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
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
65.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17015058/ |
0.25 mg/kg single, intravenous dose: 0.25 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
LEVMETAMFETAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1190.7 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17015058/ |
0.25 mg/kg single, intravenous dose: 0.25 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
LEVMETAMFETAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
13.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17015058/ |
0.25 mg/kg single, intravenous dose: 0.25 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
LEVMETAMFETAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Reinforcing effects of methamphetamine in an animal model of attention-deficit/hyperactivity disorder--the spontaneously hypertensive rat. | 2010-12-09 |
|
| Distribution and pharmacokinetics of methamphetamine in the human body: clinical implications. | 2010-12-07 |
|
| Addiction and cognition. | 2010-12 |
|
| Drug discrimination in methamphetamine-trained rats: effects of cholinergic nicotinic compounds. | 2010-12 |
|
| A neurotoxic regimen of methamphetamine exacerbates the febrile and neuroinflammatory response to a subsequent peripheral immune stimulus. | 2010-11-22 |
|
| Autoradiographic study of serotonin transporter during memory formation. | 2010-09-01 |
|
| Detection of volatile indicators of illicit substances by the olfactory receptors of Drosophila melanogaster. | 2010-09 |
|
| Enantioselective piezoelectric quartz crystal sensor for d-methamphetamine based on a molecularly imprinted polymer. | 2010-08 |
|
| Methamphetamine reduces LTP and increases baseline synaptic transmission in the CA1 region of mouse hippocampus. | 2010-06-30 |
|
| Toward a Better Understanding of Non-Addicted, Methamphetamine-Using, Men who Have Sex with Men (MSM) in Atlanta. | 2010-05-14 |
|
| Effect of an electronic control device exposure on a methamphetamine-intoxicated animal model. | 2010-04 |
|
| Regulation of the dopamine transporter: aspects relevant to psychostimulant drugs of abuse. | 2010-02 |
|
| Characterization of route specific impurities found in methamphetamine synthesized by the Leuckart and reductive amination methods. | 2009-09-01 |
|
| Cryogenic terahertz spectrum of (+)-methamphetamine hydrochloride and assignment using solid-state density functional theory. | 2009-04-30 |
|
| "Ice" use and eating disorders: a report of three cases. | 2009-03 |
|
| Rapid analysis of methamphetamine in hair by micropulverized extraction and microchip-based competitive ELISA. | 2009-01-30 |
|
| An electrochemiluminescent sensor for methamphetamine hydrochloride based on multiwall carbon nanotube/ionic liquid composite electrode. | 2009-01-01 |
|
| Applications of nanomaterials in electrogenerated chemiluminescence biosensors. | 2009 |
|
| Local hippocampal methamphetamine-induced reinforcement. | 2009 |
|
| Changes in glutamate/NMDA receptor subunit 1 expression in rat brain after acute and subacute exposure to methamphetamine. | 2009 |
|
| Myocardial lesions after long-term administration of methamphetamine in rats. | 2008-12 |
|
| Identification of impurities and statistical classification of methamphetamine hydrochloride drugs seized in China. | 2008-11-20 |
|
| Regional differences in HIV prevalence among drug users in China: potential for future spread of HIV? | 2008-08-04 |
|
| The clinical pharmacology of intranasal l-methamphetamine. | 2008-07-21 |
|
| Rapid nondestructive on-site screening of methylamphetamine seizures by attenuated total reflection fourier transform infrared spectroscopy. | 2008-06 |
|
| Environmental enrichment has no effect on the development of dopaminergic and GABAergic fibers during methylphenidate treatment of early traumatized gerbils. | 2008-05-16 |
|
| Evaluation of effects of methamphetamine repeated dosing on proliferation and apoptosis of rat germ cells. | 2008-05-01 |
|
| Redetermination of (+)-methamphetamine hydro-chloride at 90 K. | 2008-04-30 |
|
| Histopathological studies of cardiac lesions after an acute high dose administration of methamphetamine. | 2008-01 |
|
| Neurochemical consequences of dysphoric state during amphetamine withdrawal in animal models: a review. | 2008-01 |
|
| Perinatal asphyxia reduces dentate granule cells and exacerbates methamphetamine-induced hyperlocomotion in adulthood. | 2008 |
|
| Selective inhibition of cyclooxygenase-2 exacerbates methamphetamine-induced dopamine depletion in the striatum in rats. | 2007-12-19 |
|
| PET studies of d-methamphetamine pharmacokinetics in primates: comparison with l-methamphetamine and ( --)-cocaine. | 2007-10 |
|
| Methamphetamine body packer: acute poisoning death due to massive leaking of methamphetamine. | 2007-09 |
|
| Application of mixtures of tartaric acid derivatives in resolution via supercritical fluid extraction. | 2007-06 |
|
| Oral administration of (+/-)3,4-methylenedioxymethamphetamine and (+)methamphetamine alters temperature and activity in rhesus macaques. | 2007-05 |
|
| [Analysis of active components of evidence materials secured in the cases of drugs abuse associated with amphetamines and cannabis products]. | 2007-01-26 |
|
| Effects of methamphetamine on single unit activity in rat medial prefrontal cortex in vivo. | 2007 |
|
| Smokable ("ice", "crystal meth") and non smokable amphetamine-type stimulants: clinical pharmacological and epidemiological issues, with special reference to the UK. | 2007 |
|
| High doses of methamphetamine that cause disruption of the blood-brain barrier in limbic regions produce extensive neuronal degeneration in mouse hippocampus. | 2006-12-01 |
|
| Armodafinil, the R-enantiomer of modafinil: wake-promoting effects and pharmacokinetic profile in the rat. | 2006-11 |
|
| Effects of (+/-)3,4-methylenedioxymethamphetamine, (+/-)3,4-methylenedioxyamphetamine and methamphetamine on temperature and activity in rhesus macaques. | 2006-10-13 |
|
| 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. | 2006-10-02 |
|
| Human pharmacology of the methamphetamine stereoisomers. | 2006-10 |
|
| 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. | 2006-10 |
|
| Comparison of monoamine and corticosterone levels 24 h following (+)methamphetamine, (+/-)3,4-methylenedioxymethamphetamine, cocaine, (+)fenfluramine or (+/-)methylphenidate administration in the neonatal rat. | 2006-09 |
|
| The acute effects of d-amphetamine and methamphetamine on attention and psychomotor performance. | 2006-08 |
|
| NMR regulatory analysis: enantiomeric purity determination for (R)-(-)-desoxyephedrine and antipode methamphetamine. | 2006-03 |
|
| Diagnosis and treatment of sleep disorders: a brief review for clinicians. | 2003-12 |
|
| Brain mechanisms of hallucinogens and entactogens. | 2001-12 |
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
Mon Mar 31 17:45:49 GMT 2025
by
admin
on
Mon Mar 31 17:45:49 GMT 2025
|
| Record UNII |
Y24T9BT2Q2
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Preferred Name | English | ||
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
NCI_THESAURUS |
C29747
Created by
admin on Mon Mar 31 17:45:50 GMT 2025 , Edited by admin on Mon Mar 31 17:45:50 GMT 2025
|
||
|
CFR |
21 CFR 1308.22
Created by
admin on Mon Mar 31 17:45:50 GMT 2025 , Edited by admin on Mon Mar 31 17:45:50 GMT 2025
|
||
|
CFR |
21 CFR 341.20
Created by
admin on Mon Mar 31 17:45:50 GMT 2025 , Edited by admin on Mon Mar 31 17:45:50 GMT 2025
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
HH-45
Created by
admin on Mon Mar 31 17:45:50 GMT 2025 , Edited by admin on Mon Mar 31 17:45:50 GMT 2025
|
PRIMARY | |||
|
36604
Created by
admin on Mon Mar 31 17:45:50 GMT 2025 , Edited by admin on Mon Mar 31 17:45:50 GMT 2025
|
PRIMARY | |||
|
Y24T9BT2Q2
Created by
admin on Mon Mar 31 17:45:50 GMT 2025 , Edited by admin on Mon Mar 31 17:45:50 GMT 2025
|
PRIMARY | |||
|
300000034275
Created by
admin on Mon Mar 31 17:45:50 GMT 2025 , Edited by admin on Mon Mar 31 17:45:50 GMT 2025
|
PRIMARY | |||
|
DTXSID30187474
Created by
admin on Mon Mar 31 17:45:50 GMT 2025 , Edited by admin on Mon Mar 31 17:45:50 GMT 2025
|
PRIMARY | |||
|
4641
Created by
admin on Mon Mar 31 17:45:50 GMT 2025 , Edited by admin on Mon Mar 31 17:45:50 GMT 2025
|
PRIMARY | |||
|
Levomethamphetamine
Created by
admin on Mon Mar 31 17:45:50 GMT 2025 , Edited by admin on Mon Mar 31 17:45:50 GMT 2025
|
PRIMARY | |||
|
251-687-0
Created by
admin on Mon Mar 31 17:45:50 GMT 2025 , Edited by admin on Mon Mar 31 17:45:50 GMT 2025
|
PRIMARY | |||
|
33817-09-3
Created by
admin on Mon Mar 31 17:45:50 GMT 2025 , Edited by admin on Mon Mar 31 17:45:50 GMT 2025
|
PRIMARY | |||
|
1359506
Created by
admin on Mon Mar 31 17:45:50 GMT 2025 , Edited by admin on Mon Mar 31 17:45:50 GMT 2025
|
PRIMARY | |||
|
CHEMBL1927030
Created by
admin on Mon Mar 31 17:45:50 GMT 2025 , Edited by admin on Mon Mar 31 17:45:50 GMT 2025
|
PRIMARY | |||
|
Y24T9BT2Q2
Created by
admin on Mon Mar 31 17:45:50 GMT 2025 , Edited by admin on Mon Mar 31 17:45:50 GMT 2025
|
PRIMARY | |||
|
DB09571
Created by
admin on Mon Mar 31 17:45:50 GMT 2025 , Edited by admin on Mon Mar 31 17:45:50 GMT 2025
|
PRIMARY | |||
|
7900
Created by
admin on Mon Mar 31 17:45:50 GMT 2025 , Edited by admin on Mon Mar 31 17:45:50 GMT 2025
|
PRIMARY | |||
|
C75930
Created by
admin on Mon Mar 31 17:45:50 GMT 2025 , Edited by admin on Mon Mar 31 17:45:50 GMT 2025
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
TARGET -> AGONIST |
|
||
|
SALT/SOLVATE -> PARENT |
|
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
PARENT -> METABOLITE |
IN-VIVO
URINE
|
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
IMPURITY -> PARENT |
|
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |
