4688. Hexamethonium

Nomenclature

CAS number: 60-26-4
N1,N1,N1,N6,N6,N6-Hexamethyl-1,6-hexanediaminium; hexamethylenebis(trimethylammonium); α,ω-bis(trimethylammonium)hexane; hexathonide; hexamethone.
[C12H30N2]2+.

Description and references

Prepn: H. J. Barber, US 2641610 (1953 to May & Baker); H. J. Barber, K. Gaimster, J. Pharm. Pharmacol. 3, 663 (1951). Ganglion blocking agent: R. Wien, D. F. J. Mason, Br. J. Pharmacol. 6, 611 (1951).

Chemical structure

Derivative

Bromide.

Nomenclature

CAS number: 55-97-0
C-6; Bistrium bromide (BMS); Esametina; Gangliostat; Hexameton bromide (Burroughs Wellcome); Hexanium bromide (Adrian-Marinier); Simpatoblock; Vegolysen (M & B); Vegolysin.
C12H30Br2N2; mol wt 362.19.
C 39.79%, H 8.35%, Br 44.12%, N 7.73%.

Properties

Hygroscopic crystals, mp 274-276°. Sol in water, alc. Insol in acetone, chloroform, ether. pH of 1% soln: 6.2-7.0.

Derivative

Chloride.

Nomenclature

CAS number: 60-25-3
Bistrium chloride (BMS); Chloor-hexaviet; Hestrium chloride; Hexameton chloride (Burroughs Wellcome); Hexone chloride; Hiohex chloride (Keith-Victor); Methium chloride; Meton.
C12H30Cl2N2; mol wt 273.29.
C 52.74%, H 11.06%, Cl 25.95%, N 10.25%.

Properties

Hygroscopic crystals, dec 289-292°. Sol in water, alc. Practically insol in chloroform, ether. pH of 10% soln: 5.5-6.5.

Derivative

Iodide.

Nomenclature

CAS number: 870-62-2
Hexathide (Allen & Hanburys).
C12H30I2N2; mol wt 456.19.
C 31.59%, H 6.63%, I 55.64%, N 6.14%.

Properties

Hygroscopic cryst powder. Sol in water. Practically insol in alc.

Derivative

Tartrate.

Nomenclature

CAS number: 2079-78-9
Vegolysen-T (M & B).
C20H40N2O12; mol wt 500.54.
C 47.99%, H 8.05%, N 5.60%, O 38.36%.

Properties

Hygroscopic powder, dec 186°. Sol in water. Practically insol in alc. pH of 10% soln: 3.8.

Therapeutic Category

Antihypertensive.

Keywords

Antihypertensive; Quaternary Ammonium Compounds