Pilocarpine

Base Information

• Chemical Name: Pilocarpine
• CAS No.: 92-13-7
• Deprecated CAS: 91484-73-0
• Molecular Formula: C11H16N2O2
• Molecular Weight: 208.26
• Hs Code.: 2939800000
• European Community (EC) Number: 202-128-4
• UNII: 01MI4Q9DI3
• DSSTox Substance ID: DTXSID1021162
• Nikkaji Number: J9.328I
• Wikipedia: Pilocarpine
• Wikidata: Q411461
• NCI Thesaurus Code: C62068
• RXCUI: 8328
• Pharos Ligand ID: HAM15654L47L
• Metabolomics Workbench ID: 43318
• ChEMBL ID: CHEMBL550
• Mol file: 92-13-7.mol

Synonyms:Hydrochloride, Pilocarpine;Isopilocarpine;Isoptocarpine;Nitrate, Pilocarpine;Ocusert;Pilocarpine;Pilocarpine Hydrochloride;Pilocarpine Mononitrate, (3S-cis)-Isomer;Pilocarpine Nitrate;Pilocarpine, Monohydrochloride, (3S-cis)-Isomer;Salagen

Chemical Property of Pilocarpine

Chemical Property:

• Melting Point: 34°
• Refractive Index: 1.5000 (estimate)
• Boiling Point: 431.8 °C at 760 mmHg
• PKA: 6.87(at 30℃)
• Flash Point: 215 °C
• PSA: 44.12000
• Density: 1.22 g/cm³
• LogP: 1.16180
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 208.121177757
• Heavy Atom Count: 15
• Complexity: 245

Purity/Quality:

99.0% ^*data from raw suppliers

Pilocarpine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+
• Statements: 26/28
• Safety Statements: 25-45

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Sj?gren Syndrome Agents
• Canonical SMILES: CCC1C(COC1=O)CC2=CN=CN2C
• Isomeric SMILES: CC[C@H]1[C@H](COC1=O)CC2=CN=CN2C
• Recent ClinicalTrials: Safety and Efficacy of Nyxol Eye Drops as a Single Agent and With Adjunctive Low-Dose Pilocarpine Eye Drops in Subjects With Presbyopia
• Recent NIPH Clinical Trials: Clinical research on the efficacy of pilocarpine hydrochloride administration from the early stage of treatment for the reduction of oral mucositis in oral cancer radiation therapy.
• Description: Pilocarpine acts by stimulating muscarinic receptors, therefore making it similar in action to acetylcholine when systematically introduced. This compound differs from acetylcholine in that it does not react with any nicotinic receptors, but by stimulating the CNS. Its effects are blocked by atropine. It has found therapeutic use in ophthalmology as a myotic agent.
• Physical properties: Appearance: colorless crystal or white crystalline powder. Solubility: freely soluble in water; slightly soluble in ethanol; insoluble in chloroform or diethyl ether. Melting point: 174–178?°C.
• Uses: Pilocarpine occurs in the leaves of variousspecies of pilocarpus. It is used as an antidotefor atropine poisoning and in ophthalmologyto produce contraction of the pupil.
• Clinical Use: Pilocarpine nitrate is mainly used to treat glaucoma clinically. Characterized with the progressive cupping of the optic disk, hypopsia, and elevated intraocular pressure, the severe patients will go blind. Patients with angle-closure glaucoma (congestive glaucoma) generally have the narrow anterior chamber angle, the obstruction of aqueous humor outflow, and the elevation of intraocular pressure, and these can be reversed by a low-concentration pilocarpine. But it is noted that a highconcentration pilocarpine will promote the progress of glaucoma. Pilocarpine is also used to treat open-angle glaucoma. The mechanism of the action is not entirely clear. Using atropine and pilocarpine alternately prevents posterior synechiae. In addition, pilocarpine is orally used to treat Zagari’s disease after neck radiotherapy, increasing salivary secretion and sweat secretion

Technology Process of Pilocarpine

There total 68 articles about Pilocarpine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 60.0%

[(p-methylphenyl)sulfonylmethyl]isonitrile (38622-91-2,36635-61-7) + 2-[(3R,4S)-4-ethyl-5-oxo-tetrahydro-3-furanyl]acetaldehyde (144128-27-8) + methylamine (74-89-5) → pilocarpine (92-13-7)

Guidance literature:

2-[(3R,4S)-4-ethyl-5-oxo-tetrahydro-3-furanyl]acetaldehyde; methylamine; With potassium carbonate; In dichloromethane; benzene; for 3h;

[(p-methylphenyl)sulfonylmethyl]isonitrile; With triethylamine; at 25 ℃; for 168h; Further stages.;

DOI:10.1016/j.tet.2008.07.100

Reference yield:

(R)-3-ethylidene-4-[(1-methylimidazol-5-yl)methyl]tetrahydrofuran-2-one (1192231-13-2) → pilocarpine (92-13-7) + isopilocarpine (531-35-1)

Guidance literature:

With platinum(IV) oxide; hydrogen; In methanol; at 20 ℃; for 24h; optical yield given as %de;

DOI:10.1016/j.tet.2009.07.010

Reference yield:

3-ethyl-dihydro-4-[(1-methyl-1H-2-mercaptoimidazol-5-yl)methyl]-2(3H)-furanone (858221-10-0) → pilocarpine (92-13-7)

Guidance literature:

With ammonium hydroxide; nitric acid; sodium nitrite; In water;

upstream raw materials:

demethylmedicalpin

methyl iodide

isopilocarpine

(3S)-cis-3-ethyl-4-(3-methyl-2-thioxo-2,3-dihydro-1H-imidazol-4-ylmethyl)-dihydro-furan-2-one

Downstream raw materials:

(+-)-isopilocarpine

4-((3R)-4-ethyl-5-oxo-tetrahydro-furan-3t-ylmethyl)-1,3-dimethyl-imidazolium; iodide

Isopilocarpinsaeure

methylammonium carbonate

Refernces

• 1、 Davies, Stephen G.,Roberts, Paul M.,Stephenson, Peter T.,Thomson, James E.. "Syntheses of the racemic jaborandi alkaloids pilocarpine, isopilocarpine and pilosinine". scheme or table. p. 3509 - 3512. Retrieved 2009/09/30.
• 2、 Braun, Manfred,Buehne, Corinna,Cougali, Dimitrula,Schaper, Klaus,Frank, Walter. "Convergent diastereoselective synthesis of isopilocarpine by one-pot Michael-addition-alkylation reaction". . p. 2905 - 2909. Retrieved 2007/10/03.