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
SMILES
Cl.CN[C@H](C)CC1=CC=CC=C1
InChI
InChIKey=TWXDDNPPQUTEOV-SBSPUUFOSA-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-;/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 |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|---|---|---|
| Cytochrome P450 2D6.1 and cytochrome P450 2D6.10 differ in catalytic activity for multiple substrates. | 2001 Aug |
|
| Diagnosis and treatment of sleep disorders: a brief review for clinicians. | 2003 Dec |
|
| PF 9601N [N-(2-propynyl)-2-(5-benzyloxy-indolyl) methylamine], a new MAO-B inhibitor, attenuates MPTP-induced depletion of striatal dopamine levels in C57/BL6 mice. | 2003 Feb |
|
| Reduced cardiovascular effects of methamphetamine following treatment with selegiline. | 2003 Nov 24 |
|
| Protein tyrosine phosphatase alpha (PTP alpha) knockout mice show deficits in Morris water maze learning, decreased locomotor activity, and decreases in anxiety. | 2003 Sep 12 |
|
| 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 |
|
| 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 |
|
| Comparison of monoamine and corticosterone levels 24 h following (+)methamphetamine, (+/-)3,4-methylenedioxymethamphetamine, cocaine, (+)fenfluramine or (+/-)methylphenidate administration in the neonatal rat. | 2006 Sep |
|
| Histopathological studies of cardiac lesions after an acute high dose administration of methamphetamine. | 2008 Jan |
|
| Applications of nanomaterials in electrogenerated chemiluminescence biosensors. | 2009 |
|
| Local hippocampal methamphetamine-induced reinforcement. | 2009 |
|
| Cryogenic terahertz spectrum of (+)-methamphetamine hydrochloride and assignment using solid-state density functional theory. | 2009 Apr 30 |
|
| "Ice" use and eating disorders: a report of three cases. | 2009 Mar |
|
| Effect of an electronic control device exposure on a methamphetamine-intoxicated animal model. | 2010 Apr |
|
| Enantioselective piezoelectric quartz crystal sensor for d-methamphetamine based on a molecularly imprinted polymer. | 2010 Aug |
|
| Addiction and cognition. | 2010 Dec |
|
| 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 |
|
| Toward a Better Understanding of Non-Addicted, Methamphetamine-Using, Men who Have Sex with Men (MSM) in Atlanta. | 2010 May 14 |
|
| 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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 18:37:38 GMT 2023
by
admin
on
Sat Dec 16 18:37:38 GMT 2023
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| Record UNII |
WQ4872M3C8
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| Record Status |
Validated (UNII)
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| Record Version |
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RACEMATE -> ENANTIOMER |
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ENANTIOMER -> ENANTIOMER |
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |
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