Fentanyl Hydrochloride

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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 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 Formula	C₂₂H₂₉ClN₂O
Molecular Weight	372.9 g/mol
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	6
Exact Mass	372.1968412 g/mol
Monoisotopic Mass	372.1968412 g/mol
Topological Polar Surface Area	23.6 Å²
Heavy Atom Count	26
Formal Charge	0
Complexity	391
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2