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MedKoo Cat#: 592205 | Name: Pilocarpine
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Pilocarpine is a slowly hydrolyzed muscarinic agonist with no nicotinic effects. Pilocarpine is used as a miotic and in the treatment of glaucoma.

Chemical Structure

Pilocarpine
Pilocarpine
CAS#92-13-7 (free base)

Theoretical Analysis

MedKoo Cat#: 592205

Name: Pilocarpine

CAS#: 92-13-7 (free base)

Chemical Formula: C11H16N23O2

Exact Mass: 208.1212

Molecular Weight: 208.26

Elemental Analysis: C, 63.44; H, 7.74; N, 13.45; O, 15.36

Price and Availability

Size Price Availability Quantity
10mg USD 350.00 2 weeks
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Related CAS #
54-71-7 (HCl) 92-13-7 (free base) 148-72-1 (nitrate)
Synonym
Pilocarpine; AI3-50523; AI3 50523; AI350523
IUPAC/Chemical Name
2(3H)-Furanone, 3-ethyldihydro-4-((1-methyl-1H-imidazol-5-yl)methyl)-, (3S,4R)-
InChi Key
QCHFTSOMWOSFHM-WPRPVWTQSA-N
InChi Code
InChI=1S/C11H16N2O2/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/t8-,10-/m0/s1
SMILES Code
O=C1OC[C@H](CC2=CN=CN2C)[C@@H]1CC
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Pilocarpine is a selective M3-type muscarinic acetylcholine receptor (M3 muscarinic receptor) agonist.
In vitro activity:
Morphology observations and viability assay showed that pilocarpine at concentrations above 0.625 g/L induced dose- and time-dependent morphological abnormality and viability decline of HCS cells. AO/EB double-staining, DNA electrophoresis and TEM noted that pilocarpine at concentrations above 0.625 g/L induced dose- and/or time-dependent membrane permeability elevation, DNA fragmentation, and apoptotic body formation of the cells. Moreover, FCM and ELISA assays revealed that 2.5 g/L pilocarpine also induced S phase arrest, PS externalization, MTP disruption, and caspase-8, -9 and -3 activation of the cells. Reference: Int J Ophthalmol. 2016 Apr 18;9(4):505-11. https://pubmed.ncbi.nlm.nih.gov/27162720/
In vivo activity:
This study investigated pilocarpine-induced saliva secretion and AQP expression in rats after voluntary exercise. After the training period, the rats were anesthetized and pilocarpine, an M3 muscarinic receptor agonist, was intraperitoneally injected (0.5 mg·kg-1) to stimulate saliva secretion. Saliva was collected, and the SMGs were sampled and subjected to western blot, RT-PCR, and immunohistochemical analyses. Pilocarpine induced a greater amount of saliva in the exercised rats than in the CN. Expression levels of AQP1 mRNA and protein were significantly higher in SMGs of exercised rats than in those of the CN, but the expression of AQP5 was not affected by voluntary exercise. Reference: FEBS Open Bio. 2017 Dec 7;8(1):85-93. https://pubmed.ncbi.nlm.nih.gov/29321959/
Solvent mg/mL mM comments
Solubility
DMSO 100.0 480.17
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 208.26 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Yuan XL, Wen Q, Zhang MY, Fan TJ. Cytotoxicity of pilocarpine to human corneal stromal cells and its underlying cytotoxic mechanisms. Int J Ophthalmol. 2016 Apr 18;9(4):505-11. doi: 10.18240/ijo.2016.04.05. PMID: 27162720; PMCID: PMC4853343. 2. Tonta MA, Parkington HC, Tare M, Coleman HA. Pilocarpine-induced relaxation of rat tail artery by a non-cholinergic mechanism and in the absence of an intact endothelium. Br J Pharmacol. 1994 Jun;112(2):525-32. doi: 10.1111/j.1476-5381.1994.tb13105.x. PMID: 8075872; PMCID: PMC1910363. 3. Seo GY, Neal ES, Han F, Vidovic D, Nooru-Mohamed F, Dienel GA, Sullivan MA, Borges K. Brain glycogen content is increased in the acute and interictal chronic stages of the mouse pilocarpine model of epilepsy. Epilepsia Open. 2022 Jun;7(2):361-367. doi: 10.1002/epi4.12599. Epub 2022 Apr 22. PMID: 35377551; PMCID: PMC9159246. 4. Matsuzaki K, Sugimoto N, Katakura M, Sumiyoshi E, Hara T, Hashimoto M, Shido O. Daily voluntary exercise enhances pilocarpine-induced saliva secretion and aquaporin 1 expression in rat submandibular glands. FEBS Open Bio. 2017 Dec 7;8(1):85-93. doi: 10.1002/2211-5463.12353. PMID: 29321959; PMCID: PMC5757178.
In vitro protocol:
1. Yuan XL, Wen Q, Zhang MY, Fan TJ. Cytotoxicity of pilocarpine to human corneal stromal cells and its underlying cytotoxic mechanisms. Int J Ophthalmol. 2016 Apr 18;9(4):505-11. doi: 10.18240/ijo.2016.04.05. PMID: 27162720; PMCID: PMC4853343. 2. Tonta MA, Parkington HC, Tare M, Coleman HA. Pilocarpine-induced relaxation of rat tail artery by a non-cholinergic mechanism and in the absence of an intact endothelium. Br J Pharmacol. 1994 Jun;112(2):525-32. doi: 10.1111/j.1476-5381.1994.tb13105.x. PMID: 8075872; PMCID: PMC1910363.
In vivo protocol:
1. Seo GY, Neal ES, Han F, Vidovic D, Nooru-Mohamed F, Dienel GA, Sullivan MA, Borges K. Brain glycogen content is increased in the acute and interictal chronic stages of the mouse pilocarpine model of epilepsy. Epilepsia Open. 2022 Jun;7(2):361-367. doi: 10.1002/epi4.12599. Epub 2022 Apr 22. PMID: 35377551; PMCID: PMC9159246. 2. Matsuzaki K, Sugimoto N, Katakura M, Sumiyoshi E, Hara T, Hashimoto M, Shido O. Daily voluntary exercise enhances pilocarpine-induced saliva secretion and aquaporin 1 expression in rat submandibular glands. FEBS Open Bio. 2017 Dec 7;8(1):85-93. doi: 10.1002/2211-5463.12353. PMID: 29321959; PMCID: PMC5757178.
1: Quintanilha MVT, Gobbo GAM, Pinheiro GB, Souza ACB, Camargo LC, Mortari MR. Evaluating a Venom-Bioinspired Peptide, NOR-1202, as an Antiepileptic Treatment in Male Mice Models. Toxins (Basel). 2024 Aug 5;16(8):342. doi: 10.3390/toxins16080342. PMID: 39195752. 2: Ling Q, Sun W, Duan X. Case report: Topical pilocarpine ameliorated the accommodation loss and pupillary dilation after micropulse transscleral laser treatment. BMC Ophthalmol. 2024 Aug 26;24(1):371. doi: 10.1186/s12886-024-03628-x. PMID: 39187764; PMCID: PMC11346055. 3: Tan Y, Yu Y, Niu H, Wang C, Mo P, Li D, Zhang Q, Feng D, Liu C. Profile of miRNA expression in the hippocampus of epileptic mice and the prediction of potential therapeutic targets. Mol Biol Rep. 2024 Aug 22;51(1):929. doi: 10.1007/s11033-024-09861-3. PMID: 39172288. 4: Zhou F, Hu R, Wang Y, Wu X, Chen X, Xi Z, Zeng K. Calsyntenin-1 expression and function in brain tissue of lithium-pilocarpine rat seizure models. Synapse. 2024 Sep;78(5):e22307. doi: 10.1002/syn.22307. PMID: 39171546. 5: Gawel K, Hulas-Stasiak M, Marszalek-Grabska M, Grenda A, Siekierska A, Kosheva N, van der Ent W, Esguerra CV, Krawczyk P, Turski WA. Induction of seizures and initiation of epileptogenesis by pilocarpine in zebrafish larvae. Front Mol Neurosci. 2024 Aug 6;17:1418606. doi: 10.3389/fnmol.2024.1418606. PMID: 39165716; PMCID: PMC11333333. 6: Chen H, Yin J, Wu Y, Wang Y, Liu Y, Dong W, Gao B, Li R, Cheng S, Wang L. Zonular ligament abnormalities intermingled in acute primary angle closure: A diagnostic and therapeutic challenge. Heliyon. 2024 Jul 25;10(15):e34939. doi: 10.1016/j.heliyon.2024.e34939. PMID: 39161832; PMCID: PMC11332892. 7: Zhang K, Yang Z, Yang Z, Du L, Zhou Y, Fu S, Wang X, Liu D, He X. Targeting microglial GLP1R in epilepsy: A novel approach to modulate neuroinflammation and neuronal apoptosis. Eur J Pharmacol. 2024 Aug 16;981:176903. doi: 10.1016/j.ejphar.2024.176903. Epub ahead of print. PMID: 39154823. 8: Yang J, Cai JH, Wu TX, Gao ZQ, Zhou C, Wu Q, Ji MJ. Salvinorin A ameliorates pilocarpine-induced seizures by regulating hippocampal microglia polarization. J Ethnopharmacol. 2024 Aug 16;335:118697. doi: 10.1016/j.jep.2024.118697. Epub ahead of print. PMID: 39154669. 9: Cai Y, Tong F, Li K, Wang Q, Ding J, Wang X. Cannabinoid receptor 2 agonist AM1241 alleviates epileptic seizures and epilepsy-associated depression via inhibiting neuroinflammation in a pilocarpine-induced chronic epilepsy mouse model. Mol Cell Neurosci. 2024 Aug 14:103958. doi: 10.1016/j.mcn.2024.103958. Epub ahead of print. PMID: 39151841. 10: Wang J, Wu Y, Chen J, Zhang Q, Liu Y, Long H, Yu J, Wu Q, Feng L. Th1/Th2 Imbalance in Peripheral Blood Echoes Microglia State Dynamics in CNS During TLE Progression. Adv Sci (Weinh). 2024 Aug 13:e2405346. doi: 10.1002/advs.202405346. Epub ahead of print. PMID: 39136073. 11: Bojja SL, Anand S, Minz RW, Medhi B. Metformin alleviates reactive gliosis and neurodegeneration, improving cognitive deficit in a rat model of temporal lobe epilepsy. Brain Res. 2024 Aug 10;1844:149138. doi: 10.1016/j.brainres.2024.149138. Epub ahead of print. PMID: 39134259. 12: Petkar S, Chaitra MC. Correction of presbyopia using 0.5% pilocarpine eye drops among Indians. Bioinformation. 2024 May 31;20(5):532-536. doi: 10.6026/973206300200532. PMID: 39132245; PMCID: PMC11309104. 13: Kim MJ, Ibrahim MM, Jablonski MM. Deepening insights into cholinergic agents for intraocular pressure reduction: systems genetics, molecular modeling, and in vivo perspectives. Front Mol Biosci. 2024 Jul 26;11:1423351. doi: 10.3389/fmolb.2024.1423351. PMID: 39130374; PMCID: PMC11310038. 14: Gao X, Gao N, Du M, Xiang Y, Zuo H, Cao H, Zheng S, Huang R, Wan W, Hu K. Pilocarpine mediated excessive calcium accumulation leads to ciliary muscle cell senescence and apoptosis. FASEB J. 2024 Aug 15;38(15):e23878. doi: 10.1096/fj.202401286R. PMID: 39120551. 15: Mohammad A, Btrush S, Makhlouf Z, Alkasem A, Abdoh H, Kudsi M. Primary Sjögren's syndrome without ocular manifestation: a case report. Ann Med Surg (Lond). 2024 May 28;86(8):4816-4819. doi: 10.1097/MS9.0000000000002234. PMID: 39118701; PMCID: PMC11305720. 16: Wormuth C, Papazoglou A, Henseler C, Ehninger D, Broich K, Haenisch B, Hescheler J, Köhling R, Weiergräber M. A Novel Rat Infant Model of Medial Temporal Lobe Epilepsy Reveals New Insight into the Molecular Biology and Epileptogenesis in the Developing Brain. Neural Plast. 2024 Jul 25;2024:9946769. doi: 10.1155/2024/9946769. PMID: 39104708; PMCID: PMC11300100. 17: Ishida N, Katsura A, Takagaki K, Arakawa H, Shimada T, Mizuno S, Sai Y, Kato Y, Nakamura H, Suga Y, Matsushita R. Transdermal pilocarpine on the skin over salivary glands to increase salivation: an in vivo study. BMC Oral Health. 2024 Aug 2;24(1):881. doi: 10.1186/s12903-024-04667-y. PMID: 39095752; PMCID: PMC11297717. 18: Xie N, Bickley BA, Gross AD. GABA-gated chloride channel mutation (Rdl) induces cholinergic physiological compensation resulting in cross resistance in Drosophila melanogaster. Pestic Biochem Physiol. 2024 Aug;203:105972. doi: 10.1016/j.pestbp.2024.105972. Epub 2024 Jun 3. PMID: 39084765. 19: Satoh K, Ohno Y, Nagase H, Kashimata M, Adachi K. Age-related alteration of the involvement of CD36 for salivary secretion from the parotid gland in mice. J Physiol Sci. 2024 Jul 29;74(1):38. doi: 10.1186/s12576-024-00931-6. PMID: 39075341; PMCID: PMC11285320. 20: Ribeiro LR, Dos Santos AMF, da Cruz Guedes E, Bezerra TLDS, de Souza TL, Filho JMB, de Almeida RN, Salvadori MGDSS. Effects of acute administration of 4-allyl-2,6-dimethoxyphenol in mouse models of seizures. Epilepsy Res. 2024 Sep;205:107421. doi: 10.1016/j.eplepsyres.2024.107421. Epub 2024 Jul 26. PMID: 39068729.