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 |
|
| Monoamine oxidase-inhibition and MPTP-induced neurotoxicity in the non-human primate: comparison of rasagiline (TVP 1012) with selegiline. | 2001 |
|
| Cytochrome P450 2D6.1 and cytochrome P450 2D6.10 differ in catalytic activity for multiple substrates. | 2001 Aug |
|
| Brain mechanisms of hallucinogens and entactogens. | 2001 Dec |
|
| Lobeline attenuates d-methamphetamine self-administration in rats. | 2001 Jul |
|
| Comparison of ELISAs for opiates, methamphetamine, cocaine metabolite, benzodiazepines, phencyclidine, and cannabinoids in whole blood and urine. | 2001 Mar |
|
| Discrimination in resolving systems. VI. Comparison of the diastereomers of deoxyephedrinium and ephedrinium 4'-fluoromandelates. | 2001 May 15 |
|
| CYP2B6 and CYP2C19 as the major enzymes responsible for the metabolism of selegiline, a drug used in the treatment of Parkinson's disease, as revealed from experiments with recombinant enzymes. | 2001 Nov |
|
| Effects of the hallucinogen psilocybin on covert orienting of visual attention in humans. | 2002 |
|
| Impaired spatial and sequential learning in rats treated neonatally with D-fenfluramine. | 2002 Aug |
|
| Preparation of immunoaffinity columns for direct enantiomeric separation of amphetamine and/or methamphetamine. | 2002 Aug 23 |
|
| Neuroprotective effect of the monoamine oxidase inhibitor PF 9601N [N-(2-propynyl)-2-(5-benzyloxy-indolyl) methylamine] on rat nigral neurons after 6-hydroxydopamine-striatal lesion. | 2002 Aug 30 |
|
| Effect of 7-nitroindazole on drug-priming reinstatement of D-methamphetamine-induced conditioned place preference. | 2002 May 17 |
|
| Lobeline does not serve as a reinforcer in rats. | 2003 Feb |
|
| 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 |
|
| Elevated environmental temperature and methamphetamine neurotoxicity. | 2003 May |
|
| Metabolic profile of amphetamine and methamphetamine following administration of the drug famprofazone. | 2003 Oct |
|
| 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 |
|
| 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 |
|
| Effects of isradipine on methamphetamine-induced changes in attentional and perceptual-motor skills of cognition. | 2005 Mar |
|
| 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 |
|
| An evaluation of the sensitivity of the standardised field sobriety tests to detect the presence of amphetamine. | 2005 Oct |
|
| The acute effects of d-amphetamine and methamphetamine on attention and psychomotor performance. | 2006 Aug |
|
| Armodafinil, the R-enantiomer of modafinil: wake-promoting effects and pharmacokinetic profile in the rat. | 2006 Nov |
|
| Human pharmacology of the methamphetamine stereoisomers. | 2006 Oct |
|
| Effects of (+/-)3,4-methylenedioxymethamphetamine, (+/-)3,4-methylenedioxyamphetamine and methamphetamine on temperature and activity in rhesus macaques. | 2006 Oct 13 |
|
| [Analysis of active components of evidence materials secured in the cases of drugs abuse associated with amphetamines and cannabis products]. | 2006 Oct-Dec |
|
| Smokable ("ice", "crystal meth") and non smokable amphetamine-type stimulants: clinical pharmacological and epidemiological issues, with special reference to the UK. | 2007 |
|
| Oral administration of (+/-)3,4-methylenedioxymethamphetamine and (+)methamphetamine alters temperature and activity in rhesus macaques. | 2007 May |
|
| 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 |
|
| Histopathological studies of cardiac lesions after an acute high dose administration of methamphetamine. | 2008 Jan |
|
| 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 |
|
| 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 |
|
| Rapid analysis of methamphetamine in hair by micropulverized extraction and microchip-based competitive ELISA. | 2009 Jan 30 |
|
| Characterization of route specific impurities found in methamphetamine synthesized by the Leuckart and reductive amination methods. | 2009 Sep 1 |
|
| Enantioselective piezoelectric quartz crystal sensor for d-methamphetamine based on a molecularly imprinted polymer. | 2010 Aug |
|
| Drug discrimination in methamphetamine-trained rats: effects of cholinergic nicotinic compounds. | 2010 Dec |
|
| Distribution and pharmacokinetics of methamphetamine in the human body: clinical implications. | 2010 Dec 7 |
|
| Methamphetamine reduces LTP and increases baseline synaptic transmission in the CA1 region of mouse hippocampus. | 2010 Jun 30 |
|
| Toward a Better Understanding of Non-Addicted, Methamphetamine-Using, Men who Have Sex with Men (MSM) in Atlanta. | 2010 May 14 |
|
| 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
Fri Dec 15 15:05:06 GMT 2023
by
admin
on
Fri Dec 15 15:05:06 GMT 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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IN-VIVO
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ACTIVE MOIETY |
