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Record Information
Created at2022-09-05 23:38:08 UTC
Updated at2022-09-05 23:38:08 UTC
NP-MRD IDNP0221935
Secondary Accession NumbersNone
Natural Product Identification
Common Namephenazocine
DescriptionPhenazocine, also known as narphen or phenbenzorphan, belongs to the class of organic compounds known as 2,6-dimethyl-3-benzazocines. These are aromatic compounds containing a 6,7-benzomorphan skeleton, which is substituted by methyl group at the 2- and 6-positions. phenazocine is found in Papaver somniferum. It was first documented in 2015 (PMID: 25972091). Based on a literature review a small amount of articles have been published on Phenazocine (PMID: 31557052) (PMID: 27721146).
Hydrobromide, phenazocineHMDB
Phenazocine hydrobromideHMDB
Chemical FormulaC22H27NO
Average Mass321.4640 Da
Monoisotopic Mass321.20926 Da
IUPAC Name1,13-dimethyl-10-(2-phenylethyl)-10-azatricyclo[^{2,7}]trideca-2(7),3,5-trien-4-ol
Traditional Name1,13-dimethyl-10-(2-phenylethyl)-10-azatricyclo[^{2,7}]trideca-2(7),3,5-trien-4-ol
CAS Registry NumberNot Available
InChI Identifier
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species of Origin
Species NameSourceReference
Papaver somniferumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2,6-dimethyl-3-benzazocines. These are aromatic compounds containing a 6,7-benzomorphan skeleton, which is substituted by methyl group at the 2- and 6-positions.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
Sub Class2,6-dimethyl-3-benzazocines
Direct Parent2,6-dimethyl-3-benzazocines
Alternative Parents
  • 2,6-dimethyl-3-benzazocine
  • 4-hydroxy-6,7-benzomorphan
  • Benzazocine
  • Tetralin
  • Phenethylamine
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Monocyclic benzene moiety
  • Piperidine
  • Benzenoid
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
pKa (Strongest Acidic)9.96ChemAxon
pKa (Strongest Basic)10.86ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area23.47 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity100.05 m³·mol⁻¹ChemAxon
Polarizability37.92 ųChemAxon
Number of Rings4ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID14031
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhenazocine
METLIN IDNot Available
PubChem Compound14707
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]
  2. Prezzavento O, Arena E, Sanchez-Fernandez C, Turnaturi R, Parenti C, Marrazzo A, Catalano R, Amata E, Pasquinucci L, Cobos EJ: (+)-and (-)-Phenazocine enantiomers: Evaluation of their dual opioid agonist/sigma1 antagonist properties and antinociceptive effects. Eur J Med Chem. 2017 Jan 5;125:603-610. doi: 10.1016/j.ejmech.2016.09.077. Epub 2016 Sep 26. [PubMed:27721146 ]
  3. Brown R, Howard R, Candy B, Sampson EL: Opioids for agitation in dementia. Cochrane Database Syst Rev. 2015 May 14;(5):CD009705. doi: 10.1002/14651858.CD009705.pub2. [PubMed:25972091 ]
  4. LOTUS database [Link]