(2S)-2-amino-1-phenylpropan-1-one hydrochloride

• ChemBase ID: 133954
• Molecular Formular: C9H12ClNO
• Molecular Mass: 185.65068
• Monoisotopic Mass: 185.06074169
• SMILES: C[C@@H](C(=O)c1ccccc1)N.Cl
• Canonical SMILES: C[C@@H](C(=O)c1ccccc1)N.Cl
• InChI: InChI=1S/C9H11NO.ClH/c1-7(10)9(11)8-5-3-2-4-6-8;/h2-7H,10H2,1H3;1H/t7-;/m0./s1
• InChIKey: HPZCAKYHISJOIK-FJXQXJEOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-1-phenylpropan-1-one hydrochloride
• IUPAC Traditional name: cathinone hydrochloride
• Synonyms: (2S)-2-Amino-1-phenyl-1-propanone Hydrochloride; (-)-β-Aminopropiophenone Hydrochloride; (-)-Cathinone Hydrochloride; (S)-(-)-Cathinone Hydrochloride; l-Cathinone Hydrochloride; Cathinone Hydrochloride; α-Aminopropiophenone hydrochloride; S(-)-2-Amino-1-phenyl-1-propanone hydrochloride; S(-)-Cathinone hydrochloride

Database IDs

• CAS Number: 72739-14-1; 71031-15-7
• MDL Number: MFCD00673264
• PubChem SID: 162228231; 24892592
• PubChem CID: 11956149

CALCULATED PROPERTIES

• Acid pKa: 18.648869
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.83593833
• LogD (pH = 7.4): 0.793252
• Log P: 1.1755277
• Molar Refractivity: 44.3144 cm^3
• Polarizability: 17.43947 Å^3
• Polar Surface Area: 43.09 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; ethanol: soluble; H2O: soluble; Methanol
• Apperance: White Solid
• Melting Point: 176-180°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• RTECS: UC0419000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Drug Control: USDEA Schedule I; Home Office Schedule 1; stupéfiant; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: 2-8°C

DETAILS

Sigma Aldrich - C3196

Biochem/physiol Actions
Alkaloid that is the major central nervous system stimulant of the Khat shrub. Like amphetamine, it is a potent releaser of norepinephrine and dopamine from their intracellular stores.

Toronto Research Chemicals - C225700

Psychoactive alkaloid found in the leaves of the khat plant, Catha edulis Forsk., Celastraceae. Controlled substance (stimulant).

REFERENCES

• Peterson, D.W., et al.: Life Sci., 27, 2143 (1980), Brenneisen, R., et al.: J. Pharm. Pharmacol., 38, 298 (1986), Kalix, P., et al.: Pharmacol. Toxicol., 70, 77 (1992), Al-Obaid, et al.: J. Pharm. Bio med. Anal., 17, 321 (1998),