N-carbamimidoyl-2-(2,6-dichlorophenyl)acetamide hydrochloride

• ChemBase ID: 153705
• Molecular Formular: C9H10Cl3N3O
• Molecular Mass: 282.5542
• Monoisotopic Mass: 280.988945
• SMILES: c1cc(c(c(c1)Cl)CC(=O)NC(=N)N)Cl.Cl
• Canonical SMILES: O=C(Cc1c(Cl)cccc1Cl)NC(=N)N.Cl
• InChI: InChI=1S/C9H9Cl2N3O.ClH/c10-6-2-1-3-7(11)5(6)4-8(15)14-9(12)13;/h1-3H,4H2,(H4,12,13,14,15);1H
• InChIKey: DGFYECXYGUIODH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-carbamimidoyl-2-(2,6-dichlorophenyl)acetamide hydrochloride
• IUPAC Traditional name: guanfacine hydrochloride
• Synonyms: N (Aminoiminomethyl)-2,6-dichlorobenzeneacetamide; Guanfacine hydrochloride; N-(Aminoiminomethyl)-2,6-dichlorobenzeneacetamide Hydrochloride; N-Amidino-2-(2,6-dichlorophenyl)acetamide Hydrochloride; BS 100-141; [(2,6-Dichlorophenyl)acetyl]guanidine Hydrochloride; Guanfascine Hydrochloride; Guarfacine Hydrochloride; Guanfacin Hydrochloride; Tenex; SPD 503; Guanfacine Hydrochloride

Database IDs

• CAS Number: 29110-48-3
• MDL Number: MFCD00798230
• PubChem SID: 162247844; 24278452
• PubChem CID: 71401

CALCULATED PROPERTIES

• Acid pKa: 12.937506
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 0.58233494
• LogD (pH = 7.4): 1.666594
• Log P: 1.7370318
• Molar Refractivity: 69.6341 cm^3
• Polarizability: 22.76446 Å^3
• Polar Surface Area: 78.97 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble12 mg/mL at 60 °C; Methanol; Water
• Apperance: white; White Solid
• Melting Point: 211-214°C

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... ADRA2A(150), ADRA2B(151), ADRA2C(152)

Product Information

• Purity: ≥98% (TLC)
• Empirical Formula (Hill Notation): C9H9Cl2N3O · HCl

DETAILS

Sigma Aldrich - G1043

Biochem/physiol Actions
α-2 noradrenergic receptor agonist.

Toronto Research Chemicals - G816001

Guanfacine centrally acting α-adrenoceptor agonist. Guanfacine is an antihypertensive.

REFERENCES

• Urosevic, D., et al.: Br. J. Pharmacol., 142, 609 (2004)
• Remko, M., et al.: Bioorg. Med. Chem., 14, 1715 (2004)
• Nikolic, K., et al.: Bioorg. Med. Chem., 16, 7134 (2008).