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Details

Stereochemistry ACHIRAL
Molecular Formula C22H27FN2O2
Molecular Weight 370.4604
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OCFENTANIL

SMILES

COCC(=O)N(C1CCN(CCC2=CC=CC=C2)CC1)C3=C(F)C=CC=C3

InChI

InChIKey=NYISTOZKVCMVEL-UHFFFAOYSA-N
InChI=1S/C22H27FN2O2/c1-27-17-22(26)25(21-10-6-5-9-20(21)23)19-12-15-24(16-13-19)14-11-18-7-3-2-4-8-18/h2-10,19H,11-17H2,1H3

HIDE SMILES / InChI
Ocfentanil, a compound structurally similar to the opioid analgesic fentanyl, was developed in the early 1990’s with the hope that it would provide a better clinical safety profile than fentanyl. The receptor pharmacology of ocfentanil appears to share pharmacodynamic effects with fentanyl and other μ opioid agonists, including analgesia, sedation, and respiratory depression. In rodents, ocfentanil was approximately 2.5 times more potent as an analgesic than fentanyl and had a shorter duration of action. Because the preclinical research suggested that ocfentanil had a better safety profile than fentanyl, it was selected for clinical evaluation. Like other μ opioid agonists, ocfentanil has been reported to produce itching, nausea, sedation, and severe respiratory depression. Chest pain, psychosis, and agitation have also been reported. In humans, however, ocfentanil had a similar potency (3 ug/kg ocfentanil produced effects that were comparable to 5 ug/kg fentanyl) and side-effects profile as fentanyl so further clinical development was discontinued. Ocfentanil is not approved in any country for medical useand is under national control in Canada, the United Kingdom, and China.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P35372|||G8XRH8|||Q5TDA1|||Q9UN57
Gene ID: 4988.0
Gene Symbol: OPRM1
Target Organism: Homo sapiens (Human)
PubMed

PubMed

TitleDatePubMed
Ocfentanil overdose fatality in the recreational drug scene.
2016 Sep
Fentanyls continue to replace heroin in the drug arena: the cases of ocfentanil and carfentanil.
2018
Patents

Patents

Sample Use Guides

Ocfentanil was evaluated as a supplement to anesthesia in a study involving 60 patients who were 18-65 years of age and undergoing elective surgery. Intravenous doses of 1, 3, and 5 ug/kg ocfentanil were compared to 5 ug/kg fentanyl. Under these conditions, the 3 ug/kg dose of ocfentanil produced effects (analgesia and sedation) that were comparable to 5 ug/kg fentanyl.
Route of Administration: Intravenous
Name Type Language
OCFENTANIL
INN  
INN  
Official Name English
N-(2-FLUOROPHENYL)-2-METHOXY-N-(1-(2-PHENYLETHYL)-4-PIPERIDINYL)ACETAMIDE
Systematic Name English
2'-FLUORO-2-METHOXY-N-(1-PHENETHYL)-4-PIPERIDYL)ACETANILIDE
Common Name English
ACETAMIDE, N-(2-FLUOROPHENYL)-2-METHOXY-N-(1-(2-PHENYLETHYL)-4-PIPERIDINYL)-
Systematic Name English
OCFENTANYL
Common Name English
ocfentanil [INN]
Common Name English
A 3217
Code English
Classification Tree Code System Code
DEA NO. 9838
Created by admin on Fri Dec 15 16:44:02 GMT 2023 , Edited by admin on Fri Dec 15 16:44:02 GMT 2023
WIKIPEDIA List_of_fentanyl_analogues
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NCI_THESAURUS C67413
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Code System Code Type Description
CAS
101343-69-5
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NCI_THESAURUS
C84024
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PUBCHEM
60575
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SMS_ID
100000083857
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WIKIPEDIA
OCFENTANIL
Created by admin on Fri Dec 15 16:44:02 GMT 2023 , Edited by admin on Fri Dec 15 16:44:02 GMT 2023
PRIMARY In human volunteers ocfentanil induces effective analgesia at 1 .MU.g/kg, while in doses up to 3 .MU.g/kg, analgesia and respiratory depression occurred in a dose-dependent manner. While a further study suggests that ocfentanil may be as effective as morphine in post-operative relief,(4) Ocfentanil was also studied as a supplement to general anaesthesia, in which the researchers concluded that it appears to be similar in action to fentanyl, with 3 .MU.g/kg of ocfentanil approximately equivalent to 5 .MU.g/kg of fentanyl.
EPA CompTox
DTXSID00869356
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FDA UNII
MX52WBC8EV
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MESH
C071395
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EVMPD
SUB09396MIG
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ChEMBL
CHEMBL2110917
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INN
6448
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WEB RESOURCE
OCFENTANIL
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