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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

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About This Item

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

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

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_germany

WGK 3

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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Sigma-Aldrich

Sigma-Aldrich

SML1217

TG4-155

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)
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)
Biomarker profiles in serum and saliva of experimental Sjogren's syndrome: associations with specific autoimmune manifestations
Delaleu N, et al.
Arthritis Research & Therapy, 10(1), R22-R22 (2008)
Vibrational spectra of pilocarpine hydrochloride crystals
Bento RRF, et al.
Brazilian Journal of Physics, 39(1), 62-68 (2009)
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