|
|
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
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
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
* denotes mobile formatted website
Links to Resources
NLM Resources (File Locators)
Regulatory Agencies (Superlist Locators)
Other Resources (Internet Locators)
Search for this InChIKey on the Web
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/s1InChIKey
PIJVFDBKTWXHHD-HIFRSBDPSA-NSmiles
CNC(=O)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.