(2S)-2,6-diamino-N-[(2R)-1-phenyl(3,3,3-2H3)propan-2-yl]hexanamide

• ChemBase ID: 172342
• Molecular Formular: C15H25N3O
• Molecular Mass: 263.3785
• Monoisotopic Mass: 263.19976244
• SMILES: c1(C[C@H](NC(=O)[C@H](CCCCN)N)C)ccccc1
• Canonical SMILES: NCCCC[C@@H](C(=O)N[C@@H](Cc1ccccc1)C)N
• InChI: InChI=1S/C15H25N3O/c1-12(11-13-7-3-2-4-8-13)18-15(19)14(17)9-5-6-10-16/h2-4,7-8,12,14H,5-6,9-11,16-17H2,1H3,(H,18,19)/t12-,14+/m1/s1
• InChIKey: VOBHXZCDAVEXEY-OCCSQVGLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2,6-diamino-N-[(2R)-1-phenyl(3,3,3-^2H₃)propan-2-yl]hexanamide
• IUPAC Traditional name: (2S)-2,6-diamino-N-[(2R)-1-phenyl(3,3,3-^2H₃)propan-2-yl]hexanamide
• Synonyms: (2S)-2,6-Diamino-N-[(1S)-1-(methyl-d3)-2-phenylethyl]hexanamide DiHydrochloride; Lisdexamphetamine-d3 Dihydrochloride

Database IDs

• PubChem SID: 164228252
• PubChem CID: 71749818

CALCULATED PROPERTIES

• Acid pKa: 15.885676
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -4.57143
• LogD (pH = 7.4): -2.5414438
• Log P: 1.1358308
• Molar Refractivity: 78.3148 cm^3
• Polarizability: 31.178026 Å^3
• Polar Surface Area: 81.14 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Brown Solid
• Melting Point: 96-102°C

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer

DETAILS

Toronto Research Chemicals - L468882

Labelled Lisdexamfetamine. A new, novel amphetamine product, has been shown to provide efficacy upwards of 12 h in children and adults with a side effect profile similar to those of other longer-acting amphetamine products.Controlled substance.

REFERENCES

• Biederman, J., et al.: Clin. Ther., 29, 450 (2007)
• Medori, R., et al.: Biol. Psychiatry., 63, 981 (2007)
• Krishnan, S., et al.: Clin. Drug Investig., 28, 745 (2007)
• Ramos-Quiroga, J., et al.: CNS Drugs, 22, 603 (2007)