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 names	Levophenacylmorphan
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	10061-32-2^Y
PubChem CID	5362482
ChemSpider	16736786^N
UNII	7Q24AL2BR2
CompTox Dashboard (EPA)	DTXSID90881401
ECHA InfoCard	100.030.168
Chemical and physical data
Formula	C24H27NO2
Molar mass	361.485 g·mol^−1
3D model (JSmol)	Interactive image
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

• 3-Hydroxymorphinan
• Levorphanol
• Norlevorphanol
• Phenomorphan

References

1. MAY, E.L. & EDDY, N.B., A New Potent Synthetic Analgesic, J. Org. Chem., 24 : 294, 1959.
2. Fraser HF, Isbell H. Human pharmacology and addiction liabilities of phenazocine and levophenacylmorphan. UN Bulletin on Narcotics. 1960 Issue 2