5-[1-(2,3-dimethylphenyl)ethyl]-1H-imidazole

• ChemBase ID: 515
• Molecular Formular: C13H16N2
• Molecular Mass: 200.27954
• Monoisotopic Mass: 200.13134852
• SMILES: [nH]1c(C(c2c(c(ccc2)C)C)C)cnc1
• Canonical SMILES: Cc1cccc(c1C)C(c1cnc[nH]1)C
• InChI: InChI=1S/C13H16N2/c1-9-5-4-6-12(10(9)2)11(3)13-7-14-8-15-13/h4-8,11H,1-3H3,(H,14,15)
• InChIKey: CUHVIMMYOGQXCV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[1-(2,3-dimethylphenyl)ethyl]-1H-imidazole
• IUPAC Traditional name: dexmedetomidine
• Brand Name: PRECEDEX
• Synonyms: Medetomidina [Spanish]; Medetomidine; Medetomidinum [Latin]; Dexmedetomidine

Database IDs

• CAS Number: 113775-47-6
• PubChem SID: 160963978
• PubChem CID: 68602

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.1336355
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 2.5437615
• LogD (pH = 7.4): 2.9845104
• Log P: 3.102479
• Molar Refractivity: 63.3355 cm^3
• Polarizability: 23.891598 Å^3
• Polar Surface Area: 28.68 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.96
• LOG S: -3.03
• Solubility (Water): 1.85e-01 g/l

PROPERTIES

Physical Property

• Solubility: Freely soluble in water
• Hydrophobicity(logP): 2.8

DETAILS

DrugBank - DB00633

• Drug Groups: approved
• Description: An agonist of receptors, adrenergic alpha-2 that is used in veterinary medicine for its analgesic and sedative properties. It is the racemate of dexmedetomidine. [PubChem]
• Indication: For sedation of initially intubated and mechanically ventilated patients during treatment in an intensive care setting, also used in pain relief; anxiety reduction and analgesia
• Pharmacology: Dexmedetomidine activates 2-adrenoceptors, and causes the decrease of sympathetic tone, with attenuation of the neuroendocrine and hemodynamic responses to anesthesia and surgery; it reduces anesthetic and opioid requirements; and causes sedation and analgesia.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Half Life: 2 hours
• Protein Binding: 94%
• Elimination: A mass balance study demonstrated that after nine days an average of 95% of the radioactivity, following intravenous administration of radiolabeled dexmedetomidine, was recovered in the urine and 4% in the feces. Fractionation of the radioactivity excreted in urine demonstrated that products of N-glucuronidation accounted for approximately 34% of the cumulative urinary excretion. The majority of metabolites are excreted in the urine.
• Distribution: * 118 L
• Clearance: * 39 L/h [Healthy volunteers receiving IV infusion (0.2-0.7 mcg/kg/hr)]
• External Links: Wikipedia; RxList