Guanoclor

Guanoclor (INN), also known as guanochlor, is a sympatholytic drug. It is known to bind to non-adrenergic sites in pig kidney membranes.[1]

Guanoclor
Clinical data
ATC code
Identifiers
IUPAC name
  • 2-{[2-(2,6-Dichlorophenoxy)ethyl]amino}guanidine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.023.334
Chemical and physical data
FormulaC9H12Cl2N4O
Molar mass263.12 g·mol−1
3D model (JSmol)
SMILES
  • C1=CC(=C(C(=C1)Cl)OCCNNC(=N)N)Cl
InChI
  • InChI=1S/C9H12Cl2N4O/c10-6-2-1-3-7(11)8(6)16-5-4-14-15-9(12)13/h1-3,14H,4-5H2,(H4,12,13,15)
  • Key:XIHXRRMCNSMUET-UHFFFAOYSA-N
  (verify)

Synthesis

When β-(2,6-dichlorophenoxy)ethyl bromide (1) is reacted with hydrazine to give 2, and this is reacted with S-methylthiourea, guanochlor (3) results.[2][3]

Guanoclor synthesis

References
  1. Vigne P, Lazdunski M, Frelin C (January 1989). "Guanabenz, guanochlor, guanoxan and idazoxan bind with high affinity to non-adrenergic sites in pig kidney membranes". European Journal of Pharmacology. 160 (2): 295–8. doi:10.1016/0014-2999(89)90503-7. PMID 2527160.
  2. Durant GJ, Smith GM, Spickett RG, Wright SH (January 1966). "Biologically active guanidines and related compounds. II. Some antiinflammatory aminoguanidines". Journal of Medicinal Chemistry. 9 (1): 22–7. doi:10.1021/jm00319a005. PMID 5958955.
  3. Prepn of free base and sulfate: BE 629613 (1963 to Pfizer), C.A. 60, 14437d (1964).
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