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.^[2] 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.^[3]

Levophenacylmorphan

Clinical data
Other names	Levophenacylmorphan
ATC code	none
Legal status
Legal status	BR: Class A1 (Narcotic drugs)[1] 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
KEGG	D12687 Y
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. Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
2. 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.
3. Fraser HF, Isbell H (January 1960). "Human pharmacology and addiction liabilities of phenazocine and levophenacylmorphan". Bulletin on Narcotics. 12 (2): 15–23.