2-hydroxypropane-1,2,3-tricarboxylic acid; N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]propanamide

• ChemBase ID: 131217
• Molecular Formular: C28H36N2O8
• Molecular Mass: 528.59404
• Monoisotopic Mass: 528.24716612
• SMILES: CCC(=O)N(c1ccccc1)C1CCN(CC1)CCc1ccccc1.C(C(=O)O)C(CC(=O)O)(C(=O)O)O
• Canonical SMILES: OC(=O)CC(C(=O)O)(CC(=O)O)O.CCC(=O)N(c1ccccc1)C1CCN(CC1)CCc1ccccc1
• InChI: InChI=1S/C22H28N2O.C6H8O7/c1-2-22(25)24(20-11-7-4-8-12-20)21-14-17-23(18-15-21)16-13-19-9-5-3-6-10-19;7-3(8)1-6(13,5(11)12)2-4(9)10/h3-12,21H,2,13-18H2,1H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
• InChIKey: IVLVTNPOHDFFCJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxypropane-1,2,3-tricarboxylic acid; N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]propanamide
• IUPAC Traditional name: citro; fentanyl
• Synonyms: N-Phenyl-N-[1-(2-phenylethyl)-4-piperidinyl]propanamide citrate salt; Fentanyl citrate salt; N-(Phenyl)-N-(1-[2-phenylethyl]-4-piperidinyl)propanamide Citrate; Sublimaze; Oravescent; NasalFent; Oralet; Fentaz; Leptanal; Leptanol; Duragesic; Fentanyl Citrate

Database IDs

• CAS Number: 990-73-8
• EC Number: 213-588-0
• MDL Number: MFCD00058359
• PubChem SID: 162225495
• PubChem CID: 13810

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.7473339
• LogD (pH = 7.4): 2.432824
• Log P: 3.8154986
• Molar Refractivity: 103.4825 cm^3
• Polarizability: 40.300232 Å^3
• Polar Surface Area: 23.55 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 153-156°C

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer, Under Inert Atmosphere
• RTECS: UE5600000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 26/27/28-42/43
• Safety Statements: 36/37/39-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H317-H330-H334
• GHS Precautionary statements: P260-P264-P280-P284-P301 + P310-P302 + P350
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2
• Drug Control: USDEA Schedule II; Home Office Schedule 2; stupéfiant; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada

DETAILS

Sigma Aldrich - F3886

Biochem/physiol Actions
Phenylpiperidine analgesic that is 80 times more potent than morphine as an analgesic and 6000 times more potent than morphine as a μ opioid receptor agonist.

Toronto Research Chemicals - F275000

Used as an analgesic. Controlled substance

REFERENCES

• Zernig, G., et al.: Life Sci., 57, 2113 (1995)
• Bot, G., et al.: J. Pharmacol. Exper. Therap., 285, 1207 (1995)