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Pentamorphone
Systematic (IUPAC) name
4,5α-epoxy- 3-hydroxy- 14β-pentylamino- 17-methyl- 7,8-didehydro- morphinan- 6-one
Identifiers
CAS number 68616-83-1
ATC code none
PubChem 5464186
Chemical data
Formula C 22H28N2O3  
Mol. mass 368.469 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status Schedule I (US)
Routes  ?

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. In addition, pentamorphone has a particularly high dependence liability, even when compared to other potent narcotic analgesics such as morphine and heroin.

References

  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 Anaesthesia. 1994 Aug;41(8):703-9. PMID 7522977
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