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Showing metabocard for Pentazocine (HMDB0014790)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
enzymes (3) Show 3 proteins
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2017-12-20 20:32:05 UTC
HMDB IDHMDB0014790
Secondary Accession Numbers
  • HMDB14790
Metabolite Identification
Common NamePentazocine
DescriptionPentazocine is only found in individuals that have used or taken this drug. It is the first mixed agonist-antagonist analgesic to be marketed. It is an agonist at the kappa and sigma opioid receptors and has a weak antagonist action at the mu receptor. (From AMA Drug Evaluations Annual, 1991, p97)The preponderance of evidence suggests that pentazocine antagonizes the opioid effects by competing for the same receptor sites, especially the opioid mu receptor.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
FortralKegg
L-PentazocineHMDB
PentazocaineHMDB
PentazocinHMDB
TalwinMeSH
LexirMeSH
Pentazocine lactateMeSH
Hydrochloride, pentazocineMeSH
Pentazocine hydrochlorideMeSH
Lactate, pentazocineMeSH
Chemical FormulaC19H27NO
Average Molecular Weight285.4238
Monoisotopic Molecular Weight285.209264491
IUPAC Name(1R,9R,13R)-1,13-dimethyl-10-(3-methylbut-2-en-1-yl)-10-azatricyclo[7.3.1.0²,⁷]trideca-2,4,6-trien-4-ol
Traditional Namepentazocine
CAS Registry Number359-83-1
SMILES
C[C@H]1[C@H]2CC3=CC=C(O)C=C3[C@]1(C)CCN2CC=C(C)C
InChI Identifier
InChI=1S/C19H27NO/c1-13(2)7-9-20-10-8-19(4)14(3)18(20)11-15-5-6-16(21)12-17(15)19/h5-7,12,14,18,21H,8-11H2,1-4H3/t14-,18+,19+/m0/s1
InChI KeyVOKSWYLNZZRQPF-GDIGMMSISA-N
Chemical Taxonomy
DescriptionThis compound 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
Class6,7-benzomorphans
Sub Class2,6-dimethyl-3-benzazocines
Direct Parent2,6-dimethyl-3-benzazocines
Alternative Parents
Substituents
  • 2,6-dimethyl-3-benzazocine
  • 4-hydroxy-6,7-benzomorphan
  • Benzazocine
  • Tetralin
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Piperidine
  • Benzenoid
  • Tertiary amine
  • Tertiary aliphatic amine
  • Organoheterocyclic compound
  • Azacycle
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point146.3 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.12 g/LNot Available
LogP3.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP4.44ALOGPS
logP3.89ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)7.59ChemAxon
pKa (Strongest Basic)12.4ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area23.47 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity89.8 m³·mol⁻¹ChemAxon
Polarizability33.86 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00xr-4490000000-a55a414896d563e7aa3dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-6079000000-3fb9a9a9c86659fbbee2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1090000000-8390171314730328d23aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-5190000000-093358a58c8c1faab502View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9220000000-2690544e141eb42e324bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-65f24c15362c36e119a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00lr-1090000000-5cba8a2f286ab0e94fc0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gb9-3290000000-8498666fd4d422f5b9f1View in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Pentazocine Action PathwayThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00652 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00652 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0-0.4 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-0.2 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00652
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID390041
KEGG Compound IDC07421
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPentazocine
METLIN IDNot Available
PubChem Compound441278
PDB IDNot Available
ChEBI ID116117
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Mu-type opioid receptor
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. Levine JD, Gordon NC: Synergism between the analgesic actions of morphine and pentazocine. Pain. 1988 Jun;33(3):369-72. [PubMed:3419842 ]
  2. Martin BR, Katzen JS, Woods JA, Tripathi HL, Harris LS, May EL: Stereoisomers of [3H]-N-allylnormetazocine bind to different sites in mouse brain. J Pharmacol Exp Ther. 1984 Dec;231(3):539-44. [PubMed:6094791 ]
  3. Kamei J, Iwamoto Y, Misawa M, Nagase H, Kasuya Y: Effects of diabetes on the antinociceptive effect of (+/-)pentazocine in mice. Res Commun Chem Pathol Pharmacol. 1994 Apr;84(1):105-10. [PubMed:8042002 ]
  4. Picker MJ, Benyas S, Horwitz JA, Thompson K, Mathewson C, Smith MA: Discriminative stimulus effects of butorphanol: influence of training dose on the substitution patterns produced by Mu, Kappa and Delta opioid agonists. J Pharmacol Exp Ther. 1996 Dec;279(3):1130-41. [PubMed:8968334 ]
  5. Saha N, Datta H, Sharma PL: Effects of morphine, buprenorphine, pentazocine and nalorphine on acquisition and extinction of active avoidance responses in rats. Indian J Physiol Pharmacol. 1990 Jul;34(3):179-82. [PubMed:2286420 ]
Enzyme Details
2. Kappa-type opioid receptor
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. Chien CC, Pasternak GW: (-)-Pentazocine analgesia in mice: interactions with a sigma receptor system. Eur J Pharmacol. 1995 Dec 27;294(1):303-8. [PubMed:8788445 ]
Enzyme Details
3. Sigma non-opioid intracellular receptor 1
General function:
Involved in C-8 sterol isomerase activity
Specific function:
Functions in lipid transport from the endoplasmic reticulum and is involved in a wide array of cellular functions probably through regulation of the biogenesis of lipid microdomains at the plasma membrane. Involved in the regulation of different receptors it plays a role in BDNF signaling and EGF signaling. Also regulates ion channels like the potassium channel and could modulate neurotransmitter release. Plays a role in calcium signaling through modulation together with ANK2 of the ITP3R-dependent calcium efflux at the endoplasmic reticulum. Plays a role in several other cell functions including proliferation, survival and death. Originally identified for its ability to bind various psychoactive drugs it is involved in learning processes, memory and mood alteration
Gene Name:
SIGMAR1
Uniprot ID:
Q99720
Molecular weight:
25127.5
References
  1. Chien CC, Pasternak GW: (-)-Pentazocine analgesia in mice: interactions with a sigma receptor system. Eur J Pharmacol. 1995 Dec 27;294(1):303-8. [PubMed:8788445 ]
  2. Colabufo NA, Contino M, Inglese C, Niso M, Perrone R, Roperto S, Roperto F: In vitro and ex vivo characterization of sigma-1 and sigma-2 receptors: agonists and antagonists in biological assays. Cent Nerv Syst Agents Med Chem. 2009 Sep;9(3):161-71. [PubMed:20021350 ]
  3. Dun Y, Thangaraju M, Prasad P, Ganapathy V, Smith SB: Prevention of excitotoxicity in primary retinal ganglion cells by (+)-pentazocine, a sigma receptor-1 specific ligand. Invest Ophthalmol Vis Sci. 2007 Oct;48(10):4785-94. [PubMed:17898305 ]
  4. Mamolo MG, Zampieri D, Zanette C, Florio C, Collina S, Urbano M, Azzolina O, Vio L: Substituted benzylaminoalkylindoles with preference for the sigma2 binding site. Eur J Med Chem. 2008 Oct;43(10):2073-81. Epub 2007 Sep 26. [PubMed:18069094 ]
  5. Pal A, Hajipour AR, Fontanilla D, Ramachandran S, Chu UB, Mavlyutov T, Ruoho AE: Identification of regions of the sigma-1 receptor ligand binding site using a novel photoprobe. Mol Pharmacol. 2007 Oct;72(4):921-33. Epub 2007 Jul 10. [PubMed:17622576 ]