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

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 43
Synaptic vesicular amine transporter 57 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 8504
Trace amine-associated receptor 1 48 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 2752
Adrenergic receptor alpha-2 114 Target ID: CHEMBL2095158 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12453616	Agonist 2752

Conditions

Condition	Modality	Highest Phase	Product
Attention deficit hyperactivity disorder 70 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/005378s026lbl.pdf	Primary	Approved 8583	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 1943
Exogenous obesity 19 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/005378s026lbl.pdf	Palliative	Approved 8583	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 1943
Unknown 2596

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 Overdose Dose: 2 g Route: oral Route: single Dose: 2 g Sources: https://pubmed.ncbi.nlm.nih.gov/26402425/	healthy, adult Health Status: healthy Age Group: adult Sex: unknown 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 Health Status: healthy Age Group: adult Sex: unknown 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 Overdose Dose: 2 g Route: oral Route: single Dose: 2 g Sources: https://pubmed.ncbi.nlm.nih.gov/26402425/	healthy, adult Health Status: healthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/26402425/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
		substrate 1388 inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT1 725 OAT2 153 OAT3 747 OAT4 150 OCT1 620 OCT2 779		GLUT1 14

Drug as perpetrator

Target	Modality	Activity
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/005378s035lbl.pdf#page=	minor
OAT1 730	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/32109742/	no
OAT2 155	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/32109742/	no
OAT3 749	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/32109742/	no
OAT4 150	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/32109742/	no
OCT2 782	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/32109742/	yes [IC50 19.1 uM]
OCT1 656	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/32109742/	yes [IC50 6.5 uM]
GLUT1 20	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/21426580/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 1388	substrate 4014 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
Methamphetamine--properties and analytical methods of enantiomer determination.	1998 Aug 31	9800366
Selenium, an antioxidant, protects against methamphetamine-induced dopaminergic neurotoxicity.	1999 Feb 13	10082851
Brain choline acetyltransferase activity in chronic, human users of cocaine, methamphetamine, and heroin.	1999 Jan	10089005
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
Cocaine and methamphetamine: differential addiction rates.	2000 Dec	11130157
Exacerbation of psychosis by phenylpropanolamine.	2000 Jun	10831490
Adult learning deficits after neonatal exposure to D-methamphetamine: selective effects on spatial navigation and memory.	2000 Jun 15	10844042
Relation between hippocampal gamma waves and behavioral disturbances induced by phencyclidine and methamphetamine.	2000 Jun 15	10840127
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
Methamphetamine-induced striatal dopamine release, behavior changes and neurotoxicity in BALB/c mice.	2000 Oct	10884597
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
Decision-making deficits, linked to a dysfunctional ventromedial prefrontal cortex, revealed in alcohol and stimulant abusers.	2001	11164876
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
Immunohistochemical investigation of pulmonary surfactant-associated protein A in fatal poisoning.	2001 Apr 1	11248451
Increased expression of synaptophysin and stathmin mRNAs after methamphetamine administration in rat brain.	2001 Apr 17	11303745
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
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
Methamphetamine-induced rapid and reversible changes in dopamine transporter function: an in vitro model.	2001 Feb 15	11160413
Long-term effects of a high-dose methamphetamine regimen on subsequent methamphetamine-induced dopamine release in vivo.	2001 Feb 16	11172757
The effect of testosterone upon methamphetamine neurotoxicity of the nigrostriatal dopaminergic system.	2001 Feb 16	11172749
[Advanced findings on the molecular mechanisms for behavioral sensitization to psychostimulants].	2001 Jan	11233297
[Amotivational syndrome in organic solvent abusers].	2001 Jan	11233295
Elevations in plasmatic titers of corticosterone and aldosterone, in the absence of changes in ACTH, testosterone, or glial fibrillary acidic protein, 72 h following D,L-fenfluramine or D-fenfluramine administration to rats.	2001 Jan-Feb	11274873
Regulation of the vesicular monoamine transporter-2: a novel mechanism for cocaine and other psychostimulants.	2001 Mar	11181904
IGF-I and bFGF improve dopamine neuron survival and behavioral outcome in parkinsonian rats receiving cultured human fetal tissue strands.	2001 Mar	11170733
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.

Name

Type

Language

METAMFETAMINE

Preferred Name

English

METHAMPHETAMINE

Common Name

English

METAMPHETAMINE

Common 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

CFR

21 CFR 216.24