Basic information
- CAS
33817-09-3- Standard SMILES
CN[C@H](C)Cc1ccccc1- InChIKey
MYWUZJCMWCOHBA-SECBINFHSA-N- Molecular formula
- C10H15N
- Average molar mass
- 149.23 g/mol
- Monoisotopic mass
- 149.12044948
Overview
Levmetamfetamine is a member of amphetamines.
Names & identifiers
- Preferred name
- Levmetamfetamine
- IUPAC
- (2R)-N-methyl-1-phenylpropan-2-amine
- English name
- (-)-2-[Methylamino]-1-phenylpropane
- Molecular formula
- C10H15N
- Molecular weight
- 149.24
Names & synonyms
LevmetamfetamineL-Methamphetaminel-MethylamphetaminelevomethamphetamineR(-)-N-Methylamphetaminel-1-Phenyl-2-methylaminopropaneVicksLevmetamfetamine ciiNSC 6084levmetanfetaminal-1-Phenyl-2-methylamino-propanEINECS 251-687-0
Show more names
(R)-N-methyl-1-phenylpropan-2-amineL-DEOXYEPHEDRINER(-)-METHAMPHETAMINER-(-)-N-MethylamphetamineVicks Inhalermethylpropamine(-)-DEOXYEPHEDRINE
UNII-Y24T9BT2Q2Y24T9BT2Q2Benzeneethanamine, N,alpha-dimethyl-, (R)-Benzeneethanamine, N,alpha-dimethyl-, (-)-PHENETHYLAMINE, N,alpha-DIMETHYL-, (-)-(-)-(R)-N,alpha-DimethylphenethylamineDTXSID30187474Levmetamfetamine [USAN:USP:INN]
Database identifiers
- CAS
33817-09-3- PubChem CID
- 36604
- DTXSID
DTXSID30187474- ChEMBL
CHEMBL1927030
Properties
Computed structural properties
- XLogP
- 2.1
- Topological polar surface area
- 12 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 3
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 95
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Melting point
- 38 · 38-40 °C
- Boiling point
- 104 · 104-107 °C(Press: 28 Torr)
- Density
- 0.907 · 0.907±0.06 g/cm3(Predicted)
- Flash point
- 9 ℃ · 9℃
- storage temp.
- 2 · 2-8°C
- solubility
- Chloroform (Slightly), Ethanol (Slightly), Methanol (Sparingly)
- form
- Oil
- pka
- 9.99 · pKa 9.99(H2O,t =25±0.5,I=0.01)(Approximate)
- color
- Pale Yellow
- Major Application
- forensics and toxicology
- 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
- InChIKey
- MYWUZJCMWCOHBA-SECBINFHSA-N
- SMILES
- CN[C@H](C)Cc1ccccc1
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P203, P261, P262, P264, P264+P265, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P318, P321, P330, P337+P317, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 144 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 3 (100%)
Toxicology
Treatment
Management of acute methamphetamine intoxication is largely symptomatic and includes gastric evacuation, administration of activated charcoal, and sedation. Experience with hemodialysis or peritoneal dialysis is inadequate to permit recommendations in this regard. Acidification of urine increases methamphetamine excretion, but is believed to increase risk of acute renal failure if myoglobinuria is present. Intravenous phentolamine has been suggested for possible acute, severe hypertension, if this complicates methamphetamine overdosage. Usually a gradual drop in blood pressure will result when sufficient sedation has been achieved. Chlorpromazine has been reported to be useful in decreasing CNS stimulation and sympathomimetic effects. (L1712)
Health Effects
Using large amounts of these drugs can result in a condition known as amphetamine psychosis -- which can result in auditory, visual and tactile hallucinations, intense paranoia, irrational thoughts and beliefs, delusions, and mental confusion.
Exposure Routes
Chemistry & industry
Pharmacology
PharmacodynamicsLevomethamphetamine increases norepinephrine release resulting in increased vasocontriction.
Mechanism of ActionLevomethamphetamine crosses the blood-brain-barrier and acts as a TAAR1 agonist,[3] functioning as a selective norepinephrine releasing agent in the central nervous system,
Biological Half-LifeThe elimination half-life of levomethamphetamine is between 13.3 and 15 hours.
Metabolism/Metabolites
Methamphetamine is a known human metabolite of selegiline.
Hepatic. The primary site of metabolism is in the liver by aromatic hydroxylation, N-dealkylation and deamination. At least seven metabolites have been identified in the urine, with the main metabolites being amphetamine (active) and 4-hydroxymethamphetamine. Other minor metabolites include 4-hydroxyamphetamine, norephedrine, and 4-hydroxynorephedrine. Route of Elimination: Excretion occurs primarily in the urine, the rate of which is dependent on urine pH. Between 30-54% of an oral dose is excreted in urine as unchanged methamphetamine and 10-23% as unchanged amphetamine. Following an intravenous dose, 45% is excreted as unchanged parent drug and 7% amphetamine. Half Life: The biological half-life has been reported in the range of 4 to 5 hours.
Uses & manufacturing
UsesFor the treatment of Attention Deficit Disorder with Hyperactivity (ADHD) and exogenous obesity.
Applications
UsesNasal decongestant.
General DescriptionR(-)-Methamphetamine, or levomethamphetamine, is a vasoconstrictor and component of multiple over-the-counter nasal decongestants. This certified Snap-N-Spike solution is suitable for use as starting material in calibrators or controls for a variety of LC/MS or GC/MS applications such as forensic analysis, sports testing, clinical toxicology, or urine drug testing. R(-)-Methamphetamine belongs to the amphetamine and phenethylamine classes of drugs.
Related reactions
2 records
Compound notes
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