Pilocarpine

Modify Date: 2024-01-01 22:54:57

Pilocarpine Structure
Pilocarpine structure
Common Name Pilocarpine
CAS Number 92-13-7 Molecular Weight 208.257
Density 1.2±0.1 g/cm3 Boiling Point 431.8±18.0 °C at 760 mmHg
Molecular Formula C11H16N2O2 Melting Point 34℃
MSDS N/A Flash Point 215.0±21.2 °C
Symbol GHS06
GHS06
Signal Word Danger

 Use of Pilocarpine


Pilocarpine is a selective M3-type muscarinic acetylcholine receptor (M3 muscarinic receptor) agonist.

 Names

Name (+)-pilocarpine
Synonym More Synonyms

 Pilocarpine Biological Activity

Description Pilocarpine is a selective M3-type muscarinic acetylcholine receptor (M3 muscarinic receptor) agonist.
Related Catalog
Target

M3 muscarinic receptor[1]

In Vitro To evaluate the cytotoxicity of Pilocarpine, the morphology and viability of human corneal stromal (HCS) cells are examined by light microscopy and MTT assay, respectively. Morphological observations show that HCS cells exposed to Pilocarpine at a concentration from 0.625 to 20 g/L exhibit dose- and time-dependent proliferation retardation and morphological abnormality such as cellular shrinkage, cytoplasmic vacuolation, detachment from culture matrix, and eventually death, while no obvious difference is observed between those exposed to Pilocarpine below the concentration of 0.625 g/L and controls. Results of MTT assay reveal that the cell viability of HCS cells decrease with time and concentration after exposing to Pilocarpine above the concentration of 0.625 g/L (P<0.01 or 0.05), while that of HCS cells treated with Pilocarpine below the concentration of 0.625 g/L show no significant difference to controls[2]. The partial muscarinic agonist, Pilocarpine, evokes concentration-dependent relaxation with an EC50 of 2.4 mM in isolated segments of rat tail artery that were constricted with Penylephrine (10 to 200 nM)[3].
In Vivo The Pilocarpine-induced saliva secretion of the control rats (CN) and exercised (EX) rats is examined. A significantly greater amount of saliva is induced by Pilocarpine in the EX rats than in the CN rats (P<0.01). Conversely, the Na+ concentration in the saliva of the EX rats is significantly lower than that of the CN rats (P<0.05)[1].
Cell Assay Cell viability is determined by MTT assay. Briefly, HCS cells are inoculated into a 96-well culture plate (Nunc) at a density of 1×104 cells/100 µL/well, and are cultured and treated. At a 4h interval, the Pilocarpine (0.625 to 20 g/L)-containing medium is replaced entirely with 100 µL serum-free DMEM/F12 medium containing 1.0 g/L MTT, and the cells are incubated at 37°C in the dark for 4h. After the MTT-containing medium is discarded with caution, 150 µL DMSO is added to dissolve the produced formazan crystals at 37°C in the dark for 15 min, and the absorbance at 490 nm is measured with a Multiskan GO microplate reader[2].
Animal Admin Rats[1] Male, 10-week-old Wistar rats are assigned to one of two groups, exercise (EX, n=6) and control (CN, n=6). The EX rats are kept for 40 days in cages with a running wheel (SN-451), allowing them to undertake voluntary exercise, while the CN rats are kept in cages with the running wheel locked. On the 40th day, Pilocarpine-induced saliva is measured as follows. Briefly, the rats are anesthetized, preweighed cotton was placed in their mouths sublingually, and Pilocarpine (0.5 mg/kg) is intraperitoneally injected to induce saliva secretion. Each cotton ball is then changed every 10 min for 1 h. The collected cotton balls are weighed again, and the mass of saliva secreted is calculated by subtracting the initial from the final weight.
References

[1]. Matsuzaki K, et al. Daily voluntary exercise enhances pilocarpine-induced saliva secretion and aquaporin 1 expression in rat submandibular glands. FEBS Open Bio. 2017 Dec 7;8(1):85-93.

[2]. Yuan XL, et al. Cytotoxicity of pilocarpine to human corneal stromal cells and its underlying cytotoxic mechanisms. Int J Ophthalmol. 2016 Apr 18;9(4):505-11.

[3]. Tonta MA, et al. Pilocarpine-induced relaxation of rat tail artery by a non-cholinergic mechanism and in the absence of an intact endothelium. Br J Pharmacol. 1994 Jun;112(2):525-32.

 Chemical & Physical Properties

Density 1.2±0.1 g/cm3
Boiling Point 431.8±18.0 °C at 760 mmHg
Melting Point 34℃
Molecular Formula C11H16N2O2
Molecular Weight 208.257
Flash Point 215.0±21.2 °C
Exact Mass 208.121185
PSA 44.12000
LogP -0.09
Vapour Pressure 0.0±1.0 mmHg at 25°C
Index of Refraction 1.585

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
TK1400000
CHEMICAL NAME :
Pilocarpine
CAS REGISTRY NUMBER :
92-13-7
LAST UPDATED :
199701
DATA ITEMS CITED :
14
MOLECULAR FORMULA :
C11-H16-N2-O2
MOLECULAR WEIGHT :
208.29
WISWESSER LINE NOTATION :
T5OVTJ C2 D1- DT5N CNJ C1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Human
DOSE/DURATION :
143 ug/kg
TOXIC EFFECTS :
Behavioral - coma Lungs, Thorax, or Respiration - cyanosis Vascular - BP elevation not characterized in autonomic section
REFERENCE :
CONEAT Confinia Neurologica. (Basel, Switzerland) V.1-37, 1938-75. Volume(issue)/page/year: 10,8,1949
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
1143 ug/kg
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - dyspnea Gastrointestinal - changes in structure or function of salivary glands Skin and Appendages - sweating
REFERENCE :
AROPAW Archives of Ophthalmology (Chicago). (AMA, 535 N. Dearborn St., Chicago, IL 60610) New series: V.1-44(3), 1929-50; V.64- 1960- Volume(issue)/page/year: 105,25,1987
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
1912 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
85DCAI "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970 Volume(issue)/page/year: 2,73,1970
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
402 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 12,1204,1981
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
166 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,APP-16,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
366 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,APP-16,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
88500 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,APP-16,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
119 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,APP-16,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
220 mg/kg
TOXIC EFFECTS :
Nutritional and Gross Metabolic - body temperature decrease
REFERENCE :
AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 192,88,1971
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
90900 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,APP-16,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
61900 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,APP-16,1982
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
120 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
HBAMAK "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." (Leipzig, Ger. Dem. Rep.) Volume(issue)/page/year: 4,1386,1935 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X3227 No. of Facilities: 11 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 115 (estimated) No. of Female Employees: 47 (estimated)

 Safety Information

Symbol GHS06
GHS06
Signal Word Danger
Hazard Statements H300 + H330
Precautionary Statements P260-P264-P284-P301 + P310-P310
Hazard Codes T+: Very toxic;
Risk Phrases 26/28
Safety Phrases 25-45
RIDADR UN 1544
Packaging Group III
Hazard Class 6.1(b)

 Synthetic Route

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Impairment of GABA release in the hippocampus at the time of the first spontaneous seizure in the pilocarpine model of temporal lobe epilepsy.

Exp. Neurol. 257 , 39-49, (2014)

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 Synonyms

ocusertp20
PILOCARPINE
pilokarpol
3-ethyl-4-((1-methyl-1H-imidazol-5-yl)methyl)dihydro-2(3H)-furanone
Pilocarpol
2(3H)-Furanone, 3-ethyldihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-
EINECS 202-128-4
3-Ethyl-4-[(1-methyl-1H-imidazol-5-yl)methyl]dihydro-2(3H)-furanone
Pilocarpin
Syncarpine
Pilokarpin
Ocucarpine
Ocusert
MFCD00153042
actone
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