methyl 1-(3-methoxy-3-oxopropyl)-4-(N-phenylpropanamido)piperidine-4-carboxylate hydrochloride

• ChemBase ID: 153234
• Molecular Formular: C20H29ClN2O5
• Molecular Mass: 412.90766
• Monoisotopic Mass: 412.17649972
• SMILES: CCC(=O)N(c1ccccc1)C1(CCN(CC1)CCC(=O)OC)C(=O)OC.Cl
• Canonical SMILES: COC(=O)C1(CCN(CC1)CCC(=O)OC)N(c1ccccc1)C(=O)CC.Cl
• InChI: InChI=1S/C20H28N2O5.ClH/c1-4-17(23)22(16-8-6-5-7-9-16)20(19(25)27-3)11-14-21(15-12-20)13-10-18(24)26-2;/h5-9H,4,10-15H2,1-3H3;1H
• InChIKey: WFBMIPUMYUHANP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 1-(3-methoxy-3-oxopropyl)-4-(N-phenylpropanamido)piperidine-4-carboxylate hydrochloride
• IUPAC Traditional name: remifentanil hydrochloride
• Synonyms: 4-(Methoxycarbonyl)-4-[(1-oxopropyl)phenylamino]-1-piperidinepropanoic Acid Methyl Ester Hydrochloride; Remifentanyl Hydrochloride; GI 87084B; Remifentanil Hydrochloride; 3-[methoxycarbonyl-4-[(1-oxopropyl)phenylamino]1-piperidine]propanoic acid methyl ester hydrochloride; GI-87084B; Remifentanyl; Ultiva; Remifentanil hydrochloride

Database IDs

• CAS Number: 132539-07-2
• MDL Number: MFCD00910882
• PubChem SID: 162247373
• PubChem CID: 60814

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -0.48355016
• LogD (pH = 7.4): 1.1568937
• Log P: 1.5152788
• Molar Refractivity: 100.5615 cm^3
• Polarizability: 39.659138 Å^3
• Polar Surface Area: 76.15 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; H2O: ≥20 mg/mL; Methanol
• Apperance: white to off-white powder; White to Off-White Solid
• Melting Point: 192-197°C

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer
• German water hazard class: 3
• Drug Control: USDEA Schedule II
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97% (HPLC)
• Empirical Formula (Hill Notation): C20H28N2O5·HCl

DETAILS

Sigma Aldrich - R1908

Biochem/physiol Actions
Remifentanil hydrochloride is a mu opioid receptor agonist, anesthetic, and analgesic compound. Remifentanil was developed as an ultra-short-acting mu opioid receptor agonist with improved pharmacodynamic properties.

Toronto Research Chemicals - R143500

Labelled synthetic mu-opioid agonist. This is a controlled substance (opiate).

REFERENCES

• James, M.K., et al.: J. Pharmacol. Exp. Ther., 259, 712 (1991)
• Hoffman, W.E., et al.: Anesthesiology, 79, 107 (1991)
• Selinger, K., et al.: J. Pharm. Biomed. Anal., 12, 243 (1991)
• Richardson, T.D., et al.: Expert Opin. Drug Saf., 4, 643 (1991)