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54-71-7

54-71-7 structure
54-71-7 structure
  • Name: Pilocarpine Hydrochloride
  • Chemical Name: (+)-Pilocarpine hydrochloride
  • CAS Number: 54-71-7
  • Molecular Formula: C11H17ClN2O2
  • Molecular Weight: 208.257
  • Catalog: Natural product Alkaloid
  • Create Date: 2018-03-12 08:00:00
  • Modify Date: 2024-01-02 16:48:16
  • Pilocarpine Hydrochloride is a selective M3-type muscarinic acetylcholine receptor (M3 muscarinic receptor) agonist.
Name (+)-Pilocarpine hydrochloride
Synonyms (3S,4R)
pilocel
Akarpine
Pilocarpine HCl
2(3H)-Furanone, 3-ethyldihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-, (3S-cis)-
pilocarpine,2(3H)-furanone,3-ethyldihydro-4-[(1-methyl-1H-imidazol-5-yl)-methyl] monohydrochloride,(3S-cis)
Salagen
Pilocarpine
(3S,4R)-3-ethyl-4-[(1-methyl-1H-imidazol-5-yl)-methyl]dihydrofuran-2(3H)one hydrochloride
pilovisc
EINECS 200-212-5
Sanpilo
2(3H)-Furanone, 3-ethyldihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-, (3S,4R)-
Pilocarpine (Hydrochloride)
(3S,4R)-3-Ethyl-4-[(1-methyl-1H-imidazol-5-yl)methyl]dihydro-2(3H)-furanone
MFCD00012722
pilocar
ami-pilo
(+)-pilocarpine
(3S,4R)-3-Ethyl-4-[(1-methyl-1H-imidazol-5-yl)methyl]dihydrofuran-2(3H)-one
amisturap
2(3H)-Furanone, 3-ethyldihydro-4-((1-methyl-1H-imidazol-5-yl)methyl)-, (3S-cis)-
Description Pilocarpine Hydrochloride 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.

[4]. Wang RF, et al. Post-treatment with the GLP-1 analogue liraglutide alleviate chronic inflammation and mitochondrial stress induced by Status epilepticus. Epilepsy Res. 2018 Mar 9;142:45-52.
Density 1.2±0.1 g/cm3
Boiling Point 431.8±18.0 °C at 760 mmHg
Melting Point 202-205 °C(lit.)
Molecular Formula C11H17ClN2O2
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
Water Solubility soluble
Name: (+)-Pilocarpine Hydrochloride Material Safety Data Sheet
Synonym: Almocarpine; Pilocar; Pilomiotin
CAS: 54-71-7
Section 1 - Chemical Product MSDS Name:(+)-Pilocarpine Hydrochloride Material Safety Data Sheet
Synonym:Almocarpine; Pilocar; Pilomiotin
Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS
CAS# Chemical Name content EINECS#
54-71-7 (+)-Pilocarpine Hydrochloride 99% 200-212-5
Hazard Symbols: T+
Risk Phrases: 26/28
Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Very toxic by inhalation and if swallowed.Hygroscopic (absorbs moisture from the air).The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated. May be harmful if swallowed.
Inhalation:
May be fatal if inhaled. May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.
Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Never give anything by mouth to an unconscious person. SPEED IS ESSENTIAL. A DOCTOR MUST BE NOTIFIED AT ONCE. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. Wash mouth out with water.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
Notes to Physician:
Treat symptomatically and supportively.
Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. This material in sufficient quantity and reduced particle size is capable of creating a dust explosion.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam. Use agent most appropriate to extinguish fire.
Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up, then place into a suitable container for disposal. Avoid generating dusty conditions. Provide ventilation.
Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Minimize dust generation and accumulation. Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Keep container tightly closed. Use only in a chemical fume hood.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Store protected from moisture. Store protected from light.
Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 54-71-7: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.
Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystalline powder
Color: white to off-white
Odor: odorless
pH: 3.5 - 4.5 (5%aq.sol)
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 200-204 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: Freely Soluble.
Specific Gravity/Density:
Molecular Formula: C11H16N2O2.HCl
Molecular Weight: 244.72
Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable.
Conditions to Avoid:
Incompatible materials, light, dust generation, excess heat, exposure to moist air or water.
Incompatibilities with Other Materials:
Moisture, oxidizing agents.
Hazardous Decomposition Products:
Hydrogen chloride, nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, oxides of chlorine.
Hazardous Polymerization: Will not occur.
Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 54-71-7: TK1450000 LD50/LC50:
CAS# 54-71-7: Oral, mouse: LD50 = 200 mg/kg.
Carcinogenicity:
(+)-Pilocarpine Hydrochloride - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.
Section 12 - ECOLOGICAL INFORMATION

Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.
Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
IMO
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
RID/ADR
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing group: III
Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: T+
Risk Phrases:
R 26/28 Very toxic by inhalation and if swallowed.
Safety Phrases:
S 25 Avoid contact with eyes.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 54-71-7: 3
Canada
CAS# 54-71-7 is listed on Canada's NDSL List.
CAS# 54-71-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 54-71-7 is listed on the TSCA inventory.

SECTION 16 - ADDITIONAL INFORMATION
N/A

CHEMICAL IDENTIFICATION

RTECS NUMBER :
TK1450000
CHEMICAL NAME :
Pilocarpine, monohydrochloride
CAS REGISTRY NUMBER :
54-71-7
LAST UPDATED :
199701
DATA ITEMS CITED :
16
MOLECULAR FORMULA :
C11-H16-N2-O2.Cl-H
MOLECULAR WEIGHT :
244.75
WISWESSER LINE NOTATION :
T5OVTJ C2 D1- DT5N CNJ C1 &GH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Ocular
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
200 ug/kg/7H-I
TOXIC EFFECTS :
Cardiac - other changes
REFERENCE :
AIMDAP Archives of Internal Medicine. (AMA, 535 N. Dearborn St., Chicago, IL 60610) V.1- 1908- Volume(issue)/page/year: 147,586,1987
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
203 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: -,901,1990
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
230 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: -,901,1990
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
200 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: 6,646,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
155 mg/kg
TOXIC EFFECTS :
Autonomic Nervous System - other (direct) parasympathomimetic
REFERENCE :
ATXKA8 Archiv fuer Toxikologie. (Berlin, Fed. Rep. Ger.) V.15-31, 1954-74. For publisher information, see ARTODN. Volume(issue)/page/year: 29,39,1972
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
200 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: -,901,1990
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
150 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: -,901,1990
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
20 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
AEPPAE Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. (Berlin, Ger.) V.110-253, 1925-66. For publisher information, see NSAPCC. Volume(issue)/page/year: 131,171,1928
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intraarterial
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
20 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
AEPPAE Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. (Berlin, Ger.) V.110-253, 1925-66. For publisher information, see NSAPCC. Volume(issue)/page/year: 131,171,1928
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Bird - pigeon
DOSE/DURATION :
353 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: 4,1289,1935 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
130 mg/kg
SEX/DURATION :
female 7-19 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - behavioral
REFERENCE :
NYKZAU Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. (Nippon Yakuri Gakkai, c/o Kyoto Daigaku Igakubu Yakurigaku Kyoshitsu, Konoe-cho, Yoshida, Sakyo-ku, Kyoto 606, Japan) V.40- 1944- Volume(issue)/page/year: 85,79,1985
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
20 mg/kg
SEX/DURATION :
female 24-27 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - respiratory system
REFERENCE :
AJANA2 American Journal of Anatomy. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1-192, 1901-91. Volume(issue)/page/year: 154,163,1979
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
800 ug/kg
SEX/DURATION :
male 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Fertility - mating performance (e.g. # sperm positive females per # females mated; # copulations per # estrus cycles)
REFERENCE :
JRPFA4 Journal of Reproduction and Fertility. (Biochemical Soc. Book Depot, POB 32, Commerce Way, Colchester, Essex CO2 8HP, UK) V.1- 1960- Volume(issue)/page/year: 8,297,1964 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - M2736 No. of Facilities: 112 (estimated) No. of Industries: 1 No. of Occupations: 5 No. of Employees: 3136 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - M2736 No. of Facilities: 110 (estimated) No. of Industries: 1 No. of Occupations: 7 No. of Employees: 5031 (estimated) No. of Female Employees: 3716 (estimated)
Symbol GHS06
GHS06
Signal Word Danger
Hazard Statements H300 + H330
Precautionary Statements Missing Phrase - N15.00950417-P260-P304 + P340 + P310-P403 + P233
Hazard Codes T+:Verytoxic;
Risk Phrases R26/28
Safety Phrases S25-S45
RIDADR UN 1544 6.1/PG 3
WGK Germany 3
RTECS TK1450000
Packaging Group III
Hazard Class 6.1
HS Code 2934999090
HS Code 2934999090
Summary 2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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