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

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
Methamphetamine--properties and analytical methods of enantiomer determination.
1998 Aug 31
A selective dopamine D4 receptor antagonist, NRA0160: a preclinical neuropharmacological profile.
1999
HPLC with fluorescence detection of methamphetamine and amphetamine in segmentally analyzed human hair.
1999 Apr
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
The role of gamma-aminobutyric acid (GABA)-benzodiazepine neurotransmission in an animal model of methamphetamine-induced psychosis.
1999 Mar
Estrogen and progesterone distinctively modulate methamphetamine-induced dopamine and serotonin depletions in C57BL/6J mice.
2000
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
Exacerbation of psychosis by phenylpropanolamine.
2000 Jun
Dual serotonin (5-HT) projections to the nucleus accumbens core and shell: relation of the 5-HT transporter to amphetamine-induced neurotoxicity.
2000 Mar 1
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
Dopamine D1 receptor protein is elevated in nucleus accumbens of human, chronic methamphetamine users.
2000 Nov
Comparison between the role of the neuronal and inducible nitric oxide synthase in methamphetamine-induced neurotoxicity and sensitization.
2000 Sep
Retrospective study of urinalysis for dl-amphetamine and dl-methamphetamine analysis under current Department of Defense guidelines.
2000 Sep
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
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
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
Speed demons.
2001 Apr 2
Reversal effect of sulpiride on rotational behaviour of rats with unilateral frontal cortex ablation: an alternative explanation for the pharmacological mechanism of its antidepressant effect.
2001 Feb
Substance abuse and dependence in a public hospital: Hawaii.
2001 Feb
Unintentional methamphetamine intoxication.
2001 Feb
Long-term changes in basal ganglia function after a neurotoxic regimen of methamphetamine.
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
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
Susceptibility of PharmChek drugs of abuse patch to environmental contamination.
2001 Feb 15
Methamphetamine-induced rapid and reversible changes in dopamine transporter function: an in vitro model.
2001 Feb 15
The effect of testosterone upon methamphetamine neurotoxicity of the nigrostriatal dopaminergic system.
2001 Feb 16
Alterations in diurnal and nocturnal locomotor activity in rats treated with a monoamine-depleting regimen of methamphetamine or 3,4-methylenedioxymethamphetamine.
2001 Jan
[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
IGF-I and bFGF improve dopamine neuron survival and behavioral outcome in parkinsonian rats receiving cultured human fetal tissue strands.
2001 Mar
Glycine reduces novelty- and methamphetamine-induced locomotor activity in neonatal ventral hippocampal damaged rats.
2001 Mar
Dopaminergic role in stimulant-induced wakefulness.
2001 Mar 1
Differences between methamphetamine users and cocaine users in treatment.
2001 Mar 1
Delta opioid peptide [D-Ala2, D-Leu5]enkephalin causes a near complete blockade of the neuronal damage caused by a single high dose of methamphetamine: examining the role of p53.
2001 Mar 15
Protective effect of the antioxidant 6-ethoxy-2,2-pentamethylen-1,2-dihydroquinoline (S 33113) in models of cerebral neurodegeneration.
2001 Mar 23
Concentrations and ratios of amphetamine, methamphetamine, MDA, MDMA, and MDEA enantiomers determined in plasma samples from clinical toxicology and driving under the influence of drugs cases by GC-NICI-MS.
2003 Nov-Dec
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 21:47:34 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
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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
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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
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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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TRANSPORTER -> INHIBITOR
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