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Substance Name: Hexamethonium [INN]
RN: 60-26-4
UNII: 3C9PSP36Z2
InChIKey: VZJFGSRCJCXDSG-UHFFFAOYSA-N

Note

  • A nicotinic cholinergic antagonist often referred to as the prototypical ganglionic blocker. It is poorly absorbed from the gastrointestinal tract and does not cross the blood-brain barrier. It has been used for a variety of therapeutic purposes including hypertension but, like the other ganglionic blockers, it has been replaced by more specific drugs for most purposes, although it is widely used a research tool.

Molecular Formula

  • C12-H30-N2.2OH

Molecular Weight

  • 202.383
 

Classification Codes

  • Antihypertensive Agents
  • Autonomic Agents
  • Cardiovascular Agents
  • Cholinergic Agents
  • Cholinergic Antagonists
  • Drug / Therapeutic Agent
  • Ganglionic Blockers
  • Neurotransmitter Agents
  • Nicotinic Antagonists
  • Peripheral Nervous System Agents
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Names and Synonyms

Name of Substance

  • Hexamethonium
  • Hexamethonium [INN]

MeSH Heading

  • Hexamethonium

Synonyms

  • 1,6-Hexanediaminium, N,N,N,N',N',N'-hexamethyl-
  • Benzohexamethonium
  • Bistrium
  • BRN 1760389
  • Esametonio
  • Esametonio [Italian]
  • Hexamethonium
  • Hexamethonum
  • Hexane-1,6-bis(trimethylammonium)
  • Hexanium
  • Hexon
  • Hexonium
  • UNII-3C9PSP36Z2

Systematic Names

  • 1,6-Hexanediaminium, N,N,N,N',N',N'-hexamethyl-
  • Ammonium, hexamethylenebis(trimethyl-

Registry Numbers

CAS Registry Number

  • 60-26-4

FDA UNII

  • 3C9PSP36Z2

Related Registry Numbers

  • 2079-78-9 (bitartrate)
  • 55-97-0 (dibromide)
  • 60-25-3 (chloride)
  • 870-62-2 (diiodide)

System Generated Number

  • 0000060264

Molecular Formulas

Molecular Formula

  • C12-H30-N2.2OH

Molecular Formula Fragments

  • C12-H30-N2
  • COMPONENT
  • OH

Structure Descriptors

InChI

InChI=1S/C12H30N2/c1-13(2,3)11-9-7-8-10-12-14(4,5)6/h7-12H2,1-6H3/q+2

InChIKey

VZJFGSRCJCXDSG-UHFFFAOYSA-N

Smiles

C[N+](C)(C)CCCCCC[N+](C)(C)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 137mg/kg (137mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ANTIPSYCHOTIC		 Farmaco, Edizione Scientifica. Vol. 8, Pg. 317, 1953.
mouse LD50 intravenous 49mg/kg (49mg/kg)   Pharmacology and Toxicology. English translation of FATOAO. Vol. 21, Pg. 110, 1958.
mouse LD50 oral 490mg/kg (490mg/kg)   Pharmacology and Toxicology. English translation of FATOAO. Vol. 21, Pg. 110, 1958.
mouse LD50 subcutaneous 83mg/kg (83mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 Sapporo Igaku Zasshi. Sapporo Medical Journal. Vol. 6, Pg. 362, 1954.
rat LD50 intraperitoneal 230mg/kg (230mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 7, Pg. 123, 1957.
rat LD50 intravenous 35mg/kg (35mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 7, Pg. 123, 1957.
rat LD50 oral 500mg/kg (500mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 7, Pg. 123, 1957.
rat LD50 subcutaneous 165mg/kg (165mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 7, Pg. 123, 1957.