Hexamethonium

Structural formula
Dication (without illustration of the counterion)
General
Non-proprietary name	Hexamethonium
other names	N , N , N , N ′, N ′, N ′ -hexamethylhexane-1,6-diammonium ( IUPAC )
Molecular formula	C 12 H 30 N 2 +2
External identifiers / databases
CAS number 60-26-4 PubChem 3604 ChemSpider 3478 DrugBank DB08960 Wikidata Q410557
properties
Molar mass	202.38 g · mol -1
safety instructions
GHS hazard labeling no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Hexamethonium is a quaternary ammonium compound and comes from the same series of methonium compounds as decamethonium . It acts as a specific, neuronal antagonist at the nicotinic acetylcholine receptor (nAchR), which acts in autonomic ganglia by binding to the NN receptor, not directly at the Ach binding site. Hexamethonium has no direct effect on the muscarinic acetylcholine receptors (mAchR) and on the nAch receptors in the motor endplate of the neuromuscular synapse, but in higher doses it appears to act as a negative allosteric modulator on the latter, since in vitro the reaction of skeletal muscles to acetylcholine and Decamethonium weakens. The doses required for this were in the experiment over an order of magnitude higher than those at which the ganglion blockade began. Hexamethonium was used as a ganglion blocker against excessive blood pressure. The numerous side effects have made the ganglion blockers largely obsolete. Today, hexamethonium is mainly of experimental importance.

The decamethonium has between the nitrogen atoms instead of six ten carbon atoms. In contrast to hexamethonium, this has practically no blocking effect on the autonomic ganglia, but decamethonium is a potent depolarizing neuromuscular blocker and also shows very weak anti- cholinesterase activity in vitro .

Individual evidence

1. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
2. ^ ^{A b} W. D. PATON, EJ ZAIMIS: The pharmacological actions of polymethylene bistrimethyl-ammonium salts. In: British journal of pharmacology and chemotherapy. Volume 4, Number 4, December 1949, pp. 381-400, PMID 15398551 , PMC 1509928 (free full text).
3. ↑ W. Forth, D. Henschler, W. Rummel: General and special pharmacology and toxicology . 9th edition. URBAN & FISCHER, Munich 2005, ISBN 3-437-42521-8 .