Noroxymorphone

{{Short description|Chemical compound}} {{Drugbox | IUPAC_name = 7,8-Dihydro-14-hydroxynormorphinone | image = Noroxymorphone.svg | image_class = skin-invert-image | width =  | tradename = | Drugs.com = | MedlinePlus = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = Schedule II | legal_DE = | dependency_liability = High (same oxymorphone) | routes_of_administration = intravenous, intramusucular, subcutaneous, oral, rectal, intranasal | CAS_number = 33522-95-1 | PubChem = 5497189 | DrugBank = DBMET00424 | ChemSpiderID = 4593755 | UNII = 9NZ7111A9O | C = 16 | H = 17 | N = 1 | O = 4 | molecular_weight = | smiles = Oc1ccc2C[C@H]3NCC[C@@]45[C@@H](Oc1c24)C(=O)CC[C@@]35O | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = HLMSIZPQBSYUNL-IPOQPSJVSA-N | synonyms = }}

'''Noroxymorphone''' is an opioid<ref name = "Lemberg_2008">{{cite journal | vauthors = Lemberg KK, Siiskonen AO, Kontinen VK, Yli-Kauhaluoma JT, Kalso EA | title = Pharmacological characterization of noroxymorphone as a new opioid for spinal analgesia | journal = Anesthesia and Analgesia | volume = 106 | issue = 2 | pages = 463–70, table of contents | date = February 2008 | pmid = 18227301 | doi = 10.1213/ane.0b013e3181605a15 | s2cid = 16524280 | doi-access = free }}</ref> which is both a metabolite of oxymorphone and oxycodone and is manufactured specifically as an intermediate in the production of narcotic 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.<ref name="Preedy2016">{{cite book| vauthors = Preedy VR |title=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|url=https://books.google.com/books?id=Yu9eBwAAQBAJ&pg=PA462|date=25 April 2016|publisher=Elsevier Science|isbn=978-0-12-800677-1|pages=462–464}}</ref><ref name="SmithPassik2008">{{cite book| vauthors = Smith H, Passik S |title=Pain and Chemical Dependency|url=https://books.google.com/books?id=T88C-9VTDXMC&pg=PA195|date=25 April 2008|publisher=Oxford University Press, USA|isbn=978-0-19-530055-0|pages=195–}}</ref><ref name = "Lemberg_2008" />

In the United States, noroxymorphone is controlled as a Schedule II Narcotic controlled substance with an ACSCN of 9637 and in 2014 the DEA set annual aggregate manufacturing quotas of 17 500 kilogrammes for conversion and 1262.5 kg for sale.<ref>{{cite magazine |url=http://www.deadiversion.usdoj.gov/fed_regs/quotas/2014/fr0825.htm |title=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 |magazine=Federal Register |volume=79 |issue=164 |pages=50700–50704 |author=Drug Enforcement Administration |date=August 25, 2014 |author-link=Drug Enforcement Administration |access-date=February 27, 2016 |archive-date=March 4, 2016 |archive-url=https://web.archive.org/web/20160304053357/http://www.deadiversion.usdoj.gov/fed_regs/quotas/2014/fr0825.htm |url-status=dead }}</ref> In other countries, it may be similarly controlled, controlled at a lower level, or regulated in another way.

== See also == * Oxymorphone hydrazone * Oxymorphol - a metabolite of oxymorphone and an intermediate in the creation of hydromorphone * Hydromorphone * Oxycodone * Norbuprenorphine * Norbinaltorphimine

== References == {{Reflist|2}}

Category:4,5-Epoxymorphinans Category:Semisynthetic opioids Category:German inventions Category:Hydroxyarenes Category:Ketones Category:Tertiary alcohols Category:Ethers Category:Mu-opioid receptor agonists Category:Euphoriants

{{analgesic-stub}} Category:Recreational drug metabolites