Noroxymorphone

Noroxymorphone
Clinical data
Dependence; liability	High
Routes of; administration	Intravenous, intramuscular, subcutaneous, oral, rectal, intranasal
Drug class	Opioid
Legal status
Legal status	US: Schedule II;
Identifiers
	IUPAC name 7,8-Dihydro-14-hydroxynormorphinone;
CAS Number	33522-95-1;
PubChem CID	5497189;
DrugBank	DBMET00424;
ChemSpider	4593755;
UNII	9NZ7111A9O;
CompTox Dashboard (EPA)	DTXSID80955145 ;
ECHA InfoCard	100.046.859
Chemical and physical data
Formula	C16H17NO4
Molar mass	287.315 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Oc1ccc2C[C@H]3NCC[C@@]45[C@@H](Oc1c24)C(=O)CC[C@@]35O;
	InChI InChI=1S/C16H17NO4/c18-9-2-1-8-7-11-16(20)4-3-10(19)14-15(16,5-6-17-11)12(8)13(9)21-14/h1-2,11,14,17-18,20H,3-7H2/t11-,14+,15+,16-/m1/s1; Key:HLMSIZPQBSYUNL-IPOQPSJVSA-N;

Noroxymorphone is an opioid^[1] which is both a metabolite of oxymorphone and oxycodone and is manufactured specifically as an intermediate in the production of opioid antagonists such as naltrexone and others. It is a potent agonist of the μ-opioid receptor, but is poorly able to cross the blood–brain barrier into the central nervous system, and for this reason, has only minimal analgesic activity.^[2]^[3]^[1]

In the United States, noroxymorphone is controlled as a Schedule II Narcotic controlled substance with an ACSCN of 9637. In 2014, the DEA set annual aggregate manufacturing quotas of 17,500 kg for conversion and 1,262.5 kg for sale.^[4]

References

1 2 Lemberg KK, Siiskonen AO, Kontinen VK, Yli-Kauhaluoma JT, Kalso EA (February 2008). "Pharmacological characterization of noroxymorphone as a new opioid for spinal analgesia". Anesthesia and Analgesia. 106 (2): 463–70, table of contents. doi:10.1213/ane.0b013e3181605a15. PMID 18227301. S2CID 16524280.
↑ Preedy VR (25 April 2016). Neuropathology of Drug Addictions and Substance Misuse Volume 3: General Processes and Mechanisms, Prescription Medications, Caffeine and Areca, Polydrug Misuse, Emerging Addictions and Non-Drug Addictions. Elsevier Science. pp. 462–464. ISBN 978-0-12-800677-1.
↑ Smith H, Passik S (25 April 2008). Pain and Chemical Dependency. Oxford University Press, USA. pp. 195–. ISBN 978-0-19-530055-0.
↑ Drug Enforcement Administration (August 25, 2014). "Final Adjusted Aggregate Production Quotas for Schedule I and II Controlled Substances and Assessment of Annual Needs for the List I Chemicals Ephedrine, Pseudoephedrine, and Phenylpropanolamine for 2014". Federal Register. Vol. 79, no. 164. pp. 50700–50704. Archived from the original on March 4, 2016. Retrieved February 27, 2016.

[Lemberg_2008-1] 1 2 Lemberg KK, Siiskonen AO, Kontinen VK, Yli-Kauhaluoma JT, Kalso EA (February 2008). "Pharmacological characterization of noroxymorphone as a new opioid for spinal analgesia". Anesthesia and Analgesia. 106 (2): 463–70, table of contents. doi:10.1213/ane.0b013e3181605a15. PMID 18227301. S2CID 16524280.

[Preedy2016-2] Preedy VR (25 April 2016). Neuropathology of Drug Addictions and Substance Misuse Volume 3: General Processes and Mechanisms, Prescription Medications, Caffeine and Areca, Polydrug Misuse, Emerging Addictions and Non-Drug Addictions. Elsevier Science. pp. 462–464. ISBN 978-0-12-800677-1.

[SmithPassik2008-3] Smith H, Passik S (25 April 2008). Pain and Chemical Dependency. Oxford University Press, USA. pp. 195–. ISBN 978-0-19-530055-0.

[4] Drug Enforcement Administration (August 25, 2014). "Final Adjusted Aggregate Production Quotas for Schedule I and II Controlled Substances and Assessment of Annual Needs for the List I Chemicals Ephedrine, Pseudoephedrine, and Phenylpropanolamine for 2014". Federal Register. Vol. 79, no. 164. pp. 50700–50704. Archived from the original on March 4, 2016. Retrieved February 27, 2016.

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[4]

See also

References