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

Properties

• product name: Pilocarpine hydrochloride, ≥99% (titration), powder
• 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
• 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
• Gene Information: human ... CHRM1(1128) , CHRM2(1129) , CHRM3(1131) , CHRM4(1132) , CHRM5(1133)

Description

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

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.

Safety Information

• pictograms: GHS06
• signalword: Danger
• hcodes: H300 + H330
• pcodes: P260 - P264 - P271 - P284 - P304 + P340 + P310 - P403 + P233
• 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_germany: WGK 3