CAS 54-71-7|Pilocarpine Hydrochloride

Introduction：Basic information about CAS 54-71-7|Pilocarpine Hydrochloride, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Pilocarpine Hydrochloride BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Customs
7. Articles84
8. Synonyms

Common Name	Pilocarpine Hydrochloride
CAS Number	54-71-7	Molecular Weight	208.257
Density	1.2±0.1 g/cm3	Boiling Point	431.8±18.0 °C at 760 mmHg
Molecular Formula	C₁₁H₁₇ClN₂O₂	Melting Point	202-205 °C(lit.)
MSDS	ChineseUSA	Flash Point	215.0±21.2 °C
Symbol	GHS06	Signal Word	Danger

Names

Name	(+)-Pilocarpine hydrochloride
Synonym	More Synonyms

Pilocarpine Hydrochloride BiologicalActivity

Description	Pilocarpine Hydrochloride is a selective M3-type muscarinic acetylcholine receptor (M3 muscarinic receptor) agonist.
Related Catalog	Signaling Pathways >>GPCR/G Protein >>mAChRSignaling Pathways >>Neuronal Signaling >>mAChRResearch Areas >>Neurological Disease
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.

Chemical & Physical Properties

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
InChIKey	RNAICSBVACLLGM-GNAZCLTHSA-N
SMILES	CCC1C(=O)OCC1Cc1cncn1C.Cl
Water Solubility	soluble

Toxicological Information

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)

Safety Information

Symbol	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

Customs

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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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)-

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