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Substance Name: Physostigmine [USP:BAN]
RN: 57-47-6
UNII: 9U1VM840SP
InChIKey: PIJVFDBKTWXHHD-HIFRSBDPSA-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

Molecular Weight

  • 275.35
 

Classification Codes

Classification Codes

  • Autonomic Agents
  • Cholinergic (Ophthalmic)
  • Cholinergic Agents
  • Cholinesterase Inhibitors
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Human Data
  • Miotics
  • Natural Product
  • Neurotransmitter Agents
  • Peripheral Nervous System Agents
  • Reproductive Effect

Superlist Classification Code

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

Names and Synonyms

Name of Substance

  • Physostigmine
  • Physostigmine [USP:BAN]

MeSH Heading

  • Physostigmine

Synonyms

  • (3aS-cis)-1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyrrolo(2,3-b)indol-5-ol methylcarbamate (ester)
  • 1,2,3,3abeta,8abeta-Hexahydro-1,3a,8-trimethylpyrrolo(2,3-b)-indol-5-yl methylcarbamate
  • Antilirium
  • Calabarine
  • Carbamic acid, methyl-, ester with eseroline
  • CCRIS 3422
  • CS 58525
  • EINECS 200-332-8
  • Eserine
  • Eserolein, methylcarbamate (ester)
  • Esromiotin
  • Ezerin
  • Fysostigmin
  • Fysostigmin [Czech]
  • HSDB 3161
  • MCV 4484
  • Methyl-carbamic acid, ester with eseroline
  • NIH 10421
  • NSC 30782
  • Physostigmine
  • Physostol
  • Pyrrolo(2,3-b)indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, methylcarbamate (ester), (3aS-cis)
  • Pyrrolo(2,3-b)indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, methylcarbamate (ester), (3aS-cis)-
  • UNII-9U1VM840SP

Systematic Names

  • Physostigmine
  • Pyrrolo(2,3-b)indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, 5-(N-methylcarbamate), (3aS,8aR)-
  • Pyrrolo(2,3-b)indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, methylcarbamate (ester), (3aS,8aR)-

Superlist Names

  • Physostigmine
  • Pyrrolo(2,3-b)indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, methylcarbamate (ester), (3aS-cis)-
  • RCRA waste no. P204

Registry Numbers

CAS Registry Number

  • 57-47-6

FDA UNII

  • 9U1VM840SP

Other Registry Numbers

  • 50975-37-6
  • 511-49-9

System Generated Number

  • 0000057476

Structure Descriptors

InChI

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

InChIKey

PIJVFDBKTWXHHD-HIFRSBDPSA-N

Smiles

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

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 intravenous 660ug/kg (0.66mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 88, Pg. 39, 1946.
dog LDLo subcutaneous 1138ug/kg (1.138mg/kg) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

GASTROINTESTINAL: ULCERATION OR BLEEDING FROM LARGE INTESTINE		 Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 5, Pg. 184, 1946.
human TDLo oral 20mg/kg (20mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: COMA		 "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 475, 1969.
mammal (species unspecified) LD50 unreported 600ug/kg (0.6mg/kg)   United States Patent Document. Vol. #5409948,
man LDLo unreported 882ug/kg (0.882mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
man TDLo oral 12mg/kg/60D-I (12mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) Neurology. Vol. 37, Pg. 345, 1987.
mouse LD50 intramuscular 330ug/kg (0.33mg/kg)   Journal of Medicinal Chemistry. Vol. 33, Pg. 577, 1990.
mouse LD50 intraperitoneal 644ug/kg (0.644mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

LUNGS, THORAX, OR RESPIRATION: CYANOSIS

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Farmakologiya i Toksikologiya Vol. 43, Pg. 717, 1980.
mouse LD50 intravenous 400ug/kg (0.4mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 58, Pg. 337, 1936.
mouse LD50 oral 3mg/kg (3mg/kg)   "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 452, 1948.
mouse LD50 parenteral 600ug/kg (0.6mg/kg)   United States Patent Document. Vol. #5306825,
mouse LD50 subcutaneous 740ug/kg (0.74mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)		 Journal of Pharmacology and Experimental Therapeutics. Vol. 123, Pg. 121, 1958.
pigeon LDLo subcutaneous 450ug/kg (0.45mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
rabbit LD50 intramuscular 2200ug/kg (2.2mg/kg)   Drug and Chemical Toxicology. Vol. 3, Pg. 319, 1980.
rabbit LD50 intraperitoneal 2470ug/kg (2.47mg/kg)   Archives Belges de Medecine Sociale, Hygiene, Medecine du Trevail et Medecine Legale. Vol. (Suppl), Pg. 226, 1984.
rabbit LD50 intravenous 500ug/kg (0.5mg/kg)   "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 452, 1948.
rabbit LD50 oral 11200ug/kg (11.2mg/kg)   Drug and Chemical Toxicology. Vol. 3, Pg. 319, 1980.
rabbit LD50 subcutaneous 3mg/kg (3mg/kg)   "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 452, 1948.
rat LD50 intraperitoneal 2mg/kg (2mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1926, 1972.
rat LD50 oral 4500ug/kg (4.5mg/kg)   United States Patent Document. Vol. #5302593,
rat LDLo subcutaneous 1mg/kg (1mg/kg)   United States Patent Document. Vol. #5318967,
women TDLo oral 40ug/kg/5D-I (0.04mg/kg) VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION American Journal of Psychiatry. Vol. 143, Pg. 910, 1985.
women TDLo oral 3920ug/kg/2W- (3.92mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) Neurology. Vol. 37, Pg. 345, 1987.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 105.5 deg C   EXP
pKa Dissociation Constant 6.12 (none)   EXP
log P (octanol-water) 1.58 (none)   EXP
Water Solubility 7760 mg/L 25 EST
Vapor Pressure 3.66E-06 mm Hg 25 EST
Henry's Law Constant 3.03E-11 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.94E-10 cm3/molecule-sec 25 EST

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