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
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 |
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| Carbon-monoxide poisoning in young drug addicts due to indoor use of a gasoline-powered generator. | 2001 Jun |
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| Diagnosis and treatment of sleep disorders: a brief review for clinicians. | 2003 Dec |
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| Impurity profiling of methamphetamine hydrochloride drugs seized in the Philippines. | 2004 Aug 11 |
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| Microglial activation is a pharmacologically specific marker for the neurotoxic amphetamines. | 2004 Sep 9 |
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| Periadolescent rats (P41-50) exhibit increased susceptibility to D-methamphetamine-induced long-term spatial and sequential learning deficits compared to juvenile (P21-30 or P31-40) or adult rats (P51-60). | 2005 Jan-Feb |
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| Effects of isradipine on methamphetamine-induced changes in attentional and perceptual-motor skills of cognition. | 2005 Mar |
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| In vivo neuroprotective effects of the novel imidazolyl nitrone free-radical scavenger (Z)-alpha-[2-thiazol-2-yl)imidazol-4-yl]-N-tert-butylnitrone (S34176). | 2005 Mar 28 |
|
| Interactions of dopamine D1 and D2 receptor antagonists with D-methamphetamine-induced hyperthermia and striatal dopamine and serotonin reductions. | 2005 May |
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| The acute effects of d-amphetamine and methamphetamine on attention and psychomotor performance. | 2006 Aug |
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| Behavioral effects of ketamine and toxic interactions with psychostimulants. | 2006 Mar 16 |
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| Comparison of the monoamine transporters from human and mouse in their sensitivities to psychostimulant drugs. | 2006 Mar 3 |
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| Human pharmacology of the methamphetamine stereoisomers. | 2006 Oct |
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| 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 |
|
| [Analysis of active components of evidence materials secured in the cases of drugs abuse associated with amphetamines and cannabis products]. | 2006 Oct-Dec |
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| Effects of methamphetamine on single unit activity in rat medial prefrontal cortex in vivo. | 2007 |
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| Selective inhibition of cyclooxygenase-2 exacerbates methamphetamine-induced dopamine depletion in the striatum in rats. | 2007 Dec 19 |
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| 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 |
|
| Methamphetamine body packer: acute poisoning death due to massive leaking of methamphetamine. | 2007 Sep |
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| Perinatal asphyxia reduces dentate granule cells and exacerbates methamphetamine-induced hyperlocomotion in adulthood. | 2008 |
|
| 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 |
|
| Myocardial lesions after long-term administration of methamphetamine in rats. | 2008 Dec |
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| Histopathological studies of cardiac lesions after an acute high dose administration of methamphetamine. | 2008 Jan |
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| Neurochemical consequences of dysphoric state during amphetamine withdrawal in animal models: a review. | 2008 Jan |
|
| Rapid nondestructive on-site screening of methylamphetamine seizures by attenuated total reflection fourier transform infrared spectroscopy. | 2008 Jun |
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| Evaluation of effects of methamphetamine repeated dosing on proliferation and apoptosis of rat germ cells. | 2008 Mar-Apr |
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| Environmental enrichment has no effect on the development of dopaminergic and GABAergic fibers during methylphenidate treatment of early traumatized gerbils. | 2008 May 16 |
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| Identification of impurities and statistical classification of methamphetamine hydrochloride drugs seized in China. | 2008 Nov 20 |
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| Applications of nanomaterials in electrogenerated chemiluminescence biosensors. | 2009 |
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| Local hippocampal methamphetamine-induced reinforcement. | 2009 |
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| Changes in glutamate/NMDA receptor subunit 1 expression in rat brain after acute and subacute exposure to methamphetamine. | 2009 |
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| Cryogenic terahertz spectrum of (+)-methamphetamine hydrochloride and assignment using solid-state density functional theory. | 2009 Apr 30 |
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| An electrochemiluminescent sensor for methamphetamine hydrochloride based on multiwall carbon nanotube/ionic liquid composite electrode. | 2009 Jan 1 |
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| Rapid analysis of methamphetamine in hair by micropulverized extraction and microchip-based competitive ELISA. | 2009 Jan 30 |
|
| "Ice" use and eating disorders: a report of three cases. | 2009 Mar |
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| Characterization of route specific impurities found in methamphetamine synthesized by the Leuckart and reductive amination methods. | 2009 Sep 1 |
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| Effect of an electronic control device exposure on a methamphetamine-intoxicated animal model. | 2010 Apr |
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| Enantioselective piezoelectric quartz crystal sensor for d-methamphetamine based on a molecularly imprinted polymer. | 2010 Aug |
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| Addiction and cognition. | 2010 Dec |
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| Drug discrimination in methamphetamine-trained rats: effects of cholinergic nicotinic compounds. | 2010 Dec |
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| Distribution and pharmacokinetics of methamphetamine in the human body: clinical implications. | 2010 Dec 7 |
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| Reinforcing effects of methamphetamine in an animal model of attention-deficit/hyperactivity disorder--the spontaneously hypertensive rat. | 2010 Dec 9 |
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| Regulation of the dopamine transporter: aspects relevant to psychostimulant drugs of abuse. | 2010 Feb |
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| Methamphetamine reduces LTP and increases baseline synaptic transmission in the CA1 region of mouse hippocampus. | 2010 Jun 30 |
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| Toward a Better Understanding of Non-Addicted, Methamphetamine-Using, Men who Have Sex with Men (MSM) in Atlanta. | 2010 May 14 |
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| A neurotoxic regimen of methamphetamine exacerbates the febrile and neuroinflammatory response to a subsequent peripheral immune stimulus. | 2010 Nov 22 |
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| Detection of volatile indicators of illicit substances by the olfactory receptors of Drosophila melanogaster. | 2010 Sep |
|
| Autoradiographic study of serotonin transporter during memory formation. | 2010 Sep 1 |
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
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| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C29747
Created by
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CFR |
21 CFR 1308.22
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CFR |
21 CFR 341.20
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| Code System | Code | Type | Description | ||
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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
PARENT (METABOLITE)
SALT/SOLVATE (PARENT)
