(3S,4R)-3-ethyl-4-[(1-methyl-1H-imidazol-5-yl)methyl]oxolan-2-one hydrochloride

• ChemBase ID: 138368
• Molecular Formular: C11H17ClN2O2
• Molecular Mass: 244.71788
• Monoisotopic Mass: 244.09785547
• SMILES: CC[C@H]1[C@H](COC1=O)Cc1cncn1C.Cl
• Canonical SMILES: CC[C@@H]1C(=O)OC[C@@H]1Cc1cncn1C.Cl
• InChI: 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
• InChIKey: RNAICSBVACLLGM-GNAZCLTHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4R)-3-ethyl-4-[(1-methyl-1H-imidazol-5-yl)methyl]oxolan-2-one hydrochloride
• IUPAC Traditional name: pilocarpine hydrochloride
• Synonyms: (+)-Pilocarpine hydrochloride; (3S,4R)-4,5-Dihydro-3-ethyl-4-(1-methyl-1H-imidazol-5-ylmethyl)-2(3H)-furanone hydrochloride; Pilocarpine hydrochloride; (3S,4R)-3-Ethyldihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-2(3H)-furanone Hydrochloride; (+)-Pilocarpine Hydrochloride; Adsorbocarpine; Almocarpine; Isopto Carpine; NSC 5746; Pilocar; Pilocar SMP; Pilocarpal; Pilocarpine Chloride; Pilocarpine Hydrochloride; (+)-毛果芸香碱盐酸盐; (3S,4R)-4,5-二氢-3-乙基-4-(1-甲基-1H-咪唑-5-基甲基)-2(3H)-呋喃酮 盐酸盐; 匹鲁卡品 盐酸盐

Database IDs

• CAS Number: 54-71-7
• EC Number: 200-212-5
• MDL Number: MFCD00012722
• Beilstein Number: 4034491
• Merck Index: 147424
• PubChem SID: 24277862; 24898106; 162232624
• PubChem CID: 5909

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.44190395
• LogD (pH = 7.4): 0.9023369
• Log P: 0.94975144
• Molar Refractivity: 56.5342 cm^3
• Polarizability: 21.845087 Å^3
• Polar Surface Area: 44.12 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; H2O: soluble100 mg/mL; Water
• Apperance: white powder; White Solid
• Melting Point: 202-205 °C(lit.); 202-205°C; 204-205°C
• Optical Rotation: [α]25/D +90°, c = 2 in H2O

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Hygroscopic
• RTECS: TK1450000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 1544; UN1544
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3; III
• Risk Statements: 26/28
• Safety Statements: 25-45
• TSCA Listed: 是
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300 + H330; H300-H330
• GHS Precautionary statements: P260-P264-P284-P301 + P310-P310; P260-P301+P310-P304+P340-P320-P330-P405-P501A
• RID/ADR: UN 1544 6.1/PG 3
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... CHRM1(1128), CHRM2(1129), CHRM3(1131), CHRM4(1132), CHRM5(1133)

Product Information

• Purity: ≥98% (titration); ≥99.0% (AT); 99%
• Salt Data: HCl
• Suitability: meets USP testing specifications
• Description: L,L Isomer
• Empirical Formula (Hill Notation): C11H16N2O2 · HCl
• Classification: Genuine Natural Compounds

DETAILS

Sigma Aldrich - P0472

Biochem/physiol Actions
Nonselective muscarinic acetylcholine receptor agonist; used to produce an experimental model of epilepsy.

Sigma Aldrich - P6503

Biochem/physiol Actions
Nonselective muscarinic acetylcholine receptor agonist; used to produce an experimental model of epilepsy.
Caution
Hygroscopic, light sensitive
Other Notes
Shelf life of the powder is at least five years.
Packaging
5, 10, 50 g in poly bottle

Sigma Aldrich - 141887

Biochem/physiol Actions
Nonselective muscarinic acetylcholine receptor agonist; used to produce an experimental model of epilepsy.

Sigma Aldrich - 80475

Biochem/physiol Actions
Nonselective muscarinic acetylcholine receptor agonist; used to produce an experimental model of epilepsy.

Toronto Research Chemicals - P441500

Antiglaucoma agent; miotic; sialogogue.

REFERENCES

• Al-Badr, A.A., et al.: Anal. Profiles Drug Subs., 12, 385 (1983)
• Vivino, F.B., et al.: Arch. Intern. Med., 159, 174 (1983)
• Horiot, J.-C., et al.: Radiother. Oncol., 55, 233 (1983)