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Details

Stereochemistry ACHIRAL
Molecular Formula C25H31FN6O2
Molecular Weight 466.551
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TREFENTANIL

SMILES

CCN1N=NN(CCN2CCC(CC2)(N(C(=O)CC)C3=C(F)C=CC=C3)C4=CC=CC=C4)C1=O

InChI

InChIKey=RJSCINHYBGMIFT-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C25H31FN6O2
Molecular Weight 466.551
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Trefentanil is a short-acting synthetic opioid of the piperidine class. The drug caused potent analgesia with the peak effect occurring 3 min after injection. There was no significant difference in analgesic potency of trefentanil and alfentanil as measured by tolerance to tibial pressure at 3 min. Trefentanil had a pharmacokinetic and pharmacodynamic profile similar to alfentanil, with a small extent of tissue distribution and a rapid blood/brain equilibration. Trefentanil caused significant respiratory depression at doses of 32 ug/kg and 64 ug/kg. It is a mu-opioid receptor agonist. Trefentanil produced naloxone reversible anti-nociception equi-efficacious to that of fentanyl.

Approval Year

PubMed

PubMed

TitleDatePubMed
Mu opiate active substances trefentanil and naloxonazine: tritiation at high specific activity.
2005 Aug
Patents

Patents

Substance Class Chemical
Created
by admin
on Thu Jul 06 02:02:32 UTC 2023
Edited
by admin
on Thu Jul 06 02:02:32 UTC 2023
Record UNII
36QM58LVGU
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TREFENTANIL
INN   MART.   WHO-DD  
INN  
Official Name English
N-(1-(2-(4-ETHYL-4,5-DIHYDRO-5-OXO-1H-TETRAZOL-1-YL)ETHYL)-4-PHENYL-4-PIPERIDINYL)-N-(2-FLUOROPHENYL)PROPANAMIDE
Systematic Name English
trefentanil [INN]
Common Name English
A-3665
Code English
A-3665 FREE BASE
Code English
TREFENTANIL [MART.]
Common Name English
TREFENTANYL
Common Name English
Trefentanil [WHO-DD]
Common Name English
PROPANAMIDE, N-(1-(2-(4-ETHYL-4,5-DIHYDRO-5-OXO-1H-TETRAZOL-1-YL)ETHYL)-4-PHENYL-4-PIPERIDINYL)-N-(2-FLUOROPHENYL)-
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C67413
Created by admin on Thu Jul 06 02:02:32 UTC 2023 , Edited by admin on Thu Jul 06 02:02:32 UTC 2023
NCI_THESAURUS C241
Created by admin on Thu Jul 06 02:02:32 UTC 2023 , Edited by admin on Thu Jul 06 02:02:32 UTC 2023
WIKIPEDIA List_of_fentanyl_analogues
Created by admin on Thu Jul 06 02:02:32 UTC 2023 , Edited by admin on Thu Jul 06 02:02:32 UTC 2023
Code System Code Type Description
WIKIPEDIA
TREFENTANIL
Created by admin on Thu Jul 06 02:02:32 UTC 2023 , Edited by admin on Thu Jul 06 02:02:32 UTC 2023
PRIMARY Trefentanil has very similar effects to alfentanil, much like those of fentanyl itself but more potent and shorter lasting. Side effects of fentanyl analogs are similar to those of fentanyl itself, which include itching, nausea and potentially serious respiratory depression, which can be life-threatening. The risk of respiratory depression is especially high with potent fentanyl analogues such as alfentanil and trefentanil, and these drugs pose a significant risk of death if used outside of a hospital setting with appropriate artificial breathing apparatus available.
SMS_ID
100000077499
Created by admin on Thu Jul 06 02:02:32 UTC 2023 , Edited by admin on Thu Jul 06 02:02:32 UTC 2023
PRIMARY
EVMPD
SUB11229MIG
Created by admin on Thu Jul 06 02:02:32 UTC 2023 , Edited by admin on Thu Jul 06 02:02:32 UTC 2023
PRIMARY
MESH
C080498
Created by admin on Thu Jul 06 02:02:32 UTC 2023 , Edited by admin on Thu Jul 06 02:02:32 UTC 2023
PRIMARY
INN
6934
Created by admin on Thu Jul 06 02:02:32 UTC 2023 , Edited by admin on Thu Jul 06 02:02:32 UTC 2023
PRIMARY
CAS
120656-74-8
Created by admin on Thu Jul 06 02:02:32 UTC 2023 , Edited by admin on Thu Jul 06 02:02:32 UTC 2023
PRIMARY
ChEMBL
CHEMBL84617
Created by admin on Thu Jul 06 02:02:32 UTC 2023 , Edited by admin on Thu Jul 06 02:02:32 UTC 2023
PRIMARY
WEB RESOURCE
TREFENTANIL
Created by admin on Thu Jul 06 02:02:32 UTC 2023 , Edited by admin on Thu Jul 06 02:02:32 UTC 2023
PRIMARY
EPA CompTox
DTXSID80152955
Created by admin on Thu Jul 06 02:02:32 UTC 2023 , Edited by admin on Thu Jul 06 02:02:32 UTC 2023
PRIMARY
DRUG BANK
DB09181
Created by admin on Thu Jul 06 02:02:32 UTC 2023 , Edited by admin on Thu Jul 06 02:02:32 UTC 2023
PRIMARY
NCI_THESAURUS
C152720
Created by admin on Thu Jul 06 02:02:32 UTC 2023 , Edited by admin on Thu Jul 06 02:02:32 UTC 2023
PRIMARY
FDA UNII
36QM58LVGU
Created by admin on Thu Jul 06 02:02:32 UTC 2023 , Edited by admin on Thu Jul 06 02:02:32 UTC 2023
PRIMARY
PUBCHEM
60728
Created by admin on Thu Jul 06 02:02:32 UTC 2023 , Edited by admin on Thu Jul 06 02:02:32 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> AGONIST
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY