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P6503

Sigma-Aldrich

Pilocarpine hydrochloride

≥99% (titration), powder

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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:
4034491
EC Number:
200-212-5
MDL number:
MFCD00012722
UNSPSC Code:
12352200
PubChem Substance ID:
24277862
NACRES:
NA.77

Quality Level

100

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)

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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

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
GHS06

Signal Word

Danger

Hazard Statements

H300 + H330

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 2 Oral

WGK

WGK 3

Regulatory Information

监管及禁止进口产品

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Double-blind randomized, placebo-controlled study of pilocarpine to salvage salivary gland function during radiotherapy of patients with head and neck cancer
Gornitsky M, et al.
Oral Surgery, Oral Medicine, Oral Pathology, Oral Radiology, and Endodontics, 98(1), 45-52 (2004)
Karolien Goffin et al.
Experimental neurology, 217(1), 205-209 (2009-02-25)
The lithium-pilocarpine model of epilepsy in rat has been used extensively to investigate basic mechanisms of epilepsy and mimics human temporal lobe epilepsy. Our aim was to investigate longitudinal alterations in metabolism after lithium-pilocarpine induced status epilepticus (SE) using [(18)F]FDG
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)
Giovanna Paolone et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 39(11), 2144-2156 (2019-01-23)
Neurotrophic factors are candidates for treating epilepsy, but their development has been hampered by difficulties in achieving stable and targeted delivery of efficacious concentrations within the desired brain region. We have developed an encapsulated cell technology that overcomes these obstacles
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