Guanoclor

Chemical compound

C02CC05 (WHO)

Identifiers

IUPAC name

2-{[2-(2,6-Dichlorophenoxy)ethyl]amino}guanidine

CAS Number

5001-32-1

PubChem CID

71835

ChemSpider

64857

UNII

M4HBT852YO

CompTox Dashboard (EPA)

DTXSID10198184

ECHA InfoCard100.023.334

Chemical and physical dataFormulaC₉H₁₂Cl₂N₄OMolar mass263.12 g·mol⁻¹3D model (JSmol)

Interactive image

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)

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

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]

References

^ 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.
^ 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.
^ Prepn of free base and sulfate: BE 629613 (1963 to Pfizer), C.A. 60, 14437d (1964).

Sympatholytic (and closely related) antihypertensives (C02)

Sympatholytics
(antagonize α-adrenergic
vasoconstriction)

Central

α₂-Adrenergic receptor agonists	Clonidine Guanabenz Guanfacine Guanoxabenz Methyldopa^# Tiamenidine^‡
Adrenergic release inhibitors	Bethanidine Bretylium Debrisoquine Guanadrel Guanazodine Guancydine Guanethidine Guanoclor Guanoxan
Imidazoline receptor agonists	Moxonidine Rilmenidine Tolonidine
Ganglion-blocking/nicotinic antagonists	Hexamethonium^‡ Mecamylamine Pentolinium Trimethaphan

Peripheral

Indirect

Monoamine oxidase inhibitors	Pargyline^‡
VMAT inhibitors	Bietaserpine Deserpidine Methoserpidine Reserpine Syrosingopine
Tyrosine hydroxylase inhibitors	Metirosine

Direct

α₁-Adrenergic receptor blockers	Doxazosin Ketanserin Indoramin Prazosin Trimazosin Urapidil
Non-selective α-adrenergic receptor blockers	Phentolamine

Other antagonists

Serotonin receptor antagonists	Ketanserin Lidanserin
Endothelin receptor antagonists (for PHTooltip Pulmonary hypertension)	dual (Aprocitentan, Bosentan, Macitentan (+tadalafil)) selective (Ambrisentan, Sitaxentan)