METHAMPHETAMINE HYDROCHLORIDE, DL-

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-

Structure Search

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

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
HPLC with fluorescence detection of methamphetamine and amphetamine in segmentally analyzed human hair.	1999 Apr	10605878
Chronic psychotic illness from methamphetamine.	1999 Apr	10200757
RGS mRNA expression in rat striatum: modulation by dopamine receptors and effects of repeated amphetamine administration.	1999 Apr	10098858
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
Amphetamines induce apoptosis and regulation of bcl-x splice variants in neocortical neurons.	1999 Jun	10336889
Methamphetamine-related stroke: four cases.	1999 May-Jun	10338241
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
Methamphetamine-induced neurotoxicity is attenuated in transgenic mice with a null mutation for interleukin-6.	2000 Dec	11093760
Methamphetamine-induced striatal dopamine neurotoxicity and cyclooxygenase-2 protein expression in BALB/c mice.	2000 Jan 28	10698006
Exacerbation of psychosis by phenylpropanolamine.	2000 Jun	10831490
Pott puffy tumor associated with intranasal methamphetamine.	2000 Mar 8	10714727
Effects of isradipine, a dihydropyridine-class calcium channel antagonist, on D-methamphetamine-induced cognitive and physiological changes in humans.	2000 May	10731625
Comparison between the role of the neuronal and inducible nitric oxide synthase in methamphetamine-induced neurotoxicity and sensitization.	2000 Sep	11085313
Activation of an effector immediate-early gene arc by methamphetamine.	2000 Sep	11085305
Cognitive impairment in individuals currently using methamphetamine.	2000 Summer	11000918
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
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
Sensitized increase of period gene expression in the mouse caudate/putamen caused by repeated injection of methamphetamine.	2001 Apr	11259635
Increased expression of synaptophysin and stathmin mRNAs after methamphetamine administration in rat brain.	2001 Apr 17	11303745
Substance abuse and dependence in a public hospital: Hawaii.	2001 Feb	11258162
Susceptibility of PharmChek drugs of abuse patch to environmental contamination.	2001 Feb 15	11182260
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
Plasma and brain methamphetamine concentrations in neonatal rats.	2001 Jan-Feb	11274878
Analysis of amphetamine and congeners in illicit samples by liquid chromatography and capillary electrophoresis.	2001 Mar	11300514
Methamphetamine potentiates ischemia/reperfusion insults after transient middle cerebral artery ligation.	2001 Mar	11239201
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
Glycine reduces novelty- and methamphetamine-induced locomotor activity in neonatal ventral hippocampal damaged rats.	2001 Mar	11166522
Dopaminergic role in stimulant-induced wakefulness.	2001 Mar 1	11222668

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

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