2-methyl-1-phenylpropan-2-amine

• ChemBase ID: 76
• Molecular Formular: C10H15N
• Molecular Mass: 149.2328
• Monoisotopic Mass: 149.12044949
• SMILES: NC(Cc1ccccc1)(C)C
• Canonical SMILES: CC(Cc1ccccc1)(N)C
• InChI: InChI=1S/C10H15N/c1-10(2,11)8-9-6-4-3-5-7-9/h3-7H,8,11H2,1-2H3
• InChIKey: DHHVAGZRUROJKS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-methyl-1-phenylpropan-2-amine
• IUPAC Traditional name: phentermine
• Brand Name: Adipex-P; Duromine; Fastin; Inoamin; Ionamin; Linyl; Lipopill; Lonamin; Mirapront; Normephentermine; Obenix; Obestin-30; Oby-Trim; Omnibex; Ona Mast; Ona-Mast; Phentercot; Phentermine Resin 30; Phentride; Pre-Sate; Pro-Fast; Teramine; Tora; Uritone; Wilpo; Wyamine Sulfate; Zantryl
• Synonyms: Phentermine Hcl; Phentermine Hydrochloride; (alpha,alpha)-Dimethylphenethylamine; Phentermine

Database IDs

• CAS Number: 122-09-8
• PubChem SID: 160963539; 46508515
• PubChem CID: 4771

CALCULATED PROPERTIES

JChem

• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): -0.94001377
• LogD (pH = 7.4): -0.5458378
• Log P: 2.0848272
• Molar Refractivity: 48.3434 cm^3
• Polarizability: 19.211359 Å^3
• Polar Surface Area: 26.02 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.32
• LOG S: -2.29
• Solubility (Water): 7.57e-01 g/l

PROPERTIES

Physical Property

• Solubility: 18.6 g/L
• Hydrophobicity(logP): 2.2

DETAILS

DrugBank - DB00191

• Drug Groups: illicit; approved
• Description: A central nervous system stimulant and sympathomimetic with actions and uses similar to those of dextroamphetamine. It has been used most frequently in the treatment of obesity. [PubChem]
• Indication: For the treatment and management of obesity.
• Pharmacology: Phentermine is indicated in the management of exogenous obesity as a short term (a few weeks) adjunct in a regimen of weight reduction based on caloric restriction. Phentermine hydrochloride is a sympathomimetic amine with pharmacologic activity similar to the prototype drugs of this class used in obesity, the amphetamines. Actions include central nervous system stimulation and elevation of blood pressure. Tachyphylaxis and tolerance have been demonstrated with all drugs of this class in which these phenomena have been looked for.
• Toxicity: LD₅₀ is adult monkeys is 15 to 20 mg/kg. Symptoms of overdose include delirium, mania, self-injury, marked hypertension, tachycardia, arrhythmia, hyperpyrexia, convulsion, coma, and circulatory collapse.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Absorption: Phentermine is rapidly absorbed after oral ingestion.
• Half Life: 16 to 31 hours
• Protein Binding: Approximately 96.3%
• References: Bray GA: A concise review on the therapeutics of obesity. Nutrition. 2000 Oct;16(10):953-60. [Pubmed] ; Nelson DL, Gehlert DR: Central nervous system biogenic amine targets for control of appetite and energy expenditure. Endocrine. 2006 Feb;29(1):49-60. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• Nelson DL, Gehlert DR: Central nervous system biogenic amine targets for control of appetite and energy expenditure. Endocrine. 2006 Feb;29(1):49-60. Pubmed
• Bray GA: A concise review on the therapeutics of obesity. Nutrition. 2000 Oct;16(10):953-60. Pubmed