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 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
Effects of lubeluzole on the methamphetamine-induced increase in extracellular glutamate and the long-term depletion of striatal dopamine.	2001-05	11252020
Increased expression of synaptophysin and stathmin mRNAs after methamphetamine administration in rat brain.	2001-04-17	11303745
Dose-dependent protective effects of apomorphine against methamphetamine-induced nigrostriatal damage.	2001-04-13	11292446
Delta opioid peptide augments functional effects and intrastriatal graft survival of rat fetal ventral mesencephalic cells.	2001-04-11	11294472
Speed demons.	2001-04-02	11299708
Immunohistochemical investigation of pulmonary surfactant-associated protein A in fatal poisoning.	2001-04-01	11248451
Dose-related neuroprotective effects of chronic nicotine in 6-hydroxydopamine treated rats, and loss of neuroprotection in alpha4 nicotinic receptor subunit knockout mice.	2001-04	11309235
Sensitized increase of period gene expression in the mouse caudate/putamen caused by repeated injection of methamphetamine.	2001-04	11259635
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.	2001-04	11170217
Plasma and brain methamphetamine concentrations in neonatal rats.	2001-03-29	11274878
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.	2001-03-29	11274873
Protective effect of the antioxidant 6-ethoxy-2,2-pentamethylen-1,2-dihydroquinoline (S 33113) in models of cerebral neurodegeneration.	2001-03-23	11282113
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.	2001-03-15	11169780
Dopaminergic role in stimulant-induced wakefulness.	2001-03-01	11222668
Fos expression in orexin neurons varies with behavioral state.	2001-03-01	11222656
Differences between methamphetamine users and cocaine users in treatment.	2001-03-01	11173172
Analysis of amphetamine and congeners in illicit samples by liquid chromatography and capillary electrophoresis.	2001-03	11300514
[Pharmacological and physiological effects of ginseng on actions induced by opioids and psychostimulants].	2001-03	11288489
Methamphetamine potentiates ischemia/reperfusion insults after transient middle cerebral artery ligation.	2001-03	11239201
Comparison of ELISAs for opiates, methamphetamine, cocaine metabolite, benzodiazepines, phencyclidine, and cannabinoids in whole blood and urine.	2001-03	11238309
Higher cortical and lower subcortical metabolism in detoxified methamphetamine abusers.	2001-03	11229978
Association of dopamine transporter reduction with psychomotor impairment in methamphetamine abusers.	2001-03	11229977
Airway effects of marijuana, cocaine, and other inhaled illicit agents.	2001-03	11224724
Lobeline inhibits the neurochemical and behavioral effects of amphetamine.	2001-03	11181937
Regulation of the vesicular monoamine transporter-2: a novel mechanism for cocaine and other psychostimulants.	2001-03	11181904
IGF-I and bFGF improve dopamine neuron survival and behavioral outcome in parkinsonian rats receiving cultured human fetal tissue strands.	2001-03	11170733
Glycine reduces novelty- and methamphetamine-induced locomotor activity in neonatal ventral hippocampal damaged rats.	2001-03	11166522
Analysis of benzphetamine and its metabolites in rat urine by liquid chromatography-electrospray ionization mass spectrometry.	2001-02-25	11236083
Long-term effects of a high-dose methamphetamine regimen on subsequent methamphetamine-induced dopamine release in vivo.	2001-02-16	11172757
The effect of testosterone upon methamphetamine neurotoxicity of the nigrostriatal dopaminergic system.	2001-02-16	11172749
Regional distribution of methamphetamine in autopsied brain of chronic human methamphetamine users.	2001-02-15	11182268
Susceptibility of PharmChek drugs of abuse patch to environmental contamination.	2001-02-15	11182260
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.	2001-02	11270514
Substance abuse and dependence in a public hospital: Hawaii.	2001-02	11258162
Relevance of pharmacokinetic parameters in animal models of methamphetamine abuse.	2001-02	11180503
Identification of reaction products of methamphetamine and hydrogen peroxide in hair dye and decolorant treatments by high-performance liquid chromatography/mass spectrometry.	2001-02	11180300
Unintentional methamphetamine intoxication.	2001-02	11174264
Long-term changes in basal ganglia function after a neurotoxic regimen of methamphetamine.	2001-02	11160639
Clozapine, but not haloperidol, reverses social behavior deficit in mice during withdrawal from chronic phencyclidine treatment.	2001-01-22	11201068
Drug addicts treatment for ten years in Thanyarak Hospital (1989-1998).	2001-01	11281496
Alterations in diurnal and nocturnal locomotor activity in rats treated with a monoamine-depleting regimen of methamphetamine or 3,4-methylenedioxymethamphetamine.	2001-01	11271404
[Advanced findings on the molecular mechanisms for behavioral sensitization to psychostimulants].	2001-01	11233297
[Amotivational syndrome in organic solvent abusers].	2001-01	11233295
The association study of DRD2, ACE and AGT gene polymorphisms and metamphetamine dependence.	2001	11300226
Anti-apoptotic and apoptotic action of (-)-deprenyl and its metabolites.	2001	11261744
Postnatal maturation of prefrontal pyramidal neurones is sensitive to a single early dose of methamphetamine in gerbils (Meriones unguiculatus).	2001	11261741
Estrogen protects against the synergistic toxicity by HIV proteins, methamphetamine and cocaine.	2001	11252157
Tamoxifen abolishes estrogen's neuroprotective effect upon methamphetamine neurotoxicity of the nigrostriatal dopaminergic system.	2001	11246153
Differential effects of cocaine and methamphetamine on neurotensin/neuromedin N and preprotachykinin messenger RNA expression in unique regions of the striatum.	2001	11182247
Decision-making deficits, linked to a dysfunctional ventromedial prefrontal cortex, revealed in alcohol and stimulant abusers.	2001	11164876

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 `Wed Apr 02 09:23:55 GMT 2025` Edited by `admin` on `Wed Apr 02 09:23:55 GMT 2025`
Record UNII	44RAL3456C
Record Status	`Validated (UNII)`
Record Version

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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