Levophenacylmorphan

Levophenacylmorphan is a morphinan derivative that acts as an opioid agonist. It has potent analgesic effects and is around 10x more potent than morphine.[1] Adverse effects associated with its use are those of the opioids as a whole, including pruritus, nausea, respiratory depression, euphoria and development of tolerance and dependence to its effects.[2]

Levophenacylmorphan
Clinical data
Other namesLevophenacylmorphan
ATC code
  • none
Legal status
Legal status
  • CA: Schedule I
  • DE: Anlage I (Authorized scientific use only)
  • US: Schedule I
Identifiers
IUPAC name
  • (−)-3-Hydroxy-N-phenacylmorphinan
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.030.168
Chemical and physical data
FormulaC24H27NO2
Molar mass361.485 g·mol−1
3D model (JSmol)
SMILES
  • C1CC[C@@]23CCN([C@@H]([C@@H]2C1)CC4=C3C=C(C=C4)O)CC(=O)C5=CC=CC=C5
InChI
  • InChI=1S/C24H27NO2/c26-19-10-9-18-14-22-20-8-4-5-11-24(20,21(18)15-19)12-13-25(22)16-23(27)17-6-2-1-3-7-17/h1-3,6-7,9-10,15,20,22,26H,4-5,8,11-14,16H2/t20-,22+,24+/m0/s1 N
  • Key:RCYBMSQOSGJZLO-BGWNEDDSSA-N N
 NY (what is this?)  (verify)

See also

References
  1. May E, Eddy N (February 1959). "A New Potent Synthetic Analgesic". Communications. The Journal of Organic Chemistry. 24 (2): 294–5. doi:10.1021/jo01084a655.
  2. Fraser HF, Isbell H (January 1960). "Human pharmacology and addiction liabilities of phenazocine and levophenacylmorphan". Bulletin on Narcotics. 12 (2): 15–23.


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