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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 (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 Formula	C₂₅H₃₁FN₆O₂
Molecular Weight	466.6 g/mol
XLogP3	4.1
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	8
Exact Mass	466.24925241 g/mol
Monoisotopic Mass	466.24925241 g/mol
Topological Polar Surface Area	71.8 Å²
Heavy Atom Count	34
Formal Charge	0
Complexity	735
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	1