Guanoclor

Guanoclor
Clinical data
ATC code	C02CC05 (WHO) ;
Identifiers
	IUPAC name 2-{[2-(2,6-Dichlorophenoxy)ethyl]amino}guanidine;
CAS Number	5001-32-1;
PubChem CID	71835;
ChemSpider	64857;
CompTox Dashboard (EPA)	DTXSID10198184 ;
ECHA InfoCard	100.023.334
Chemical and physical data
Formula	C9H12Cl2N4O
Molar mass	263.12 g·mol−1
3D 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]

Guanoclor synthesis

References

Vigne, Paul; Michael Lazdunski; Christian Frelin (31 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): 295–298. doi:10.1016/0014-2999(89)90503-7. PMID 2527160.
Durant, G. J.; Smith, G. M.; Spickett, R. G. W.; Wright, S. H. B. (1966). "Biologically Active Guanidines and Related Compounds. II. Some Antiinflammatory Aminoguanidines1". 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).

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[Guanabenz-1] Vigne, Paul; Michael Lazdunski; Christian Frelin (31 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): 295–298. doi:10.1016/0014-2999(89)90503-7. PMID 2527160.

[2] Durant, G. J.; Smith, G. M.; Spickett, R. G. W.; Wright, S. H. B. (1966). "Biologically Active Guanidines and Related Compounds. II. Some Antiinflammatory Aminoguanidines1". 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).