METHAMPHETAMINE HYDROCHLORIDE

Details

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

SHOW SMILES / InChI

Structure of METHAMPHETAMINE HYDROCHLORIDE

Structure Search

SMILES

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

InChI

InChIKey=TWXDDNPPQUTEOV-FVGYRXGTSA-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/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 42
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 8297
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 2678
Adrenergic receptor alpha-2 113 Target ID: CHEMBL2095158 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12453616	Agonist 2678

Conditions

Condition	Modality	Highest Phase	Product
Attention deficit hyperactivity disorder 68 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/005378s026lbl.pdf	Primary	Approved 8429	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 8429	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 2578

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 1217 inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT1 599 OAT2 145 OAT3 642 OAT4 146 OCT1 512 OCT2 647		GLUT1 9

Drug as perpetrator

Target	Modality	Activity
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/005378s035lbl.pdf#page=	minor
OAT1 603	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/32109742/	no
OAT2 147	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/32109742/	no
OAT3 644	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/32109742/	no
OAT4 146	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/32109742/	no
OCT2 648	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/32109742/	yes [IC50 19.1 uM]
OCT1 543	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/32109742/	yes [IC50 6.5 uM]
GLUT1 15	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/21426580/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 1217	substrate 3367 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
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
Evaluation of the effects of alpha-phenyl-N-tert-butyl nitrone pretreatment on the neurobehavioral effects of methamphetamine.	2000 Aug 18	10983851
Methamphetamine-induced neurotoxicity is attenuated in transgenic mice with a null mutation for interleukin-6.	2000 Dec	11093760
Dual serotonin (5-HT) projections to the nucleus accumbens core and shell: relation of the 5-HT transporter to amphetamine-induced neurotoxicity.	2000 Mar 1	10684896
Pott puffy tumor associated with intranasal methamphetamine.	2000 Mar 8	10714727
Effect of temperature on dopamine transporter function and intracellular accumulation of methamphetamine: implications for methamphetamine-induced dopaminergic neurotoxicity.	2000 Oct 15	11027249
nNOS inhibitors attenuate methamphetamine-induced dopaminergic neurotoxicity but not hyperthermia in mice.	2000 Sep 11	11006970
The association study of DRD2, ACE and AGT gene polymorphisms and metamphetamine dependence.	2001	11300226
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
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
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
Substance abuse and dependence in a public hospital: Hawaii.	2001 Feb	11258162
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
Unintentional methamphetamine intoxication.	2001 Feb	11174264
Highly sensitive analysis of methamphetamine and amphetamine in human whole blood using headspace solid-phase microextraction and gas chromatography-mass spectrometry.	2001 Feb 1	11118748
Methamphetamine-induced rapid and reversible changes in dopamine transporter function: an in vitro model.	2001 Feb 15	11160413
Analysis of benzphetamine and its metabolites in rat urine by liquid chromatography-electrospray ionization mass spectrometry.	2001 Feb 25	11236083
Alterations in diurnal and nocturnal locomotor activity in rats treated with a monoamine-depleting regimen of methamphetamine or 3,4-methylenedioxymethamphetamine.	2001 Jan	11271404
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
Regulation of the vesicular monoamine transporter-2: a novel mechanism for cocaine and other psychostimulants.	2001 Mar	11181904
Effects of lubeluzole on the methamphetamine-induced increase in extracellular glutamate and the long-term depletion of striatal dopamine.	2001 May	11252020

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

Common Name

English

Metamfetamine hydrochloride [WHO-DD]

Common Name

English

METAMFETAMINE HYDROCHLORIDE [MART.]

Common Name

English

METHAMPHETAMINE HYDROCHLORIDE [JAN]

Common Name

English

METHAMPHETAMINE HCL

Common Name

English

BENZENEETHANAMINE, N,.ALPHA.-DIMETHYL-, HYDROCHLORIDE, (S)-

Systematic Name

English

METHAMPHETAMINE HYDROCHLORIDE CII

Common Name

English

METHAMPHETAMINE HYDROCHLORIDE [VANDF]

Common Name

English

DESOXYEPHEDRINE HYDROCHLORIDE

Common Name

English

NSC-169505

Code

English

METHAMPHETAMINE HYDROCHLORIDE [ORANGE BOOK]

Common Name

English

METHAMPEX

Brand Name

English

(+)-METHAMPHETAMINE HYDROCHLORIDE

Common Name

English

METHAMPHETAMINE HYDROCHLORIDE [MI]

Common Name

English

(+)-(S)-N,.ALPHA.-DIMETHYLPHENETHYLAMINE HYDROCHLORIDE

Systematic Name

English

METHAMPHETAMINE HYDROCHLORIDE CII [USP-RS]

Common Name

English

METHAMPHETAMINE HYDROCHLORIDE [USP MONOGRAPH]

Common Name

English

DESOXYN

Brand Name

English

METAMFETAMINE HYDROCHLORIDE

Common Name

English

Classification Tree Code System Code

DEA NO.

1105