Hydromorphinol

Hydromorphinol
Clinical data
Other namesHydromorphinol,
14-hydroxy-7,8-dihydromorphine,
RAM-320
ATC code
  • none
Legal status
Legal status
  • AU: S8 (Controlled drug)
  • CA: Schedule I
  • DE: Anlage I (Authorized scientific use only)
  • US: Schedule I
Identifiers
IUPAC name
  • (5α,6α)-3,6,14-Trihydroxy-4,5-epoxy-17-methylmorphinan
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.016.878
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Chemical and physical data
FormulaC17H21NO4
Molar mass303.358 g·mol−1
3D model (JSmol)
SMILES
  • CN1CC[C@]23[C@@H]4[C@H](CC[C@]2([C@H]1CC5=C3C(=C(C=C5)O)O4)O)O
InChI
  • InChI=1S/C17H21NO4/c1-18-7-6-16-13-9-2-3-10(19)14(13)22-15(16)11(20)4-5-17(16,21)12(18)8-9/h2-3,11-12,15,19-21H,4-8H2,1H3/t11-,12+,15-,16-,17+/m0/s1 ☒N
  • Key:AABLHGPVOULICI-BRJGLHKUSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Hydromorphinol (RAM-320, 14-Hydroxydihydromorphine),[1] also is an opiate analogue that is a derivative of morphine, where the 14-position has been hydroxylated and the 7,8- double bond saturated.[2] It has similar effects to morphine such as sedation, analgesia and respiratory depression, but is twice as potent as morphine[1] and has a steeper dose-response curve and longer half-life.[3] It is used in medicine as the bitartrate salt (free base conversion ratio 0.643, molecular weight 471.5) and hydrochloride (free base conversion ratio 0.770, molecular weight 393.9)

It is also called α-Oxymorphol, and oxymorphol is itself a mixture of hydromorphinol and 4,5α-Epoxy-17-methylmorphinan-3,6β,14-triol, β-Oxymorphol, which is different at position 6 on the morphine carbon skeleton.[4]

Hydromorphinol was developed in Austria in 1932. In the United States, it was never available and is classified as a Schedule I drug with a DEA ACSCN of 9301. The salts in use are the bitartrate (free base conversion ratio 0.643) and hydrochloride (0.770). The 2014 national aggregate manufacturing quota was 2 grams, unchanged from prior years.[5]

Hydromorphinol is metabolised mainly in the liver in the same fashion as many other opioids and is itself a minor active metabolite of 14-Hydroxydihydrocodeine, an uncommonly used opiate (but is therefore also an active metabolite of a first-order active metabolite of oxycodone).

It is distributed under the trade name Numorphan in some countries. It is controlled under the Single Convention On Narcotic Drugs.

See also

References

  1. 1 2 US 2960505, Weiss U, "Morphine derivative", published 11/15/1960
  2. ↑ Weiss U, Daum SJ (January 1965). "Derivatives of Morphine. IV.114-Hydroxymorphine and 14-Hydroxydihydromorphine". Journal of Medicinal Chemistry. 8: 123–5. doi:10.1021/jm00325a028. PMID 14287245.
  3. ↑ Plummer JL, Cmielewski PL, Reynolds GD, Gourlay GK, Cherry DA (March 1990). "Influence of polarity on dose-response relationships of intrathecal opioids in rats". Pain. 40 (3): 339–47. doi:10.1016/0304-3959(90)91131-2. PMID 2326098. S2CID 2100412.
  4. ↑ "Hydromorphinol CAS#: 2183-56-4". Chemical Book.
  5. ↑ "Quotas 2014". DEA Diversion Control Division.
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