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Pilocarpinhydrochlorid Produkt Beschreibung

(+)-Pilocarpine hydrochloride Struktur
54-71-7
CAS-Nr.
54-71-7
Bezeichnung:
Pilocarpinhydrochlorid
Englisch Name:
(+)-Pilocarpine hydrochloride
Synonyma:
Sanpilo;Salagen;pilocar;pilocel;(3S,4R)-;Akarpine;ami-pilo;pilovisc;NSC 5746;amisturap
CBNumber:
CB1236112
Summenformel:
C11H17ClN2O2
Molgewicht:
244.72
MOL-Datei:
54-71-7.mol

Pilocarpinhydrochlorid Eigenschaften

Schmelzpunkt:
202-205 °C(lit.)
alpha 
89 º (C=5, H2O)
storage temp. 
2-8°C
Löslichkeit
H2O: 100 mg/mL
Aggregatzustand
powder
Farbe
white
Wasserlöslichkeit
soluble
Sensitive 
Hygroscopic
Merck 
14,7424
BRN 
4034491
Stabilität:
Hygroscopic
CAS Datenbank
54-71-7(CAS DataBase Reference)
EPA chemische Informationen
Pilocarpine monohydrochloride (54-71-7)

Sicherheit

Kennzeichnung gefährlicher T+,T
R-Sätze: 26/28-25-23
S-Sätze: 25-45
RIDADR  UN 1544 6.1/PG 3
WGK Germany  3
RTECS-Nr. TK1450000
3-8-10
HazardClass  6.1
PackingGroup  III
HS Code  29399990

Pilocarpinhydrochlorid Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:

R26/28:Sehr giftig beim Einatmen und Verschlucken.

S-Sätze Betriebsanweisung:

S25:Berührung mit den Augen vermeiden.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).

Chemische Eigenschaften

Crystalline Solid

Originator

Andre Carpine, Andre Laboratries Pvt. Ltd., India

Verwenden

Antiglaucoma agent; miotic; sialogogue.

Verwenden

Acetylcholine receptor agonist

Verwenden

(+)-Pilocarpine hydrochloride is a muscarinic M1 and M2 acetylcholine receptor agonist with pKB values of 5 and 3.7, respectively. Systemic administration of (+)-Pilocarpine hydrochloride is typically used as an animal model for temporal lobe epilepsy and can mimic the generation of complex partial seizures by producing changes in hippocampal neuron morphology, membrane properties, and synaptic responses.

Manufacturing Process

The 1-methylimidazole-5-aldehyde is easily accessible from sarcosine methyl ester hydrochloride and dimethylamino-2-azaprop-2-en-1 Pilocarpine ylidenedimethylammonium.
0.14 mol of ethyl diethylphosphonoethoxyacetate is slowly added dropwise with stirring and under inert gas to a suspension of 0.14 mol of NaH (paraffinfree) in 250 ml of abs. THF, the mixture is stirred for 1 h at 20°C and a solution of 0.093 mol of 1-methylimidazole-5-aldehyde in 100 ml of abs. THF is added dropwise. After stirring at 20°C for 10 min, the solvent is distilled off in vacuo, the residue is taken up in a little H2O, and the solution is acidified with 1 N HCl and washed several times with ether. The aqueous phase is rendered alkaline using 2 N NaOH with cooling (0°-5°C) and extracted several times with CH2Cl2. After drying of the organic extracts with Na2SO4, the solvent is removed in vacuo and 2-ethoxy-3-[(1-methyl-1H-imidazol-5yl)methyl]-acrilic acid ethyl ester. Yield: 99% of theory.
122 ml of 45% diisobutylaluminum hydride solution (328 mmol) are slowly added dropwise under inert gas, with stirring and ice cooling, to a solution of 137 mmol of 2-ethoxy-3-[(1-methyl-1H-imidazol-5-yl)methyl]-acrilic acid ethyl ester in 600 ml of abs. C6H6. Stirring of the mixture is continued for a further 30 min at 0°-5°C and 600 ml of CH3OH, then 100 ml of H2O, are slowly added. The hydroxide precipitate is filtered off with suction and washed several times with hot CH3OH. After drying of the combined filtrates the solvents are distilled off in vacuo and the residue is crystallized using C2H5OH. 2-ethoxy-3-[(1-methyl-1H-imidazol-5-yl)methyl]-prop-2-en-1-ol was obtained. Yield: 100% of theory. The crude product is pure enough for the subsequent reaction. Recrystallization of an analytical sample from CH3OH/acetone: melting point 129°C.
A solution of 58 mmol of 2-ethoxy-3-[(1-methyl-1H-imidazol-5-yl)methyl]prop-2-en-1-ol in 116.6 ml of HCl (= 116.6 mmol) is stirred at 30°-35°C for 1.5 h and concentrated in vacuo at the same temperature. The residual HCl is removed by distillation with CHCl3 in vacuo. After seeding, the residue crystallizes at 20°C (15 h) 1-hydroxy-3-[(1-methyl-1H-imidazol-5-yl)methyl]propan-2-one hydrochloride. The crystallizate is filtered off with suction, washed with a little CH3OH and dried in vacuo. Yield: 86% of theory; melting point 190°C.
About 80-90% of the equivalent amount of NaOCH3 solution in CH3OH is slowly added dropwise at 20°C with stirring and exclusion of moisture to a suspension of 21.24 mmol of 1-hydroxy-3-[(1-methyl-1H-imidazol-5yl)methyl]-propan-2-one hydrochloride in 80 ml of CH3OH, in the course of which the pH of 6.5 is not to be exceeded. The solvent is distilled off in vacuo at a maximum of 30°C and the residue of 1-hydroxy-3-[(1-methyl-1Himidazol-5-yl)methyl]-propan-2-one is purified by flash chromatography (silica gel; CHCl3/CH3OH). Yield: 100% of theory; viscous, orange-colored oil.
Catalytic amounts of 4-dimethylaminopyridine and a solution of 21.3 mmol of 1-hydroxy-3-[(1-methyl-1H-imidazol-5-yl)methyl]-propan-2-one in 80 ml of CH2Cl2 are added to a solution of 26.44 mmol of 2-diethylphosphonobutyric acid in 40 ml of purified CH2Cl2. After cooling to 0°-5°C, a solution of 23.5 mmol of dicyclohexylcarbodiimide in 60 ml of CH2Cl2 is added dropwise and the mixture is stirred for 1 h at 0°-5°C and for 2 h at 20°C. The crystallizeddicyclohexylurea is filtered off with suction and the filtrate is washed with H2O and saturated NaHCO3 solution. After drying of the organic phase the solvent is distilled off at 30°C in vacuo and the residue of 2-diethoxy-phosphoryl)butyric acid 3-[(1-methyl-1H-imidazol-5-yl)methyl]-2-oxo-propyl ester is purified by flash chromatography (silica gel; ethyl acetate/CH3OH). Yield: 95% of theory of a viscous, orange-colored oil.
A mixture of 5 mmol each of 80% NaH and 15-crown-5 in 50 ml of absol. toluene is stirred at 20°C under inert gas for 10 min and a solution of 5 mm

Trademarks

Pilopine (Alcon); Salagen (Millot Laboratories, France).

Therapeutic Function

Cholinergic

Allgemeine Beschreibung

Pilocarpine monohydrochlorideis the hydrochloride of an alkaloid obtainedfrom the dried leaflets of Pilocarpus jaborandi or P. microphyllus,in which it occurs to the extent of about 0.5% togetherwith other alkaloids.

Biologische Aktivität

Muscarinic agonist.

Clinical Use

Pilocarpine, the salt of an alkaloid obtained from Pilocarpus jaborandi, is an example of a muscarinic agonist that does not adhere to the traditional SAR. In 1876, Langley reported that extracts containing the alkaloid stimulated the end organs of parasympathetic neurons. The structure of pilocarpine was reported in 1901.
Pilocarpine is marketed as tablets (Salogen), an ophthalmic solution, and gel. It penetrates the eye well and is the miotic of choice for open-angle glaucoma and to terminate acute angle closure attacks. It also is used for the treatment of xerostomia (dryness of the mouth) caused by radiation therapy of the head and neck, Sjogren's syndrome, or as a side effect of some psychotropic drugs.

Sicherheitsprofil

Poison by ingestion, intraperitoneal, and intravenous routes. Experimental teratogenic and reproductive effects. Human systemic effects: cardiac changes. When heated to decomposition it emits very toxic fumes of HCl and NOx. See also PILOCARPINE.

Veterinary Drugs and Treatments

Pilocarpine is a miotic agent that is rarely used in the treatment of canine primary glaucoma. Pilocarpine causes the ciliary body muscle to constrict placing posteriorly directed tension on the base of the iris to mechanically pull open the iridocorneal angle structures. By causing miosis, it may prevent closure of the iridocorneal angle by preventing excess iris tissue from peripherally compromising the outflow of aqueous humor. Pilocarpine has also been used for diagnostic localization of parasympathetic denervation of the iris sphincter caused by lesions or trauma to Cranial Nerve III.
The popularity of treatment of KCS with ophthalmic cyclosporine and tacrolimus has been associated with a decline in the use of pilocarpine for this disease; however, pilocarpine is still used orally as the primary treatment of neurogenic keratoconjunctivitis sicca in dogs as this condition does not respond to cyclosporine or tacrolimus.

Pilocarpinhydrochlorid Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Pilocarpinhydrochlorid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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54-71-7(Pilocarpinhydrochlorid)Verwandte Suche:


  • Pilocarpine HCL & Nitrate
  • PIEFELTARRAENIN IA(SH)
  • Pilocarpine Hydrochloride (200 mg)
  • Pilocarpin Hydrochloride
  • (3S,4R)-
  • PILOCARPINE HCL(P)
  • Akarpine
  • AlMocarpin
  • Pilopine VS
  • (3S,4R)-3-Ethyldihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-2(3H)-furanone Hydrochloride
  • Pilocarpine Chloride
  • 2(3H)-Furanone, 3-ethyldihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-, hydrochloride (1:1), (3S,4R)-
  • NSC 5746 HCl
  • Sanpilo
  • Pilocarpal
  • Pilocarpine, monohydrochloride (8CI)
  • Salagen
  • Pilocarpinhydrochlorid
  • ALMOCARPINE HYDROCHLORIDE
  • 3-ETHYL-4-[(1-METHYL-5-IMIDAZOLYL)METHYL]TETRAHYDROFURAN-2-ONE HYDROCHLORIDE
  • (3S,4R)-4,5-DIHYDRO-3-ETHYL-4-(1-METHYL-1H-IMIDAZOL-5-YLMETHYL)-2(3H)-FURANONE HYDROCHLORIDE
  • (3S-CIS)-3-ETHYLDIHYDRO-4-[(1-METHYL-1H-IMIDAZOL-5-YL)METHYL]-2(3H)-FURANONE HYDROCHLORIDE
  • PILOCARPINE HCL
  • (+)-PILOCARPINE HYDROCHLORIDE
  • (3s-cis)-ochlorid
  • 3-ethyldihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-,monohydrochloride,(3S-cis)-2(3H)-Furanone
  • 3-ethyldihydro-4-[(1-methyl-1h-imidazol-5-yl)methyl]-2(3h)-furanonmonohydr
  • almocarpine
  • ami-pilo
  • amisturap
  • isopto-carpine
  • mi-piloophthsol
  • pilocar
  • pilocarpine,monohydrochloride
  • pilocarpinemuriate
  • pilocel
  • pilomiotin
  • pilovisc
  • PILOCARPINE HCL. USP
  • PILOCARPINE HYDROCHLORIDE USP
  • (+)-Pilocarpinehydrochloride,99%
  • Pilocarpine hydrochlororide
  • 2(3H)-Furanone, 3-ethyldihydro-4-(1-methyl-1H-imidazol-5-yl)methyl-, monohydrochloride, (3S,4R)-
  • PILOCARPINEHYDROCHLORIDE,CRYSTAL,USP
  • PILOCARPINE HCL(RG)
  • 2(3H)-Furanone, 3-ethyldihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-, monohydrochloride, (3S,4R)- (9CI)
  • 2(3H)-Furanone, 3-ethyldihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-, monohydrochloride, (3S-cis)-
  • Adsorbocarpine
  • NSC 5746
  • Pilocar SMP
  • Pilocarpine hydrocholoride
  • Pilocarpine-d3 HCl
  • 3-ethyl-4-[(1-methyl-1H-imidazol-5-yl)methyl]dihydro-2(3H)-furanone hydrochloride
  • Pilocarpine hydrochloride CRS
  • Pilocarpine hydrochl
  • PILOCARPINE HYDROCHLORIDE
  • 54-71-7
  • C11H16N2O2xHCl
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