METHAMPHETAMINE

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

Structure Search

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

HIDE SMILES / InChI

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

Description
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
Monoamine transporter 10 Target ID: CHEMBL2363064 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19897077	Negative Allosteric Modulator 42
Synaptic vesicular amine transporter 53 Target ID: Q05940 Gene ID: 6571.0 Gene Symbol: SLC18A2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/24484975	Inhibitor 8146
Trace amine-associated receptor 1 47 Target ID: Q96RJ0 Gene ID: 134864.0 Gene Symbol: TAAR1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/17218486	Agonist 2637
Adrenergic receptor alpha-2 113 Target ID: CHEMBL2095158 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12453616	Agonist 2637

Conditions

Condition	Modality	Highest Phase	Product
Attention deficit hyperactivity disorder 66 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/005378s026lbl.pdf	Primary	Approved 8307	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
Exogenous obesity 19 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/005378s026lbl.pdf	Palliative	Approved 8307	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
Unknown 2554

C_max

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

T_1/2

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 Dose: 2 g Route: oral Route: single Dose: 2 g Sources: https://pubmed.ncbi.nlm.nih.gov/26402425/	healthy, adult n = 25 Health Status: healthy Condition: methamphetamine dependence Age Group: adult Sex: unknown Population Size: 25 Sources: https://pubmed.ncbi.nlm.nih.gov/26402425/	Disc. AE: Intoxication... AEs leading to discontinuation/dose reduction: Intoxication (25 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/26402425/
40 mg single, oral Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: https://pubmed.ncbi.nlm.nih.gov/32986459/	healthy, adult n = 19 Health Status: healthy Age Group: adult Sex: unknown Population Size: 19 Sources: https://pubmed.ncbi.nlm.nih.gov/32986459/	Sources: https://pubmed.ncbi.nlm.nih.gov/32986459/

AEs

AE	Significance	Dose	Population
Intoxication	25 patients Disc. AE	2 g single, oral (max) Overdose Dose: 2 g Route: oral Route: single Dose: 2 g Sources: https://pubmed.ncbi.nlm.nih.gov/26402425/	healthy, adult n = 25 Health Status: healthy Condition: methamphetamine dependence Age Group: adult Sex: unknown Population Size: 25 Sources: https://pubmed.ncbi.nlm.nih.gov/26402425/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
		substrate 1168 inhibitor 1789

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT1 584 OAT2 144 OAT3 625 OAT4 145 OCT1 498 OCT2 630		GLUT1 9

Drug as perpetrator

Target	Modality	Activity
CYP2D6 1826	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/005378s035lbl.pdf#page=	minor
OAT1 588	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/32109742/	no
OAT2 146	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/32109742/	no
OAT3 627	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/32109742/	no
OAT4 145	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/32109742/	no
OCT2 631	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/32109742/	yes [IC50 19.1 uM]
OCT1 513	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/32109742/	yes [IC50 6.5 uM]
GLUT1 15	inducer 1515 Sources: https://pubmed.ncbi.nlm.nih.gov/21426580/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 1168	substrate 3264 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/005378s035lbl.pdf#page=	yes

Sourcing

Vendor/Aggregator	ID	URL
ChemIDplus	7563486	https://chem.nlm.nih.gov/chemidplus/id/0007563486
EPA DSSTox	DTXSID20226543	https://comptox.epa.gov/dashboard/DTXSID20226543
PubChem	71586915	https://pubchem.ncbi.nlm.nih.gov/compound/71586915
Wikidata	Q27281863

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	7119715
Chronic psychotic illness from methamphetamine.	1999 Apr	10200757
Methamphetamine generates peroxynitrite and produces dopaminergic neurotoxicity in mice: protective effects of peroxynitrite decomposition catalyst.	1999 Aug 7	10433983
Brain choline acetyltransferase activity in chronic, human users of cocaine, methamphetamine, and heroin.	1999 Jan	10089005
Distinct features of seizures induced by cocaine and amphetamine analogs.	1999 Jul 21	10456426
The role of gamma-aminobutyric acid (GABA)-benzodiazepine neurotransmission in an animal model of methamphetamine-induced psychosis.	1999 Mar	10386162
Methamphetamine-related stroke: four cases.	1999 May-Jun	10338241
Null mutation of c-fos causes exacerbation of methamphetamine-induced neurotoxicity.	1999 Nov 15	10559418
Methamphetamine-induced neurotoxicity alters locomotor activity, stereotypic behavior, and stimulated dopamine release in the rat.	1999 Oct 15	10516332
Hydroxyl radical formation following methamphetamine administration to rats.	1999 Sep	10522753
Estrogen and progesterone distinctively modulate methamphetamine-induced dopamine and serotonin depletions in C57BL/6J mice.	2000	11129103
Time-course of methamphetamine-induced neurotoxicity in rat caudate-putamen after single-dose treatment.	2000 Apr 28	10773198
Regional heterogeneity of dopaminergic deficits in vervet monkey striatum and substantia nigra after methamphetamine exposure.	2000 Aug	10958525
Evaluation of the effects of alpha-phenyl-N-tert-butyl nitrone pretreatment on the neurobehavioral effects of methamphetamine.	2000 Aug 18	10983851
Methamphetamine-induced neurotoxicity is attenuated in transgenic mice with a null mutation for interleukin-6.	2000 Dec	11093760
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	10684896
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	10731628
Age-dependent differential responses of monoaminergic systems to high doses of methamphetamine.	2000 Nov	11032899
Methamphetamine-induced striatal dopamine release, behavior changes and neurotoxicity in BALB/c mice.	2000 Oct	10884597
Effect of temperature on dopamine transporter function and intracellular accumulation of methamphetamine: implications for methamphetamine-induced dopaminergic neurotoxicity.	2000 Oct 15	11027249
The effects of single dose of methamphetamine on lipid peroxidation levels in the rat striatum and prefrontal cortex.	2000 Sep	10974615
Retrospective study of urinalysis for dl-amphetamine and dl-methamphetamine analysis under current Department of Defense guidelines.	2000 Sep	10999353
Direct effects of methamphetamine on hypertrophy and microtubules in cultured adult rat ventricular myocytes.	2000 Sep 11	10978632
Estrogen protects against the synergistic toxicity by HIV proteins, methamphetamine and cocaine.	2001	11252157
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	11309235
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	11170217
Dose-dependent protective effects of apomorphine against methamphetamine-induced nigrostriatal damage.	2001 Apr 13	11292446
Speed demons.	2001 Apr 2	11299708
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	11270514
Relevance of pharmacokinetic parameters in animal models of methamphetamine abuse.	2001 Feb	11180503
Identification of reaction products of methamphetamine and hydrogen peroxide in hair dye and decolorant treatments by high-performance liquid chromatography/mass spectrometry.	2001 Feb	11180300
Unintentional methamphetamine intoxication.	2001 Feb	11174264
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	11158245
Contrasting responses by basal ganglia met-enkephalin systems to low and high doses of methamphetamine in a rat model.	2001 Feb	11158242
Highly sensitive analysis of methamphetamine and amphetamine in human whole blood using headspace solid-phase microextraction and gas chromatography-mass spectrometry.	2001 Feb 1	11118748
Regional distribution of methamphetamine in autopsied brain of chronic human methamphetamine users.	2001 Feb 15	11182268
Long-term effects of a high-dose methamphetamine regimen on subsequent methamphetamine-induced dopamine release in vivo.	2001 Feb 16	11172757
Analysis of benzphetamine and its metabolites in rat urine by liquid chromatography-electrospray ionization mass spectrometry.	2001 Feb 25	11236083
Drug addicts treatment for ten years in Thanyarak Hospital (1989-1998).	2001 Jan	11281496
Alterations in diurnal and nocturnal locomotor activity in rats treated with a monoamine-depleting regimen of methamphetamine or 3,4-methylenedioxymethamphetamine.	2001 Jan	11271404
[Advanced findings on the molecular mechanisms for behavioral sensitization to psychostimulants].	2001 Jan	11233297
Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin.	2001 Jan	11071707
Neurotoxic regimen of methamphetamine produces evidence of behavioral sensitization in the rat.	2001 Jan	11071703
Delta opioid peptide augments functional effects and intrastriatal graft survival of rat fetal ventral mesencephalic cells.	2001 Jan-Feb	11294472
Plasma and brain methamphetamine concentrations in neonatal rats.	2001 Jan-Feb	11274878
Comparison of ELISAs for opiates, methamphetamine, cocaine metabolite, benzodiazepines, phencyclidine, and cannabinoids in whole blood and urine.	2001 Mar	11238309
Lobeline inhibits the neurochemical and behavioral effects of amphetamine.	2001 Mar	11181937
IGF-I and bFGF improve dopamine neuron survival and behavioral outcome in parkinsonian rats receiving cultured human fetal tissue strands.	2001 Mar	11170733
Dopaminergic role in stimulant-induced wakefulness.	2001 Mar 1	11222668
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	14670133

Patents

Sample Use Guides

In Vivo Use Guide

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

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 `Sun Dec 18 20:36:32 UTC 2022` Edited by `admin` on `Sun Dec 18 20:36:32 UTC 2022`
Record UNII	44RAL3456C
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

METHAMPHETAMINE

Common Name

English

METAMFETAMINE

Official Name

English

J6.362B

Code

English

METHYLAMPHETAMINE

Systematic Name

English

Metamfetamine [WHO-DD]

Common Name

English

metamfetamine [INN]

Common Name

English

NSC-25115

Code

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