Stereochemistry | ABSOLUTE |
Molecular Formula | C25H35NO4 |
Molecular Weight | 413.5497 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 7 / 7 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12OC3=C4C(C[C@H]5NCC[C@@]14[C@@]56CC[C@@]2(OC)[C@]([H])(C6)[C@](C)(O)C(C)(C)C)=CC=C3O
InChI
InChIKey=YOYLLRBMGQRFTN-IOMBULRVSA-N
InChI=1S/C25H35NO4/c1-21(2,3)22(4,28)16-13-23-8-9-25(16,29-5)20-24(23)10-11-26-17(23)12-14-6-7-15(27)19(30-20)18(14)24/h6-7,16-17,20,26-28H,8-13H2,1-5H3/t16-,17-,20-,22+,23-,24+,25-/m1/s1
Molecular Formula | C25H35NO4 |
Molecular Weight | 413.5497 |
Charge | 0 |
Count |
MOL RATIO
1 MOL RATIO (average) |
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 7 / 7 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Norbuprenorphine is a major metabolite of buprenorphine and potent agonist of μ, δ, and κ opioid receptors. Norbuprenorphine is the only known active metabolite of buprenorphine. It has been shown to be a respiratory depressant in rats, but only at concentrations at least 50-fold greater than those observed following application to humans of BuTrans 20 mcg/h. Compared with buprenorphine, norbuprenorphine causes minimal antinociception but greater respiratory depression. In rats, nor-buprenorphine had 1/50th the analgesic potency of buprenor-phine but 10-fold greater respiratory depressant potency. Norbuprenorphine is an in vitro substrate of the efflux transporter P-glycoprotein (Mdr1). Norbuprenorphine is an in vitro and in vivo substrate of P-glycoprotein. P-glycoprotein-mediated efflux influences brain access and antinociceptive, but not the respiratory, effects of norbuprenorphine.
CNS Activity
Approval Year
PubMed
Sample Use Guides
Sheep were administered 0.6 mg kg(-1) Norbuprenorphine as 4-min i.v. infusions.
Route of Administration:
Intravenous