Pentamorphone

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Pentamorphone
220px
Systematic (IUPAC) name
4,5α-Epoxy-3-hydroxy-14β-pentylamino-17-methyl-7,8-didehydromorphinan-6-one
Clinical data
Legal status
Identifiers
CAS Number 68616-83-1
ATC code none
PubChem CID: 5464186
ChemSpider 4576571
UNII MM4487B4MW YesY
KEGG D05416 YesY
Chemical data
Formula C22H28N2O3
Molecular mass 368.469 g/mol
  • 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)

Pentamorphone (14β-pentylaminomorphinone, RX-77989) is a semi-synthetic opiate derivative related to compounds such as morphine, hydromorphone 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.

References

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