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Chemistry

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Also known as: 120656-74-8, Trefentanil [inn], 36qm58lvgu, A-3665, N-[1-[2-(4-ethyl-5-oxotetrazol-1-yl)ethyl]-4-phenylpiperidin-4-yl]-n-(2-fluorophenyl)propanamide, Unii-36qm58lvgu
Molecular Formula
C25H31FN6O2
Molecular Weight
466.6  g/mol
InChI Key
RJSCINHYBGMIFT-UHFFFAOYSA-N
FDA UNII
36QM58LVGU

Trefentanil
Trefentanil (A-3665) is a fentanyl analogue opioid developed in 1992. It is more potent and shorter acting than alfentanil. Trefentanil is not used in clinics due to the severity of its respiratory depression, though it is still used in research.
1 2D Structure

Trefentanil

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
N-[1-[2-(4-ethyl-5-oxotetrazol-1-yl)ethyl]-4-phenylpiperidin-4-yl]-N-(2-fluorophenyl)propanamide
2.1.2 InChI
InChI=1S/C25H31FN6O2/c1-3-23(33)32(22-13-9-8-12-21(22)26)25(20-10-6-5-7-11-20)14-16-29(17-15-25)18-19-31-24(34)30(4-2)27-28-31/h5-13H,3-4,14-19H2,1-2H3
2.1.3 InChI Key
RJSCINHYBGMIFT-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCC(=O)N(C1=CC=CC=C1F)C2(CCN(CC2)CCN3C(=O)N(N=N3)CC)C4=CC=CC=C4
2.2 Other Identifiers
2.2.1 UNII
36QM58LVGU
2.3 Synonyms
2.3.1 MeSH Synonyms

1. A 3665

2. A-3665

2.3.2 Depositor-Supplied Synonyms

1. 120656-74-8

2. Trefentanil [inn]

3. 36qm58lvgu

4. A-3665

5. N-[1-[2-(4-ethyl-5-oxotetrazol-1-yl)ethyl]-4-phenylpiperidin-4-yl]-n-(2-fluorophenyl)propanamide

6. Unii-36qm58lvgu

7. Trefentanyl

8. Trefentanil [mart.]

9. Trefentanil [who-dd]

10. Chembl84617

11. Schembl397177

12. A-3665 Free Base

13. Dtxsid80152955

14. Db09181

15. L001379

16. Q7837766

17. N-(1-(2-(4-ethyl-4,5-dihydro-5-oxo-1h-tetrazol-1-yl)ethyl)-4-phenyl-4-piperidinyl)-n-(2-fluorophenyl)propanamide

18. Propanamide, N-(1-(2-(4-ethyl-4,5-dihydro-5-oxo-1h-tetrazol-1-yl)ethyl)-4-phenyl-4-piperidinyl)-n-(2-fluorophenyl)-

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 466.6 g/mol
Molecular Formula C25H31FN6O2
XLogP34.1
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count6
Rotatable Bond Count8
Exact Mass466.24925241 g/mol
Monoisotopic Mass466.24925241 g/mol
Topological Polar Surface Area71.8 Ų
Heavy Atom Count34
Formal Charge0
Complexity735
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1

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