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Details

Stereochemistry RACEMIC
Molecular Formula C19H27NO
Molecular Weight 285.4238
Optical Activity ( + / - )
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PENTAZOCINE

SMILES

C[C@H]1[C@H]2CC3=CC=C(O)C=C3[C@]1(C)CCN2CC=C(C)C

InChI

InChIKey=VOKSWYLNZZRQPF-GDIGMMSISA-N
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

HIDE SMILES / InChI

Molecular Formula C19H27NO
Molecular Weight 285.4238
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12379919 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/016194s079s080lbl.pdf | https://www.drugbank.ca/drugs/DB00652

Pentazocine is a synthetically prepared prototypical mixed agonist-antagonist narcotic (opioid analgesic) drug of the benzomorphan class of opioids used to treat moderate to moderately severe pain. Pentazocine is sold under several brand names, such as Fortral, Sosegon, Talwin NX. Pentazocine acts as an agonist of κ-opioid receptors and as an antagonist of μ-opioid receptors. This compound may exist as one of two enantiomers, named (+)-pentazocine and (−)-pentazocine. Side effects are similar to those of morphine, but pentazocine, due to its action at the kappa opioid receptor is more likely to invoke psychotomimetic effects. High dose may cause high blood pressure or high heart rate.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
6.9 nM [Ki]
75.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TALWIN

Approved Use

Pentazocine Hydrochloride and Naloxone Hydrochloride Tablets, USP is indicated for the relief of moderate to severe pain. Pentazocine Hydrochloride and Naloxone Hydrochloride Tablets, USP is indicated for oral use only.

Launch Date

1967
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
102 ng/mL
40 mg single, intramuscular
dose: 40 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
PENTAZOCINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
227 ng/mL
80 mg single, intramuscular
dose: 80 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
PENTAZOCINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
536 ng × h/mL
40 mg single, intramuscular
dose: 40 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
PENTAZOCINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
1311 ng × h/mL
80 mg single, intramuscular
dose: 80 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
PENTAZOCINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4.6 h
40 mg single, intramuscular
dose: 40 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
PENTAZOCINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
5.3 h
80 mg single, intramuscular
dose: 80 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
PENTAZOCINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
30 mg single, intramuscular
Dose: 30 mg
Route: intramuscular
Route: single
Dose: 30 mg
Sources:
unhealthy
Disc. AE: Respiratory depression, Hypotension...
AEs leading to
discontinuation/dose reduction:
Respiratory depression
Hypotension (severe)
Sources:
30 mg single, intramuscular
Dose: 30 mg
Route: intramuscular
Route: single
Dose: 30 mg
Sources:
unhealthy
Disc. AE: Sedation, Coma...
AEs leading to
discontinuation/dose reduction:
Sedation
Coma
Sources:
AEs

AEs

AESignificanceDosePopulation
Respiratory depression Disc. AE
30 mg single, intramuscular
Dose: 30 mg
Route: intramuscular
Route: single
Dose: 30 mg
Sources:
unhealthy
Hypotension severe
Disc. AE
30 mg single, intramuscular
Dose: 30 mg
Route: intramuscular
Route: single
Dose: 30 mg
Sources:
unhealthy
Coma Disc. AE
30 mg single, intramuscular
Dose: 30 mg
Route: intramuscular
Route: single
Dose: 30 mg
Sources:
unhealthy
Sedation Disc. AE
30 mg single, intramuscular
Dose: 30 mg
Route: intramuscular
Route: single
Dose: 30 mg
Sources:
unhealthy
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as victim

Drug as victim

Tox targets

Tox targets

PubMed

PubMed

TitleDatePubMed
Pentazocine addict nephropathy: a case report.
1992 Mar
Anti-inflammatory and analgesic activity of Indian Hypericum perforatum L.
2001 Apr
Pharmacological actions of AH-9700 on micturition reflex in anesthetized rats.
2001 Jan 26
The opioid peptide analogue biphalin induces less physical dependence than morphine.
2001 Jul 20
[Analysis of prehospital analgesia administered to victims with traumatic injuries].
2001 Jul-Aug
Post operative pain therapy: a survey of prescribing patterns and adequacy of analgesia in Ibadan, Nigeria.
2001 Mar
[Influence of intubation maneuver with or without premedication for intracranial hemorrhage with unconsciousness].
2001 Mar
Chitosan based pentazocine microspheres for intranasal systemic delivery: development and biopharmaceutical evaluation.
2001 Mar
[UV-densitometry determination of pentazocine hydrochloride in tablets after low temperature extraction].
2001 May-Jun
Modulation of serotonergic neurotransmission by short- and long-term treatments with sigma ligands.
2001 Oct
[Biopharmaceutical studies on molecular mechanisms of membrane transport].
2002 Dec
Fibromyositis after intramuscular pentazocine abuse.
2002 Jul-Sep
Synthesis and evaluation of [18F]fluoroethyl SA4503 as a PET ligand for the sigma receptor.
2002 Mar 15
Synthesis and evaluation of 3-(4-chlorobenzyl)-8-[11C]methoxy-1,2,3,4-tetrahydrochromeno[3,4-c]pyridin-5-one: a PET tracer for imaging sigma(1) receptors.
2002 May
Investigation of transport mechanism of pentazocine across the blood-brain barrier using the in situ rat brain perfusion technique.
2002 Nov
Investigation on the influx transport mechanism of pentazocine at the blood-brain barrier in rats using the carotid injection technique.
2002 Oct
Antidiarrhoeal properties of a novel sigma ligand (JO 2871) on toxigenic diarrhoea in mice: mechanisms of action.
2002 Oct
Subarachnoid block for lower abdominal and lower limb surgery: UITH experience.
2002 Oct-Dec
Agonist/antagonist properties of nalbuphine, butorphanol and (-)-pentazocine in male vs. female rats.
2003 Apr
Enhanced sensitivity to the antinociceptive effects of kappa opioids in naltrexone-treated rats: dose- and time-dependent effects.
2003 Dec
Differential effects of agonists on adenylyl cyclase superactivation mediated by the kappa opioid receptors: adenylyl cyclase superactivation is independent of agonist-induced phosphorylation, desensitization, internalization, and down-regulation.
2003 Dec
SR31747A is a sigma receptor ligand exhibiting antitumoural activity both in vitro and in vivo.
2003 Feb 10
Analgesic activity of Piper longum Linn. root.
2003 Jun
[Neurochemical analysis and pharmacological regulation of the corticofugal control of the nociceptive signals in the afferent pathways].
2003 Mar-Apr
Opioid agonists have different efficacy profiles for G protein activation, rapid desensitization, and endocytosis of mu-opioid receptors.
2003 May 23
Modulation of Fas receptor proteins and dynamin during opiate addiction and induction of opiate withdrawal in rat brain.
2003 Nov
Dose ratio is important in maximizing naloxone enhancement of nalbuphine analgesia in humans.
2003 Nov 6
Procaine hydrochloride fails to relieve pain in patients with acute pancreatitis.
2004
Antiproliferative and cytotoxic effects of some sigma2 agonists and sigma1 antagonists in tumour cell lines.
2004 Aug
[Intermittent complete left bundle branch block during general anesthesia].
2004 Dec
Molecular modeling of sigma 1 receptor ligands: a model of binding conformational and electrostatic considerations.
2004 Jan
Pentazocine-induced cutaneous sclerosis and panniculitis in an Indian male.
2004 Jul
Involvement of P-glycoprotein in blood-brain barrier transport of pentazocine in rats using brain uptake index method.
2004 Jun
Sigma-2 receptors are specifically localized to lipid rafts in rat liver membranes.
2004 Jun 16
Sternoclavicular septic arthritis: review of 180 cases.
2004 May
Intrathecal morphine, but not buprenorphine or pentazocine, can induce spastic paraparesis after a noninjurious interval of spinal cord ischemia in the rat.
2004 Nov
Modulation of bradykinin-induced calcium changes in SH-SY5Y cells by neurosteroids and sigma receptor ligands via a shared mechanism.
2004 Nov
[Case report of pentazocine dependence from a standpoint of the cognitive therapy].
2004 Oct
Retroperitoneoscopic live donor nephrectomy: extended experience in a single center.
2004 Sep
Vitamin B12-associated localized scleroderma and its treatment.
2004 Sep
Sex-related psychological predictors of baseline pain perception and analgesic responses to pentazocine.
2005 Apr
Using mixed agonist-antagonists.
2005 Feb
Patents

Sample Use Guides

In Vivo Use Guide
Initial dose: 30 mg by intramuscular, subcutaneous, or intravenous route. This may be repeated every 3 to 4 hours. Doses in excess of 30 mg intravenously or 60 mg intramuscularly or subcutaneously are not recommended. Maximum daily dose: 360 mg
Route of Administration: Other
Cultured bovine adrenal medullary cells (1 × 10^6 / well) or SK-N-SH cells (0.3 × 10^6 / well) were preincubated with or without PTZ (Pentazocine) for the indicated times and further incubated at 37°C for another 12 min in KRH buffer containing 100 μM pargyline, 1 mM ascorbic acid, and [3H]NE (500 or 100 nM, respectively, 0.1 μCi) in the presence or absence of desipramine and PTZ. KRH buffer was composed of 154 mM NaCl, 5.6 mM KCl, 1.1 mM MgSO4, 2.2 mM CaCl2, 10 mM HEPES-Tris, and 10 mM glucose, adjusted to pH 7.4. After incubation, the cells were rapidly washed three times with 250 μl of ice-cold KRH buffer and solubilized in 500 μl of 10% Triton X-100. The radioactivity in the solubilized cells was counted with a liquid scintillation counter.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:48:17 GMT 2025
Edited
by admin
on Mon Mar 31 17:48:17 GMT 2025
Record UNII
RP4A60D26L
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PENTAZOCINE
EP   HSDB   INN   MART.   MI   USAN   USP   VANDF   WHO-DD  
USAN   INN  
Official Name English
PENTAZOCINE CIV
USP-RS  
Preferred Name English
(±)-PENTAZOCINE
Common Name English
TALWIN
Brand Name English
PENTAZOCINE [JAN]
Common Name English
PENTAZOCINE [EP IMPURITY]
Common Name English
PENTAZOCINE [HSDB]
Common Name English
PENTAZOCINE [MART.]
Common Name English
CIS-(±)-PENTAZOCINE
Common Name English
NSC-107430
Code English
WIN 20,228
Code English
DL-PENTAZOCINE
Common Name English
NIH-7958
Code English
2,6-METHANO-3-BENZAZOCIN-8-OL, 1,2,3,4,5,6-HEXAHYDRO-6,11-DIMETHYL-3-(3-METHYL-2-BUTEN-1-YL)-, (2R,6R,11R)-REL-
Common Name English
PENTAZOCINE [VANDF]
Common Name English
pentazocine [INN]
Common Name English
2,6-METHANO-3-BENZAZOCIN-8-OL, 1,2,3,4,5,6-HEXAHYDRO-6,11-DIMETHYL-3-(3-METHYL-2-BUTENYL)-, (2.ALPHA.,6.ALPHA.,11R*)-
Common Name English
WIN-20228
Code English
PENTAZOCINE CIV [USP-RS]
Common Name English
Pentazocine [WHO-DD]
Common Name English
(2R*,6R*,11R*)-1,2,3,4,5,6-HEXAHYDRO-6,11-DIMETHYL-3-(3-METHYL-2-BUTENYL)-2,6-METHANO-3-BENZAZOCIN-8-OL
Common Name English
PENTAZOCINE [EP MONOGRAPH]
Common Name English
PENTAZOCINE [USAN]
Common Name English
PENTAZOCINE [MI]
Common Name English
PENTAZOCINE [USP MONOGRAPH]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C67413
Created by admin on Mon Mar 31 17:48:17 GMT 2025 , Edited by admin on Mon Mar 31 17:48:17 GMT 2025
WHO-VATC QN02AD01
Created by admin on Mon Mar 31 17:48:17 GMT 2025 , Edited by admin on Mon Mar 31 17:48:17 GMT 2025
LIVERTOX NBK548498
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NDF-RT N0000175686
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WHO-ATC N02AD01
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DEA NO. 9709
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NDF-RT N0000175685
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NCI_THESAURUS C1506
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NDF-RT N0000175688
Created by admin on Mon Mar 31 17:48:17 GMT 2025 , Edited by admin on Mon Mar 31 17:48:17 GMT 2025
Code System Code Type Description
DRUG CENTRAL
3424
Created by admin on Mon Mar 31 17:48:17 GMT 2025 , Edited by admin on Mon Mar 31 17:48:17 GMT 2025
PRIMARY
SMS_ID
100000082491
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PRIMARY
MESH
D010423
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PRIMARY
HSDB
3150
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PRIMARY
MERCK INDEX
m8503
Created by admin on Mon Mar 31 17:48:17 GMT 2025 , Edited by admin on Mon Mar 31 17:48:17 GMT 2025
PRIMARY Merck Index
WIKIPEDIA
PENTAZOCINE
Created by admin on Mon Mar 31 17:48:17 GMT 2025 , Edited by admin on Mon Mar 31 17:48:17 GMT 2025
PRIMARY
DRUG BANK
DB00652
Created by admin on Mon Mar 31 17:48:17 GMT 2025 , Edited by admin on Mon Mar 31 17:48:17 GMT 2025
PRIMARY
FDA UNII
RP4A60D26L
Created by admin on Mon Mar 31 17:48:17 GMT 2025 , Edited by admin on Mon Mar 31 17:48:17 GMT 2025
PRIMARY
EVMPD
SUB09688MIG
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PRIMARY
ChEMBL
CHEMBL560
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PRIMARY
RS_ITEM_NUM
1505007
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PRIMARY
CAS
359-83-1
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PRIMARY
DAILYMED
RP4A60D26L
Created by admin on Mon Mar 31 17:48:17 GMT 2025 , Edited by admin on Mon Mar 31 17:48:17 GMT 2025
PRIMARY
LACTMED
Pentazocine
Created by admin on Mon Mar 31 17:48:17 GMT 2025 , Edited by admin on Mon Mar 31 17:48:17 GMT 2025
PRIMARY
INN
1674
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PRIMARY
NCI_THESAURUS
C61884
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PRIMARY
RXCUI
8001
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PRIMARY RxNorm
NSC
107430
Created by admin on Mon Mar 31 17:48:17 GMT 2025 , Edited by admin on Mon Mar 31 17:48:17 GMT 2025
PRIMARY
ECHA (EC/EINECS)
206-634-6
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PRIMARY
EPA CompTox
DTXSID7023433
Created by admin on Mon Mar 31 17:48:17 GMT 2025 , Edited by admin on Mon Mar 31 17:48:17 GMT 2025
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
TARGET -> AGONIST
(+)-pentazocine is active
ENANTIOMER -> RACEMATE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
USP
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
Related Record Type Details
ACTIVE MOIETY