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Substance Name: Physostigmine sulfate [USP]
RN: 64-47-1
UNII: G63V2J2N71
InChIKey: YYBNDIVPHIWTPK-KYJQVDHRSA-N

Classification Codes

  • Cholinergic (Ophthalmic)
  • Drug / Therapeutic Agent
  • Human Data
  • Reproductive Effect

Molecular Formula

  • C15-H21-N3-O2.1/2H2-O4-S

Molecular Weight

  • 648.778
 
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Names and Synonyms

Name of Substance

  • Physostigmine sulfate [USP]

Synonyms

  • EINECS 200-585-4
  • Eserine sulfate
  • Eserine sulphate
  • Physostigmine hemisulfate
  • Physostigmine SO4
  • Physostigmine sulfate
  • Physostigmine sulfate (2:1)
  • Physostigmine sulphate
  • Pyrrolo(2,3-b)indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, methylcarbamate (ester), (3aS-cis)-, sulfate (2:1)
  • UNII-G63V2J2N71

Systematic Names

  • Physostigmine sulphate
  • Pyrrolo(2,3-b)indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, 5-(N-methylcarbamate), (3aS,8aR)-, sulfate (2:1)
  • Pyrrolo(2,3-b)indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, methylcarbamate (ester), (3aS,8aR)-, sulfate (2:1) (salt)
  • Pyrrolo(2,3-b)indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, methylcarbamate (ester), (3aS-cis)-, sulfate (2:1)
  • Pyrrolo(2,3-b)indole, 1,2,3,3a,8,8a-hexahydro-5-hydroxy-1,3a,8-trimethyl-, methylcarbamate (ester), (3aS-cis)-, sulfate (2:1)

Registry Numbers

CAS Registry Number

  • 64-47-1

FDA UNII

  • G63V2J2N71

Other Registry Numbers

  • 11036-67-2
  • 11041-29-5

System Generated Number

  • 0000064471

Molecular Formulas

Molecular Formula

  • C15-H21-N3-O2.1/2H2-O4-S

Molecular Formula Fragments

  • C15-H21-N3-O2
  • COMPONENT
  • H2-O4-S

Structure Descriptors

InChI

1S/2C15H21N3O2.H2O4S/c2*1-15-7-8-17(3)13(15)18(4)12-6-5-10(9-11(12)15)20-14(19)16-2;1-5(2,3)4/h2*5-6,9,13H,7-8H2,1-4H3,(H,16,19);(H2,1,2,3,4)/t2*13-,15+;/m11./s1

InChIKey

YYBNDIVPHIWTPK-KYJQVDHRSA-N

Smiles

c12[C@@]3([C@@H](N(C)c1ccc(c2)OC(NC)=O)[N@@H+](C)CC3)C.c12[C@@]3([C@@H](N(C)c1ccc(c2)OC(NC)=O)[N@@H+](C)CC3)C.S(=O)(=O)([O-])[O-]

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo subcutaneous 1250ug/kg (1.25mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA Journal of Pharmacology and Experimental Therapeutics. Vol. 44, Pg. 95, 1932.
frog LDLo parenteral 325mg/kg (325mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 44, Pg. 95, 1932.
frog LDLo subcutaneous 1gm/kg (1000mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 207, Pg. 547, 1949.
man TDLo subcutaneous 191ng/kg (0.000191mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

GASTROINTESTINAL: NAUSEA OR VOMITING

GASTROINTESTINAL: OTHER CHANGES
Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 53, Pg. 313, 1905.
mouse LD50 intraperitoneal 510ug/kg (0.51mg/kg)   Archiv fuer Toxikologie. Vol. 29, Pg. 39, 1972.
mouse LD50 intravenous 178ug/kg (0.178mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#03167,
mouse LD50 oral 1680ug/kg (1.68mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 137, 1972.
mouse LD50 subcutaneous 700ug/kg (0.7mg/kg)   Annales Pharmaceutiques Francaises. Vol. 11, Pg. 286, 1953.
rabbit LDLo subcutaneous 1500ug/kg (1.5mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA Journal of Pharmacology and Experimental Therapeutics. Vol. 44, Pg. 95, 1932.
rat LD50 intraperitoneal 1621ug/kg (1.621mg/kg)   Fundamental and Applied Toxicology. Vol. 4, Pg. S195, 1984.
rat LD50 intravenous 450ug/kg (0.45mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 259, Pg. 153, 1982.
rat LD50 oral 4mg/kg (4mg/kg)   Annales Pharmaceutiques Francaises. Vol. 11, Pg. 286, 1953.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 105-106 deg C   EXP
log P (octanol-water) -2.250 (none)   EST
Water Solubility 1.00E+06 mg/L 25 EXP
Vapor Pressure 1.08E-25 mm Hg 25 EST
Henry's Law Constant 5.67E-27 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 3.97E-10 cm3/molecule-sec 25 EST

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