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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

DL-Methamphetamine (also known as +/- Methamphetamin) is a central nervous system stimulant and sympathomimetic with actions and uses similar to DEXTROAMPHETAMINE. The smokable form is a drug of abuse and is referred to as crank, crystal, crystal meth, ice, and speed. Methamphetamine is a mixture of two isomers. One isomer called Dextro, or D Methamphetamine, is active as a central nervous system stimulant and it is a DEA Schedule 2 controlled drug commonly called “Meth” or “Speed”. Desoxyn, a prescription drug also contains D Methamphetamine. The other isomer, Levo, or L Methamphetamine is not a DEA controlled drug. It is found in an over the counter medicine called “Vicks Inhaler” or as the prescription drug, Selegiline. (+)-methamphetamine is the more physiologically active isomer. In addition to some medications, L Methamphetamine can be produced in the illegal production of street Methamphetamine.

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
Estrogen and progesterone distinctively modulate methamphetamine-induced dopamine and serotonin depletions in C57BL/6J mice.
2000
Time-course of methamphetamine-induced neurotoxicity in rat caudate-putamen after single-dose treatment.
2000 Apr 28
Regional heterogeneity of dopaminergic deficits in vervet monkey striatum and substantia nigra after methamphetamine exposure.
2000 Aug
Cocaine and methamphetamine: differential addiction rates.
2000 Dec
Methamphetamine-induced neurotoxicity is attenuated in transgenic mice with a null mutation for interleukin-6.
2000 Dec
Psychiatric comorbidity of methamphetamine dependence in a forensic sample.
2000 Fall
Methamphetamine-induced striatal dopamine neurotoxicity and cyclooxygenase-2 protein expression in BALB/c mice.
2000 Jan 28
Exacerbation of psychosis by phenylpropanolamine.
2000 Jun
Adult learning deficits after neonatal exposure to D-methamphetamine: selective effects on spatial navigation and memory.
2000 Jun 15
Relation between hippocampal gamma waves and behavioral disturbances induced by phencyclidine and methamphetamine.
2000 Jun 15
Pott puffy tumor associated with intranasal methamphetamine.
2000 Mar 8
Carbamazepine suppresses methamphetamine-induced Fos expression in a regionally specific manner in the rat brain. Possible neural substrates responsible for antimanic effects of mood stabilizers.
2000 May
Effects of isradipine, a dihydropyridine-class calcium channel antagonist, on D-methamphetamine-induced cognitive and physiological changes in humans.
2000 May
Dopamine D1 receptor protein is elevated in nucleus accumbens of human, chronic methamphetamine users.
2000 Nov
Age-dependent differential responses of monoaminergic systems to high doses of methamphetamine.
2000 Nov
Methamphetamine-induced striatal dopamine release, behavior changes and neurotoxicity in BALB/c mice.
2000 Oct
Effect of temperature on dopamine transporter function and intracellular accumulation of methamphetamine: implications for methamphetamine-induced dopaminergic neurotoxicity.
2000 Oct 15
Comparison between the role of the neuronal and inducible nitric oxide synthase in methamphetamine-induced neurotoxicity and sensitization.
2000 Sep
Activation of an effector immediate-early gene arc by methamphetamine.
2000 Sep
Repeated adenosine pre-treatment potentiates the acute effect of methamphetamine in rats.
2000 Sep
Dopamine deficiency in mice.
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
Cognitive impairment in individuals currently using methamphetamine.
2000 Summer
The association study of DRD2, ACE and AGT gene polymorphisms and metamphetamine dependence.
2001
Estrogen protects against the synergistic toxicity by HIV proteins, methamphetamine and cocaine.
2001
Tamoxifen abolishes estrogen's neuroprotective effect upon methamphetamine neurotoxicity of the nigrostriatal dopaminergic system.
2001
Differential effects of cocaine and methamphetamine on neurotensin/neuromedin N and preprotachykinin messenger RNA expression in unique regions of the striatum.
2001
Dose-related neuroprotective effects of chronic nicotine in 6-hydroxydopamine treated rats, and loss of neuroprotection in alpha4 nicotinic receptor subunit knockout mice.
2001 Apr
Immunohistochemical investigation of pulmonary surfactant-associated protein A in fatal poisoning.
2001 Apr 1
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
Unintentional methamphetamine intoxication.
2001 Feb
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
Susceptibility of PharmChek drugs of abuse patch to environmental contamination.
2001 Feb 15
Analysis of benzphetamine and its metabolites in rat urine by liquid chromatography-electrospray ionization mass spectrometry.
2001 Feb 25
[Advanced findings on the molecular mechanisms for behavioral sensitization to psychostimulants].
2001 Jan
Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin.
2001 Jan
Neurotoxic regimen of methamphetamine produces evidence of behavioral sensitization in the rat.
2001 Jan
Clozapine, but not haloperidol, reverses social behavior deficit in mice during withdrawal from chronic phencyclidine treatment.
2001 Jan 22
Delta opioid peptide augments functional effects and intrastriatal graft survival of rat fetal ventral mesencephalic cells.
2001 Jan-Feb
Analysis of amphetamine and congeners in illicit samples by liquid chromatography and capillary electrophoresis.
2001 Mar
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
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
Fos expression in orexin neurons varies with behavioral state.
2001 Mar 1
Effects of lubeluzole on the methamphetamine-induced increase in extracellular glutamate and the long-term depletion of striatal dopamine.
2001 May
Patents

Sample Use Guides

Attention Deficit Disorder with Hyperactivity: For treatment of children 6 years or older with a behavioral syndrome characterized by moderate to severe distractibility, short attention span, hyperactivity, emotional lability and impulsivity: an initial dose of 5 mg DESOXYN once or twice a day is recommended. Daily dosage may be raised in increments of 5 mg at weekly intervals until an optimum clinical response is achieved. The usual effective dose is 20 to 25 mg daily. The total daily dose may be given in two divided doses daily. Where possible, drug administration should be interrupted occasionally to determine if there is a recurrence of behavioral symptoms sufficient to require continued therapy. For Obesity: One 5 mg tablet should be taken one-half hour before each meal. Treatment should not exceed a few weeks in duration. Methamphetamine is not recommended for use as an anorectic agent in children under 12 years of age.
Route of Administration: Oral
It was investigated whether the psychostimulant methamphetamine (METH) has a cytotoxic effect on oligodendrocytes and which cell-death pathways are involved in the cytotoxic process. METH caused concentration- and time-dependent cytotoxicity in rat oligodendrocyte cultures. METH induced apoptotic cell death and mRNA expression of pro-apoptotic proteins (bax and DP5), but not anti-apoptotic proteins (bcl-2 and bcl-XL). These results suggest that METH induces cytotoxicity in rat oligodendrocytes via the differential regulation of the expression of genes involved in the apoptotic process.
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
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC Elimination
PHARMACOKINETIC