Dezocine

Common Name

Dezocine Description

Dezocine is a partial opiate drug and is used for pain management. Dezocine is a very effective alternative to fentanyl when administered during outpatient laparoscopy, although is associated with an increased incidence of postoperative nausea. Structure

Synonyms

Value Source (-)-13beta-amino-5,6,7,8,9,10,11alpha,12-octahydro-5alpha-Methyl-5,11-methanobenzocyclodecen-3-olChEBI DezocinaChEBI DezocinumChEBI (-)-13b-amino-5,6,7,8,9,10,11a,12-octahydro-5a-Methyl-5,11-methanobenzocyclodecen-3-olGenerator (-)-13β-amino-5,6,7,8,9,10,11α,12-octahydro-5α-methyl-5,11-methanobenzocyclodecen-3-olGenerator (-5alpha, 11alpha,13S)-13-amino-5,6,7,8,9,10,11,12-octahydro-5-Methyl-5,11-methanobenzocyclodecen-3-olMeSH Dezocine hydrobromide, (5R-(5alpha,11alpha,13S*))-isomerMeSH Dezocine hydrobromide, (5S-(5alpha,11alpha,13*))-isomerMeSH Dezocine hydrobromide, (5alpha,11alpha,13*)-isomerMeSH Dezocine hydrobromide, (5alpha,11alpha,13S*)-isomerMeSH Dezocine, (5alpha,11alpha,13S*)-isomerMeSH

Chemical Formlia

C₁₆H₂₃NO Average Molecliar Weight

245.3599 Monoisotopic Molecliar Weight

245.177964363 IUPAC Name

(1R,9S,15S)-15-amino-1-methyltricyclo[7.5.1.0²,⁷]pentadeca-2,4,6-trien-4-ol Traditional Name

dezocina CAS Registry Number

53648-55-8 SMILES

InChI Identifier

InChI Key

VTMVHDZWSFQSQP-VBNZEHGJSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane. Kingdom

Chemical entities Super Class

Organic compounds Class

Benzenoids Sub Class

Tetralins Direct Parent

Tetralins Alternative Parents

Aralkylamines

1-hydroxy-2-unsubstituted benzenoids

Organopnictogen compounds

Organooxygen compounds

Monoalkylamines

Hydrocarbon derivatives

Substituents

Tetralin

1-hydroxy-2-unsubstituted benzenoid

Aralkylamine

Organic nitrogen compound

Organic oxygen compound

Organopnictogen compound

Hydrocarbon derivative

Primary amine

Organooxygen compound

Organonitrogen compound

Primary aliphatic amine

Amine

Aromatic homopolycyclic compound

Molecliar Framework

Aromatic homopolycyclic compounds External Descriptors

phenols (CHEBI:4474 )

primary amino compound (CHEBI:4474 )

Ontology Status

Expected but not Quantified Origin

Drug

Biofunction

Analgesics, Opioid

Application

Pharmaceutical

Cellliar locations

Membrane

Physical Properties State

Solid Experimental Properties

Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility1.40e-02 g/LNot Available LogP3.3Not Available

Predicted Properties

Property Value Source Water Solubility0.014 mg/mLALOGPS logP3.77ALOGPS logP3.23ChemAxon logS-4.2ALOGPS pKa (Strongest Acidic)10.43ChemAxon pKa (Strongest Basic)9.67ChemAxon Physiological Charge1ChemAxon Hydrogen Acceptor Count2ChemAxon Hydrogen Donor Count2ChemAxon Polar Surface Area46.25 ŲChemAxon Rotatable Bond Count0ChemAxon Refractivity74.19 m³·mol^-1ChemAxon Polarizability28.49 ųChemAxon Number of Rings3ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

Spectra Spectra

Spectrum Type Description Splash Key Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

Biological Properties Cellliar Locations

Membrane

Biofluid Locations

Blood

Urine

Tissue Location

Not Available Pathways

Name SMPDB Link KEGG Link Dezocine Action PathwaySMP00676Not Available

Normal Concentrations

Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01209

21059682

details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01209

21059682

details

Abnormal Concentrations

Not Available Associated Disorders and Diseases Disease References

None Associated OMIM IDs

None External Links DrugBank ID

DB01209 DrugBank Metabolite ID

Not Available Phenol Explorer Compound ID

Not Available Phenol Explorer Metabolite ID

Not Available FoodDB ID

Not Available KNApSAcK ID

Not Available Chemspider ID

2297867 KEGG Compound ID

C08010 BioCyc ID

Not Available BiGG ID

Not Available Wikipedia Link

Not Available NuGOwiki Link

HMDB15340 Metagene Link

HMDB15340 METLIN ID

Not Available PubChem Compound

3033053 PDB ID

Not Available ChEBI ID

4474

Product: Methylene Blue

References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

Enzymes

General function:

Involved in G-protein coupled receptor protein signaling pathway

Specific function:

Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for beta-endorphin

Gene Name:

OPRM1

Uniprot ID:

P35372

Molecular weight:

44778.9

References

1. Picker MJ: Discriminative stimulus effects of the mixed-opioid agonist/antagonist dezocine: cross-substitution by mu and delta opioid agonists. J Pharmacol Exp Ther. 1997 Dec;283(3):1009-17. [PubMed:9399970 ]
2. Barrett AC, Cook CD, Terner JM, Craft RM, Picker MJ: Importance of sex and relative efficacy at the mu opioid receptor in the development of tolerance and cross-tolerance to the antinociceptive effects of opioids. Psychopharmacology (Berl). 2001 Nov;158(2):154-64. [PubMed:11702089 ]
3. Cook CD, Barrett AC, Roach EL, Bowman JR, Picker MJ: Sex-related differences in the antinociceptive effects of opioids: importance of rat genotype, nociceptive stimulus intensity, and efficacy at the mu opioid receptor. Psychopharmacology (Berl). 2000 Jul;150(4):430-42. [PubMed:10958085 ]
4. Gharagozlou P, Demirci H, David Clark J, Lameh J: Activity of opioid ligands in cells expressing cloned mu opioid receptors. BMC Pharmacol. 2003 Jan 4;3:1. Epub 2003 Jan 4. [PubMed:12513698 ]
5. Morgan D, Cook CD, Smith MA, Picker MJ: An examination of the interactions between the antinociceptive effects of morphine and various mu-opioids: the role of intrinsic efficacy and stimulus intensity. Anesth Analg. 1999 Feb;88(2):407-13. [PubMed:9972766 ]
6. Jacobs AM, Youngblood F: Opioid receptor affinity for agonist-antagonist analgesics. J Am Podiatr Med Assoc. 1992 Oct;82(10):520-4. [PubMed:1361946 ]

General function:

Involved in G-protein coupled receptor protein signaling pathway

Specific function:

Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for dynorphins. May play a role in arousal and regulation of autonomic and neuroendocrine functions

Gene Name:

OPRK1

Uniprot ID:

P41145

Molecular weight:

42644.7

References

1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
3. Gharagozlou P, Hashemi E, DeLorey TM, Clark JD, Lameh J: Pharmacological profiles of opioid ligands at kappa opioid receptors. BMC Pharmacol. 2006 Jan 25;6:3. [PubMed:16433932 ]
4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

PMID: 1315463

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