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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H13N
Molecular Weight 135.2062
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVAMFETAMINE

SMILES

C[C@@H](N)CC1=CC=CC=C1

InChI

InChIKey=KWTSXDURSIMDCE-MRVPVSSYSA-N
InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3/t8-/m1/s1

HIDE SMILES / InChI

Molecular Formula C9H13N
Molecular Weight 135.2062
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

LEVAMFETAMINE the levorotatory form of amphetamine. L-amphetamine, is a central nervous system (CNS) stimulant 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. L-Amphetamine succinate was sold in Hungary between 1952 and 1955 under the brand name Cydril.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
1.3 µM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PAREDRINE
Primary
PAREDRINE
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
14.6 ng/mL
7.5 mg single, oral
LEVAMFETAMINE plasma
Homo sapiens
16.4 ng/mL
7.5 mg single, oral
LEVAMFETAMINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
357.4 ng × h/mL
7.5 mg single, oral
LEVAMFETAMINE plasma
Homo sapiens
370.9 ng × h/mL
7.5 mg single, oral
LEVAMFETAMINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
14.84 h
7.5 mg single, oral
LEVAMFETAMINE plasma
Homo sapiens
14.47 h
7.5 mg single, oral
LEVAMFETAMINE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
82%
LEVAMFETAMINE plasma
Homo sapiens

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
In children from 3 to 5 years of age, start with 2.5 mg daily; daily dosage may be raised in increments of 2.5 mg at weekly intervals until optimal response is obtained. In children 6 years of age and older, start with 5 mg once or twice daily; daily dosage may be raised in increments of 5 mg at weekly intervals until optimal response is obtained. Only in rare cases will it be necessary to exceed a total of 40 mg per day. Give first dose on awakening; additional doses (1 or 2) at intervals of 4 to 6 hours.
Route of Administration: Oral
In Vitro Use Guide
TAAR1 receptor activation was assayed in CHO cells stably expressing Gα16 and the hTAAR1 receptor. 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 LEVAMFETAMINE 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. LEVAMFETAMINE were evaluated using 10 different concentrations run in duplicate.
Substance Class Chemical
Record UNII
R87US8P740
Record Status Validated (UNII)
Record Version