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Substance Name: Physostigmine salicylate [USP:JAN]
RN: 57-64-7
UNII: 2046ZRO9VU
InChIKey: HZOTZTANVBDFOF-PBCQUBLHSA-N

Note

  • A cholinesterase inhibitor that is rapidly absorbed through membranes. It can be applied topically to the conjunctiva. It also can cross the blood-brain barrier and is used when central nervous system effects are desired, as in the treatment of severe anticholinergic toxicity.

Molecular Formula

  • C15-H21-N3-O2.C7-H6-O3

Molecular Weight

  • 413.4713
 

Classification Codes

Classification Codes

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

Superlist Classification Code

  • Threshold Planning Quantity (TPQ) = 100/10000 lb
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Names and Synonyms

Name of Substance

  • Physostigmine salicylate
  • Physostigmine salicylate [USP:JAN]

Synonyms

  • Antilirium
  • AR-44
  • CCRIS 3405
  • EINECS 200-343-8
  • Eserine salicylate
  • Isopto Eserine
  • NSC 757275
  • Physostigmine monosalicylate
  • Physostigmine salicylate
  • Physostol salicylate
  • Pyrrolo(2,3-b)indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, methylcarbamate (ester), (3aS-cis)-, mono(2-hydroxybenzoate)
  • Salicylic acid, compd. with physostigmine (1:1)
  • TL-1380
  • UNII-2046ZRO9VU

Systematic Names

  • Benzoic acid, 2-hydroxy-, compd. with (3aS,8aR)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo(2,3-b)indol-5-yl methylcarbamate (1:1)
  • Benzoic acid, 2-hydroxy-, compd. with (3aS,8aR)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo(2,3-b)indol-5-yl N-methylcarbamate (1:1)
  • Physostigmine salicylate
  • Physostigmine, salicylate (1:1)
  • Pyrrolo(2,3-b)indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, methylcarbamate (ester), (3aS-cis)-, mono(2-hydroxybenzoate)

Superlist Names

  • Benzoic acid, 2-hydroxy-, compd. with (3aS-cis)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo(2,3-b)indol-5-yl methylcarbamate ester (1:1)
  • Physostigmine salicylate
  • Physostigmine, salicylate (1:1)
  • RCRA waste no. P188

Mixture Name

  • Isopto P-ES

Registry Numbers

CAS Registry Number

  • 57-64-7

FDA UNII

  • 2046ZRO9VU

Other Registry Numbers

  • 11033-04-8
  • 11036-66-1

System Generated Number

  • 0000057647

Molecular Formulas

Molecular Formula

  • C15-H21-N3-O2.C7-H6-O3

Molecular Formula Fragments

  • C15-H21-N3-O2
  • C7-H6-O3
  • COMPONENT

Structure Descriptors

InChI

InChI=1S/C15H21N3O2.C7H6O3/c1-15-7-8-17(3)13(15)18(4)12-6-5-10(9-11(12)15)20-14(19)16-2;8-6-4-2-1-3-5(6)7(9)10/h5-6,9,13H,7-8H2,1-4H3,(H,16,19);1-4,8H,(H,9,10)/t13-,15+;/m1./s1

InChIKey

HZOTZTANVBDFOF-PBCQUBLHSA-N

Smiles

CNC(=O)Oc1ccc2N(C)[C@H]3N(C)CC[C@@]3(C)c2c1.OC(=O)c4ccccc4O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo subcutaneous 800ug/kg (0.8mg/kg) BEHAVIORAL: COMA

AUTONOMIC NERVOUS SYSTEM: OTHER (DIRECT) PARASYMPATHOMIMETIC

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
National Technical Information Service. Vol. PB158-508,
dog LDLo subcutaneous 1200ug/kg (1.2mg/kg) BEHAVIORAL: COMA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

AUTONOMIC NERVOUS SYSTEM: OTHER (DIRECT) PARASYMPATHOMIMETIC
National Technical Information Service. Vol. PB158-508,
man TDLo intravenous 14ug/kg (0.014mg/kg) CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)

GASTROINTESTINAL: NAUSEA OR VOMITING
Journal of Clinical Psychiatry. Vol. 46, Pg. 446, 1985.
mouse LD50 intraperitoneal 640ug/kg (0.64mg/kg)   Toxicology and Applied Pharmacology. Vol. 28, Pg. 227, 1974.
mouse LD50 intravenous 310ug/kg (0.31mg/kg)   Toxicology and Applied Pharmacology. Vol. 20, Pg. 474, 1971.
mouse LD50 oral 2500ug/kg (2.5mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 81, Pg. 276, 1950.
mouse LD50 subcutaneous 800ug/kg (0.8mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: TREMOR

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Journal of Pharmacy and Pharmacology. Vol. 34, Pg. 603, 1982.
rabbit LD50 intramuscular 1570ug/kg (1.57mg/kg) BEHAVIORAL: TREMOR Archives Internationales de Pharmacodynamie et de Therapie. Vol. 81, Pg. 276, 1950.
rabbit LD50 intravenous 910ug/kg (0.91mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Toxicology and Applied Pharmacology. Vol. 165, Pg. 27, 2000.
rabbit LDLo subcutaneous 2mg/kg (2mg/kg)   Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 53, Pg. 313, 1905.
rat LD50 intramuscular 1280ug/kg (1.28mg/kg)   Drug and Chemical Toxicology. Vol. 7, Pg. 507, 1984.
rat LD50 subcutaneous 2mg/kg (2mg/kg)   Toxicology and Applied Pharmacology. Vol. 25, Pg. 569, 1973.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 150.1 deg C   EXP
log P (octanol-water) 2.380 (none)   EST
Water Solubility 1.38E+04 mg/L 25 EXP
Vapor Pressure 3.10E-16 mm Hg 25 EST
Henry's Law Constant 3.36E-22 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.58E-10 cm3/molecule-sec 25 EST

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