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
SMILES
CN[C@H](C)CC1=CC=CC=C1
InChI
InChIKey=MYWUZJCMWCOHBA-SECBINFHSA-N
InChI=1S/C10H15N/c1-9(11-2)8-10-6-4-3-5-7-10/h3-7,9,11H,8H2,1-2H3/t9-/m1/s1
| 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 |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/22037049 | https://www.drugs.com/uk/vicks-inhaler-leaflet.html | https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=38849 | https://www.ncbi.nlm.nih.gov/pubmed/17015058
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/22037049 | https://www.drugs.com/uk/vicks-inhaler-leaflet.html | https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=38849 | https://www.ncbi.nlm.nih.gov/pubmed/17015058
Levomethamphetamine is the levorotary (L-enantiomer) form of methamphetamine. Levomethamphetamine is a sympathomimetic vasoconstrictor which is the active ingredient in some over-the-counter (OTC) nasal decongestant inhalers in the United States. Levomethamphetamine crosses the blood-brain-barrier and acts as a TAAR1 agonist, functioning as a selective norepinephrine releasing agent (with few or no effects on the release of dopamine), so it affects the central nervous system, although its effects are qualitatively distinct relative to those of dextromethamphetamine. Levomethamphetamine does not possess the potential for euphoria or addiction that dextromethamphetamine possesses. Among its physiological effects are the vasoconstriction that makes it useful for nasal decongestion. The elimination half-life of levomethamphetamine is between 13.3 and 15 hours, whereas dextromethamphetamine has a half-life of about 10.5 hours. When the nasal decongestant is taken in excess, levomethamphetamine has potential side effects resembling those of other sympathomimetic drugs; these effects include hypertension (elevated blood pressure), tachycardia (rapid heart rate), nausea, stomach cramps, dizziness, headache, sweating, muscle tension, and tremors. Central side effects may include anxiety, insomnia, and anorexia
CNS Activity
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Brain mechanisms of hallucinogens and entactogens. | 2001 Dec |
|
| Carbon-monoxide poisoning in young drug addicts due to indoor use of a gasoline-powered generator. | 2001 Jun |
|
| Preparation of immunoaffinity columns for direct enantiomeric separation of amphetamine and/or methamphetamine. | 2002 Aug 23 |
|
| Diagnosis and treatment of sleep disorders: a brief review for clinicians. | 2003 Dec |
|
| Neurochemical and behavioral differences between d-methamphetamine and d-amphetamine in rats. | 2003 Feb |
|
| Lobeline does not serve as a reinforcer in rats. | 2003 Feb |
|
| Screening for and validated quantification of amphetamines and of amphetamine- and piperazine-derived designer drugs in human blood plasma by gas chromatography/mass spectrometry. | 2003 Jun |
|
| Chiral analysis of amphetamine-type stimulants using reversed-polarity capillary electrophoresis/positive ion electrospray ionization tandem mass spectrometry. | 2003 Jun |
|
| Developmental D-methamphetamine treatment selectively induces spatial navigation impairments in reference memory in the Morris water maze while sparing working memory. | 2003 Jun 1 |
|
| Elevated environmental temperature and methamphetamine neurotoxicity. | 2003 May |
|
| Differences between d-methamphetamine and d-amphetamine in rats: working memory, tolerance, and extinction. | 2003 Nov |
|
| Reduced cardiovascular effects of methamphetamine following treatment with selegiline. | 2003 Nov 24 |
|
| Metabolic profile of amphetamine and methamphetamine following administration of the drug famprofazone. | 2003 Oct |
|
| Impurity profiling of methamphetamine hydrochloride drugs seized in the Philippines. | 2004 Aug 11 |
|
| Detection of methamphetamine in the presence of nicotine using in situ chemical derivatization and ion mobility spectrometry. | 2004 Feb 15 |
|
| Analysis of pyrolysis products of methamphetamine. | 2004 Nov-Dec |
|
| Microglial activation is a pharmacologically specific marker for the neurotoxic amphetamines. | 2004 Sep 9 |
|
| Parkin-deficient mice are not more sensitive to 6-hydroxydopamine or methamphetamine neurotoxicity. | 2005 Dec 24 |
|
| Interactions of dopamine D1 and D2 receptor antagonists with D-methamphetamine-induced hyperthermia and striatal dopamine and serotonin reductions. | 2005 May |
|
| An evaluation of the sensitivity of the standardised field sobriety tests to detect the presence of amphetamine. | 2005 Oct |
|
| Potential marker for smoked methamphetamine hydrochloride based on a gas chromatography-mass spectrometry quantification method for trans-phenylpropene. | 2005 Sep |
|
| High doses of methamphetamine that cause disruption of the blood-brain barrier in limbic regions produce extensive neuronal degeneration in mouse hippocampus. | 2006 Dec 1 |
|
| Epoxidation of the methamphetamine pyrolysis product, trans-phenylpropene, to trans-phenylpropylene oxide by CYP enzymes and stereoselective glutathione adduct formation. | 2006 Mar 1 |
|
| Behavioral effects of ketamine and toxic interactions with psychostimulants. | 2006 Mar 16 |
|
| Comparison of the monoamine transporters from human and mouse in their sensitivities to psychostimulant drugs. | 2006 Mar 3 |
|
| Armodafinil, the R-enantiomer of modafinil: wake-promoting effects and pharmacokinetic profile in the rat. | 2006 Nov |
|
| Phosphodiesterase 1B differentially modulates the effects of methamphetamine on locomotor activity and spatial learning through DARPP32-dependent pathways: evidence from PDE1B-DARPP32 double-knockout mice. | 2006 Oct |
|
| Effects of (+/-)3,4-methylenedioxymethamphetamine, (+/-)3,4-methylenedioxyamphetamine and methamphetamine on temperature and activity in rhesus macaques. | 2006 Oct 13 |
|
| Chiral separation and quantification of R/S-amphetamine, R/S-methamphetamine, R/S-MDA, R/S-MDMA, and R/S-MDEA in whole blood by GC-EI-MS. | 2006 Oct 2 |
|
| Smokable ("ice", "crystal meth") and non smokable amphetamine-type stimulants: clinical pharmacological and epidemiological issues, with special reference to the UK. | 2007 |
|
| Application of mixtures of tartaric acid derivatives in resolution via supercritical fluid extraction. | 2007 Jun |
|
| PET studies of d-methamphetamine pharmacokinetics in primates: comparison with l-methamphetamine and ( --)-cocaine. | 2007 Oct |
|
| Redetermination of (+)-methamphetamine hydro-chloride at 90 K. | 2008 Apr 30 |
|
| Regional differences in HIV prevalence among drug users in China: potential for future spread of HIV? | 2008 Aug 4 |
|
| Histopathological studies of cardiac lesions after an acute high dose administration of methamphetamine. | 2008 Jan |
|
| The clinical pharmacology of intranasal l-methamphetamine. | 2008 Jul 21 |
|
| Rapid nondestructive on-site screening of methylamphetamine seizures by attenuated total reflection fourier transform infrared spectroscopy. | 2008 Jun |
|
| Environmental enrichment has no effect on the development of dopaminergic and GABAergic fibers during methylphenidate treatment of early traumatized gerbils. | 2008 May 16 |
|
| Applications of nanomaterials in electrogenerated chemiluminescence biosensors. | 2009 |
|
| Local hippocampal methamphetamine-induced reinforcement. | 2009 |
|
| An electrochemiluminescent sensor for methamphetamine hydrochloride based on multiwall carbon nanotube/ionic liquid composite electrode. | 2009 Jan 1 |
|
| "Ice" use and eating disorders: a report of three cases. | 2009 Mar |
|
| Characterization of route specific impurities found in methamphetamine synthesized by the Leuckart and reductive amination methods. | 2009 Sep 1 |
|
| Addiction and cognition. | 2010 Dec |
|
| Distribution and pharmacokinetics of methamphetamine in the human body: clinical implications. | 2010 Dec 7 |
|
| Reinforcing effects of methamphetamine in an animal model of attention-deficit/hyperactivity disorder--the spontaneously hypertensive rat. | 2010 Dec 9 |
|
| Regulation of the dopamine transporter: aspects relevant to psychostimulant drugs of abuse. | 2010 Feb |
|
| Methamphetamine reduces LTP and increases baseline synaptic transmission in the CA1 region of mouse hippocampus. | 2010 Jun 30 |
|
| A neurotoxic regimen of methamphetamine exacerbates the febrile and neuroinflammatory response to a subsequent peripheral immune stimulus. | 2010 Nov 22 |
|
| Detection of volatile indicators of illicit substances by the olfactory receptors of Drosophila melanogaster. | 2010 Sep |
Patents
Sample Use Guides
adults and children 12 years of age and over 2 inhalations in each nostril
children 6 to under 12 years of age 1 inhalation in each nostril (with adult supervision).
The product delivers in each 800 ml of air 0.04 to 0.150 mg of levmetamfetamine
Route of Administration:
Nasal
TA receptor activation was assayed in RD-HGA16cells stably expressing Gα16 and the hTAAR1 receptor. These cells were plated in HAM’s F-12 medium with 10% fetal bovine serum, 400 µg/ml hygromycin, and 400 µg/ml geneticin at 30,000 cells/well in 96-well, black, clear-bottom plates and incubated at 37 °C 5% CO2 overnight. Activation of hTAAR1 via Levomethamphetamine ((R)-10) was assessed the next day using the Calcium 3 Assay Kit (Molecular Devices). On the day of assay, the culture medium was removed and the cells washed once in 100 µl HBSS buffer containing 0.78 mg/ml probenicid, followed by the addition of 100 µl HBSS buffer plus probenicid and 100 µl of Calcium 3 dye (one-third the suggested concentration). The cells were incubated with the dye at 37 °C for 1 h. Levomethamphetamine were evaluated using 10 different concentrations run in duplicate. These were added to cells at 5 times the final concentration in HBSS/probenicid containing 1.25% DMSO (0.25% final concentration). The effect of test compound on internal calcium mobilization was determined with a FlexStation set for bottom read with 485-nm excitation and 525-nm emission wavelengths
| Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 22:37:08 UTC 2023
by
admin
on
Wed Jul 05 22:37:08 UTC 2023
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| Record UNII |
Y24T9BT2Q2
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C29747
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CFR |
21 CFR 1308.22
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CFR |
21 CFR 341.20
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HH-45
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36604
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Y24T9BT2Q2
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300000034275
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DTXSID30187474
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4641
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Levomethamphetamine
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251-687-0
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33817-09-3
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1359506
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CHEMBL1927030
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Y24T9BT2Q2
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DB09571
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7900
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C75930
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ACTIVE MOIETY |
