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
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
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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/9800366 | http://www.legacyhealth.org/for-health-professionals/refer-a-patient/laboratory-services/test-table/dl-methamphetamine-isomers-confirmation-urine.aspxhttps://www.accessdata.fda.gov/drugsatfda_docs/label/2007/005378s026lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/24484975
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9800366 | http://www.legacyhealth.org/for-health-professionals/refer-a-patient/laboratory-services/test-table/dl-methamphetamine-isomers-confirmation-urine.aspxhttps://www.accessdata.fda.gov/drugsatfda_docs/label/2007/005378s026lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/24484975
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).
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2363064 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19897077 |
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Target ID: Q05940 Gene ID: 6571.0 Gene Symbol: SLC18A2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/24484975 |
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Target ID: Q96RJ0 Gene ID: 134864.0 Gene Symbol: TAAR1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/17218486 |
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Target ID: CHEMBL2095158 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12453616 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | DESOXYN Approved UseAttention 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 |
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Palliative | DESOXYN Approved UseAttention 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 |
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Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
19.8 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1362938/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
330 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1362938/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
8.46 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1362938/ |
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
Dose | Population | Adverse events |
---|---|---|
2 g single, oral (max) Overdose |
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 |
healthy, adult n = 19 Health Status: healthy Age Group: adult Sex: unknown Population Size: 19 Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Intoxication | 25 patients Disc. AE |
2 g single, oral (max) Overdose |
healthy, adult n = 25 Health Status: healthy Condition: methamphetamine dependence Age Group: adult Sex: unknown Population Size: 25 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
minor | ||||
no | ||||
no | ||||
no | ||||
no | ||||
yes [IC50 19.1 uM] | ||||
yes [IC50 6.5 uM] | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/21426580/ |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes |
PubMed
Title | Date | PubMed |
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Determination of d-methamphetamine in urine after administration of d- or dl-methamphetamine to rats by radioimmunoassay using optically sensitive antiserum. | 1982 Jul |
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Methamphetamine--properties and analytical methods of enantiomer determination. | 1998 Aug 31 |
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HPLC with fluorescence detection of methamphetamine and amphetamine in segmentally analyzed human hair. | 1999 Apr |
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Methamphetamine generates peroxynitrite and produces dopaminergic neurotoxicity in mice: protective effects of peroxynitrite decomposition catalyst. | 1999 Aug 7 |
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Methamphetamine administration causes overexpression of nNOS in the mouse striatum. | 1999 Dec 18 |
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The role of gamma-aminobutyric acid (GABA)-benzodiazepine neurotransmission in an animal model of methamphetamine-induced psychosis. | 1999 Mar |
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Null mutation of c-fos causes exacerbation of methamphetamine-induced neurotoxicity. | 1999 Nov 15 |
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Methamphetamine-induced neurotoxicity alters locomotor activity, stereotypic behavior, and stimulated dopamine release in the rat. | 1999 Oct 15 |
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Estrogen and progesterone distinctively modulate methamphetamine-induced dopamine and serotonin depletions in C57BL/6J mice. | 2000 |
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Time-course of methamphetamine-induced neurotoxicity in rat caudate-putamen after single-dose treatment. | 2000 Apr 28 |
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Cocaine and methamphetamine: differential addiction rates. | 2000 Dec |
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Psychiatric comorbidity of methamphetamine dependence in a forensic sample. | 2000 Fall |
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Exacerbation of psychosis by phenylpropanolamine. | 2000 Jun |
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Relation between hippocampal gamma waves and behavioral disturbances induced by phencyclidine and methamphetamine. | 2000 Jun 15 |
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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 |
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Effects of isradipine, a dihydropyridine-class calcium channel antagonist, on D-methamphetamine-induced cognitive and physiological changes in humans. | 2000 May |
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Age-dependent differential responses of monoaminergic systems to high doses of methamphetamine. | 2000 Nov |
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Effect of temperature on dopamine transporter function and intracellular accumulation of methamphetamine: implications for methamphetamine-induced dopaminergic neurotoxicity. | 2000 Oct 15 |
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Retrospective study of urinalysis for dl-amphetamine and dl-methamphetamine analysis under current Department of Defense guidelines. | 2000 Sep |
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Comparison between the role of the neuronal and inducible nitric oxide synthase in methamphetamine-induced neurotoxicity and sensitization. | 2000 Sep |
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Dopamine deficiency in mice. | 2000 Sep |
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The effects of single dose of methamphetamine on lipid peroxidation levels in the rat striatum and prefrontal cortex. | 2000 Sep |
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Anti-apoptotic and apoptotic action of (-)-deprenyl and its metabolites. | 2001 |
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Postnatal maturation of prefrontal pyramidal neurones is sensitive to a single early dose of methamphetamine in gerbils (Meriones unguiculatus). | 2001 |
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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 |
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Sensitized increase of period gene expression in the mouse caudate/putamen caused by repeated injection of methamphetamine. | 2001 Apr |
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Dose-dependent protective effects of apomorphine against methamphetamine-induced nigrostriatal damage. | 2001 Apr 13 |
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Increased expression of synaptophysin and stathmin mRNAs after methamphetamine administration in rat brain. | 2001 Apr 17 |
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Speed demons. | 2001 Apr 2 |
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Identification of reaction products of methamphetamine and hydrogen peroxide in hair dye and decolorant treatments by high-performance liquid chromatography/mass spectrometry. | 2001 Feb |
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Long-term changes in basal ganglia function after a neurotoxic regimen of methamphetamine. | 2001 Feb |
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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 |
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Drug addicts treatment for ten years in Thanyarak Hospital (1989-1998). | 2001 Jan |
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Alterations in diurnal and nocturnal locomotor activity in rats treated with a monoamine-depleting regimen of methamphetamine or 3,4-methylenedioxymethamphetamine. | 2001 Jan |
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[Advanced findings on the molecular mechanisms for behavioral sensitization to psychostimulants]. | 2001 Jan |
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[Amotivational syndrome in organic solvent abusers]. | 2001 Jan |
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Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin. | 2001 Jan |
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Neurotoxic regimen of methamphetamine produces evidence of behavioral sensitization in the rat. | 2001 Jan |
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Clozapine, but not haloperidol, reverses social behavior deficit in mice during withdrawal from chronic phencyclidine treatment. | 2001 Jan 22 |
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Plasma and brain methamphetamine concentrations in neonatal rats. | 2001 Jan-Feb |
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Analysis of amphetamine and congeners in illicit samples by liquid chromatography and capillary electrophoresis. | 2001 Mar |
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[Pharmacological and physiological effects of ginseng on actions induced by opioids and psychostimulants]. | 2001 Mar |
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Methamphetamine potentiates ischemia/reperfusion insults after transient middle cerebral artery ligation. | 2001 Mar |
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Association of dopamine transporter reduction with psychomotor impairment in methamphetamine abusers. | 2001 Mar |
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IGF-I and bFGF improve dopamine neuron survival and behavioral outcome in parkinsonian rats receiving cultured human fetal tissue strands. | 2001 Mar |
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Glycine reduces novelty- and methamphetamine-induced locomotor activity in neonatal ventral hippocampal damaged rats. | 2001 Mar |
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Dopaminergic role in stimulant-induced wakefulness. | 2001 Mar 1 |
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Differences between methamphetamine users and cocaine users in treatment. | 2001 Mar 1 |
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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 |
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Protective effect of the antioxidant 6-ethoxy-2,2-pentamethylen-1,2-dihydroquinoline (S 33113) in models of cerebral neurodegeneration. | 2001 Mar 23 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4377016
in rats: 10mg/kg i.p
Route of Administration:
Intraperitoneal
Substance Class |
Chemical
Created
by
admin
on
Edited
Thu Jul 06 22:59:32 UTC 2023
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on
Thu Jul 06 22:59:32 UTC 2023
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Record UNII |
44RAL3456C
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000007883
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WHO-VATC |
QN06BA03
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NDF-RT |
N0000175425
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CFR |
21 CFR 862.3610
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DEA NO. |
1105
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NDF-RT |
N0000175372
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N0000175729
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WHO-ATC |
N06BA03
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LIVERTOX |
612
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NDF-RT |
N0000175651
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CFR |
21 CFR 250.101
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NDF-RT |
N0000175739
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NCI_THESAURUS |
C47795
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NDF-RT |
N0000175372
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1732
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208-668-7
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6816
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C61840
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100000081196
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6809
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M7290
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44RAL3456C
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537-46-2
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1879
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25115
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DB01577
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10836
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CHEMBL1201201
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44RAL3456C
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D008694
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4803
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METHAMPHETAMINE
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Methamphetamine
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DTXSID8037128
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SUB08809MIG
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Related Record | Type | Details | ||
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TRANSPORTER -> SUBSTRATE | |||
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PRECURSOR->PARENT |
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SALT/SOLVATE -> PARENT | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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REAGENT->PARENT |
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TRANSPORTER -> INHIBITOR |
IC50
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LIGAND->TARGET |
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REAGENT->PARENT |
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PRECURSOR->PARENT |
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PRECURSOR->PARENT |
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TRANSPORTER -> SUBSTRATE | |||
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TRANSPORTER -> INHIBITOR |
IC50
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TARGET -> AGONIST |
SHORT-ACTING
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TRANSPORTER -> SUBSTRATE | |||
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PRECURSOR->PARENT |
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TRANSPORTER -> INHIBITOR |
IC50
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PRECURSOR->PARENT |
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REAGENT->PARENT |
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TRANSPORTER -> INHIBITOR |
IC50
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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METABOLITE -> PARENT |
N.D. to 41.8 mcmol/dm3 in Methamphetamine abuser's urine samples (n=6)
IN-VIVO
URINE
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PARENT -> METABOLITE |
MAJOR
PLASMA
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METABOLITE -> PARENT |
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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |