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Chemistry

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Also known as: Fentanyl hcl, 1443-54-5, 59h156xy46, Fentanyl hydrochloride (jan), Fentanyl hydrochloride [jan], N-phenyl-n-[1-(2-phenylethyl)piperidin-4-yl]propanamide;hydrochloride
Molecular Formula
C22H29ClN2O
Molecular Weight
372.9  g/mol
InChI Key
LHCBOXPPRUIAQT-UHFFFAOYSA-N
FDA UNII
59H156XY46

Fentanyl Hydrochloride
Fentanyl Hydrochloride is the hydrochloride salt form of fentanyl, a synthetic, lipophilic phenylpiperidine opioid agonist with analgesic and anesthetic properties. Fentanyl selectively binds to the mu-receptor in the central nervous system (CNS) thereby mimicking the effects of endogenous opiates. Stimulation of the mu-subtype opioid receptor stimulates the exchange of GTP for GDP on the G-protein complex and subsequently inhibits adenylate cyclase. This results in a decrease in intracellular cAMP and leads to a reduction in the release of neurotransmitters such as substance P, GABA, dopamine, acetylcholine and noradrenaline. The analgesic effect of fentanyl is likely due to its metabolite morphine, which induces opening of G-protein-coupled inwardly rectifying potassium (GIRK) channels and blocks the opening of N-type voltage-gated calcium channels, thereby resulting in hyperpolarization and reduced neuronal excitability.
1 2D Structure

Fentanyl Hydrochloride

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]propanamide;hydrochloride
2.1.2 InChI
InChI=1S/C22H28N2O.ClH/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;/h3-12,21H,2,13-18H2,1H3;1H
2.1.3 InChI Key
LHCBOXPPRUIAQT-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3.Cl
2.2 Other Identifiers
2.2.1 UNII
59H156XY46
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. Fentanyl Hcl

2. 1443-54-5

3. 59h156xy46

4. Fentanyl Hydrochloride (jan)

5. Fentanyl Hydrochloride [jan]

6. N-phenyl-n-[1-(2-phenylethyl)piperidin-4-yl]propanamide;hydrochloride

7. Unii-59h156xy46

8. Ionsys (tn)

9. N-(1-phenethyl-4-piperidyl)propionanilide Hydrochloride

10. Mls002320669

11. Schembl242876

12. Chembl1201159

13. Dtxsid90162666

14. Propionanilide, N-(1-phenethyl-4-piperidyl)-, Hydrochloride

15. Fentanyl Hydrochloride [mart.]

16. Fentanyl Hydrochloride [who-dd]

17. Fentanyl Hydrochloride [ema Epar]

18. Smr001338815

19. Fentanyl Hydrochloride [orange Book]

20. D10811

21. Q27261701

22. Propanamide, N-phenyl-n-(1-(2-phenylethyl)-4-piperidinyl)-, Monohydrochloride

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 372.9 g/mol
Molecular Formula C22H29ClN2O
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count6
Exact Mass372.1968412 g/mol
Monoisotopic Mass372.1968412 g/mol
Topological Polar Surface Area23.6 Ų
Heavy Atom Count26
Formal Charge0
Complexity391
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Indication

Ionsys is indicated for the management of acute moderate to severe post-operative pain in adult patients.


Management of acute moderate to severe post-operative pain for use in a hospital setting only


Treatment of acute pain


5 Pharmacology and Biochemistry
5.1 ATC Code

N02AB03


N02AB03


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