All Photos(4)

P6503

Sigma-Aldrich

Pilocarpine hydrochloride

≥99% (titration), powder

Synonym(s):
(3S,4R)-4,5-Dihydro-3-ethyl-4-(1-methyl-1H-imidazol-5-ylmethyl)-2(3H)-furanone hydrochloride
Empirical Formula (Hill Notation):
C11H16N2O2 · HCl
CAS Number:
Molecular Weight:
244.72
Beilstein:
4034491
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥99% (titration)

form

powder

application(s)

HPLC: suitable
gas chromatography (GC): suitable

color

white

mp

202-205 °C (lit.)

solubility

H2O: 100 mg/mL

Featured Industry

Forensics and Toxicology
Veterinary

relevant disease(s)

epilepsy

SMILES string

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

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

InChI key

RNAICSBVACLLGM-GNAZCLTHSA-N

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Related Categories

Application

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

Packaging

5, 10, 50 g in poly bottle

Biochem/physiol Actions

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.
Nonselective muscarinic acetylcholine receptor agonist; used to produce an experimental model of epilepsy.

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.

Caution

Hygroscopic, light sensitive

Other Notes

Shelf life of the powder is at least five years.

pictograms

Skull and crossbones

signalword

Danger

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 2 Oral

Storage Class Code

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

WGK Germany

WGK 3

Certificate of Analysis

Certificate of Origin

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)
Vibrational spectra of pilocarpine hydrochloride crystals
Bento RRF, et al.
Brazilian Journal of Physics, 39(1), 62-68 (2009)
Pilocarpine hydrochloride for the treatment of xerostomia in patients with Sjogren's syndrome in Taiwan?a double-blind, placebo-controlled trial
Wu CH, et al.
Journal of the Formosan Medical Association = Taiwan Yi Zhi, 105(10), 796-803 (2006)
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...
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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