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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H15N.C6H10O8
Molecular Weight 359.3716
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHAMPHETAMINE SACCHARATE

SMILES

CN[C@@H](C)CC1=CC=CC=C1.O[C@@H]([C@H](O)[C@@H](O)C(O)=O)[C@H](O)C(O)=O

InChI

InChIKey=RACLVLZTMNZFLJ-SSNDBKPTSA-N
InChI=1S/C10H15N.C6H10O8/c1-9(11-2)8-10-6-4-3-5-7-10;7-1(3(9)5(11)12)2(8)4(10)6(13)14/h3-7,9,11H,8H2,1-2H3;1-4,7-10H,(H,11,12)(H,13,14)/t9-;1-,2-,3-,4+/m00/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

Molecular Formula C6H10O8
Molecular Weight 210.1388
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

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

1943
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

1943
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
Regional heterogeneity of dopaminergic deficits in vervet monkey striatum and substantia nigra after methamphetamine exposure.
2000 Aug
Cocaine and methamphetamine: differential addiction rates.
2000 Dec
Psychiatric comorbidity of methamphetamine dependence in a forensic sample.
2000 Fall
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
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
The effects of single dose of methamphetamine on lipid peroxidation levels in the rat striatum and prefrontal cortex.
2000 Sep
Cognitive impairment in individuals currently using methamphetamine.
2000 Summer
The association study of DRD2, ACE and AGT gene polymorphisms and metamphetamine dependence.
2001
Anti-apoptotic and apoptotic action of (-)-deprenyl and its metabolites.
2001
Postnatal maturation of prefrontal pyramidal neurones is sensitive to a single early dose of methamphetamine in gerbils (Meriones unguiculatus).
2001
Tamoxifen abolishes estrogen's neuroprotective effect upon methamphetamine neurotoxicity of the nigrostriatal dopaminergic system.
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
Immunohistochemical investigation of pulmonary surfactant-associated protein A in fatal poisoning.
2001 Apr 1
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
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
Substance abuse and dependence in a public hospital: Hawaii.
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
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
Long-term effects of a high-dose methamphetamine regimen on subsequent methamphetamine-induced dopamine release in vivo.
2001 Feb 16
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
Alterations in diurnal and nocturnal locomotor activity in rats treated with a monoamine-depleting regimen of methamphetamine or 3,4-methylenedioxymethamphetamine.
2001 Jan
[Advanced findings on the molecular mechanisms for behavioral sensitization to psychostimulants].
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
Plasma and brain methamphetamine concentrations in neonatal rats.
2001 Jan-Feb
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
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
Methamphetamine potentiates ischemia/reperfusion insults after transient middle cerebral artery ligation.
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
IGF-I and bFGF improve dopamine neuron survival and behavioral outcome in parkinsonian rats receiving cultured human fetal tissue strands.
2001 Mar
Differences between methamphetamine users and cocaine users in treatment.
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 14:59:01 GMT 2023
Edited
by admin
on Fri Dec 15 14:59:01 GMT 2023
Record UNII
K2J544L5HP
Record Status Validated (UNII)
Record Version
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Name Type Language
METHAMPHETAMINE SACCHARATE
WHO-DD  
Common Name English
GLUCARIC ACID, COMPD. WITH N,.ALPHA.-DIMETHYLPHENETHYLAMINE
Common Name English
METAMFETAMINE SACCHARATE
Common Name English
Methamphetamine saccharate [WHO-DD]
Common Name English
PHENETHYLAMINE, N,.ALPHA.-DIMETHYL-, GLUCARATE
Common Name English
D-METHAMPHETAMINE SACCHARATE
Common Name English
BENZENEETHANAMINE, N,.ALPHA.-DIMETHYL-, D-GLUCARATE
Common Name English
D-GLUCARIC ACID, COMPD. WITH N,.ALPHA.-DIMETHYLBENZENEETHANAMINE
Common Name English
Code System Code Type Description
SMS_ID
100000085947
Created by admin on Fri Dec 15 14:59:01 GMT 2023 , Edited by admin on Fri Dec 15 14:59:01 GMT 2023
PRIMARY
CAS
7563-48-6
Created by admin on Fri Dec 15 14:59:01 GMT 2023 , Edited by admin on Fri Dec 15 14:59:01 GMT 2023
PRIMARY
PUBCHEM
71586915
Created by admin on Fri Dec 15 14:59:01 GMT 2023 , Edited by admin on Fri Dec 15 14:59:01 GMT 2023
PRIMARY
EVMPD
SUB03204MIG
Created by admin on Fri Dec 15 14:59:01 GMT 2023 , Edited by admin on Fri Dec 15 14:59:01 GMT 2023
PRIMARY
EPA CompTox
DTXSID20226543
Created by admin on Fri Dec 15 14:59:01 GMT 2023 , Edited by admin on Fri Dec 15 14:59:01 GMT 2023
PRIMARY
FDA UNII
K2J544L5HP
Created by admin on Fri Dec 15 14:59:01 GMT 2023 , Edited by admin on Fri Dec 15 14:59:01 GMT 2023
PRIMARY
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