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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:35:42 UTC
Update Date2019-07-23 06:05:59 UTC
HMDB IDHMDB0030251
Secondary Accession Numbers
  • HMDB30251
Metabolite Identification
Common NameOripavine
DescriptionOripavine belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic. Oripavine is a very strong basic compound (based on its pKa). The simple bridged oripavine parent compound 6,14-Endoethenotetrahydrooripavine is already 40 times the potency of morphine, but adding a branched tertiary alcohol substituent on the C7 position results in a wide range of highly potent compounds. Outside of the human body, oripavine has been detected, but not quantified in, several different foods, such as radish, cocoa beans, black radish, alpine sweetvetchs, and rocket salad. This could make oripavine a potential biomarker for the consumption of these foods. Replacing the N-methyl group with cyclopropylmethyl results in opioid antagonists such as diprenorphine (M5050, which is used as an antidote to reverse the effects of etorphine, M99), and partial agonists such as buprenorphine, which is widely used in the treatment of opioid addiction. Due to its use in manufacture of strong opioids, oripavine is a controlled substance in some jurisdictions. Oripavine possesses an analgesic potency comparable to morphine; however, it is not clinically useful due to severe toxicity and low therapeutic index. It is the parent compound from which a series of semi-synthetic opioids are derived, which includes the compounds etorphine and buprenorphine. On September 24, 2007, the Drug Enforcement Administration formally added oripavine to Schedule II.Under the Controlled Substances Act 1970, oripavine has an ACSCN of 9330 and a 2013 manufacturing quota of 22,750 kg (50,160 lb). Oripavine has a potential for dependence which is significantly greater than that of thebaine but slightly less than that of morphine. Oripavine is an opiate and the major metabolite of thebaine. Of much greater relevance are the properties of the orvinols, a large family of semi-synthetic oripavine derivatives classically synthesized by the Diels-Alder reaction of thebaine with an appropriate dienophile followed by 3-O-demethylation to the corresponding bridged oripavine. This molecule is biosynthetically related to the morphinane derivatives metabolism, where thebaine and morphine are implicated. These compounds were developed by the group led by K. W. Bentley in the 1960s, and these Bentley compounds represent the first series of "super-potent" μ-opioid agonists, with some compounds in the series being over 10,000 times the potency of morphine as an analgesic. On March 14, 2007, the United Nations Commission on Narcotic Drugs formally decided to accept these recommendations, and placed oripavine in the Schedule I.Until recently, oripavine was a Schedule II drug in the United States by default as a thebaine derivative, although it was not explicitly listed.
Structure
Data?1563861959
Synonyms
ValueSource
6,7,8,14-Tetradehydro-4,5-epoxy-6-methoxy-17-methylmorphinan-3-olHMDB
Chemical FormulaC18H19NO3
Average Molecular Weight297.3484
Monoisotopic Molecular Weight297.136493479
IUPAC Name14-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,14,16-pentaen-10-ol
Traditional Name14-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,14,16-pentaen-10-ol
CAS Registry Number467-04-9
SMILES
COC1=CC=C2C3CC4=C5C(OC1C25CCN3C)=C(O)C=C4
InChI Identifier
InChI=1S/C18H19NO3/c1-19-8-7-18-11-4-6-14(21-2)17(18)22-16-13(20)5-3-10(15(16)18)9-12(11)19/h3-6,12,17,20H,7-9H2,1-2H3
InChI KeyZKLXUUYLEHCAMF-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassMorphinans
Sub ClassNot Available
Direct ParentMorphinans
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point201 - 202 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.87 g/LALOGPS
logP2.58ALOGPS
logP1.25ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)7.36ChemAxon
pKa (Strongest Basic)11.09ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.93 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity86.18 m³·mol⁻¹ChemAxon
Polarizability31.58 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001l-0090000000-fa6976ff06a0709a568eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0uka-3029000000-e16785ea0b5328feaa68Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-d6fbb5a289eda927d73dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0090000000-6e5324047e5f47efb371Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pbi-4090000000-9b0dacc89bfff3dbe683Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-081253287a6e95e02428Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-d085105127d814824e05Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a5l-2090000000-bab6d89f58af7274f5b9Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002075
KNApSAcK IDC00028775
Chemspider ID544349
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOripavine
METLIN IDNot Available
PubChem Compound626667
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .