Pentamorphone

Pentamorphone (14β-pentylaminomorphinone, RX-77989) is a semi-synthetic opiate derivative related to compounds such as Morphinone and oxymorphone. Developed in 1984, it is a potent opioid analgesic several times stronger than fentanyl, and with a similarly fast onset of effects and short duration of action.[1][2] It was found to produce relatively little respiratory depression compared to other potent opioid agonists,[3] but its analgesic effects were somewhat disappointing in human trials,[4] and while pentamorphone had some slight advantages over fentanyl[5] these were not sufficient to warrant its introduction into clinical use.

Pentamorphone
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
  • 4,5α-Epoxy-3-hydroxy-14β-pentylamino-17-methyl-7,8-didehydromorphinan-6-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
Chemical and physical data
FormulaC22H28N2O3
Molar mass368.477 g·mol−1
3D model (JSmol)
  • CCCCCN[C@@]12C=CC(=O)[C@H]3[C@@]14CCN([C@@H]2CC5=C4C(=C(C=C5)O)O3)C
  • InChI=1S/C22H28N2O3/c1-3-4-5-11-23-22-9-8-16(26)20-21(22)10-12-24(2)17(22)13-14-6-7-15(25)19(27-20)18(14)21/h6-9,17,20,23,25H,3-5,10-13H2,1-2H3/t17-,20+,21+,22-/m1/s1
  • Key:NRPCWSUJMWEFOK-KDXIVRHGSA-N
  (verify)

References
  1. Glass PS, Camporesi EM, Shafron D, Quill T, Reves JG (March 1989). "Evaluation of pentamorphone in humans: a new potent opiate". Anesthesia and Analgesia. 68 (3): 302–7. doi:10.1213/00000539-198903000-00021. PMID 2465708. S2CID 35949040.
  2. Rudo FG, Wynn RL, Ossipov M, Ford RD, Kutcher BA, Carter A, Spaulding TC (October 1989). "Antinociceptive activity of pentamorphone, a 14-beta-aminomorphinone derivative, compared to fentanyl and morphine". Anesthesia and Analgesia. 69 (4): 450–6. doi:10.1213/00000539-198910000-00005. PMID 2476953. S2CID 6715423.
  3. Afifi MS, Glass PS, Cohen NA, Shook JE, Camporesi EM (October 1990). "Depression of ventilatory responses to hypoxia and hypercapnia after pentamorphone". Anesthesia and Analgesia. 71 (4): 377–83. doi:10.1213/00000539-199010000-00010. PMID 1698039. S2CID 30738025.
  4. Wong HY, Parker RK, Fragen R, White PF (May 1991). "Pentamorphone for management of postoperative pain". Anesthesia and Analgesia. 72 (5): 656–60. doi:10.1213/00000539-199105000-00015. PMID 1708214. S2CID 30636072.
  5. Kelly WB, Howie MB, Romanelli VA, Duarte JA, Rezaei H, McSweeney TD (August 1994). "A comparison of pentamorphone and fentanyl in balanced anaesthesia during general surgery". Canadian Journal of Anaesthesia. 41 (8): 703–9. doi:10.1007/BF03015625. PMID 7522977.
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