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Chemistry

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Also known as: Brifentanil [inn], 101345-71-5, 6gdt77pqbw, N-[(3r,4s)-1-[2-(4-ethyl-5-oxotetrazol-1-yl)ethyl]-3-methylpiperidin-4-yl]-n-(2-fluorophenyl)-2-methoxyacetamide, Brifentanilum, Brifentanyl
Molecular Formula
C20H29FN6O3
Molecular Weight
420.5  g/mol
InChI Key
KKMGCTVJCQYQPV-WBVHZDCISA-N
FDA UNII
6GDT77PQBW

Brifentanil
Brifentanil (also known as A-3331) is an analog of fentanyl, a potent opioid. This drug is classified as an opioid analgesic and was developed in the early 1990s. The effects of brifentanil are very similar to those of alfentanil, with strong but short lasting analgesia and sedation, and particularly notable itching and respiratory depression.
1 2D Structure

Brifentanil

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
N-[(3R,4S)-1-[2-(4-ethyl-5-oxotetrazol-1-yl)ethyl]-3-methylpiperidin-4-yl]-N-(2-fluorophenyl)-2-methoxyacetamide
2.1.2 InChI
InChI=1S/C20H29FN6O3/c1-4-25-20(29)26(23-22-25)12-11-24-10-9-17(15(2)13-24)27(19(28)14-30-3)18-8-6-5-7-16(18)21/h5-8,15,17H,4,9-14H2,1-3H3/t15-,17+/m1/s1
2.1.3 InChI Key
KKMGCTVJCQYQPV-WBVHZDCISA-N
2.1.4 Canonical SMILES
CCN1C(=O)N(N=N1)CCN2CCC(C(C2)C)N(C3=CC=CC=C3F)C(=O)COC
2.1.5 Isomeric SMILES
CCN1C(=O)N(N=N1)CCN2CC[C@@H]([C@@H](C2)C)N(C3=CC=CC=C3F)C(=O)COC
2.2 Other Identifiers
2.2.1 UNII
6GDT77PQBW
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1-(2-(4-ethyl-4,5-dihydro-5-oxo1h-tetrazolyl)ethyl)-3-methyl-4-(n-(2-fluorophenyl)methoxyacetamido)piperidine

2. A 3331

3. A-3331

4. A-3331.hcl

5. Brifentanil Hydrochloride

2.3.2 Depositor-Supplied Synonyms

1. Brifentanil [inn]

2. 101345-71-5

3. 6gdt77pqbw

4. N-[(3r,4s)-1-[2-(4-ethyl-5-oxotetrazol-1-yl)ethyl]-3-methylpiperidin-4-yl]-n-(2-fluorophenyl)-2-methoxyacetamide

5. Brifentanilum

6. Brifentanyl

7. N-[(3s,4r)-1-[2-(4-ethyl-5-oxotetrazol-1-yl)ethyl]-3-methylpiperidin-4-yl]-n-(2-fluorophenyl)-2-methoxyacetamide

8. Brifentanilo

9. Unii-6gdt77pqbw

10. Brifentanilum [inn-latin]

11. Brifentanilo [inn-spanish]

12. A-3331-

13. Brifentanil [who-dd]

14. Schembl488879

15. Dtxsid20143867

16. Db09172

17. Q4967117

18. (+/-)-cis-n-(1-(2-(4-ethyl-5-oxo-2-tetrazolin-1-yl)ethyl)-3-methyl-4-piperidyl)-2'-fluoro-2-methoxyacetanilide

19. Acetamide, N-((3r,4s)-1-(2-(4-ethyl-4,5-dihydro-5-oxo-1h-tetrazol-1-yl)ethyl)-3-methyl-4-piperidinyl)-n-(2-fluorophenyl)-2-methoxy-, Rel-

20. Acetamide, N-(1-(2-(4-ethyl-4,5-dihydro-5-oxo-1h-tetrazol-1-yl)ethyl)-3-methyl-4-piperidinyl)-n-(2-fluorophenyl)-2-methoxy-, Cis-

21. Acetamide, N-(1-(2-(4-ethyl-4,5-dihydro-5-oxo-1h-tetrazol-1-yl)ethyl)-3-methyl-4-piperidinyl)-n-(2-fluorophenyl)-2-methoxy-, Cis-(+/-)-

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 420.5 g/mol
Molecular Formula C20H29FN6O3
XLogP32.7
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count7
Rotatable Bond Count8
Exact Mass420.22851697 g/mol
Monoisotopic Mass420.22851697 g/mol
Topological Polar Surface Area81 Ų
Heavy Atom Count30
Formal Charge0
Complexity636
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1

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