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Substance Name: Pilocarpine [USP:BAN:JAN]
RN: 92-13-7
UNII: 01MI4Q9DI3
InChIKey: QCHFTSOMWOSFHM-WPRPVWTQSA-N

Note

  • A slowly hydrolyzed muscarinic agonist with no nicotinic effects. Pilocarpine is used as a miotic and in the treatment of glaucoma.

Molecular Formula

  • C11-H16-N2-O2

Molecular Weight

  • 208.2594
 

Classification Codes

  • Antiglaucoma Agent
  • Autonomic Agents
  • Cholinergic (Ophthalmic)
  • Cholinergic Agents
  • Cholinergic Agonists
  • Drug / Therapeutic Agent
  • Human Data
  • Miotics
  • Muscarinic Agonists
  • Natural Product
  • Neurotransmitter Agents
  • Peripheral Nervous System Agents

Names and Synonyms

Name of Substance

  • Pilocarpine
  • Pilocarpine [USP:BAN:JAN]

MeSH Heading

  • Pilocarpine

Synonyms

  • (3S-cis)-3-Ethyldihydro-4-((1-methyl-1H-imidazol-5-yl)methyl)-2(3H)-furanone
  • 2(3H)-Furanone, 3-ethyldihydro-4-((1-methyl-1H-imidazol-5-yl)methyl)-, (3S-cis)-
  • AI3-50523
  • EINECS 202-128-4
  • HSDB 3163
  • Imidazole-5-butyric acid, alpha-ethyl-beta-(hydroxymethyl)-1-methyl-, gamma-lactone
  • Ocusert P 20
  • Ocusert pilo
  • Ocusert Pilo-20
  • Ocusert Pilo-40
  • Pilocarpin
  • Pilocarpine
  • Pilocarpol
  • Pilokarpin
  • Pilokarpol
  • Syncarpine
  • UNII-01MI4Q9DI3

Systematic Names

  • 2(3H)-Furanone, 3-ethyldihydro-4-((1-methyl-1H-imidazol-5-yl)methyl)-, (3S,4R)-
  • Pilocarpine

Registry Numbers

CAS Registry Number

  • 92-13-7

FDA UNII

  • 01MI4Q9DI3

Other Registry Number

  • 91484-73-0

System Generated Number

  • 0000092137

Structure Descriptors

InChI

1S/C11H16N2O2/c1-3-10-8(6-15-11(10)14)4-9-5-12-7-13(9)2/h5,7-8,10H,3-4,6H2,1-2H3/t8-,10-/m0/s1

InChIKey

QCHFTSOMWOSFHM-WPRPVWTQSA-N

Smiles

CC[C@H]1[C@H](COC1=O)Cc2cncn2C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human LDLo subcutaneous 143ug/kg (0.143mg/kg) BEHAVIORAL: COMA

LUNGS, THORAX, OR RESPIRATION: CYANOSIS

VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION
Confinia Neurologica. Vol. 10, Pg. 8, 1949.
man LDLo unreported 1912ug/kg (1.912mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
mouse LD50 intraperitoneal 220mg/kg (220mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 192, Pg. 88, 1971.
mouse LD50 intravenous 61900ug/kg (61.9mg/kg)   Drugs in Japan Vol. 6, Pg. APP-16, 1982.
mouse LD50 oral 119mg/kg (119mg/kg)   Drugs in Japan Vol. 6, Pg. APP-16, 1982.
mouse LD50 subcutaneous 90900ug/kg (90.9mg/kg)   Drugs in Japan Vol. 6, Pg. APP-16, 1982.
rabbit LDLo intravenous 120mg/kg (120mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1386, 1935.
rat LD50 intraperitoneal 166mg/kg (166mg/kg)   Drugs in Japan Vol. 6, Pg. APP-16, 1982.
rat LD50 intravenous 88500ug/kg (88.5mg/kg)   Drugs in Japan Vol. 6, Pg. APP-16, 1982.
rat LD50 oral 402mg/kg (402mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 12, Pg. 1204, 1981.
rat LD50 subcutaneous 366mg/kg (366mg/kg)   Drugs in Japan Vol. 6, Pg. APP-16, 1982.
women TDLo subcutaneous 1143ug/kg (1.143mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

SKIN AND APPENDAGES (SKIN): SWEATING: OTHER
Archives of Ophthalmology Vol. 105, Pg. 25, 1987.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 34 deg C   EXP
pKa Dissociation Constant 6.78 (none)   EXP
log P (octanol-water) 0.12 (none)   EXP
Water Solubility 3.13E+04 mg/L 25 EST
Vapor Pressure 1.83E-06 mm Hg 25 EST
Henry's Law Constant 2.88E-07 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 9.61E-11 cm3/molecule-sec 25 EST

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