Hexamethonium chloride

• CAT Number: I028719
• CAS Number: 60-25-3
• Molecular Formula: C12H30Cl2N2
• Molecular Weight: 273.286
• Purity: 98%
• Synonyms: Hexamethonium chloride; NSC 21643; NSC-21643; NSC21643
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: N1,N1,N1,N6,N6,N6-hexamethylhexane-1,6-diaminium chloride
• InChI: InChI=1S/C12H30N2.2ClH/c1-13(2,3)11-9-7-8-10-12-14(4,5)6;;/h7-12H2,1-6H3;2*1H/q+2;;/p-2
• InChIKey: PYIHTIJNCRKDBV-UHFFFAOYSA-L
• SMILES: C[N+](C)(CCCCCC[N+](C)(C)C)C.[Cl-].[Cl-]

Hexamethonium chloride is a preferential nicotinic receptor blocker at the level of autonomic ganglia. It has been shown to cross the blood-brain barrier only in high doses.

Reference

1: Miyazaki C, Shimizu K, Nagasawa Y, Chiba T, Sakuma K, Aimoto M, Yamamoto T, Takahashi M, Sugo N, Takahara A, Shirai K. Effects of Enhanced Intracranial Pressure on Blood Pressure and the Cardio-Ankle Vascular Index in Rabbits. J Atheroscler Thromb. 2021 Jan 20. doi: 10.5551/jat.59451. Epub ahead of print. PMID: 33473056.
2: Yang Y, Li Y, Wang J, Hong L, Qiao S, Wang C, An J. Cholinergic receptors play a role in the cardioprotective effects of anesthetic preconditioning: Roles of nitric oxide and the CaMKKβ/AMPK pathway. Exp Ther Med. 2021 Feb;21(2):137. doi: 10.3892/etm.2020.9569. Epub 2020 Dec 14. PMID: 33456504; PMCID: PMC7791965.
3: Asirvatham-Jeyaraj N, Gauthier MM, Banek CT, Ramesh A, Garver H, Fink GD, Osborn JW. Renal Denervation and Celiac Ganglionectomy Decrease Mean Arterial Pressure Similarly in Genetically Hypertensive Schlager (BPH/2J) Mice. Hypertension. 2021 Feb;77(2):519-528. doi: 10.1161/HYPERTENSIONAHA.119.14069. Epub 2021 Jan 4. PMID: 33390041; PMCID: PMC7803455.
4: de Souza JA, Becker LK, Batista MAC, de Assis Braga DC, Gomes PM, Alzamora AC, Vieira MAR, de Lima WG, Andrade MGC, de Lima Sanches B, Totou NL, de Assis Dias Martins Júnior F, de Oliveira LB, Antunes VR, Cardoso LM. Swimming training improves cardiovascular autonomic dysfunctions and prevents renal damage in rats fed a high-sodium diet from weaning. Exp Physiol. 2021 Feb;106(2):412-426. doi: 10.1113/EP088892. Epub 2020 Dec 24. PMID: 33347659.
5: Jones BS, Keightley LJ, Harris JO, Wiklendt L, Spencer NJ, Dinning PG. Identification of neurogenic intestinal motility patterns in silver perch (Bidyanus bidyanus) that persist over wide temperature ranges. Neurogastroenterol Motil. 2020 Dec 19:e14037. doi: 10.1111/nmo.14037. Epub ahead of print. PMID: 33340207.
6: Barrera A, Morales-Loredo H, Garcia JM, Fregoso G, Pace CE, Mendiola PJ, Naik JS, Gonzalez Bosc LV, Kanagy NL. Simulated sleep apnea alters hydrogen sulfide regulation of blood flow and pressure. Am J Physiol Heart Circ Physiol. 2021 Feb 1;320(2):H511-H519. doi: 10.1152/ajpheart.00672.2019. Epub 2020 Dec 4. PMID: 33275519.
7: Matsuo N, Matsuo S, Nakamura Y, Ezomo FO, Kawai Y. Regulatory effects of cervical sympathetic trunk and renal sympathetic nerve activities on cerebral blood flow during head-down postural rotations. Auton Neurosci. 2020 Dec;229:102738. doi: 10.1016/j.autneu.2020.102738. Epub 2020 Nov 4. PMID: 33197695.
8: Ventura-Martinez R, Angeles-Lopez GE, Gonzalez-Trujano ME, Carrasco OF, Deciga-Campos M. Study of Antispasmodic and Antidiarrheal Activities of Tagetes lucida (Mexican Tarragon) in Experimental Models and Its Mechanism of Action. Evid Based Complement Alternat Med. 2020 Oct 28;2020:7140642. doi: 10.1155/2020/7140642. PMID: 33193797; PMCID: PMC7641699.
9: Ralph AF, Grenier C, Costello HM, Stewart K, Ivy JR, Dhaun N, Bailey MA. Activation of the Sympathetic Nervous System Promotes Blood Pressure Salt- Sensitivity in C57BL6/J Mice. Hypertension. 2021 Jan;77(1):158-168. doi: 10.1161/HYPERTENSIONAHA.120.16186. Epub 2020 Nov 16. PMID: 33190558; PMCID: PMC7720873.
10: Chaudhry MA, Alamgeer, Mushtaq MN, Bukhari IA, Assiri AM. Ipomoea hederacea Jacq.: A plant with promising antihypertensive and cardio-protective effects. J Ethnopharmacol. 2021 Mar 25;268:113584. doi: 10.1016/j.jep.2020.113584. Epub 2020 Nov 12. PMID: 33189838.
11: Li H, An C. Exploring the role of neurogenic pathway-linked cholecystokinin release in remote preconditioning-induced cardioprotection. Acta Cir Bras. 2020 Oct 30;35(9):e202000906. doi: 10.1590/s0102-865020200090000006. PMID: 33146235; PMCID: PMC7727451.
12: Imanishi A, Ichise H, Fan C, Nakagawa Y, Kuwahara K, Sumiyama K, Matsuda M, Terai K. Visualization of Spatially-Controlled Vasospasm by Sympathetic Nerve- Mediated ROCK Activation. Am J Pathol. 2021 Jan;191(1):194-203. doi: 10.1016/j.ajpath.2020.09.012. Epub 2020 Oct 16. PMID: 33069718.
13: Spencer NJ, Travis L, Hibberd T, Kelly N, Feng J, Hu H. Effects of optogenetic activation of the enteric nervous system on gastrointestinal motility in mouse small intestine. Auton Neurosci. 2020 Dec;229:102733. doi: 10.1016/j.autneu.2020.102733. Epub 2020 Sep 19. PMID: 32980660.
14: Metin M, Altun A, Köylüoğlu G. The effect of probiotics on ıntestinal motility in an experimental short bowel model. Acta Cir Bras. 2020 Sep 7;35(8):e202000804. doi: 10.1590/s0102-865020200080000004. PMID: 32901681; PMCID: PMC7478466.
15: Efimova SS, Khaleneva DA, Litasova EV, Piotrovskiy LB, Ostroumova OS. The mechanisms of action of water-soluble aminohexanoic and malonic adducts of fullerene C60 with hexamethonium on model lipid membranes. Biochim Biophys Acta Biomembr. 2020 Nov 1;1862(11):183433. doi: 10.1016/j.bbamem.2020.183433. Epub 2020 Aug 5. PMID: 32763244.
16: Johnson K, Yin J, In JG, Kulkarni S, Pasricha P, Tse CM, Donowitz M. Cholinergic-induced anion secretion in murine jejunal enteroids involves synergy between muscarinic and nicotinic pathways. Am J Physiol Cell Physiol. 2020 Aug 1;319(2):C321-C330. doi: 10.1152/ajpcell.00179.2020. Epub 2020 Jun 17. PMID: 32551856; PMCID: PMC7500216.
17: Matucci R, Bellucci C, Martino MV, Nesi M, Manetti D, Welzel J, Bartz U, Holze J, Tränkle C, Mohr K, Mazzolari A, Vistoli G, Dei S, Teodori E, Romanelli MN. Carbachol dimers with primary carbamate groups as homobivalent modulators of muscarinic receptors. Eur J Pharmacol. 2020 Sep 15;883:173183. doi: 10.1016/j.ejphar.2020.173183. Epub 2020 Jun 10. PMID: 32534072.
18: Liu JYH, Du P, Rudd JA. Acetylcholine exerts inhibitory and excitatory actions on mouse ileal pacemaker activity: role of muscarinic versus nicotinic receptors. Am J Physiol Gastrointest Liver Physiol. 2020 Jul 1;319(1):G97-G107. doi: 10.1152/ajpgi.00003.2020. Epub 2020 Jun 1. PMID: 32475128.
19: Sartim MA, Souza COS, Diniz CRAF, da Fonseca VMB, Sousa LO, Peti APF, Costa TR, Lourenço AG, Borges MC, Sorgi CA, Faccioli LH, Sampaio SV. Crotoxin-Induced Mice Lung Impairment: Role of Nicotinic Acetylcholine Receptors and COX-Derived Prostanoids. Biomolecules. 2020 May 20;10(5):794. doi: 10.3390/biom10050794. PMID: 32443924; PMCID: PMC7277605.
20: Rosli RM, Heitmann PT, Kumar R, Hibberd TJ, Costa M, Wiklendt L, Wattchow DA, Arkwright J, de Fontgalland D, Brookes SJH, Spencer NJ, Dinning PG. Distinct patterns of myogenic motor activity identified in isolated human distal colon with high-resolution manometry. Neurogastroenterol Motil. 2020 Oct;32(10):e13871. doi: 10.1111/nmo.13871. Epub 2020 May 6. PMID: 32374068; PMCID: PMC7529858.