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 |
|---|---|---|
| The effect of low oral doses of (-)-deprenyl and its metabolites on DSP-4 toxicity. | 2001 |
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| Cytochrome P450 2D6.1 and cytochrome P450 2D6.10 differ in catalytic activity for multiple substrates. | 2001 Aug |
|
| Generation of anti-(+)methamphetamine antibodies is not impeded by (+)methamphetamine administration during active immunization of rats. | 2001 Feb |
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| Lobeline attenuates d-methamphetamine self-administration in rats. | 2001 Jul |
|
| Carbon-monoxide poisoning in young drug addicts due to indoor use of a gasoline-powered generator. | 2001 Jun |
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| Patterns of methamphetamine abuse and their consequences. | 2002 |
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| Impaired spatial and sequential learning in rats treated neonatally with D-fenfluramine. | 2002 Aug |
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| Phosphodiesterase 1B knock-out mice exhibit exaggerated locomotor hyperactivity and DARPP-32 phosphorylation in response to dopamine agonists and display impaired spatial learning. | 2002 Jun 15 |
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| Neurochemical and behavioral differences between d-methamphetamine and d-amphetamine in rats. | 2003 Feb |
|
| Microbial degradation of illicit drugs, their precursors, and manufacturing by-products: implications for clandestine drug laboratory investigation and environmental assessment. | 2003 Jun 24 |
|
| Effects of isradipine on methamphetamine-induced changes in attentional and perceptual-motor skills of cognition. | 2005 Mar |
|
| 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 |
|
| 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 |
|
| Selective inhibition of cyclooxygenase-2 exacerbates methamphetamine-induced dopamine depletion in the striatum in rats. | 2007 Dec 19 |
|
| Neurochemical consequences of dysphoric state during amphetamine withdrawal in animal models: a review. | 2008 Jan |
|
| The clinical pharmacology of intranasal l-methamphetamine. | 2008 Jul 21 |
|
| Identification of impurities and statistical classification of methamphetamine hydrochloride drugs seized in China. | 2008 Nov 20 |
|
| Local hippocampal methamphetamine-induced reinforcement. | 2009 |
|
| Toward a Better Understanding of Non-Addicted, Methamphetamine-Using, Men who Have Sex with Men (MSM) in Atlanta. | 2010 May 14 |
|
| A neurotoxic regimen of methamphetamine exacerbates the febrile and neuroinflammatory response to a subsequent peripheral immune stimulus. | 2010 Nov 22 |
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
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admin
on
Edited
Fri Dec 15 15:05:06 GMT 2023
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admin
on
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| Record UNII |
Y24T9BT2Q2
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| Record Status |
Validated (UNII)
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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 |
