Page last updated: 2024-11-05

etorphine

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Description

Etorphine: A narcotic analgesic morphinan used as a sedative in veterinary practice. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID644209
CHEMBL ID140050
CHEBI ID4912
SCHEMBL ID20507
MeSH IDM0007932
PubMed CID26721
MeSH IDM0007932

Synonyms (55)

Synonym
etorphinum [inn-latin]
6,14-ethenomorphinan-7-methanol, 4,5-epoxy-3-hydroxy-6-methoxy-alpha,17-dimethyl-alpha-propyl-, (5alpha,7alpha(r))-
einecs 238-535-9
7-alpha-etorphine
etorphine [inn:ban]
CHEBI:4912
etorfina
(7r)-7-[(2r)-2-hydroxypentan-2-yl]-6-methoxy-17-methyl-5alpha-4,5-epoxy-6,14-ethenomorphinan-3-ol
etorphinum
7,8-dihydro-7-alpha-(1-(r)-hydroxy-1-methylbutyl)-o(sup 6)-methyl-6,14-endo-ethenomorphine
7alpha-etorphine
6,14-ethenomorphinan-3-ol, 7,8-didehydro-4,5-epoxy-18,19-dihydro-18-[(1r)-1-hydroxy-1-methylbutyl]-6-methoxy-17-methyl-, (5alpha,6beta,14beta,18r)-
tetrahydro-7-alpha-(1-hydroxy-1-methylbutyl)-6,14-endo-ethenooripavine
dea no. 9056
7-alpha-(1-(r)-hydroxy-1-methylbutyl)-6,14-endo-ethenotetrahydrooripavine
(-)-etorphine
oripavine, 6,14-endo-ethylenetetrahydro-7-(1-hydroxy-1-methylbutyl)- (7ci)
etorphine (except hydrochloride salt)
19-propylorvinol
m99 injection
6,14-ethenomorphinan-7-methanol, 4,5-epoxy-3-hydroxy-6-methoxy-alpha,17-dimethyl-alpha-propyl-, (alphar,5alpha,7alpha)- (9ci)
6,14-endo-ethenotetrahydrooripavine, 7-alpha-(1-hydroxy-1-methylbutyl)-
tetrahydro-7-alpha-(2-hydroxy-2-pentyl)-6,14-endo-ethenooripavine
6,14-endo-ethenotetrahydrooripavine, 7alpha-((r)-1-hydroxy-1-methylbutyl)- (8ci)
etorfina [dcit]
6,14-ethenomorphinan-7-methanol, 4,5-epoxy-3-hydroxy-6-methoxy-alpha,17-dimethyl-a-propyl-, [5alpha,7alpha(r)]-
6,7,8,14-tetrahydro-7alpha-(1-hydroxy-1-methylbutyl)-6,14-endo-ethenooripavine
42m2y6nu9o ,
hsdb 7601
m. 99 [as hydrochloride]
unii-42m2y6nu9o
CHEMBL140050
SCHEMBL20507
tetrahydro-7.alpha.-(1-hydroxy-1-methylbutyl)-6,14-endo-ethenooripavine
etorphine [hsdb]
tetrahydro-7.alpha.-(2-hydroxy-2-pentyl)-6,14-endo-ethenooripavine
7,8-dihydro-7.alpha.-(1(r)-hydroxy-1-methylbutyl)-o sup(6)-methyl-6,14-endo-ethenomorphine
etorphine [mi]
(5.alpha.,7.alpha.(r))-4,5-epoxy-3-hydroxy-6-methoxy-.alpha.,17-dimethyl-.alpha.-propyl-6,14-ethenomorphinan-7-methanol
etorphine [inn]
7.alpha.-(1(r)-hydroxy-1-methylbutyl)-6,14-endo-ethenotetrahydrooripavine
ids-ne-007
ids-ne-007(sect.3)
m. 99 free base
propylorvinol
m-99 free base
bdbm50123599
DTXSID40878669
PDSP2_001571
14521-96-1
etorphine
DB01497
Q416827
(1r,2s,6r,14r,15r,19r)-19-[(2s)-2-hydroxypentan-2-yl]-15-methoxy-5-methyl-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11,16-tetraen-11-ol
(1r,2s,6r)-19-(2-hydroxypentan-2-yl)-15-methoxy-5-methyl-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11,16-tetraen-11-ol

Research Excerpts

Overview

Etorphine is an non-selective opioid receptor agonist with very potent analgesic effect. It is usually used in veterinary medicine.

ExcerptReferenceRelevance
"Etorphine is an non-selective opioid receptor agonist with very potent analgesic effect. "( Barium elicits reversal of low-concentration etorphine-induced decrease of potassium conductance in cultures of dissociated dorsal root ganglion neurons.
Crain, SM; Fan, S, 1997
)
2
"Etorphine is a synthetic narcotic analgesic usually used in veterinary medicine. "( Analysis of etorphine in postmortem samples by HPLC with UV diode-array detection.
Elliott, SP; Hale, KA, 1999
)
2.13

Treatment

Etorphine treatment decreased ( approximately 25-40%) mu-receptor density similarly in both strains throughout treatment. Treatment with etorphine, but not morphine, produced a significant increase in protein levels of G protein-coupled receptor kinase 2, dynamin II, beta-arrestin 2 and phosphorylated-conventional protein kinase C.

ExcerptReferenceRelevance
"Etorphine-azaperone (treatment EA; 0.015 and 0.15 mg kg"( Immobilization of African buffaloes (Syncerus caffer) using etorphine-midazolam compared with etorphine-azaperone.
Buss, PE; Grace, JF; Laubscher, LL; Miller, MA; Raath, JP; Zeiler, GE, 2021
)
2.31
"Etorphine treatment decreased ( approximately 25-40%) mu-receptor density similarly in both strains throughout treatment."( In vivo regulation of mu-opioid receptor density and gene expression in CXBK and outbred Swiss Webster mice.
Duttaroy, A; Yoburn, BC, 2000
)
1.03
"treatment with etorphine, but not morphine, produced a significant increase in protein levels of G protein-coupled receptor kinase 2, dynamin II, beta-arrestin 2 and phosphorylated-conventional protein kinase C in membranes of the mouse spinal cord, suggesting that the etorphine-induced mu-opioid receptor desensitization may result from G protein-coupled receptor kinase 2/dynaminII/beta-arrestin2-dependent phosphorylation of mu-opioid receptors."( mu-Opioid receptor internalization-dependent and -independent mechanisms of the development of tolerance to mu-opioid receptor agonists: Comparison between etorphine and morphine.
Miyatake, M; Nakamura, A; Narita, M; Niikura, K; Suzuki, M; Suzuki, T; Yajima, Y, 2006
)
0.87

Pharmacokinetics

This study provides pharmacokinetic data and insight into the effects of propofol in rhinoceros anesthetized using etorphine, butorphanol, medetomidine, and azaperone.

ExcerptReferenceRelevance
"To evaluate the pharmacokinetic and pharmacodynamic characteristics of a novel opioid analgesic, dihydroetorphine (DHE), concentrations of DHE and its glucuronide (DG) in plasma and central nervous system (by liquid chromatography-tandem mass spectrometry) and the antinociceptive effect (by tail-immersion test) were measured after intravenous (i."( Pharmacokinetic and pharmacodynamic evaluations of a potent analgesic, dihydroetorphine, in hairless rat.
Hayashi, T; Kawase, M; Morimoto, Y; Ohmori, S; Saito, S, 2001
)
0.75
" These characteristics are accounted for by the pharmacokinetic properties of DHE in the rat, namely, by rapid distribution of DHE from the injection site to the brain and rapid metabolism by glucuronidation in the gut and liver followed by elimination into the bile."( Dihydroetorphine: a potent analgesic: pharmacology, toxicology, pharmacokinetics, and clinical effects.
Morimoto, Y; Ohmori, S, 2002
)
0.77
" The authors measured isohypercapnic ventilation, pain threshold, and tolerance responses to electrical noxious stimulation and arterial blood samples for pharmacokinetic analysis."( Analgesic and Respiratory Depressant Effects of R-dihydroetorphine: A Pharmacokinetic-Pharmacodynamic Analysis in Healthy Male Volunteers.
Baily, P; Boom, M; Dahan, A; Niesters, M; Oksche, A; Olofsen, E; Sarton, E; Smith, KJ; van Velzen, M, 2019
)
0.76
"7 ml/min/kg, the mean terminal half-life was 82."( Pharmacokinetics of intravenous propofol in southern white rhinoceros (Ceratotherium simum simum) after intramuscular etorphine-butorphanol-medetomidine-azaperone.
Berlin, ER; Clancy, MM; Ferris, RL; Howard, LL; Kinney, ME; Knych, HK; Mama, KR; Perrin, KL; Phair, KA, 2023
)
1.12
"This study provides pharmacokinetic data and insight into the effects of propofol in rhinoceros anesthetized using etorphine, butorphanol, medetomidine, and azaperone."( Pharmacokinetics of intravenous propofol in southern white rhinoceros (Ceratotherium simum simum) after intramuscular etorphine-butorphanol-medetomidine-azaperone.
Berlin, ER; Clancy, MM; Ferris, RL; Howard, LL; Kinney, ME; Knych, HK; Mama, KR; Perrin, KL; Phair, KA, 2023
)
1.33

Compound-Compound Interactions

ExcerptReferenceRelevance
"To study the analgesia efficacy of drugs combined with acupuncture analgesia for painless labor, 462 normal pregnancy women were observed."( [Clinical study on painless labor under drugs combined with acupuncture analgesia].
Jin, Y; Wu, L; Xia, Y, 1996
)
0.29
" Potent opioids combined with neuroleptic drugs are most often used for this purpose."( Evaluation of two different etorphine doses combined with azaperone in blesbok (Damaliscus pygargus phillipsi) immobilisation.
Gaudio, E; Hoffman, LC; Laubscher, LL; Meyer, LCR; Pfitzer, S; Raath, JP, 2021
)
0.92

Dosage Studied

Five anesthetic agents (C1744, etorphine, fentanyl, ketamine hydrochloride, and halothane) were tested to establish the dosage of a safe, effective, short-acting anesthetic for use in the sea otter. The shift to the right of the dose-response curves was greater for morphine and oxycodone compared to Etorphine.

ExcerptRelevanceReference
"Five anesthetic agents (C1744, etorphine, fentanyl, ketamine hydrochloride, and halothane) were tested to establish the dosage of a safe, effective, short-acting anesthetic for use in the sea otter."( Comparison of anesthetic agents in the sea otter.
Kocher, FH; Williams, TD, 1978
)
0.54
" It was found that 10 mg of naloxone was sufficient to antagonize wide dosage ranges of etorphine hydrochloride or fentanyl, used in combination with a variety of tranquilizers."( An appraisal of naloxone hydrochloride as a narcotic antagonist in the capture and release of wild herbivores.
Smuts, GL, 1975
)
0.48
" morphine dose-response line was shown to be displaced progressively to the right with decreasing maximal effect (i."( Modulation of the potency and efficacy of mu-mediated antinociception by delta agonists in the mouse.
Mosberg, HI; Porreca, F; Qi, JN, 1990
)
0.28
" injection of the drug at a dosage rate of 20 micrograms/kg."( Neurochemical changes in the brain and spinal cord of sheep: a basis for the immobilizing action of etorphine.
Kania, BF, 1985
)
0.49
" Complete dose-response data for morphine, heroin, etorphine, d- and l-ethylketazocine, d- and l-pentazocine, and d- and l-N-allylnormetazocine revealed a predominant response of hyperthermia."( Body temperature effects of opioids in rats: intracerebroventricular administration.
Adler, MW; Geller, EB; Rowan, CH, 1986
)
0.52
" Antagonism by competition at same opioid receptor subtypes is suggested from parallel shifts of the dose-response curve of etorphine or beta h-EP in the presence of increasing doses of beta h-EP-(1-28)."( Inhibition of analgesia by C-terminal deletion analogs of human beta-endorphin.
Li, CH; Nicolas, P, 1985
)
0.48
" Antagonism by competition at the same site(s) is suggested from parallel shifts of the dose-response curves of etorphine or beta-endorphin in the presence of beta-endorphin-(1-27)."( Beta-endorphin-(1-27) is a naturally occurring antagonist to etorphine-induced analgesia.
Li, CH; Nicolas, P, 1985
)
0.72
" The dose-response curves for the biological response were suggestive of positive cooperativity and systematically occurred at lower ligand concentrations than those for the binding of [3H] [D-Ala2, D-Leu5]enkephalin (DADLE), which were instead shallow and suggestive of a site heterogeneity or of a cooperative phenomenon."( Multiple states of opioid receptors may modulate adenylate cyclase in intact neuroblastoma X glioma hybrid cells.
Costa, T; Gramsch, C; Herz, A; Wüster, M, 1985
)
0.27
"Systemic administration of beta-funaltrexamine (beta-FNA) 24 hr before analgesic testing produced approximately a 10-fold parallel shift in the dose-response curves of the prototypic mu agonists morphine, I-methadone, fentanyl and etorphine in the mouse abdominal constriction test."( Use of beta-funaltrexamine to determine mu opioid receptor involvement in the analgesic activity of various opioid ligands.
Hynes, MD; Leander, JD; Reel, JK; Zimmerman, DM, 1987
)
0.46
" The dosage rates of the immobilization combinations for mammmals, birds and reptiles are presented in tabular form."( [Practical advice concerning the immobilization of wild and zoo animals].
von Hegel, G; Wiesner, H, 1985
)
0.27
" In contrast, removal of the morphine pellet 3 hours prior to the analgesic evaluation apparently unmasked the expression of tolerance and cross-tolerance as evidenced by a three fold, parallel shift to the right of the analgesic dose-response curve for subcutaneously administered etorphine and methadone and a seven fold shift to intracerebroventricularly administered morphine."( Differential analgesic cross-tolerance to morphine between lipophilic and hydrophilic narcotic agonists.
Paktor, J; Vaught, JL, 1984
)
0.44
" Morphine's direct effect on activity is believed to have a biphasic dose-response curve; therefore, the relation of dose to conditioning was also studied."( Conditioned increases in locomotor activity produced with morphine as an unconditioned stimulus, and the relation of conditioning to acute morphine effect and tolerance.
Kalant, H; Mucha, RF; Volkovskis, C, 1981
)
0.26
" It increased the IC50 values and slopes of their dose-response curve for enkephalins and their analogs, and shifted to the right the curves for FK33824, levorphanol and normorphine."( Functional opiate receptor in mouse vas deferens: evidence for a complex interaction.
Garzón, J; Lee, NM; Sánchez-Blázquez, P, 1983
)
0.27
", delayed nociceptive reaction on a 55 degrees C hot-plate with a dose-response curve not readily fitting a single straight line; this effect was antagonized by high doses of naloxone."( Bremazocine induces antinociception, but prevents opioid-induced constipation and catatonia in rats and precipitates withdrawal in morphine-dependent rats.
Gambino, MC; Petrillo, P; Tavani, A, 1984
)
0.27
", dose-response curves were shifted to the right) but failed to block the effects of diprenorphine."( Effects of naloxone, diprenorphine, buprenorphine and etorphine on unpunished and punished food-reinforced responding in the squirrel monkey.
DeRossett, SE; Holtzman, SG, 1984
)
0.52
" The dose-response curves for both were shifted to the right in non-parallel fashion with decreased slopes and antidiuretic efficacies."( Cross tolerance to etorphine in rats tolerant to morphine-induced antidiuresis.
Fuhrman-Lane, C; Fujimoto, JM; Tseng, LF, 1982
)
0.59
" At higher dosage levels respiratory rate was reduced to 2/minute."( Immobilization of coastal grizzly bears with etorphine hydrochloride.
Herbert, DM; Lay, DW; Turnbull, WG, 1980
)
0.52
" To achieve an excellent pain relief by higher dosage of DHE and tramadol need further randomized investigation."( [Influence of dihydroetorphine hydrochloride and tramadol on labor pain and umbilical blood gas].
Li, E; Weng, L, 1995
)
0.61
" However, the effect of differences in dosing protocol on tolerance to opioid analgesics of high or low efficacy has not been addressed."( The effect of intrinsic efficacy on opioid tolerance.
Duttaroy, A; Yoburn, BC, 1995
)
0.29
" At the end of treatment, the pumps and placebos were removed, and 4-24 h later, mice were tested in dose-response studies (tail flick) using the same drug that had been chronically administered."( The effect of intrinsic efficacy on opioid tolerance.
Duttaroy, A; Yoburn, BC, 1995
)
0.29
" Mice were injected intracerebroventricularly (ICV), or intrathecally (IT), or IT and ICV with PTX, and dose-response studies of the antinociceptive action of systemic (SC) morphine, fentanyl, and etorphine were conducted 10 days later."( Spinal and supraspinal effects of pertussis toxin on opioid analgesia.
Davis, T; Duttaroy, A; Shah, S; Yoburn, BC, 1994
)
0.48
" A good dose-response relationship was found between the 100% suppressive withdrawal sign doses of DHE and the degree of withdrawal sign in heroin addicts."( [Clinical assessment of physical dependence potential of dihydroetorphine hydrochloride (DHE)].
Cai, ZJ; Ge, Y; Li, M; Sun, WL, 1994
)
0.53
" The present study provides systematic dose-response analyses indicating that NTX elicited optimal enhancement of morphine's antinociceptive potency in mice when co-administered (i."( Ultra-low doses of naltrexone or etorphine increase morphine's antinociceptive potency and attenuate tolerance/dependence in mice.
Crain, SM; Shen, KF, 1997
)
0.58
" Dose-response and time-course determinations were performed with various opioids."( Sex-related differences in the antinociceptive effects of opioids: importance of rat genotype, nociceptive stimulus intensity, and efficacy at the mu opioid receptor.
Barrett, AC; Bowman, JR; Cook, CD; Picker, MJ; Roach, EL, 2000
)
0.31
" Using three human cancer cell lines: MIA PaCa-2 pancreatic adenocarcinoma, HT-29 colon adenocarcinoma, and CAL-27 squamous cell carcinoma of the head and neck, and OGF and the opioid antagonist naltrexone (NTX) at a dosage (10(-6)M) selected because it is known to repress or increase, respectively, cell replication, the effects on apoptosis (TUNEL, Annexin V) and necrosis (trypan blue) were investigated on days 2, 5, and 7 of exposure."( Opioids and the apoptotic pathway in human cancer cells.
McLaughlin, PJ; Zagon, IS, 2003
)
0.32
" Furthermore, the differences between intermittent and continuous dosing protocols were evaluated."( Opioid agonist and antagonist treatment differentially regulates immunoreactive mu-opioid receptors and dynamin-2 in vivo.
Patel, K; Purohit, V; Yoburn, BC; Zhang, Q, 2004
)
0.32
" Recommendation on dosage are given."( Experience with drugs for capture and restraint of wildebeest, impala, eland and hartebeest in Kenya.
Drevemo, SA; Grootenhuis, JG; Karstad, L, 1976
)
0.26
" The shift to the right of the dose-response curves was greater for morphine and oxycodone compared to etorphine and the highest dose of clocinnamox reduced the maximal effect of morphine and oxycodone, but not etorphine."( Opioid agonist efficacy predicts the magnitude of tolerance and the regulation of mu-opioid receptors and dynamin-2.
Kumar, P; Pawar, M; Sirohi, S; Sunkaraneni, S; Walker, EA; Yoburn, BC, 2007
)
0.55
"Analgesic efficacy of opioids and dosing protocol have been shown to influence analgesic tolerance."( Dosing protocol and analgesic efficacy determine opioid tolerance in the mouse.
Dighe, SV; Madia, PA; Sirohi, S; Walker, EA; Yoburn, BC, 2009
)
0.35
" Dose-response studies were conducted using morphine following treatment."( Dosing protocol and analgesic efficacy determine opioid tolerance in the mouse.
Dighe, SV; Madia, PA; Sirohi, S; Walker, EA; Yoburn, BC, 2009
)
0.35
" These results suggest that opioid analgesic tolerance may be increased when sustained release dosing formulations or continuous infusions are employed clinically."( Dosing protocol and analgesic efficacy determine opioid tolerance in the mouse.
Dighe, SV; Madia, PA; Sirohi, S; Walker, EA; Yoburn, BC, 2009
)
0.35
" In this experiment, similar effects could be seen in impala at the higher dosage rates of R-8-OH-DPAT."( Dose-effect study of the serotonin agonist R-8-OH-DPAT on opioid-induced respiratory depression in blesbok (Damaliscus pygargus philipsi) and impala (Aepyceros melampus).
Laubscher, L; Laurence, M; Meyer, L; Pfitzer, S; Raath, JP; Vaughan-Higgins, R; Warren, K, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
opioid analgesicA narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
sedativeA central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.
opioid receptor agonistAn agent that selectively binds to and activates an opioid receptor.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
alcoholA compound in which a hydroxy group, -OH, is attached to a saturated carbon atom.
morphinane alkaloidAn isoquinoline alkaloid based on a morphinan skeleton and its substituted derivatives.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (6)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Delta-type opioid receptorMus musculus (house mouse)Ki0.00290.00000.53939.4000AID1250603; AID415678
Delta-type opioid receptorRattus norvegicus (Norway rat)IC50 (µMol)0.00740.00030.38877.0000AID149505
Delta-type opioid receptorRattus norvegicus (Norway rat)Ki0.00030.00000.60689.2330AID149669
Mu-type opioid receptorRattus norvegicus (Norway rat)IC50 (µMol)0.00010.00010.887410.0000AID151303
Mu-type opioid receptorRattus norvegicus (Norway rat)Ki0.20020.00000.38458.6000AID1250605; AID151608; AID415677; AID415683
Kappa-type opioid receptorRattus norvegicus (Norway rat)Ki0.00020.00000.18683.9500AID148461
Kappa-type opioid receptorCavia porcellus (domestic guinea pig)IC50 (µMol)0.00180.00030.71237.0700AID148565
Kappa-type opioid receptorHomo sapiens (human)Ki0.00050.00000.362410.0000AID1250604; AID415679
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Delta-type opioid receptorRattus norvegicus (Norway rat)Activity0.04000.00000.11931.2200AID310939
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (30)

Processvia Protein(s)Taxonomy
immune responseKappa-type opioid receptorHomo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathwayKappa-type opioid receptorHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayKappa-type opioid receptorHomo sapiens (human)
chemical synaptic transmissionKappa-type opioid receptorHomo sapiens (human)
sensory perceptionKappa-type opioid receptorHomo sapiens (human)
locomotory behaviorKappa-type opioid receptorHomo sapiens (human)
sensory perception of painKappa-type opioid receptorHomo sapiens (human)
adenylate cyclase-inhibiting opioid receptor signaling pathwayKappa-type opioid receptorHomo sapiens (human)
response to insulinKappa-type opioid receptorHomo sapiens (human)
positive regulation of dopamine secretionKappa-type opioid receptorHomo sapiens (human)
negative regulation of luteinizing hormone secretionKappa-type opioid receptorHomo sapiens (human)
response to nicotineKappa-type opioid receptorHomo sapiens (human)
G protein-coupled opioid receptor signaling pathwayKappa-type opioid receptorHomo sapiens (human)
maternal behaviorKappa-type opioid receptorHomo sapiens (human)
eating behaviorKappa-type opioid receptorHomo sapiens (human)
response to estrogenKappa-type opioid receptorHomo sapiens (human)
estrous cycleKappa-type opioid receptorHomo sapiens (human)
response to ethanolKappa-type opioid receptorHomo sapiens (human)
regulation of saliva secretionKappa-type opioid receptorHomo sapiens (human)
behavioral response to cocaineKappa-type opioid receptorHomo sapiens (human)
sensory perception of temperature stimulusKappa-type opioid receptorHomo sapiens (human)
defense response to virusKappa-type opioid receptorHomo sapiens (human)
cellular response to lipopolysaccharideKappa-type opioid receptorHomo sapiens (human)
cellular response to glucose stimulusKappa-type opioid receptorHomo sapiens (human)
positive regulation of p38MAPK cascadeKappa-type opioid receptorHomo sapiens (human)
positive regulation of potassium ion transmembrane transportKappa-type opioid receptorHomo sapiens (human)
response to acrylamideKappa-type opioid receptorHomo sapiens (human)
positive regulation of eating behaviorKappa-type opioid receptorHomo sapiens (human)
conditioned place preferenceKappa-type opioid receptorHomo sapiens (human)
neuropeptide signaling pathwayKappa-type opioid receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
G protein-coupled opioid receptor activityKappa-type opioid receptorHomo sapiens (human)
protein bindingKappa-type opioid receptorHomo sapiens (human)
receptor serine/threonine kinase bindingKappa-type opioid receptorHomo sapiens (human)
dynorphin receptor activityKappa-type opioid receptorHomo sapiens (human)
neuropeptide bindingKappa-type opioid receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (14)

Processvia Protein(s)Taxonomy
nucleoplasmKappa-type opioid receptorHomo sapiens (human)
mitochondrionKappa-type opioid receptorHomo sapiens (human)
cytosolKappa-type opioid receptorHomo sapiens (human)
plasma membraneKappa-type opioid receptorHomo sapiens (human)
membraneKappa-type opioid receptorHomo sapiens (human)
sarcoplasmic reticulumKappa-type opioid receptorHomo sapiens (human)
T-tubuleKappa-type opioid receptorHomo sapiens (human)
dendriteKappa-type opioid receptorHomo sapiens (human)
synaptic vesicle membraneKappa-type opioid receptorHomo sapiens (human)
presynaptic membraneKappa-type opioid receptorHomo sapiens (human)
perikaryonKappa-type opioid receptorHomo sapiens (human)
axon terminusKappa-type opioid receptorHomo sapiens (human)
postsynaptic membraneKappa-type opioid receptorHomo sapiens (human)
plasma membraneKappa-type opioid receptorHomo sapiens (human)
neuron projectionKappa-type opioid receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (36)

Assay IDTitleYearJournalArticle
AID1147847Analgesic activity in rat assessed as pressure in tail relative to morphine1979Journal of medicinal chemistry, Jun, Volume: 22, Issue:6
Intramolecular hydrogen bonding and conformational studies of bridged thebaine and oripavine opiate narcotic agonists and antagonists.
AID227718Binding energy by using the equation deltaG obsd = -RT ln KD1984Journal of medicinal chemistry, Dec, Volume: 27, Issue:12
Functional group contributions to drug-receptor interactions.
AID310939Displacement of [3H]naltrindole from rat delta opioid receptor expressed in C6 cells2007Journal of medicinal chemistry, Apr-19, Volume: 50, Issue:8
Quantitative conformationally sampled pharmacophore for delta opioid ligands: reevaluation of hydrophobic moieties essential for biological activity.
AID151608Binding affinity against Opioid receptor mu 1 isolated from rat brain membrane was determined using [3H]DAMGO as radioligand2003Journal of medicinal chemistry, Sep-11, Volume: 46, Issue:19
Synthesis and biological evaluation of 14-alkoxymorphinans. 20. 14-phenylpropoxymetopon: an extremely powerful analgesic.
AID415678Displacement of [3H]diprenorphine from mouse delta opioid receptor expressed in CHO cells2009Bioorganic & medicinal chemistry letters, Mar-01, Volume: 19, Issue:5
Synthesis and biological evaluation of C-12 triazole and oxadiazole analogs of salvinorin A.
AID148625Evaluated the ability to protect against the irreversible antagonism of morphines effects by beta-FNA in guinea pig ileal longitudinal muscle.1983Journal of medicinal chemistry, Oct, Volume: 26, Issue:10
Different receptor sites mediate opioid agonism and antagonism.
AID113188In vivo antinociceptive potency determined in tail-flick test in mice2003Journal of medicinal chemistry, Sep-11, Volume: 46, Issue:19
Synthesis and biological evaluation of 14-alkoxymorphinans. 20. 14-phenylpropoxymetopon: an extremely powerful analgesic.
AID415677Displacement of [3H]diprenorphine from rat mu opioid receptor expressed in CHO cells2009Bioorganic & medicinal chemistry letters, Mar-01, Volume: 19, Issue:5
Synthesis and biological evaluation of C-12 triazole and oxadiazole analogs of salvinorin A.
AID149033Compound was tested for inhibition of [3H]naloxone receptor binding to opioid receptor in the absence of 100 mM NaCl1986Journal of medicinal chemistry, Apr, Volume: 29, Issue:4
N-substituent modulation of opiate agonist/antagonist activity in resolved 3-methyl-3-(m-hydroxyphenyl)piperidines.
AID231885Compound was tested for ability to protect against the irreversible antagonism of morphine''s effects by beta-FNA in guinea pig ileum at 1 nM concentration1983Journal of medicinal chemistry, Oct, Volume: 26, Issue:10
Different receptor sites mediate opioid agonism and antagonism.
AID1250603Displacement of [3H]diprenorphine from FLAG-tagged mouse delta opioid receptor expressed in CHO cell membranes2015Bioorganic & medicinal chemistry letters, Oct-15, Volume: 25, Issue:20
Synthesis and biological evaluation of 2-alkyl-2-methoxymethyl-salvinorin ethers as selective κ-opioid receptor agonists.
AID149630Inhibition of Opioid receptor delta 1 by displacing 1 nM [3H]DPDPE in guinea pig brain membrane1992Journal of medicinal chemistry, Nov-27, Volume: 35, Issue:24
O3-(2-carbomethoxyallyl) ethers of opioid ligands derived from oxymorphone, naltrexone, etorphine, diprenorphine, norbinaltorphimine, and naltrindole. Unexpected O3-dealkylation in the opioid radioligand displacement assay.
AID113186In vivo antinociceptive potency determined in hot plate assay in mice2003Journal of medicinal chemistry, Sep-11, Volume: 46, Issue:19
Synthesis and biological evaluation of 14-alkoxymorphinans. 20. 14-phenylpropoxymetopon: an extremely powerful analgesic.
AID149035Inhibition of [3H]naloxone receptor binding to opioid receptor in the presence of 100 mM NaCl1986Journal of medicinal chemistry, Apr, Volume: 29, Issue:4
N-substituent modulation of opiate agonist/antagonist activity in resolved 3-methyl-3-(m-hydroxyphenyl)piperidines.
AID1250608Displacement of [3H]diprenorphine from human kappa opioid receptor expressed in CHO cell membranes at 3 uM2015Bioorganic & medicinal chemistry letters, Oct-15, Volume: 25, Issue:20
Synthesis and biological evaluation of 2-alkyl-2-methoxymethyl-salvinorin ethers as selective κ-opioid receptor agonists.
AID311367Permeability coefficient in human skin2007Bioorganic & medicinal chemistry, Nov-15, Volume: 15, Issue:22
Transdermal penetration behaviour of drugs: CART-clustering, QSPR and selection of model compounds.
AID1250605Displacement of [3H]diprenorphine from rat mu opioid receptor expressed in CHO cell membranes2015Bioorganic & medicinal chemistry letters, Oct-15, Volume: 25, Issue:20
Synthesis and biological evaluation of 2-alkyl-2-methoxymethyl-salvinorin ethers as selective κ-opioid receptor agonists.
AID148993Inhibition of opioid receptor mu by displacing 1 nM [3H]DAGO in guinea pig brain membrane1992Journal of medicinal chemistry, Nov-27, Volume: 35, Issue:24
O3-(2-carbomethoxyallyl) ethers of opioid ligands derived from oxymorphone, naltrexone, etorphine, diprenorphine, norbinaltorphimine, and naltrindole. Unexpected O3-dealkylation in the opioid radioligand displacement assay.
AID1250609Displacement of [3H]diprenorphine from FLAG-tagged mouse delta opioid receptor expressed in CHO cell membranes Displacement of [3H]diprenorphine from human kappa opioid receptor expressed in CHO cell membranes at 3 uM2015Bioorganic & medicinal chemistry letters, Oct-15, Volume: 25, Issue:20
Synthesis and biological evaluation of 2-alkyl-2-methoxymethyl-salvinorin ethers as selective κ-opioid receptor agonists.
AID229952Relative affinity for rat brain kappa1 and guinea pig delta opioid receptors1996Journal of medicinal chemistry, May-10, Volume: 39, Issue:10
Probes for narcotic receptor-mediated phenomena. 21. Novel derivatives of 3-(1,2,3,4,5,11-hexahydro-3-methyl-2,6-methano-6H-azocino[4,5-b]indol- 6-yl)-phenols with improved delta opioid receptor selectivity.
AID1250610Displacement of [3H]diprenorphine from rat mu opioid receptor expressed in CHO cell membranes Displacement of [3H]diprenorphine from human kappa opioid receptor expressed in CHO cell membranes at 3 uM2015Bioorganic & medicinal chemistry letters, Oct-15, Volume: 25, Issue:20
Synthesis and biological evaluation of 2-alkyl-2-methoxymethyl-salvinorin ethers as selective κ-opioid receptor agonists.
AID191072Analgesic activity was measured using tail-flick test in Sprague-Dawley rats and expressed as response value1981Journal of medicinal chemistry, Jul, Volume: 24, Issue:7
6-Demethoxythebaine and its conversion to analgesics of the 6,14-ethenomorphinan type.
AID147960Inhibition of opioid receptor kappa by displacing 0.5 nM [3H]bremazocine in guinea pig brain membrane1992Journal of medicinal chemistry, Nov-27, Volume: 35, Issue:24
O3-(2-carbomethoxyallyl) ethers of opioid ligands derived from oxymorphone, naltrexone, etorphine, diprenorphine, norbinaltorphimine, and naltrindole. Unexpected O3-dealkylation in the opioid radioligand displacement assay.
AID151303Inhibition of [3H]- DAMGO binding to Rat brain Opioid receptor mu 11996Journal of medicinal chemistry, May-10, Volume: 39, Issue:10
Probes for narcotic receptor-mediated phenomena. 21. Novel derivatives of 3-(1,2,3,4,5,11-hexahydro-3-methyl-2,6-methano-6H-azocino[4,5-b]indol- 6-yl)-phenols with improved delta opioid receptor selectivity.
AID149046The ratio between [3H]naloxone binding in the presence and absence of 100 mM NaCl1986Journal of medicinal chemistry, Apr, Volume: 29, Issue:4
N-substituent modulation of opiate agonist/antagonist activity in resolved 3-methyl-3-(m-hydroxyphenyl)piperidines.
AID229954Relative affinity mu and delta opioid receptors of rat brain1996Journal of medicinal chemistry, May-10, Volume: 39, Issue:10
Probes for narcotic receptor-mediated phenomena. 21. Novel derivatives of 3-(1,2,3,4,5,11-hexahydro-3-methyl-2,6-methano-6H-azocino[4,5-b]indol- 6-yl)-phenols with improved delta opioid receptor selectivity.
AID113187In vivo antinociceptive potency determined in paraphenylquinone writhing test in mice2003Journal of medicinal chemistry, Sep-11, Volume: 46, Issue:19
Synthesis and biological evaluation of 14-alkoxymorphinans. 20. 14-phenylpropoxymetopon: an extremely powerful analgesic.
AID415679Displacement of [3H]diprenorphine from human kappa opioid receptor expressed in CHO cells2009Bioorganic & medicinal chemistry letters, Mar-01, Volume: 19, Issue:5
Synthesis and biological evaluation of C-12 triazole and oxadiazole analogs of salvinorin A.
AID148565Inhibition of [3H]- U69,593 binding to Guinea pig Opioid receptor kappa 11996Journal of medicinal chemistry, May-10, Volume: 39, Issue:10
Probes for narcotic receptor-mediated phenomena. 21. Novel derivatives of 3-(1,2,3,4,5,11-hexahydro-3-methyl-2,6-methano-6H-azocino[4,5-b]indol- 6-yl)-phenols with improved delta opioid receptor selectivity.
AID310938Agonist activity at rat delta opioid receptor expressed in C6 cells assessed as stimulation of [35S]GTP-gamma-S binding relative to BW373U862007Journal of medicinal chemistry, Apr-19, Volume: 50, Issue:8
Quantitative conformationally sampled pharmacophore for delta opioid ligands: reevaluation of hydrophobic moieties essential for biological activity.
AID148461Binding affinity against Opioid receptor kappa 1 isolated from rat brain membrane was determined using [3H]U-69593 as radioligand2003Journal of medicinal chemistry, Sep-11, Volume: 46, Issue:19
Synthesis and biological evaluation of 14-alkoxymorphinans. 20. 14-phenylpropoxymetopon: an extremely powerful analgesic.
AID148475Inhibition of total opioid receptor by displacing 0.5 nM [3H]bremazocine in guinea pig brain membrane1992Journal of medicinal chemistry, Nov-27, Volume: 35, Issue:24
O3-(2-carbomethoxyallyl) ethers of opioid ligands derived from oxymorphone, naltrexone, etorphine, diprenorphine, norbinaltorphimine, and naltrindole. Unexpected O3-dealkylation in the opioid radioligand displacement assay.
AID415683Displacement of [3H]DAMGO from rat mu opioid receptor expressed in CHO cells at 1 uM2009Bioorganic & medicinal chemistry letters, Mar-01, Volume: 19, Issue:5
Synthesis and biological evaluation of C-12 triazole and oxadiazole analogs of salvinorin A.
AID149505Inhibition of [3H]- DADLE binding to Rat brain Opioid receptor delta 11996Journal of medicinal chemistry, May-10, Volume: 39, Issue:10
Probes for narcotic receptor-mediated phenomena. 21. Novel derivatives of 3-(1,2,3,4,5,11-hexahydro-3-methyl-2,6-methano-6H-azocino[4,5-b]indol- 6-yl)-phenols with improved delta opioid receptor selectivity.
AID1250604Displacement of [3H]diprenorphine from human kappa opioid receptor expressed in CHO cell membranes2015Bioorganic & medicinal chemistry letters, Oct-15, Volume: 25, Issue:20
Synthesis and biological evaluation of 2-alkyl-2-methoxymethyl-salvinorin ethers as selective κ-opioid receptor agonists.
AID149669Binding affinity against Opioid receptor delta 1 isolated from rat brain membrane was determined using [3H][Ile]-deltorphin as radioligand2003Journal of medicinal chemistry, Sep-11, Volume: 46, Issue:19
Synthesis and biological evaluation of 14-alkoxymorphinans. 20. 14-phenylpropoxymetopon: an extremely powerful analgesic.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (785)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990458 (58.34)18.7374
1990's168 (21.40)18.2507
2000's91 (11.59)29.6817
2010's49 (6.24)24.3611
2020's19 (2.42)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 58.23

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index58.23 (24.57)
Research Supply Index6.71 (2.92)
Research Growth Index4.31 (4.65)
Search Engine Demand Index98.45 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (58.23)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials23 (2.88%)5.53%
Reviews0 (0.00%)6.00%
Reviews12 (1.50%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies20 (2.51%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other12 (100.00%)84.16%
Other743 (93.11%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]