U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C17H24N2O3
Molecular Weight 304.3847
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of N-METHYLCARFENTANIL

SMILES

CCC(=O)N(c1ccccc1)C2(CCN(C)CC2)C(=O)OC

InChI

InChIKey=KKEVIELPQLXPRR-UHFFFAOYSA-N
InChI=1S/C17H24N2O3/c1-4-15(20)19(14-8-6-5-7-9-14)17(16(21)22-3)10-12-18(2)13-11-17/h5-9H,4,10-13H2,1-3H3

HIDE SMILES / InChI

Molecular Formula C17H24N2O3
Molecular Weight 304.3847
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

Substance Class Chemical
Created
by admin
on Sat Jun 26 09:39:21 UTC 2021
Edited
by admin
on Sat Jun 26 09:39:21 UTC 2021
Record UNII
85WEL251JZ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
N-METHYLCARFENTANIL
Common Name English
METHYL 1-METHYL-4-(PHENYL(PROPANOYL)AMINO)PIPERIDINE-4-CARBOXYLATE
Common Name English
R 32395
Code English
R-32395
Common Name English
N-METHYLNORCARFENTANIL
Common Name English
N-METHYLNORCARFENTANYL
Common Name English
REMIFENTANIL HYDROCHLORIDE IMPURITY K [EP]
Common Name English
N-METHYLCARFENTANYL
Common Name English
4-PIPERIDINECARBOXYLIC ACID, 1-METHYL-4-((1-OXOPROPYL)PHENYLAMINO)-, METHYL ESTER
Systematic Name English
Classification Tree Code System Code
WIKIPEDIA List_of_fentanyl_analogues
Created by admin on Sat Jun 26 09:39:21 UTC 2021 , Edited by admin on Sat Jun 26 09:39:21 UTC 2021
Code System Code Type Description
FDA UNII
85WEL251JZ
Created by admin on Sat Jun 26 09:39:21 UTC 2021 , Edited by admin on Sat Jun 26 09:39:21 UTC 2021
PRIMARY
PUBCHEM
12298013
Created by admin on Sat Jun 26 09:39:21 UTC 2021 , Edited by admin on Sat Jun 26 09:39:21 UTC 2021
PRIMARY
CAS
59708-50-8
Created by admin on Sat Jun 26 09:39:21 UTC 2021 , Edited by admin on Sat Jun 26 09:39:21 UTC 2021
PRIMARY
WEB RESOURCE
N-METHYLCARFENTANIL
Created by admin on Sat Jun 26 09:39:21 UTC 2021 , Edited by admin on Sat Jun 26 09:39:21 UTC 2021
PRIMARY
WIKIPEDIA
N-Methylnorcarfentanil
Created by admin on Sat Jun 26 09:39:21 UTC 2021 , Edited by admin on Sat Jun 26 09:39:21 UTC 2021
PRIMARY N-Methylnorcarfentanil (R-32395) is an opioid analgesic drug related to the highly potent animal tranquilizer carfentanil, but several thousand times weaker, being only slightly stronger than morphine. It was first synthesised by a team of chemists at Janssen Pharmaceutica led by Paul Janssen, who were investigating the structure-activity relationships of the fentanyl family of drugs. They found that replacing the phenethyl group attached to the piperidine nitrogen of fentanyl with a smaller methyl group, made it so much weaker that it was inactive as an analgesic in animals. However the same change made to the more potent analogue carfentanil retained reasonable opioid receptor activity, reflecting the higher binding affinity produced by the 4-carbomethoxy group.
Related Record Type Details
TARGET -> AGONIST
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY