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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H21NO4.ClH.2H2O
Molecular Weight 399.866
Optical Activity ( - )
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NALOXONE HYDROCHLORIDE DIHYDRATE

SMILES

O.O.Cl.OC1=CC=C2C[C@H]3N(CC=C)CC[C@@]45[C@@H](OC1=C24)C(=O)CC[C@@]35O

InChI

InChIKey=TXMZWEASFRBVKY-IOQDSZRYSA-N
InChI=1S/C19H21NO4.ClH.2H2O/c1-2-8-20-9-7-18-15-11-3-4-12(21)16(15)24-17(18)13(22)5-6-19(18,23)14(20)10-11;;;/h2-4,14,17,21,23H,1,5-10H2;1H;2*1H2/t14-,17+,18+,19-;;;/m1.../s1

HIDE SMILES / InChI

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C19H21NO4
Molecular Weight 327.3743
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Naloxone, sold under the brand name Narcan among others, is a medication used to block the effects of opioids, especially in overdose. Naloxone has an extremely high affinity for μ-opioid receptors in the central nervous system (CNS). Naloxone is a μ-opioid receptor (MOR) inverse agonist, and its rapid blockade of those receptors often produces rapid onset of withdrawal symptoms. Naloxone also has an antagonist action, though with a lower affinity, at κ- (KOR) and δ-opioid receptors (DOR). If administered in the absence of concomitant opioid use, no functional pharmacological activity occurs (except the inability for the body to combat pain naturally). In contrast to direct opiate agonists, which elicit opiate withdrawal symptoms when discontinued in opiate-tolerant people, no evidence indicates the development of tolerance or dependence on naloxone. The mechanism of action is not completely understood, but studies suggest it functions to produce withdrawal symptoms by competing for opiate receptor sites within the CNS (a competitive antagonist, not a direct agonist), thereby preventing the action of both endogenous and xenobiotic opiates on these receptors without directly producing any effects itself. When administered parenterally (e.g. intravenously or by injection), as is most common, naloxone has a rapid distribution throughout the body. The mean serum half-life has been shown to range from 30 to 81 minutes, shorter than the average half-life of some opiates, necessitating repeat dosing if opioid receptors must be stopped from triggering for an extended period. Naloxone is primarily metabolized by the liver. Its major metabolite is naloxone-3-glucuronide, which is excreted in the urine. Naloxone is useful both in acute opioid overdose and in reducing respiratory or mental depression due to opioids. Whether it is useful in those in cardiac arrest due to an opioid overdose is unclear. Naloxone is poorly absorbed when taken by mouth, so it is commonly combined with a number of oral opioid preparations, including buprenorphine and pentazocine, so that when taken orally, just the opioid has an effect, but if misused by injecting, the naloxone blocks the effect of the opioid. In a meta-analysis of people with shock, including septic, cardiogenic, hemorrhagic, or spinal shock, those who received naloxone had improved blood flow. Naloxone is also experimentally used in the treatment for congenital insensitivity to pain with anhidrosis, an extremely rare disorder (one in 125 million) that renders one unable to feel pain or differentiate temperatures. Naloxone can also be used as an antidote in overdose of clonidine, a medication that lowers blood pressure.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
7.3 nM [IC50]
49.8 nM [IC50]
138.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
NARCAN

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

1971
Primary
NARCAN

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

1971
Primary
NARCAN

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

1971
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.09 ng/mL
10 mg/kg single, nasal
dose: 10 mg/kg
route of administration: Nasal
experiment type: SINGLE
co-administered:
NALOXONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
4.83 ng/mL
4 mg single, nasal
dose: 4 mg
route of administration: Nasal
experiment type: SINGLE
co-administered:
NALOXONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
0.87 ng/mL
0.4 mg single, intramuscular
dose: 0.4 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
NALOXONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
9.62 ng/mL
8 mg single, nasal
dose: 8 mg
route of administration: Nasal
experiment type: SINGLE
co-administered:
NALOXONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
37.1 ng × min/mL
10 mg/kg single, nasal
dose: 10 mg/kg
route of administration: Nasal
experiment type: SINGLE
co-administered:
NALOXONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
7.9 ng × h/mL
4 mg single, nasal
dose: 4 mg
route of administration: Nasal
experiment type: SINGLE
co-administered:
NALOXONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
1.68 ng × h/mL
0.4 mg single, intramuscular
dose: 0.4 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
NALOXONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
15 ng × h/mL
8 mg single, nasal
dose: 8 mg
route of administration: Nasal
experiment type: SINGLE
co-administered:
NALOXONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
28.2 min
10 mg/kg single, nasal
dose: 10 mg/kg
route of administration: Nasal
experiment type: SINGLE
co-administered:
NALOXONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
1.2 h
0.4 mg single, intramuscular
dose: 0.4 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
NALOXONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
2.1 h
8 mg single, nasal
dose: 8 mg
route of administration: Nasal
experiment type: SINGLE
co-administered:
NALOXONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
0.8 mg single, intramuscular
Dose: 0.8 mg
Route: intramuscular
Route: single
Dose: 0.8 mg
Sources:
healthy, 23.8 years (range: 22.6–25 years)
Health Status: healthy
Age Group: 23.8 years (range: 22.6–25 years)
Sex: M+F
Sources:
160 mg/m2 single, intravenous
Highest studied dose
Dose: 160 mg/m2
Route: intravenous
Route: single
Dose: 160 mg/m2
Sources:
unhealthy, 35-85 years
Health Status: unhealthy
Age Group: 35-85 years
Sources:
Disc. AE: Hypotension, Bradycardia...
Other AEs: Nausea, Emesis...
AEs leading to
discontinuation/dose reduction:
Hypotension (3 patients)
Bradycardia (2 patients)
Myoclonus (1 patient)
Hypertension (1 patient)
Other AEs:
Nausea (32%)
Emesis (5%)
Seizures (5%)
Headache (5%)
Confusion (5%)
Agitation (3%)
Sources:
8 mg single, intranasal
Dose: 8 mg
Route: intranasal
Route: single
Dose: 8 mg
Sources:
healthy, adult
AEs

AEs

AESignificanceDosePopulation
Hypertension 1 patient
Disc. AE
160 mg/m2 single, intravenous
Highest studied dose
Dose: 160 mg/m2
Route: intravenous
Route: single
Dose: 160 mg/m2
Sources:
unhealthy, 35-85 years
Health Status: unhealthy
Age Group: 35-85 years
Sources:
Myoclonus 1 patient
Disc. AE
160 mg/m2 single, intravenous
Highest studied dose
Dose: 160 mg/m2
Route: intravenous
Route: single
Dose: 160 mg/m2
Sources:
unhealthy, 35-85 years
Health Status: unhealthy
Age Group: 35-85 years
Sources:
Bradycardia 2 patients
Disc. AE
160 mg/m2 single, intravenous
Highest studied dose
Dose: 160 mg/m2
Route: intravenous
Route: single
Dose: 160 mg/m2
Sources:
unhealthy, 35-85 years
Health Status: unhealthy
Age Group: 35-85 years
Sources:
Hypotension 3 patients
Disc. AE
160 mg/m2 single, intravenous
Highest studied dose
Dose: 160 mg/m2
Route: intravenous
Route: single
Dose: 160 mg/m2
Sources:
unhealthy, 35-85 years
Health Status: unhealthy
Age Group: 35-85 years
Sources:
Agitation 3%
160 mg/m2 single, intravenous
Highest studied dose
Dose: 160 mg/m2
Route: intravenous
Route: single
Dose: 160 mg/m2
Sources:
unhealthy, 35-85 years
Health Status: unhealthy
Age Group: 35-85 years
Sources:
Nausea 32%
160 mg/m2 single, intravenous
Highest studied dose
Dose: 160 mg/m2
Route: intravenous
Route: single
Dose: 160 mg/m2
Sources:
unhealthy, 35-85 years
Health Status: unhealthy
Age Group: 35-85 years
Sources:
Confusion 5%
160 mg/m2 single, intravenous
Highest studied dose
Dose: 160 mg/m2
Route: intravenous
Route: single
Dose: 160 mg/m2
Sources:
unhealthy, 35-85 years
Health Status: unhealthy
Age Group: 35-85 years
Sources:
Emesis 5%
160 mg/m2 single, intravenous
Highest studied dose
Dose: 160 mg/m2
Route: intravenous
Route: single
Dose: 160 mg/m2
Sources:
unhealthy, 35-85 years
Health Status: unhealthy
Age Group: 35-85 years
Sources:
Headache 5%
160 mg/m2 single, intravenous
Highest studied dose
Dose: 160 mg/m2
Route: intravenous
Route: single
Dose: 160 mg/m2
Sources:
unhealthy, 35-85 years
Health Status: unhealthy
Age Group: 35-85 years
Sources:
Seizures 5%
160 mg/m2 single, intravenous
Highest studied dose
Dose: 160 mg/m2
Route: intravenous
Route: single
Dose: 160 mg/m2
Sources:
unhealthy, 35-85 years
Health Status: unhealthy
Age Group: 35-85 years
Sources:
PubMed

PubMed

TitleDatePubMed
Antagonism by naloxone of morphine-induced single-dose dependence and antinociception in mice.
1976 Dec
The NMDA receptor antagonist MK-801 prevents long-lasting non-associative morphine tolerance in the rat.
1992 Mar 20
The calcium antagonist diltiazem has antiarrhythmic effects which are mediated in the brain through endogenous opioids.
1992 May
[Experimental study on the effect of abstinence with herbal preparation qingjunyin].
1998 May
Seizure and electroencephalographic changes in the newborn period induced by opiates and corrected by naloxone infusion.
1999 Mar
Morphine inhibits human microglial cell production of, and migration towards, RANTES.
2000
Acute detoxification of opioid-addicted patients with naloxone during propofol or methohexital anesthesia: a comparison of withdrawal symptoms, neuroendocrine, metabolic, and cardiovascular patterns.
2000 Apr
The effect of spinal ibuprofen on opioid withdrawal in the rat.
2000 Aug
A peripheral, intracerebral, or intrathecal administration of an opioid receptor antagonist blocks illness-induced hyperalgesia in the rat.
2000 Dec
Phenytoin, midazolam, and naloxone protect against fentanyl-induced brain damage in rats.
2000 Dec
Methadone, ciprofloxacin, and adverse drug reactions.
2000 Dec 16
Orphanin FQ/nociceptin inhibits morphine withdrawal.
2000 Jan 14
Fentanyl-induced chest wall rigidity and laryngospasm in preterm and term infants.
2000 Mar
Hypertensive crisis and myocardial infarction following massive clonidine overdose.
2000 May
Systemic naloxone enhances cerebral blood flow in anesthetized morphine-dependent rats.
2000 Nov 24
Enhanced spinal nociceptin receptor expression develops morphine tolerance and dependence.
2000 Oct 15
Differential cardiorespiratory effects of endomorphin 1, endomorphin 2, DAMGO, and morphine.
2000 Sep
Opioid peptides alleviated while naloxone potentiated methamphetamine-induced striatal dopamine depletion in mice.
2001
Effect of whole-body vibration in the vertical axis on cortisol and adrenocorticotropic hormone levels in piglets.
2001 Apr
Opioid peptides attenuate blood pressure increase in acute respiratory failure.
2001 Apr
Relief by naloxone of morphine-induced spasm of the sphincter of Oddi in a post-cholecystectomy patient.
2001 Aug
Opioid-induced hyperalgesia and incisional pain.
2001 Jul
Inverse agonists and neutral antagonists at mu opioid receptor (MOR): possible role of basal receptor signaling in narcotic dependence.
2001 Jun
Morphine-induced dependence and sensitization are altered in mice deficient in AMPA-type glutamate receptor-A subunits.
2001 Jun 15
Naloxone improves arterial blood pressure and hypoxic ventilatory depression, but not survival, of rats during acute hypoxia.
2001 Mar
Delta9-tetrahydrocannabinol releases and facilitates the effects of endogenous enkephalins: reduction in morphine withdrawal syndrome without change in rewarding effect.
2001 May
Effects of Ferula gummosa Boiss. fractions on morphine dependence in mice.
2001 Sep
Effect of naloxone-precipitated morphine withdrawal on CRH and vasopressin mRNA expression in the rat hypothalamic paraventricular nucleus.
2002 Dec 6
The role of spinal neuropeptides and prostaglandins in opioid physical dependence.
2002 May
Cocaine/heroin induced rhabdomyolysis and ventricular fibrillation.
2002 May
Nicotine potentiation of morphine-induced catalepsy in mice.
2002 May
Attitudes about prescribing take-home naloxone to injection drug users for the management of heroin overdose: a survey of street-recruited injectors in the San Francisco Bay Area.
2003 Jun
Heroin addicts to receive CPR training and Narcan.
2003 May
Structural basis of heroin and cocaine metabolism by a promiscuous human drug-processing enzyme.
2003 May
Naloxone provokes similar pain facilitation as observed after short-term infusion of remifentanil in humans.
2003 Nov
Influence of sweet tasting solutions on opioid withdrawal.
2004 Dec 15
Identification of UGT2B9*2 and UGT2B33 isolated from female rhesus monkey liver.
2004 Jun 1
Magnesium influence on morphine--induced pharmacodependence in rats.
2004 Mar
Testosterone and luteinizing hormone responses to naloxone help predict sexual performance in rams.
2004 Nov
Evaluation of fresh and cryopreserved hepatocytes as in vitro drug metabolism tools for the prediction of metabolic clearance.
2004 Nov
Effect of agmatine on the development of morphine dependence in rats: potential role of cAMP system.
2004 Nov 19
Effects of L-745,870, a dopamine D4 receptor antagonist, on naloxone-induced morphine dependence in mice.
2004 Oct
Differential roles of peripheral and spinal endothelin receptors in the micturition reflex in rats.
2004 Oct
Rapid, transient, and dose-dependent expression of hsp70 messenger RNA in the rat brain after morphine treatment.
2004 Summer
[Combination of morphine with low-dose naloxone for intravenous patient-controlled analgesia].
2005 Apr
Ventricular tachycardia following naloxone administration in an illicit drug misuse.
2005 Aug
[Effect of naloxone on expression of Bcl-2 protein and tumor necrosis factor-alpha in rats with acute myocardial ischemia/reperfusion injury].
2005 Jul
The opioid fentanyl affects light input, electrical activity and Per gene expression in the hamster suprachiasmatic nuclei.
2005 Jun
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Ultrafine particles cross cellular membranes by nonphagocytic mechanisms in lungs and in cultured cells.
2005 Nov
Patents

Sample Use Guides

Opioid Overdose–Known or Suspected: An initial dose of 0.4 mg to 2 mg of NARCAN may be administered intravenously. If the desired degree of counteraction and improvement in respiratory functions are not obtained, it may be repeated at two- to three-minute intervals. If no response is observed after 10 mg of NARCAN have been administered, the diagnosis of opioid-induced or partial opioid-induced toxicity should be questioned. Intramuscular or subcutaneous administration may be necessary if the intravenous route is not available. Postoperative Opioid Depression: For the partial reversal of opioid depression following the use of opioids during surgery, smaller doses of NARCAN are usually sufficient. The dose of NARCAN should be titrated according to the patient’s response. For the initial reversal of respiratory depression, NARCAN should be injected in increments of 0.1 to 0.2 mg intravenously at two- to three-minute intervals to the desired degree of reversal, i.e., adequate ventilation and alertness without significant pain or discomfort. Larger than necessary dosage of NARCAN may result in significant reversal of analgesia and increase in blood pressure. Similarly, too rapid reversal may induce nausea, vomiting, sweating or circulatory stress. Repeat doses of NARCAN may be required within one- to two-hour intervals depending upon the amount, type (i.e., short or long acting) and time interval since last administration of an opioid. Supplemental intramuscular doses have been shown to produce a longer lasting effect.
Route of Administration: Other
MDCKII-MDR1 assay. Stock solutions of Naloxone (20 mM) were prepared in 100% DMSO and then diluted to the final concentration of 10 mkM, in Dulbecco’s PBS. Naloxone were tested in both directions, apicalto-basolateral (A→B) and basolateral-to-apical (B→A), in duplicate. The ratio BA/AB >2 indicates an efflux phenomena. Permeability studies were conducted at 37 ◦C in incubator for 60 min. The monolayer integrity was evaluated by measuring the TransEpithelial Electrical Resistance (TEER) by using the Millicell-ERS system (Millipore Corporation) and it was considered integer if the resistancewas between 200 and 300 cm2. After the transport study the monolayer integrity was measured in each well by adding a 0.02 mg/mL solution of lucifer yellow (LY); the test was conducted at 37 ◦C for 60 min, and the fluorescence (RFU) was measured at 485/535 nm.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:34:16 GMT 2025
Edited
by admin
on Mon Mar 31 17:34:16 GMT 2025
Record UNII
5Q187997EE
Record Status Validated (UNII)
Record Version
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Name Type Language
NALOXONE HYDROCHLORIDE DIHYDRATE
EP   MI   WHO-IP  
Common Name English
BUNAVAIL COMPONENT NALOXONE HYDROCHLORIDE DIHYDRATE
Preferred Name English
(-)-N-ALLYL-14-HYDROXYNORDIHYDROMORPHINONE HYDROCHLORIDE DIHYDRATE
Common Name English
NALOXONE CHLORHYDRATE
Common Name English
NALOXONE HYDROCHLORIDE DIHYDRATE [MI]
Common Name English
17-ALLYL-4,5.ALPHA.-EPOXY-3,14-DIHYDROXYMORPHINAN-6-ONE HYDROCHLORIDE DIHYDRATE
Systematic Name English
NALOXONI HYDROCHLORIDUM DIHYDRATE [WHO-IP LATIN]
Common Name English
CASSIPA COMPONENT NALOXONE HYDROCHLORIDE DIHYDRATE
Brand Name English
NALOXONE HYDROCHLORIDE DIHYDRATE [EP MONOGRAPH]
Common Name English
NALOXONE HYDROCHLORIDE DIHYDRATE [WHO-IP]
Common Name English
Classification Tree Code System Code
EU-Orphan Drug EU/3/12/1057
Created by admin on Mon Mar 31 17:34:16 GMT 2025 , Edited by admin on Mon Mar 31 17:34:16 GMT 2025
Code System Code Type Description
RXCUI
1010598
Created by admin on Mon Mar 31 17:34:16 GMT 2025 , Edited by admin on Mon Mar 31 17:34:16 GMT 2025
PRIMARY RxNorm
DAILYMED
5Q187997EE
Created by admin on Mon Mar 31 17:34:16 GMT 2025 , Edited by admin on Mon Mar 31 17:34:16 GMT 2025
PRIMARY
MERCK INDEX
m7717
Created by admin on Mon Mar 31 17:34:16 GMT 2025 , Edited by admin on Mon Mar 31 17:34:16 GMT 2025
PRIMARY
EPA CompTox
DTXSID90199452
Created by admin on Mon Mar 31 17:34:16 GMT 2025 , Edited by admin on Mon Mar 31 17:34:16 GMT 2025
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
NALOXONE HYDROCHLORIDE DIHYDRATE
Created by admin on Mon Mar 31 17:34:16 GMT 2025 , Edited by admin on Mon Mar 31 17:34:16 GMT 2025
PRIMARY Description: A white or almost white powder. Solubility: Soluble in water; slightly soluble in ethanol (~750 g/l) TS; practically insoluble in ether R. Category: Narcotic antagonist. Storage: Naloxone hydrochloride should be kept in a tightly closed container, protected from light. Labelling: The designation on the container of Naloxone hydrochloride should state whether the substance is in the anhydrous form or is the dihydrate. Additional information: Even in the absence of light, Naloxone hydrochloride is gradually degraded on exposure to a humid atmosphere, the decomposition being faster at higher temperatures. It melts at about 177?C.
SMS_ID
100000089225
Created by admin on Mon Mar 31 17:34:16 GMT 2025 , Edited by admin on Mon Mar 31 17:34:16 GMT 2025
PRIMARY
CAS
51481-60-8
Created by admin on Mon Mar 31 17:34:16 GMT 2025 , Edited by admin on Mon Mar 31 17:34:16 GMT 2025
PRIMARY
EVMPD
SUB12168MIG
Created by admin on Mon Mar 31 17:34:16 GMT 2025 , Edited by admin on Mon Mar 31 17:34:16 GMT 2025
PRIMARY
FDA UNII
5Q187997EE
Created by admin on Mon Mar 31 17:34:16 GMT 2025 , Edited by admin on Mon Mar 31 17:34:16 GMT 2025
PRIMARY
DRUG BANK
DBSALT001497
Created by admin on Mon Mar 31 17:34:16 GMT 2025 , Edited by admin on Mon Mar 31 17:34:16 GMT 2025
PRIMARY
PUBCHEM
20112022
Created by admin on Mon Mar 31 17:34:16 GMT 2025 , Edited by admin on Mon Mar 31 17:34:16 GMT 2025
PRIMARY
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