Pentolinium

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Wikipedia

Pentolinium
Identifiers
  • 1-Methyl-1-[5-(1-methylpyrrolidin-1-ium-1-yl)pentyl]pyrrolidin-1-ium
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H32N22+
Molar mass240.435 g·mol−1
  • InChI=1S/C15H32N2/c1-16(12-6-7-13-16)10-4-3-5-11-17(2)14-8-9-15-17/h3-15H2,1-2H3/q+2
  • Key:XSBSKEQEUFOSDD-UHFFFAOYSA-N

Pentolinium, also known as pentapyrrolidinium, is a ganglionic blocking agent which acts as a nicotinic acetylcholine receptor antagonist. Formulated as the pentolinium tartrate salt, it was marketed under the trade name Ansolysen.[1] It can be used as an antihypertensive drug during surgery or to control hypertensive crises. It works by binding to the acetylcholine receptor of adrenergic nerves and thereby inhibiting the release of noradrenaline and adrenaline. Blocking this receptor leads to smooth muscle relaxation and vasodilation.

Route of administration and dose

Pentolinium can be given orally (20mg three times a day), injected intramuscularly, or administered intravenously.[2]

Use

Pentolinium and hexamethonium combined with Rauvolfia was reported in 1955 to be effective in the outpatient management of moderate to severe hypertension, with satisfactory orthostatic reduction in blood pressure but there are significant untoward effects attributable to the use of the hexamethonium. Pentolinium has been reported to offer more prolonged ganglionic blockade and has less severe untoward effects than hexamethonium.[3]

History

Pentolinium was developed in the early 1950s at May & Baker among several other related compounds with potential ganglionic blocking activity.[4] It was assigned the code name M. & B. 2050A. The first clinical trials were conducted by F. H. Smirk at Dunedin Hospital in 1952.[5][6]

References

  1. ↑ Agrest A, Hoobler SW (March 1955). "Long-term management of hypertension with pentolinium tartrate (ansolysen)". Journal of the American Medical Association. 157 (12): 999–1003. doi:10.1001/jama.1955.02950290019006. PMID 14353636.
  2. ↑ Budhiraja RD (2009). Elementary Pharmacology & Toxicology. Popular Prakashan. p. 189. ISBN 97881-7991-472-4.
  3. ↑ Dennis E, Ford R, Herschberger R, Moyer JH (October 1955). "Pentolinium and hexamethonium combined with Rauwolfia in the treatment of hypertension". The New England Journal of Medicine. 253 (14): 597–600. doi:10.1056/NEJM195510062531404. PMID 13266002.
  4. ↑ Libman DD, Pain DL, Slack R (1952). "Some bisquaternary salts". J Chem Soc. 430: 2305–7. doi:10.1039/JR9520002305.
  5. ↑ Smirk FH (March 1953). "Action of a new methonium compound in arterial hypertension; pentamethylene 1:5-bis-n-(n-methyl-pyrrolidinium) bitartrate (M. & B. 2050A)". Lancet. 1 (6758): 457–64. doi:10.1016/s0140-6736(53)91640-7. PMID 13036030.
  6. ↑ Smirk FH (December 1954). "Blood pressure reduction in arterial hypertension by hexamethonium and pentapyrrolidinium salts". Am J Med. 17 (6): 839–50. doi:10.1016/0002-9343(54)90228-4. PMID 13207165.