3-Hydroxymorphinan

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3-Hydroxymorphinan
Skeletal formula
Ball-and-stick model
Clinical data
ATC code
  • None
Pharmacokinetic data
Bioavailability18%
Identifiers
  • (±)-morphinan-3-ol
JSmol)
  • Oc3ccc4C[C@H]1NCC[C@@]2(CCCC[C@@H]12)c4c3
  • InChI=1S/C16H21NO/c18-12-5-4-11-9-15-13-3-1-2-6-16(13,7-8-17-15)14(11)10-12/h4-5,10,13,15,17-18H,1-3,6-9H2/t13-,15+,16+/m0/s1 checkY
  • Key:IYNWSQDZXMGGGI-NUEKZKHPSA-N checkY
 ☒NcheckY (what is this?)  (verify)

3-Hydroxymorphinan (3-HM), or morphinan-3-ol, is a

racemic counterpart to norlevorphanol
.

The

presynaptic voltage-dependent Ca2+ entry and protein kinase C activity.[7] In any case, as such, the compound has been investigated as a potential management of Parkinson's disease medication (antiparkinsonian agent). A prodrug, GCC1290K, has been developed on account of 3-HM's poor bioavailability (18%), and a New Drug Application has been approved for it by the United States Food and Drug Administration.[6] It is currently undergoing clinical trials for the treatment of Parkinson's disease.[6] It does not have a Controlled Substances Act 1970 schedule, ACSCN, or annual aggregate manufacturing quota and may not necessarily be controlled, whilst norlevorphanol is; none of the dextrorotary derivatives of the dromoran and norlevorphanol sub-families of morphinan derivatives are controlled as they do not have opioid activity but the other racemic compounds are.[8]

3-HM's

analogue levorphanol.[10]

(+)-3-Hydroxymorphinan the Dextro isomer of 3-hydroxymorphinan. The Dextro form is metabolite of 3-methoxymorphinan which is metabolite of Dextromethorphan

References

  1. ISBN 978-0-412-46630-4
    . Retrieved 29 November 2011.
  2. PMID 1306804
    .
  3. S2CID 13513164
    .
  4. S2CID 23032934
    .
  5. PMID 18198471
    .
  6. ^
    PMID 21606622
    .
  7. S2CID 23428637
    .
  8. ^ "Conversion Factors for Controlled Substances". Diversion Control Division. Drug Enforcement Agency, U.S. Department of Justice. Archived from the original on 2016-03-02. Retrieved 2016-02-27.
  9. ISBN 0-412-54090-8
    .
  10. ^ Bentham Science Publishers (April 1995). Current Medicinal Chemistry. Bentham Science Publishers. p. 425. Retrieved 29 November 2011.
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