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Substance Name: Methacholine chloride [USP:INN:BAN]
RN: 62-51-1
UNII: 0W5ETF9M2K
InChIKey: JHPHVAVFUYTVCL-UHFFFAOYSA-M

Note

  • A quaternary ammonium parasympathomimetic agent with the muscarinic actions of ACETYLCHOLINE. It is hydrolyzed by ACETYLCHOLINESTERASE at a considerably slower rate than ACETYLCHOLINE and is more resistant to hydrolysis by nonspecific CHOLINESTERASES so that its actions are more prolonged. It is used as a parasympathomimetic bronchoconstrictor agent and as a diagnostic aid for bronchial asthma. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1116)

Molecular Formula

  • C8-H18-N-O2.Cl

Molecular Weight

  • 195.688
 

Classification Codes

  • Autonomic Agents
  • Bronchoconstrictor Agents
  • Cholinergic
  • Cholinergic Agents
  • Cholinergic Agonists
  • Drug / Therapeutic Agent
  • Miotics
  • Muscarinic Agonists
  • Neurotransmitter Agents
  • Parasympathomimetics
  • Peripheral Nervous System Agents
  • Respiratory System Agents
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Names and Synonyms

Name of Substance

  • Methacholine chloride
  • Methacholine chloride [USP:INN:BAN]

MeSH Heading

  • Methacholine chloride

Synonyms

  • (+-)-(2-Hydroxypropyl)trimethylammonium chloride acetate
  • (+-)-Acetyl-beta-methylcholine chloride
  • (2-Acetoxypropyl)trimethylammonium chloride
  • (2-Hydroxypropyl)trimethylammonium chloride acetate
  • 1-Propanaminium, 2-(acetyloxy)-N,N,N-trimethyl-, chloride, (+-)-
  • Acetyl-beta-methylcholine chloride
  • AI3-51680
  • Amechol
  • beta-Methylacetylcholine chloride
  • Chlorure de methacholine
  • Chlorure de methacholine [French]
  • Chlorure de methacholine [INN-French]
  • Cloruro de metacolina
  • Cloruro de metacolina [INN-Spanish]
  • Cloruro de metacolina [Spanish]
  • DL-Acetyl-beta-methylcholine chloride
  • EINECS 200-537-2
  • Mecholine chloride
  • Mecholyl
  • Mecholyl chloride
  • Metacolina cloruro
  • Metacolina cloruro [DCIT]
  • Methacholine chloride
  • Methacholini chloridum
  • Methacholini chloridum [INN-Latin]
  • Methacholinium chloride
  • O-Acetyl-beta-methylcholine chloride
  • Provocholine
  • Provokit
  • Trimethyl-beta-acetoxypropylammonium chloride
  • UNII-0W5ETF9M2K

Systematic Names

  • 1-Propanaminium, 2-(acetyloxy)-N,N,N-trimethyl-, chloride
  • 1-Propanaminium, 2-(acetyloxy)-N,N,N-trimethyl-, chloride (1:1)
  • Ammonium, (2-hydroxypropyl)trimethyl-, chloride, acetate
  • Methacholine chloride

Registry Numbers

CAS Registry Number

  • 62-51-1

FDA UNII

  • 0W5ETF9M2K

Other Registry Number

  • 2410-07-3

Related Registry Number

  • 55-92-5 (parent)

System Generated Number

  • 0000062511

Molecular Formulas

Molecular Formula

  • C8-H18-N-O2.Cl

Molecular Formula Fragments

  • C8-H18-N-O2
  • Cl
  • COMPONENT

Structure Descriptors

InChI

1S/C8H18NO2.ClH/c1-7(11-8(2)10)6-9(3,4)5;/h7H,6H2,1-5H3;1H/q+1;/p-1

InChIKey

JHPHVAVFUYTVCL-UHFFFAOYSA-M

Smiles

C([N+](C)(C)C)[C@@H](OC(C)=O)C.[ClH-]

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LDLo intravenous 3750ug/kg (3.75mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION Archives Internationales de Pharmacodynamie et de Therapie. Vol. 106, Pg. 245, 1956.
mouse LD50 intraperitoneal 160mg/kg (160mg/kg)   Toxicology and Applied Pharmacology. Vol. 28, Pg. 227, 1974.
mouse LD50 intravenous 15mg/kg (15mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 58, Pg. 337, 1936.
mouse LD50 oral 740mg/kg (740mg/kg)   Pharmacology and Toxicology. English translation of FATOAO. Vol. 22, Pg. 210, 1959.
mouse LD50 subcutaneous 90mg/kg (90mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 58, Pg. 337, 1936.
rat LD50 intravenous 20mg/kg (20mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 58, Pg. 337, 1936.
rat LD50 oral 750mg/kg (750mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 58, Pg. 337, 1936.
rat LD50 subcutaneous 75mg/kg (75mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 58, Pg. 337, 1936.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 172 deg C   EXP
log P (octanol-water) -3.030 (none)   EST
Atmospheric OH Rate Constant 1.85E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.