Hydromorphinol

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)

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
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
 NY (what is this?)  (verify)

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. 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. Archived from the original on 2016-03-04. Retrieved 2016-02-27.
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