Compounds > n-(cyclobutylmethyl)-8 beta-methyl-6-methylenemorphinan-3-ol
Page last updated: 2024-11-11

n-(cyclobutylmethyl)-8 beta-methyl-6-methylenemorphinan-3-ol

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

N-(cyclobutylmethyl)-8 beta-methyl-6-methylenemorphinan-3-ol: has potent mixed agonist-antagonist narcotic properties; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5488631
CHEMBL ID606566
SCHEMBL ID1653472
MeSH IDM0095576

Synonyms (21)

Synonym
xorphanol
PDSP2_000327
CHEMBL606566
tr 5379
77287-89-9
17-(cyclobutylmethyl)-8beta-methyl-6-methylenmorphinan-3-ol
xorfanol [spanish]
xorphanolum
n-(cyclobutylmethyl)-8 beta-methyl-6-methylenemorphinan-3-ol
xorphanolum [latin]
unii-l415991p58
xorphanol [inn]
9a-cyclobutylmethyl-8beta-methyl-6-methylen-3-morphinanol
xorfanol
l415991p58 ,
morphinan-3-ol, 17-(cyclobutylmethyl)-8-methyl-6-methylene-, (8beta)-
17-(cyclobutylmethyl)-8.beta.-methyl-6-methylenemorphinan-3-ol
SCHEMBL1653472
(1r,9r,10r,11s)-17-(cyclobutylmethyl)-11-methyl-13-methylidene-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-4-ol
Q8044946
AKOS040754467

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"The narcotic antagonist TR5379M had po LD50 values of 365 and 750 mg/kg and iv LD50 values of 35."( Preclinical toxicity and teratogenicity studies with the narcotic antagonist analgesic drug TR5379M.
Bare, JJ; Clemens, GR; Halliwell, WE; Hartnagel, RE; Kitchen, DN; Kowalski, RL; Porter, MC, )		0.13

Dosage Studied

ExcerptRelevanceReference
" Dose-response curves were constructed using the rat tail pressure test for analgesia which indicated a rank order of potency of buprenorphine much greater than morphine greater than butorphanol greater than xorphanol = nalbuphine."( Physical dependence induced by opiate partial agonists in the rat.
Howlett, GJ; McCarthy, PS, 1984)		0.27
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (1)

Assay IDTitleYearJournalArticle
AID139099Analgesic Potency was tested against mice1990Journal of medicinal chemistry, Oct, Volume: 33, Issue:10
A Free-Wilson/Fujita-Ban analysis and prediction of the analgesic potency of some 3-hydroxy- and 3-methoxy-N-alkylmorphinan-6-one opioids.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904 (80.00)18.7374
1990's1 (20.00)18.2507
2000's0 (0.00)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.36

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.36 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.31 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.36)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
buprenorphine
Buprenorphine: A derivative of the opioid alkaloid THEBAINE that is a more potent and longer lasting analgesic than MORPHINE. It appears to act as a partial agonist at mu and kappa opioid receptors and as an antagonist at delta receptors. The lack of delta-agonist activity has been suggested to account for the observation that buprenorphine tolerance may not develop with chronic use.. buprenorphine : A morphinane alkaloid that is 7,8-dihydromorphine 6-O-methyl ether in which positions 6 and 14 are joined by a -CH2CH2- bridge, one of the hydrogens of the N-methyl group is substituted by cyclopropyl, and a hydrogen at position 7 is substituted by a 2-hydroxy-3,3-dimethylbutan-2-yl group. It is highly effective for the treatment of opioid use disorder and is also increasingly being used in the treatment of chronic pain.		1.9610morphinane alkaloiddelta-opioid receptor antagonist;
kappa-opioid receptor antagonist;
mu-opioid receptor agonist;
opioid analgesic
morphine
Meconium: The thick green-to-black mucilaginous material found in the intestines of a full-term fetus. It consists of secretions of the INTESTINAL GLANDS; BILE PIGMENTS; FATTY ACIDS; AMNIOTIC FLUID; and intrauterine debris. It constitutes the first stools passed by a newborn.		2.8840morphinane alkaloid;
organic heteropentacyclic compound;
tertiary amino compound		anaesthetic;
drug allergen;
environmental contaminant;
geroprotector;
mu-opioid receptor agonist;
opioid analgesic;
plant metabolite;
vasodilator agent;
xenobiotic
nalbuphine
Nalbuphine: A narcotic used as a pain medication. It appears to be an agonist at KAPPA RECEPTORS and an antagonist or partial agonist at MU RECEPTORS.		1.9610organic heteropentacyclic compoundmu-opioid receptor antagonist;
opioid analgesic
cyclorphan
cyclorphan: was heading 1965-94 (see under MORPHINANS 1965-90); use MORPHINANS to search CYCLORPHAN 1966-94		1.9710
butorphanol
Butorphanol: A synthetic morphinan analgesic with narcotic antagonist action. It is used in the management of severe pain.. butorphanol : Levorphanol in which a hydrogen at position 14 of the morphinan skeleton is substituted by hydroxy and one of the hydrogens of the N-methyl group is substituted by cyclopropyl. A semi-synthetic opioid agonist-antagonist analgesic, it is used as its (S,S)-tartaric acid salt for relief or moderate to severe pain.		1.9610morphinane alkaloidantitussive;
kappa-opioid receptor agonist;
mu-opioid receptor agonist;
opioid analgesic
morphinans
Morphinans: Compounds based on a partially saturated iminoethanophenanthrene, which can be described as ethylimino-bridged benzo-decahydronaphthalenes. They include some of the OPIOIDS found in PAPAVER that are used as ANALGESICS.		2.8840isoquinoline alkaloid fundamental parent;
morphinane alkaloid
sodium selenate
[no description available]		1.9710
ConditionIndicatedRelationship StrengthStudiesTrials
Chemical Dependence
[description not available]		02.3720
Substance-Related Disorders
Disorders related to substance use or abuse.		02.3720
Morphine Abuse
[description not available]		02.3620
Morphine Dependence
Strong dependence, both physiological and emotional, upon morphine.		02.3620
Drug Withdrawal Symptoms
[description not available]		01.9610
Substance Withdrawal Syndrome
Physiological and psychological symptoms associated with withdrawal from the use of a drug after prolonged administration or habituation. The concept includes withdrawal from smoking or drinking, as well as withdrawal from an administered drug.		01.9610
Ache
[description not available]		01.9610
Pain
An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.		01.9610