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Substance Name: Muscarine
RN: 300-54-9
UNII: 7T101UWZ5W
InChIKey: UQOFGTXDASPNLL-XHNCKOQMSA-N

Note

  • A toxic alkaloid found in Amanita muscaria (fly fungus) and other fungi of the Inocybe species. It is the first parasympathomimetic substance ever studied and causes profound parasympathetic activation that may end in convulsions and death. The specific antidote is atropine.

Molecular Formula

  • C9-H20-N-O2

Molecular Weight

  • 174.262
 

Classification Codes

  • Autonomic Agents
  • Cholinergic Agents
  • Cholinergic Agonists
  • Human Data
  • Muscarinic Agonists
  • Neurotransmitter Agents
  • Parasympathomimetics
  • Peripheral Nervous System Agents
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Names and Synonyms

Name of Substance

  • Muscarine

MeSH Heading

  • Muscarine

Synonyms

  • (+)-(2S,4R,5S)-Muscarine
  • (+)-Muscarine
  • Ammonium, trimethyl(tetrahydro-4-hydroxy-5-methylfurfuryl)-
  • EINECS 206-094-1
  • L-(+)-Muscarine
  • Muscarin
  • Muscarine (alkaloid)
  • Muscarine (the alkaloid)
  • Muskarin
  • UNII-7T101UWZ5W

Systematic Names

  • (2S-(2alpha,4beta,5alpha))-(Tetrahydro-4-hydroxy-5-methylfurfuryl)trimethylammonium
  • 2-Furanmethanaminium, tetrahydro-4-hydroxy-N,N,N,5-tetramethyl-, (2S-(2alpha,4beta,5alpha))-
  • D-ribo-Hexitol, 2,5-anhydro-1,4,6-trideoxy-6-(trimethyl)ammonio)-
  • Muscarine

Registry Numbers

CAS Registry Number

  • 300-54-9

FDA UNII

  • 7T101UWZ5W

System Generated Number

  • 0000300549

Structure Descriptors

InChI

1S/C9H20NO2/c1-7-9(11)5-8(12-7)6-10(2,3)4/h7-9,11H,5-6H2,1-4H3/q+1/t7-,8-,9+/m0/s1

InChIKey

UQOFGTXDASPNLL-XHNCKOQMSA-N

Smiles

C[C@@H]1O[C@H](C[N+](C)(C)C)C[C@H]1O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 1100ug/kg (1.1mg/kg)   Science. Vol. 144, Pg. 1100, 1964.
cat LDLo oral 7mg/kg (7mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
cat LDLo subcutaneous 2mg/kg (2mg/kg)   "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 406, 1948.
frog LDLo parenteral 160ug/kg (0.16mg/kg)   Justus Leibigs Annalen der Chemie. Vol. 489, Pg. 156, 1931.
frog LDLo unreported 160ug/kg (0.16mg/kg)   "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 407, 1948.
man LDLo unreported 735ug/kg (0.735mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
mouse LD50 intraperitoneal 5mg/kg (5mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 192, Pg. 88, 1971.
mouse LD50 intravenous 230ug/kg (0.23mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: EXCITEMENT
Toxicology Letters. Vol. 1000(Sp,
mouse LD50 subcutaneous 1100ug/kg (1.1mg/kg)   Naturwissenschaften. Vol. 56, Pg. 615, 1969.
mouse LDLo oral 750mg/kg (750mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 167, 1973.
rabbit LDLo oral 150mg/kg (150mg/kg) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

VASCULAR: REGIONAL OR GENERAL ARTERIOLAR OR VENOUS DILATION
Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 61, Pg. 283, 1909.
rabbit LDLo subcutaneous 27mg/kg (27mg/kg)   Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 61, Pg. 283, 1909.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) -3.530 (none)   EST
Atmospheric OH Rate Constant 4.30E-11 cm3/molecule-sec 25 EST

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