Compound: Levamfetamine
SMILES: N[C@@H](Cc1ccccc1)C
InChIKey: KWTSXDURSIMDCE-MRVPVSSYSA-N
Synonyms: Levamfetamine, (-)-Amphetamine, 156-34-3, Levanfetamina, (R)-alpha-Methylbenzeneethanamine, (-)-Phenylisopropylamine, (R)-alpha-Methylphenethylamine, Levamfetamina, Levamfetaminum, Amfetamine, (r)-, R87US8P740, DTXSID20166016, lAvamphAtamine, Amphetamine l-, RefChem:1049081, DTXCID4088507, 205-850-8, L-Amphetamine, Levamphetamine, (R)-Amphetamine, (2R)-1-phenylpropan-2-amine, (R)-1-Phenylpropan-2-amine, l-(R)-Amphetamine, l-alpha-Methylphenethylamine, Amphetamine l-form, CHEMBL19393, Levamphetaminum, Levamfetamina [DCIT], r-amphetamine, Levamfetamine [INN:BAN], R(-)amphetamine, Levamfetaminum [INN-Latin], Levanfetamina [INN-Spanish], (-)-alpha-Methylphenethylamine, EINECS 205-850-8, l-Amphetamine Hydrochloride, UNII-R87US8P740, (R)-Phenaminum, Phenethylamine, alpha-methyl-, (-)-, Benzeneethanamine, alpha-methyl-, (R)-, l-a-Methylphenethylamine, Selegiline Impurity 18, (R)-phenylisopropylamine, (R)-a-methylphenethylamine, LEVAMFETAMINE [INN], SCHEMBL2636, (R)-a-methylbenzeneethanamine, (R)-a-Methyl-benzeneethanamine, GTPL2146, SCHEMBL6931237, AMPHETAMINE L-FORM [MI], SCHEMBL10567690, SCHEMBL27959917, CHEBI:42724, (R)-alpha-Methyl-benzeneethanamine, BDBM50022721, PDSP1_001510, PDSP2_001494, AKOS022172419, C105, (R)-1-METHYL-2-PHENYL-ETHYLAMINE, NS00070159, (-)-(R)-.ALPHA.-METHYLPHENETHYLAMINE, (-)-(R)-.ALPHA.-METHYLBENZENEETHANAMINE, Q2506823, R(-)-Amphetamine (levo-Amphetamine), 1.0 mg/mL in methanol, ampule of 1 mL, certified reference material
Theoretical properties:
molecular_formula: C9H13N
molecular_weight: 135.21 g/mol
exact_mass: 135.104799419 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 1
rotatable_bond_count: 2
heavy_atom_count: 10
topological_polar_surface_area: 26 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: (R)-amphetamine is a 1-phenylpropan-2-amine that has R configuration. It is an enantiomer of a (S)-amphetamine.
chebi: A 1-phenylpropan-2-amine that has <i>R</i> configuration.
chembl: LEVAMFETAMINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Levoamphetamine is a stimulant medication which is used in the treatment of certain medical conditions. It was previously marketed by itself under the brand name Cydril, but is now available only in combination with dextroamphetamine in varying ratios under brand names such as Adderall. The drug is known to increase wakefulness and concentration in association with decreased appetite and fatigue. Pharmaceuticals that contain levoamphetamine are currently indicated and prescribed for the treatment of attention deficit hyperactivity disorder (ADHD), obesity, and narcolepsy in some countries. Levoamphetamine is taken by mouth.
Levoamphetamine acts as a releasing agent of the monoamine neurotransmitters norepinephrine and dopamine. It is similar to dextroamphetamine in its ability to release norepinephrine and in its sympathomimetic effects but is a few times weaker than dextroamphetamine in its capacity to release dopamine and in its psychostimulant effects. Levoamphetamine is the levorotatory stereoisomer of the racemic amphetamine molecule, whereas dextroamphetamine is the dextrorotatory isomer.
Levoamphetamine was first introduced in the form of racemic amphetamine under the brand name Benzedrine in 1935 and as an enantiopure drug under the brand name Cydril in the 1970s. While pharmaceutical formulations containing enantiopure levoamphetamine are no longer manufactured, levomethamphetamine (levmetamfetamine) is still marketed and sold over-the-counter as a nasal decongestant. In addition to being used in pharmaceutical drugs itself, levoamphetamine is a known active metabolite of certain other drugs, such as selegiline (L-deprenyl).