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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:44 UTC
HMDB IDHMDB0014790
Secondary Accession Numbers
  • HMDB14790
Metabolite Identification
Common NamePentazocine
DescriptionPentazocine, also known as fortral or talwin, 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. Pentazocine is a drug which is used for the relief of moderate to severe pain. The petition was filed by Joseph L. Fink III, a pharmacist and law student at Georgetown University Law Center as part of the course Lawyering in the Public Interest. Pentazocine is a very strong basic compound (based on its pKa). Pentazocine is used primarily to treat pain, although its analgesic effects are subject to a ceiling effect. In humans, pentazocine is involved in pentazocine action pathway. In addition, animal studies have demonstrated that Pentazocine is tolerated less well subcutaneously than intramuscularly. Pentazocine is a potentially toxic compound. U.S. testing was conducted between 1961 and 1967.
Structure
Data?1582753221
Synonyms
ValueSource
FortralKegg
L-PentazocineHMDB
PentazocaineHMDB
PentazocinHMDB
TalwinHMDB
LexirHMDB
Pentazocine lactateHMDB
Hydrochloride, pentazocineHMDB
Pentazocine hydrochlorideHMDB
Lactate, pentazocineHMDB
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
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
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
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point146.3 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.12 g/LNot Available
LogP3.7Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM173.530932474
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+169.42131661259
DarkChem[M-H]-170.19431661259
DeepCCS[M+H]+172.91530932474
DeepCCS[M-H]-170.55730932474
DeepCCS[M-2H]-205.01530932474
DeepCCS[M+Na]+179.93930932474
AllCCS[M+H]+171.332859911
AllCCS[M+H-H2O]+168.032859911
AllCCS[M+NH4]+174.332859911
AllCCS[M+Na]+175.132859911
AllCCS[M-H]-179.432859911
AllCCS[M+Na-2H]-179.432859911
AllCCS[M+HCOO]-179.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PentazocineC[C@H]1[C@H]2CC3=CC=C(O)C=C3[C@]1(C)CCN2CC=C(C)C3396.9Standard polar33892256
PentazocineC[C@H]1[C@H]2CC3=CC=C(O)C=C3[C@]1(C)CCN2CC=C(C)C2344.8Standard non polar33892256
PentazocineC[C@H]1[C@H]2CC3=CC=C(O)C=C3[C@]1(C)CCN2CC=C(C)C2285.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Pentazocine,1TMS,isomer #1CC(C)=CCN1CC[C@@]2(C)C3=CC(O[Si](C)(C)C)=CC=C3C[C@@H]1[C@@H]2C2220.3Semi standard non polar33892256
Pentazocine,1TBDMS,isomer #1CC(C)=CCN1CC[C@@]2(C)C3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3C[C@@H]1[C@@H]2C2465.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Pentazocine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00xr-4490000000-a55a414896d563e7aa3d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pentazocine GC-MS (1 TMS) - 70eV, Positivesplash10-0006-6079000000-3fb9a9a9c86659fbbee22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pentazocine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Pentazocine 35V, Positive-QTOFsplash10-014r-0390000000-31bc6b49bbe03cc8b27b2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentazocine 10V, Positive-QTOFsplash10-000i-1090000000-8390171314730328d23a2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentazocine 20V, Positive-QTOFsplash10-014r-5190000000-093358a58c8c1faab5022016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentazocine 40V, Positive-QTOFsplash10-014i-9220000000-2690544e141eb42e324b2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentazocine 10V, Negative-QTOFsplash10-001i-0090000000-65f24c15362c36e119a92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentazocine 20V, Negative-QTOFsplash10-00lr-1090000000-5cba8a2f286ab0e94fc02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentazocine 40V, Negative-QTOFsplash10-0gb9-3290000000-8498666fd4d422f5b9f12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentazocine 10V, Positive-QTOFsplash10-000i-0090000000-6c52ebfcebbeb27c1aa22021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentazocine 20V, Positive-QTOFsplash10-00kr-0090000000-040bd3fa35cc831fbfac2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentazocine 40V, Positive-QTOFsplash10-0006-9100000000-000bbfae8da629b629a52021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentazocine 10V, Negative-QTOFsplash10-001i-0090000000-c2113612e96dcf956da52021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentazocine 20V, Negative-QTOFsplash10-001i-1090000000-c793d7bec665f34e1f132021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentazocine 40V, Negative-QTOFsplash10-0udi-0190000000-a21f5a18b58d692cf8c02021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00652 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00652 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot 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. 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 ]
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 ]
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 ]