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.accessdata.fda.gov/drugsatfda_docs/label/2007/005378s026lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/24484975https://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.aspx
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/005378s026lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/24484975https://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.aspx
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.
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 |
---|---|---|---|
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 |
---|---|---|
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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Chronic psychotic illness from methamphetamine. | 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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Brain choline acetyltransferase activity in chronic, human users of cocaine, methamphetamine, and heroin. | 1999 Jan |
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Distinct features of seizures induced by cocaine and amphetamine analogs. | 1999 Jul 21 |
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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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Methamphetamine-related stroke: four cases. | 1999 May-Jun |
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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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Hydroxyl radical formation following methamphetamine administration to rats. | 1999 Sep |
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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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Regional heterogeneity of dopaminergic deficits in vervet monkey striatum and substantia nigra after methamphetamine exposure. | 2000 Aug |
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Evaluation of the effects of alpha-phenyl-N-tert-butyl nitrone pretreatment on the neurobehavioral effects of methamphetamine. | 2000 Aug 18 |
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Methamphetamine-induced neurotoxicity is attenuated in transgenic mice with a null mutation for interleukin-6. | 2000 Dec |
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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 |
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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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Age-dependent differential responses of monoaminergic systems to high doses of methamphetamine. | 2000 Nov |
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Methamphetamine-induced striatal dopamine release, behavior changes and neurotoxicity in BALB/c mice. | 2000 Oct |
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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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The effects of single dose of methamphetamine on lipid peroxidation levels in the rat striatum and prefrontal cortex. | 2000 Sep |
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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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Direct effects of methamphetamine on hypertrophy and microtubules in cultured adult rat ventricular myocytes. | 2000 Sep 11 |
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Estrogen protects against the synergistic toxicity by HIV proteins, methamphetamine and cocaine. | 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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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 |
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Dose-dependent protective effects of apomorphine against methamphetamine-induced nigrostriatal damage. | 2001 Apr 13 |
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Speed demons. | 2001 Apr 2 |
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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 |
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Relevance of pharmacokinetic parameters in animal models of methamphetamine abuse. | 2001 Feb |
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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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Unintentional methamphetamine intoxication. | 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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Contrasting responses by basal ganglia met-enkephalin systems to low and high doses of methamphetamine in a rat model. | 2001 Feb |
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Highly sensitive analysis of methamphetamine and amphetamine in human whole blood using headspace solid-phase microextraction and gas chromatography-mass spectrometry. | 2001 Feb 1 |
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Regional distribution of methamphetamine in autopsied brain of chronic human methamphetamine users. | 2001 Feb 15 |
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Long-term effects of a high-dose methamphetamine regimen on subsequent methamphetamine-induced dopamine release in vivo. | 2001 Feb 16 |
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Analysis of benzphetamine and its metabolites in rat urine by liquid chromatography-electrospray ionization mass spectrometry. | 2001 Feb 25 |
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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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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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Delta opioid peptide augments functional effects and intrastriatal graft survival of rat fetal ventral mesencephalic cells. | 2001 Jan-Feb |
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Plasma and brain methamphetamine concentrations in neonatal rats. | 2001 Jan-Feb |
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Comparison of ELISAs for opiates, methamphetamine, cocaine metabolite, benzodiazepines, phencyclidine, and cannabinoids in whole blood and urine. | 2001 Mar |
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Lobeline inhibits the neurochemical and behavioral effects of amphetamine. | 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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Dopaminergic role in stimulant-induced wakefulness. | 2001 Mar 1 |
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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 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12915247
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
Edited
Sun Dec 18 20:36:32 UTC 2022
by
admin
on
Sun Dec 18 20:36:32 UTC 2022
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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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NDF-RT |
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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PRIMARY | RxNorm | ||
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C61840
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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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3359
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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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SALT/SOLVATE -> PARENT | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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TRANSPORTER -> INHIBITOR |
IC50
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LIGAND->TARGET |
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TRANSPORTER -> SUBSTRATE | |||
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TRANSPORTER -> INHIBITOR |
IC50
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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 -> INHIBITOR |
IC50
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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PARENT -> METABOLITE |
MAJOR
PLASMA
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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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METABOLITE -> PARENT |
Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |