47:35 UTC 2021 , Edited by admin on Fri Jun 25 21:47:35 UTC 2021
LIVERTOX 612
Created by admin on Fri Jun 25 21:47:35 UTC 2021 , Edited by admin on Fri Jun 25 21:47:35 UTC 2021
NDF-RT N0000175651
Created by admin on Fri Jun 25 21:47:35 UTC 2021 , Edited by admin on Fri Jun 25 21:47:35 UTC 2021
CFR 21 CFR 250.101
Created by admin on Fri Jun 25 21:47:35 UTC 2021 , Edited by admin on Fri Jun 25 21:47:35 UTC 2021
NDF-RT N0000175739
Created by admin on Fri Jun 25 21:47:35 UTC 2021 , Edited by admin on Fri Jun 25 21:47:35 UTC 2021
NCI_THESAURUS C47795
Created by admin on Fri Jun 25 21:47:35 UTC 2021 , Edited by admin on Fri Jun 25 21:47:35 UTC 2021
NDF-RT N0000175372
Created by admin on Fri Jun 25 21:47:35 UTC 2021 , Edited by admin on Fri Jun 25 21:47:35 UTC 2021
Code System Code Type Description
DRUG CENTRAL
1732
Created by admin on Fri Jun 25 21:47:35 UTC 2021 , Edited by admin on Fri Jun 25 21:47:35 UTC 2021
PRIMARY
ECHA (EC/EINECS)
208-668-7
Created by admin on Fri Jun 25 21:47:35 UTC 2021 , Edited by admin on Fri Jun 25 21:47:35 UTC 2021
PRIMARY
RXCUI
6816
Created by admin on Fri Jun 25 21:47:35 UTC 2021 , Edited by admin on Fri Jun 25 21:47:35 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C61840
Created by admin on Fri Jun 25 21:47:35 UTC 2021 , Edited by admin on Fri Jun 25 21:47:35 UTC 2021
PRIMARY
MERCK INDEX
M7290
Created by admin on Fri Jun 25 21:47:35 UTC 2021 , Edited by admin on Fri Jun 25 21:47:35 UTC 2021
PRIMARY Merck Index
CAS
537-46-2
Created by admin on Fri Jun 25 21:47:35 UTC 2021 , Edited by admin on Fri Jun 25 21:47:35 UTC 2021
PRIMARY
INN
1879
Created by admin on Fri Jun 25 21:47:35 UTC 2021 , Edited by admin on Fri Jun 25 21:47:35 UTC 2021
PRIMARY
HSDB
3359
Created by admin on Fri Jun 25 21:47:35 UTC 2021 , Edited by admin on Fri Jun 25 21:47:35 UTC 2021
PRIMARY
DRUG BANK
DB01577
Created by admin on Fri Jun 25 21:47:35 UTC 2021 , Edited by admin on Fri Jun 25 21:47:35 UTC 2021
PRIMARY
PUBCHEM
10836
Created by admin on Fri Jun 25 21:47:35 UTC 2021 , Edited by admin on Fri Jun 25 21:47:35 UTC 2021
PRIMARY
ChEMBL
CHEMBL1201201
Created by admin on Fri Jun 25 21:47:35 UTC 2021 , Edited by admin on Fri Jun 25 21:47:35 UTC 2021
PRIMARY
FDA UNII
44RAL3456C
Created by admin on Fri Jun 25 21:47:35 UTC 2021 , Edited by admin on Fri Jun 25 21:47:35 UTC 2021
PRIMARY
MESH
D008694
Created by admin on Fri Jun 25 21:47:35 UTC 2021 , Edited by admin on Fri Jun 25 21:47:35 UTC 2021
PRIMARY
IUPHAR
4803
Created by admin on Fri Jun 25 21:47:35 UTC 2021 , Edited by admin on Fri Jun 25 21:47:35 UTC 2021
PRIMARY
WIKIPEDIA
METHAMPHETAMINE
Created by admin on Fri Jun 25 21:47:35 UTC 2021 , Edited by admin on Fri Jun 25 21:47:35 UTC 2021
PRIMARY
LACTMED
Methamphetamine
Created by admin on Fri Jun 25 21:47:35 UTC 2021 , Edited by admin on Fri Jun 25 21:47:35 UTC 2021
PRIMARY
EPA CompTox
537-46-2
Created by admin on Fri Jun 25 21:47:35 UTC 2021 , Edited by admin on Fri Jun 25 21:47:35 UTC 2021
PRIMARY
EVMPD
SUB08809MIG
Created by admin on Fri Jun 25 21:47:35 UTC 2021 , Edited by admin on Fri Jun 25 21:47:35 UTC 2021
PRIMARY
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