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Merck
CN

P6503

Pilocarpine hydrochloride

≥99% (titration), powder, muscarinic acetylcholine receptor agonist

Synonym(s):

(3S,4R)-4,5-Dihydro-3-ethyl-4-(1-methyl-1H-imidazol-5-ylmethyl)-2(3H)-furanone hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C11H16N2O2 · HCl
CAS Number:
54-71-7
Molecular Weight:
244.72
NACRES:
NA.77
PubChem Substance ID:
24277862
UNSPSC Code:
12352200
EC Number:
200-212-5
MDL number:
MFCD00012722
Beilstein/REAXYS Number:
4034491

Key Documents

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Product Name

Pilocarpine hydrochloride, ≥99% (titration), powder

InChI key

RNAICSBVACLLGM-GNAZCLTHSA-N

InChI

1S/C11H16N2O2.ClH/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;1H/t8-,10-;/m0./s1

SMILES string

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

assay

≥99% (titration)

form

powder

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

color

white

mp

202-205 °C (lit.)

solubility

H2O: 100 mg/mL

application(s)

forensics and toxicology
veterinary

relevant disease(s)

epilepsy

Quality Level

100

Gene Information

human ... CHRM1(1128), CHRM2(1129), CHRM3(1131), CHRM4(1132), CHRM5(1133)

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Application

Pilocarpine hydrochloride has been used to stimulate salivary secretions in mice. It has also been used to induce status epilepticus(SE) in rat.

Biochem/physiol Actions

Nonselective muscarinic acetylcholine receptor agonist; used to produce an experimental model of epilepsy.
Pilocarpine is alkaloid isolated from the shrub Pilocarpus species. It comprises imidazole ring and γ- lactone rings in its structure. It has cholinergic potential and it stimulates the parasympathetic system. Pilocarpine is also effective for treating glaucoma. It stimulates ciliary muscle contraction by binding to muscarinic M3 receptors. It is effective in treating corneal dryness in Sjogren′s syndrome. It is a secretagogue, which improves salivary secretions in Xerostomia or a dry mouth condition in Sjogren′s syndrome patients and in radiotherapy patients with head and neck carcinoma.

Disclaimer

Hygroscopic, light sensitive

Features and Benefits

This compound is a featured product for ADME Tox and Neuroscience research. Discover more featured ADME Tox and Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Acetylcholine Receptors (Muscarinic) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Other Notes

Shelf life of the powder is at least five years.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 2 Oral

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

Regulatory Information

涉药品监管产品
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Certificates of Analysis (COA)

Lot/Batch Number
MKCV5224
MKCT8868
MKCV0237
MKCS4466
MKCN8798

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Oral pilocarpine for the treatment of ocular symptoms in patients with Sjogren?s syndrome: a randomised 12 week controlled study
Tsifetaki N, et al.
Annals of the Rheumatic Diseases, 62(12), 1204-1207 (2003)
Longitudinal microPET imaging of brain glucose metabolism in rat lithium-pilocarpine model of epilepsy
Goffin K, et al.
Experimental neurology, 217(1), 205-209 (2009)
Lin Zhu et al.
ASN neuro, 12, 1759091420926836-1759091420926836 (2020-05-20)
Nuclear-distribution element-like 1 (NDEL1) is associated with the proliferation and migration of neurons. Vascular endothelial growth factor (VEGF) in combination with VEGF receptor-2 (VEGFR-2) regulates the proliferation and migration of neurons. This study was performed to explore undefined alterations in
Vibrational spectra of pilocarpine hydrochloride crystals
Bento RRF, et al.
Brazilian Journal of Physics, 39(1), 62-68 (2009)
Effect of pilocarpine hydrochloride on the Schlemm canal in healthy eyes and eyes with open-angle glaucoma
Skaat A, et al.
JAMA Ophthalmology, 134(9), 976-981 (2016)
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Product Information Sheet - P6503

Product Information Sheet

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