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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H15N.ClH
Molecular Weight 185.6941
Optical Activity ( + )
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHAMPHETAMINE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=TWXDDNPPQUTEOV-FVGYRXGTSA-N
InChI=1S/C10H15N.ClH/c1-9(11-2)8-10-6-4-3-5-7-10;/h3-7,9,11H,8H2,1-2H3;1H/t9-;/m0./s1

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Methamphetamine exposure from postnatal day 11 to 20 causes impairments in both behavioral strategies and spatial learning in adult rats.
2002 Dec 27
Neurochemical and behavioral differences between d-methamphetamine and d-amphetamine in rats.
2003 Feb
Chiral analysis of amphetamine-type stimulants using reversed-polarity capillary electrophoresis/positive ion electrospray ionization tandem mass spectrometry.
2003 Jun
Developmental D-methamphetamine treatment selectively induces spatial navigation impairments in reference memory in the Morris water maze while sparing working memory.
2003 Jun 1
Microbial degradation of illicit drugs, their precursors, and manufacturing by-products: implications for clandestine drug laboratory investigation and environmental assessment.
2003 Jun 24
Elevated environmental temperature and methamphetamine neurotoxicity.
2003 May
Reduced cardiovascular effects of methamphetamine following treatment with selegiline.
2003 Nov 24
Protein tyrosine phosphatase alpha (PTP alpha) knockout mice show deficits in Morris water maze learning, decreased locomotor activity, and decreases in anxiety.
2003 Sep 12
Impurity profiling of methamphetamine hydrochloride drugs seized in the Philippines.
2004 Aug 11
Analysis of pyrolysis products of methamphetamine.
2004 Nov-Dec
Microglial activation is a pharmacologically specific marker for the neurotoxic amphetamines.
2004 Sep 9
Periadolescent rats (P41-50) exhibit increased susceptibility to D-methamphetamine-induced long-term spatial and sequential learning deficits compared to juvenile (P21-30 or P31-40) or adult rats (P51-60).
2005 Jan-Feb
Effects of isradipine on methamphetamine-induced changes in attentional and perceptual-motor skills of cognition.
2005 Mar
In vivo neuroprotective effects of the novel imidazolyl nitrone free-radical scavenger (Z)-alpha-[2-thiazol-2-yl)imidazol-4-yl]-N-tert-butylnitrone (S34176).
2005 Mar 28
Interactions of dopamine D1 and D2 receptor antagonists with D-methamphetamine-induced hyperthermia and striatal dopamine and serotonin reductions.
2005 May
An evaluation of the sensitivity of the standardised field sobriety tests to detect the presence of amphetamine.
2005 Oct
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
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
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
[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
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
Redetermination of (+)-methamphetamine hydro-chloride at 90 K.
2008 Apr 30
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
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
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
Characterization of route specific impurities found in methamphetamine synthesized by the Leuckart and reductive amination methods.
2009 Sep 1
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
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
Autoradiographic study of serotonin transporter during memory formation.
2010 Sep 1
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 21:05:07 UTC 2021
Edited
by admin
on Fri Jun 25 21:05:07 UTC 2021
Record UNII
997F43Z9CV
Record Status Validated (UNII)
Record Version
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Name Type Language
METHAMPHETAMINE HYDROCHLORIDE
MI   ORANGE BOOK   USP   VANDF  
Common Name English
METAMFETAMINE HYDROCHLORIDE [MART.]
Common Name English
METHAMPHETAMINE HYDROCHLORIDE [JAN]
Common Name English
METHAMPHETAMINE HCL
Common Name English
BENZENEETHANAMINE, N,.ALPHA.-DIMETHYL-, HYDROCHLORIDE, (S)-
Systematic Name English
METHAMPHETAMINE HYDROCHLORIDE CII
USP-RS  
Common Name English
METHAMPHETAMINE HYDROCHLORIDE [VANDF]
Common Name English
DESOXYEPHEDRINE HYDROCHLORIDE
Common Name English
NSC-169505
Code English
METHAMPHETAMINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
METHAMPEX
Brand Name English
(+)-METHAMPHETAMINE HYDROCHLORIDE
Common Name English
METHAMPHETAMINE HYDROCHLORIDE [MI]
Common Name English
(+)-(S)-N,.ALPHA.-DIMETHYLPHENETHYLAMINE HYDROCHLORIDE
Systematic Name English
METHAMPHETAMINE HYDROCHLORIDE CII [USP-RS]
Common Name English
METHAMPHETAMINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
METAMFETAMINE HYDROCHLORIDE [WHO-DD]
Common Name English
DESOXYN
Brand Name English
METAMFETAMINE HYDROCHLORIDE
MART.   WHO-DD  
Common Name English
Classification Tree Code System Code
DEA NO. 1105
Created by admin on Fri Jun 25 21:05:07 UTC 2021 , Edited by admin on Fri Jun 25 21:05:07 UTC 2021
NCI_THESAURUS C47795
Created by admin on Fri Jun 25 21:05:07 UTC 2021 , Edited by admin on Fri Jun 25 21:05:07 UTC 2021
Code System Code Type Description
PUBCHEM
66124
Created by admin on Fri Jun 25 21:05:07 UTC 2021 , Edited by admin on Fri Jun 25 21:05:07 UTC 2021
PRIMARY
FDA UNII
997F43Z9CV
Created by admin on Fri Jun 25 21:05:07 UTC 2021 , Edited by admin on Fri Jun 25 21:05:07 UTC 2021
PRIMARY
DRUG BANK
DBSALT000734
Created by admin on Fri Jun 25 21:05:07 UTC 2021 , Edited by admin on Fri Jun 25 21:05:07 UTC 2021
PRIMARY
EPA CompTox
51-57-0
Created by admin on Fri Jun 25 21:05:07 UTC 2021 , Edited by admin on Fri Jun 25 21:05:07 UTC 2021
PRIMARY
RXCUI
82044
Created by admin on Fri Jun 25 21:05:07 UTC 2021 , Edited by admin on Fri Jun 25 21:05:07 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C47609
Created by admin on Fri Jun 25 21:05:07 UTC 2021 , Edited by admin on Fri Jun 25 21:05:07 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-106-9
Created by admin on Fri Jun 25 21:05:07 UTC 2021 , Edited by admin on Fri Jun 25 21:05:07 UTC 2021
PRIMARY
CAS
51-57-0
Created by admin on Fri Jun 25 21:05:07 UTC 2021 , Edited by admin on Fri Jun 25 21:05:07 UTC 2021
PRIMARY
USP_CATALOG
1399001
Created by admin on Fri Jun 25 21:05:07 UTC 2021 , Edited by admin on Fri Jun 25 21:05:07 UTC 2021
PRIMARY USP-RS
MERCK INDEX
M7290
Created by admin on Fri Jun 25 21:05:07 UTC 2021 , Edited by admin on Fri Jun 25 21:05:07 UTC 2021
PRIMARY Merck Index
EVMPD
SUB03186MIG
Created by admin on Fri Jun 25 21:05:07 UTC 2021 , Edited by admin on Fri Jun 25 21:05:07 UTC 2021
PRIMARY
ChEMBL
CHEMBL1201201
Created by admin on Fri Jun 25 21:05:07 UTC 2021 , Edited by admin on Fri Jun 25 21:05:07 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
ENANTIOMER -> ENANTIOMER
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC Elimination
PHARMACOKINETIC