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Details

Stereochemistry RACEMIC
Molecular Formula C10H15N.ClH
Molecular Weight 185.694
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHAMPHETAMINE HYDROCHLORIDE, DL-

SMILES

Cl.CNC(C)CC1=CC=CC=C1

InChI

InChIKey=TWXDDNPPQUTEOV-UHFFFAOYSA-N
InChI=1S/C10H15N.ClH/c1-9(11-2)8-10-6-4-3-5-7-10;/h3-7,9,11H,8H2,1-2H3;1H

HIDE SMILES / InChI
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q05940
Gene ID: 6571.0
Gene Symbol: SLC18A2
Target Organism: Homo sapiens (Human)
Target ID: Q96RJ0
Gene ID: 134864.0
Gene Symbol: TAAR1
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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
Palliative
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
19.8 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
330 ng × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
8.46 h
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

Doses

DosePopulationAdverse events​
2 g single, oral (max)
Overdose
Dose: 2 g
Route: oral
Route: single
Dose: 2 g
Sources:
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
Dose: 40 mg
Route: oral
Route: single
Dose: 40 mg
Sources:
healthy, adult
n = 19
Health Status: healthy
Age Group: adult
Sex: unknown
Population Size: 19
Sources:
AEs

AEs

AESignificanceDosePopulation
Intoxication 25 patients
Disc. AE
2 g single, oral (max)
Overdose
Dose: 2 g
Route: oral
Route: single
Dose: 2 g
Sources:
healthy, adult
n = 25
Health Status: healthy
Condition: methamphetamine dependence
Age Group: adult
Sex: unknown
Population Size: 25
Sources:
PubMed

PubMed

TitleDatePubMed
Estrogen and progesterone distinctively modulate methamphetamine-induced dopamine and serotonin depletions in C57BL/6J mice.
2000
Evaluation of the effects of alpha-phenyl-N-tert-butyl nitrone pretreatment on the neurobehavioral effects of methamphetamine.
2000 Aug 18
Cocaine and methamphetamine: differential addiction rates.
2000 Dec
Methamphetamine-induced neurotoxicity is attenuated in transgenic mice with a null mutation for interleukin-6.
2000 Dec
Psychiatric comorbidity of methamphetamine dependence in a forensic sample.
2000 Fall
Dopamine D1 receptor protein is elevated in nucleus accumbens of human, chronic methamphetamine users.
2000 Nov
Age-dependent differential responses of monoaminergic systems to high doses of methamphetamine.
2000 Nov
Effect of temperature on dopamine transporter function and intracellular accumulation of methamphetamine: implications for methamphetamine-induced dopaminergic neurotoxicity.
2000 Oct 15
Directed coherence of EEG on ICSS rats with methamphetamine-induced hyperactivity and stereotyped behavior.
2000 Sep
Comparison between the role of the neuronal and inducible nitric oxide synthase in methamphetamine-induced neurotoxicity and sensitization.
2000 Sep
Activation of an effector immediate-early gene arc by methamphetamine.
2000 Sep
Repeated adenosine pre-treatment potentiates the acute effect of methamphetamine in rats.
2000 Sep
Dopamine deficiency in mice.
2000 Sep
nNOS inhibitors attenuate methamphetamine-induced dopaminergic neurotoxicity but not hyperthermia in mice.
2000 Sep 11
Cognitive impairment in individuals currently using methamphetamine.
2000 Summer
The association study of DRD2, ACE and AGT gene polymorphisms and metamphetamine dependence.
2001
Decision-making deficits, linked to a dysfunctional ventromedial prefrontal cortex, revealed in alcohol and stimulant abusers.
2001
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
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
Dose-dependent protective effects of apomorphine against methamphetamine-induced nigrostriatal damage.
2001 Apr 13
Increased expression of synaptophysin and stathmin mRNAs after methamphetamine administration in rat brain.
2001 Apr 17
Speed demons.
2001 Apr 2
Relevance of pharmacokinetic parameters in animal models of methamphetamine abuse.
2001 Feb
Identification of reaction products of methamphetamine and hydrogen peroxide in hair dye and decolorant treatments by high-performance liquid chromatography/mass spectrometry.
2001 Feb
Long-term changes in basal ganglia function after a neurotoxic regimen of methamphetamine.
2001 Feb
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
Contrasting responses by basal ganglia met-enkephalin systems to low and high doses of methamphetamine in a rat model.
2001 Feb
Highly sensitive analysis of methamphetamine and amphetamine in human whole blood using headspace solid-phase microextraction and gas chromatography-mass spectrometry.
2001 Feb 1
Regional distribution of methamphetamine in autopsied brain of chronic human methamphetamine users.
2001 Feb 15
Susceptibility of PharmChek drugs of abuse patch to environmental contamination.
2001 Feb 15
Methamphetamine-induced rapid and reversible changes in dopamine transporter function: an in vitro model.
2001 Feb 15
The effect of testosterone upon methamphetamine neurotoxicity of the nigrostriatal dopaminergic system.
2001 Feb 16
Analysis of benzphetamine and its metabolites in rat urine by liquid chromatography-electrospray ionization mass spectrometry.
2001 Feb 25
Drug addicts treatment for ten years in Thanyarak Hospital (1989-1998).
2001 Jan
[Amotivational syndrome in organic solvent abusers].
2001 Jan
Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin.
2001 Jan
Neurotoxic regimen of methamphetamine produces evidence of behavioral sensitization in the rat.
2001 Jan
Clozapine, but not haloperidol, reverses social behavior deficit in mice during withdrawal from chronic phencyclidine treatment.
2001 Jan 22
Delta opioid peptide augments functional effects and intrastriatal graft survival of rat fetal ventral mesencephalic cells.
2001 Jan-Feb
Analysis of amphetamine and congeners in illicit samples by liquid chromatography and capillary electrophoresis.
2001 Mar
[Pharmacological and physiological effects of ginseng on actions induced by opioids and psychostimulants].
2001 Mar
Comparison of ELISAs for opiates, methamphetamine, cocaine metabolite, benzodiazepines, phencyclidine, and cannabinoids in whole blood and urine.
2001 Mar
Higher cortical and lower subcortical metabolism in detoxified methamphetamine abusers.
2001 Mar
Association of dopamine transporter reduction with psychomotor impairment in methamphetamine abusers.
2001 Mar
IGF-I and bFGF improve dopamine neuron survival and behavioral outcome in parkinsonian rats receiving cultured human fetal tissue strands.
2001 Mar
Glycine reduces novelty- and methamphetamine-induced locomotor activity in neonatal ventral hippocampal damaged rats.
2001 Mar
Dopaminergic role in stimulant-induced wakefulness.
2001 Mar 1
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
Protective effect of the antioxidant 6-ethoxy-2,2-pentamethylen-1,2-dihydroquinoline (S 33113) in models of cerebral neurodegeneration.
2001 Mar 23
Effects of lubeluzole on the methamphetamine-induced increase in extracellular glutamate and the long-term depletion of striatal dopamine.
2001 May
Patents

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
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
METHAMPHETAMINE HYDROCHLORIDE, DL-
Common Name English
DL-DESOXYEPHEDRINE HYDROCHLORIDE
Common Name English
(DL)-METHAMPHETAMINE HYDROCHLORIDE
Common Name English
METAMFETAMINE HYDROCHLORIDE, DL-
Common Name English
(±)-N-METHYLAMPHETAMINE HYDROCHLORIDE
Systematic Name English
N,.ALPHA.-DIMETHYLPHENETHYLAMINE HYDROCHLORIDE
Systematic Name English
BENZENEETHANAMINE, N,.ALPHA.-DIMETHYL-, HYDROCHLORIDE (1:1)
Systematic Name English
2-METHYLAMINO-1-PHENYLPROPANE HYDROCHLORIDE
Systematic Name English
NSC-22367
Code English
BENZENEETHANAMINE, N,.ALPHA.-DIMETHYL-, HYDROCHLORIDE
Systematic Name English
OBESIN
Common Name English
PHENETHYLAMINE, N,.ALPHA.-DIMETHYL-, HYDROCHLORIDE
Systematic Name English
DL-METHAMPHETAMINE HYDROCHLORIDE
Common Name English
OBESINE
Common Name English
(±)-METHAMPHETAMINE HYDROCHLORIDE
Common Name English
NSC-169506
Code English
Code System Code Type Description
PUBCHEM
9306
Created by admin on Fri Dec 15 18:56:48 UTC 2023 , Edited by admin on Fri Dec 15 18:56:48 UTC 2023
PRIMARY
FDA UNII
24GNZ56D62
Created by admin on Fri Dec 15 18:56:48 UTC 2023 , Edited by admin on Fri Dec 15 18:56:48 UTC 2023
PRIMARY
ECHA (EC/EINECS)
206-093-6
Created by admin on Fri Dec 15 18:56:48 UTC 2023 , Edited by admin on Fri Dec 15 18:56:48 UTC 2023
PRIMARY
NSC
169506
Created by admin on Fri Dec 15 18:56:48 UTC 2023 , Edited by admin on Fri Dec 15 18:56:48 UTC 2023
PRIMARY
NSC
22367
Created by admin on Fri Dec 15 18:56:48 UTC 2023 , Edited by admin on Fri Dec 15 18:56:48 UTC 2023
PRIMARY
EPA CompTox
DTXSID3048865
Created by admin on Fri Dec 15 18:56:48 UTC 2023 , Edited by admin on Fri Dec 15 18:56:48 UTC 2023
PRIMARY
CAS
300-42-5
Created by admin on Fri Dec 15 18:56:47 UTC 2023 , Edited by admin on Fri Dec 15 18:56:47 UTC 2023
PRIMARY