methyl 1-(2-phenylethyl)-4-(N-phenylpropanamido)piperidine-4-carboxylate

• ChemBase ID: 1322
• Molecular Formular: C24H30N2O3
• Molecular Mass: 394.5066
• Monoisotopic Mass: 394.22564283
• SMILES: O(C(=O)C1(N(c2ccccc2)C(=O)CC)CCN(CC1)CCc1ccccc1)C
• Canonical SMILES: CCC(=O)N(C1(CCN(CC1)CCc1ccccc1)C(=O)OC)c1ccccc1
• InChI: InChI=1S/C24H30N2O3/c1-3-22(27)26(21-12-8-5-9-13-21)24(23(28)29-2)15-18-25(19-16-24)17-14-20-10-6-4-7-11-20/h4-13H,3,14-19H2,1-2H3
• InChIKey: YDSDEBIZUNNPOB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 1-(2-phenylethyl)-4-(N-phenylpropanamido)piperidine-4-carboxylate
• IUPAC Traditional name: carfentanil
• Synonyms: 4-[(1-Oxopropyl)phenylamino]-1-(2-phenylethyl)-4-piperidinecarboxylic Acid Methyl Ester; Carfentanyl; R 31833; Carfentanil

Database IDs

• CAS Number: 59708-52-0
• PubChem SID: 160964782; 46505501
• PubChem CID: 62156
• CHEBI ID: 61084
• CHEMBL: 290429
• Chemspider ID: 55986
• DrugBank ID: DB01535
• Unique Ingredient Identifier: LA9DTA2L8F
• Wikipedia Title: Carfentanil

CALCULATED PROPERTIES

JChem

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.1664388
• LogD (pH = 7.4): 2.9341178
• Log P: 3.6675231
• Molar Refractivity: 114.376 cm^3
• Polarizability: 44.70643 Å^3
• Polar Surface Area: 49.85 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.7
• LOG S: -4.18
• Solubility (Water): 2.59e-02 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: Pale Yellow Oil

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer

Pharmacology Properties

• Admin Routes: Oral
• Half Life: 7.7 hrs
• Protein Bound: ?
• Legal Status: Class A (UK); Schedule II (US)

DETAILS

DrugBank - DB01535

• Drug Groups: illicit; experimental
• Indication: Carfentanil is similar (but more potent) to the opioid analgesic fentanyl. It is used as a tranquilizer for large animals.
• Pharmacology: Carfentanil acts primarily on the mu (some kappa and delta) opioid receptors as an agonist. It will induce similar effects of analgesia as other opioids, however, due to its potency, it will also induce strong side effects such as sedation. Consequently, that is why it is used as a tranquilizer for large animals.; ; Carfentanil interacts predominately with the opioid mu-receptor. These mu-binding sites are discretely distributed in the brain, spinal cord, and other tissues. It exerts its principal pharmacologic effects on the central nervous system. Its primary actions of therapeutic value are analgesia and sedation. Carfentanil also depresses the respiratory centers, depresses the cough reflex, and constricts the pupils.
• References: Wax PM, Becker CE, Curry SC: Unexpected "gas" casualties in Moscow: a medical toxicology perspective. Ann Emerg Med. 2003 May;41(5):700-5. [Pubmed]
• External Links: Wikipedia

Toronto Research Chemicals - C183480

A Fentanyl analogue as opioid receptor agonist.Controlled Substance.

REFERENCES

• Wax PM, Becker CE, Curry SC: Unexpected "gas" casualties in Moscow: a medical toxicology perspective. Ann Emerg Med. 2003 May;41(5):700-5. Pubmed
• Gear, et al.: Neuroscience, 66, 5 (1995)
• Boronat, et al.: Br. J. Pharmacol., 125, 175 ( 1998), Ozdogan., et al.: Eur. J. Pharmacol., 460, 127 (1995)