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

• ChemBase ID: 1344
• Molecular Formular: C9H11NO
• Molecular Mass: 149.18974
• Monoisotopic Mass: 149.08406398
• SMILES: O=C([C@@H](N)C)c1ccccc1
• Canonical SMILES: C[C@@H](C(=O)c1ccccc1)N
• InChI: InChI=1S/C9H11NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7H,10H2,1H3/t7-/m0/s1
• InChIKey: PUAQLLVFLMYYJJ-ZETCQYMHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-1-phenylpropan-1-one
• IUPAC Traditional name: cathinone
• Synonyms: D-Cathinone; β-ketoamphetamine; Cathinone

Database IDs

• CAS Number: 71031-15-7
• PubChem SID: 46508478; 160964804
• PubChem CID: 62258
• CHEBI ID: 4110
• Chemspider ID: 56062
• DrugBank ID: DB01560
• KEGG ID: C08301
• Unique Ingredient Identifier: 540EI4406J
• Wikipedia Title: Cathinone

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: 0.51
• LOG S: -1.78
• Solubility (Water): 2.46e+00 g/l

PROPERTIES

Pharmacology Properties

• Legal Status: Class C (UK); Schedule I (US); Schedule III (Canada)

DETAILS

DrugBank - DB01560

• Drug Groups: illicit; experimental
• Description: Cathinone (β-ketoamphetamine) is a monoamine alkaloid found in the shrub Catha edulis (Khat). Closely related to ephedrine, cathine and other amphetamines, it is probably the main contributor to the stimulant effect of Catha edulis. Cathinone differs from many other amphetamines in that its structure is a ketone. Other amphetamines to share this structure include the antidepressant bupropion and the stimulant methcathinone, among others. Internationally, cathinone is a Schedule I drug under the Convention on Psychotropic Substances. Circa 1993, the DEA added cathinone to the Controlled Substances Act's Schedule I in order to fulfill the requirements of international law. [Wikipedia]
• Affected Organisms: Humans and other mammals
• References: Bentur Y, Bloom-Krasik A, Raikhlin-Eisenkraft B: Illicit cathinone ("Hagigat") poisoning. Clin Toxicol (Phila). 2007 Aug 15;:1-5. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Bentur Y, Bloom-Krasik A, Raikhlin-Eisenkraft B: Illicit cathinone ("Hagigat") poisoning. Clin Toxicol (Phila). 2007 Aug 15;:1-5. Pubmed