Compounds > jwh-073
Page last updated: 2024-11-12

jwh-073

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

Cross-References

ID SourceID
PubMed CID10471670
CHEMBL ID2380416
CHEBI ID181123
SCHEMBL ID11983320
MeSH IDM0568640

Synonyms (47)

Synonym
HY-32733
208987-48-8
(1-butylindol-3-yl)-naphthalen-1-ylmethanone
CHEBI:181123
1-butyl-3-(1-naphthoyl)indole
PDSP2_000253
PDSP1_000254
AKOS005146537
FT-0664155
FT-0664154
(1-butyl-1h-indol-3-yl)(naphthalen-1-yl)methanone;jwh-073
A4544
(1-butyl-1h-indol-3-yl)(naphthalen-1-yl)methanone
CHEMBL2380416
1-naphthyl(1-butyl-1h-indole-3-yl)methanone
jwh-073
bdbm85804
jwh073
1-butyl-3-(1-naphthoyl) indole
unii-bbx3bp2772
dea no.7173
(1-butyl-1h-indole-3-yl)-1-naphthalenyl methanone
methanone, (1-butyl-1h-indol-3-yl)-1-naphthalenyl-
bbx3bp2772 ,
hsdb 7999
jwh 073
CS-0827
CCG-208716
naphthaten-1-yl-(1-butylindol-3-yl)methanone
SCHEMBL11983320
VCHHHSMPMLNVGS-UHFFFAOYSA-N
(1-butyl-1h-indole-3-yl)(naphthalene-1-yl)methanone
naphthalen-1-yl-(1-butylindol-3-yl)methanone
j2.856.750b ,
DTXSID20175042
NCGC00378993-02
c23h21no
1-butyl-3-(1-naphthoyl)-1h-indole
Q423476
1-naphthalenyl(1-butyl-1h-indol-3-yl)methanone
doi:10.14272/vchhhsmpmlnvgs-uhfffaoysa-n.1
10.14272/VCHHHSMPMLNVGS-UHFFFAOYSA-N.1
BCP24000
jwh-073; jwh073
ctdp-32476 hcl
jwh-073, 1mg/ml in methanol
jwh-073, 0.1mg/ml in methanol

Research Excerpts

Compound-Compound Interactions

ExcerptReferenceRelevance
" Because SCBs are frequently used in combinations, we hypothesized that coadministering multiple SCBs induces synergistic drug-drug interactions."( Differential drug-drug interactions of the synthetic Cannabinoids JWH-018 and JWH-073: implications for drug abuse liability and pain therapy.
Brents, LK; Fantegrossi, WE; Prather, PL; Saffell, AR; Zimmerman, SM, 2013)		0.62

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019)		0.51

Dosage Studied

ExcerptRelevanceReference
" Drug deliveries calculated as percent vehicle followed a prototypical inverted-U shaped dose-response curve for cannabinoids and heroin except for THC and JWH-018 (in males)."( Self-administration of inhaled delta-9-tetrahydrocannabinol and synthetic cannabinoids in non-human primates.
Cooper, ZD; Evans, SM; Foltin, RW, 2021)		0.62
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
indolecarboxamide
[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 (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Cannabinoid receptor 2 Homo sapiens (human)Ki0.00980.00000.415610.0000AID747706
Cannabinoid receptor 1Mus musculus (house mouse)Ki0.01290.00060.72467.2000AID747707
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (12)

Processvia Protein(s)Taxonomy
response to amphetamineCannabinoid receptor 2 Homo sapiens (human)
inflammatory responseCannabinoid receptor 2 Homo sapiens (human)
immune responseCannabinoid receptor 2 Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerCannabinoid receptor 2 Homo sapiens (human)
leukocyte chemotaxisCannabinoid receptor 2 Homo sapiens (human)
negative regulation of synaptic transmission, GABAergicCannabinoid receptor 2 Homo sapiens (human)
response to lipopolysaccharideCannabinoid receptor 2 Homo sapiens (human)
negative regulation of mast cell activationCannabinoid receptor 2 Homo sapiens (human)
cannabinoid signaling pathwayCannabinoid receptor 2 Homo sapiens (human)
negative regulation of action potentialCannabinoid receptor 2 Homo sapiens (human)
regulation of metabolic processCannabinoid receptor 2 Homo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayCannabinoid receptor 2 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (2)

Processvia Protein(s)Taxonomy
protein bindingCannabinoid receptor 2 Homo sapiens (human)
cannabinoid receptor activityCannabinoid receptor 2 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
plasma membraneCannabinoid receptor 2 Homo sapiens (human)
dendriteCannabinoid receptor 2 Homo sapiens (human)
extrinsic component of cytoplasmic side of plasma membraneCannabinoid receptor 2 Homo sapiens (human)
perikaryonCannabinoid receptor 2 Homo sapiens (human)
endoplasmic reticulumCannabinoid receptor 2 Homo sapiens (human)
plasma membraneCannabinoid receptor 2 Homo sapiens (human)
cytoplasmCannabinoid receptor 2 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (8)

Assay IDTitleYearJournalArticle
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1347160Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347159Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID747706Agonist activity at human CB2 receptor transfected in CHO cells assessed as inhibition of forskolin-stimulated adenylyl cyclase activity after 15 mins by liquid scintillation spectrophotometry2013Journal of medicinal chemistry, Jun-13, Volume: 56, Issue:11
Design, synthesis, and biological evaluation of aminoalkylindole derivatives as cannabinoid receptor ligands with potential for treatment of alcohol abuse.
AID747707Agonist activity at CB1 receptor in mouse Neuro2a cells assessed as inhibition of forskolin-stimulated adenylyl cyclase activity after 15 mins by liquid scintillation spectrophotometry2013Journal of medicinal chemistry, Jun-13, Volume: 56, Issue:11
Design, synthesis, and biological evaluation of aminoalkylindole derivatives as cannabinoid receptor ligands with potential for treatment of alcohol abuse.
AID747703Agonist activity at CB1 receptor in Swiss mouse assessed as hypothermic effect at 10 mg/kg, ip2013Journal of medicinal chemistry, Jun-13, Volume: 56, Issue:11
Design, synthesis, and biological evaluation of aminoalkylindole derivatives as cannabinoid receptor ligands with potential for treatment of alcohol abuse.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (45)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's40 (88.89)24.3611
2020's5 (11.11)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 35.92

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

MetricThis Compound (vs All)
Research Demand Index35.92 (24.57)
Research Supply Index3.85 (2.92)
Research Growth Index4.52 (4.65)
Search Engine Demand Index50.49 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (35.92)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (4.35%)6.00%
Case Studies2 (4.35%)4.05%
Observational0 (0.00%)0.25%
Other42 (91.30%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
methanol
Methanol: A colorless, flammable liquid used in the manufacture of FORMALDEHYDE and ACETIC ACID, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness.. primary alcohol : A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.. methanol : The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group.		2.0810alkyl alcohol;
one-carbon compound;
primary alcohol;
volatile organic compound		amphiprotic solvent;
Escherichia coli metabolite;
fuel;
human metabolite;
mouse metabolite;
Mycoplasma genitalium metabolite
mianserin
Mianserin: A tetracyclic compound with antidepressant effects. It may cause drowsiness and hematological problems. Its mechanism of therapeutic action is not well understood, although it apparently blocks alpha-adrenergic, histamine H1, and some types of serotonin receptors.. mianserin : A dibenzoazepine (specifically 1,2,3,4,10,14b-hexahydrodibenzo[c,f]pyrazino[1,2-a]azepine) methyl-substituted on N-2. Closely related to (and now mostly superseded by) the tetracyclic antidepressant mirtazapinean, it is an atypical antidepressant used in the treatment of depression throughout Europe and elsewhere.		2.1310dibenzoazepineadrenergic uptake inhibitor;
alpha-adrenergic antagonist;
antidepressant;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
geroprotector;
H1-receptor antagonist;
histamine agonist;
sedative;
serotonergic antagonist
sibutramine
sibutramine: serotonin and norepinephrine transporter inhibitor; Meridia is tradename for sibutramine hydrochloride		2.1710organochlorine compound;
tertiary amino compound		anti-obesity agent;
serotonin uptake inhibitor
tetraethoxysilane
[no description available]		2.2510
rhodamine b
rhodamine B: RN & N1 from 9th CI Form Index; RN given refers to parent cpd; structure in Merck Index, 9th ed, #7973; TETRAETHYLRHODAMINE was see RHODAMINES 1975-93; use RHODAMINES to search TETRAETHYLRHODAMINE 1975-93. rhodamine B : An organic chloride salt having N-[9-(2-carboxyphenyl)-6-(diethylamino)-3H-xanthen-3-ylidene]-N-ethylethanaminium as the counterion. An amphoteric dye commonly used as a fluorochrome.		2.3110organic chloride salt;
xanthene dye		fluorescent probe;
fluorochrome;
histological dye
cyclohexanol
Cyclohexanols: Monohydroxy derivatives of cyclohexanes that contain the general formula R-C6H11O. They have a camphorlike odor and are used in making soaps, insecticides, germicides, dry cleaning, and plasticizers.. cyclohexanols : An alcohol in which one or more hydroxy groups are attached to a cyclohexane skeleton.		4.1140cyclohexanols;
secondary alcohol		solvent
n-pentanoic acid
n-pentanoic acid: RN given refers to unlabeled parent cpd. valeric acid : A straight-chain saturated fatty acid containing five carbon atoms.		2.0810short-chain fatty acid;
straight-chain saturated fatty acid		plant metabolite
indazoles
Indazoles: A group of heterocyclic aromatic organic compounds consisting of the fusion of BENZENE and PYRAZOLES.		2.5320indazole
adamantane
Adamantane: A tricyclo bridged hydrocarbon.		2.1510adamantanes;
polycyclic alkane
dronabinol
Dronabinol: A psychoactive compound extracted from the resin of Cannabis sativa (marihuana, hashish). The isomer delta-9-tetrahydrocannabinol (THC) is considered the most active form, producing characteristic mood and perceptual changes associated with this compound.. Delta(9)-tetrahydrocannabinol : A diterpenoid that is 6a,7,8,10a-tetrahydro-6H-benzo[c]chromene substituted at position 1 by a hydroxy group, positions 6, 6 and 9 by methyl groups and at position 3 by a pentyl group. The principal psychoactive constituent of the cannabis plant, it is used for treatment of anorexia associated with AIDS as well as nausea and vomiting associated with cancer chemotherapy.		3.4970benzochromene;
diterpenoid;
phytocannabinoid;
polyketide		cannabinoid receptor agonist;
epitope;
hallucinogen;
metabolite;
non-narcotic analgesic
selegiline
Selegiline: A selective, irreversible inhibitor of Type B monoamine oxidase that is used for the treatment of newly diagnosed patients with PARKINSON DISEASE, and for the treatment of depressive disorders. The compound without isomeric designation is Deprenyl.		2.1710selegiline;
terminal acetylenic compound		geroprotector
glucuronic acid
Glucuronic Acid: A sugar acid formed by the oxidation of the C-6 carbon of GLUCOSE. In addition to being a key intermediate metabolite of the uronic acid pathway, glucuronic acid also plays a role in the detoxification of certain drugs and toxins by conjugating with them to form GLUCURONIDES.. D-glucuronic acid : The D-enantiomer of glucuronic acid.. D-glucopyranuronic acid : A D-glucuronic acid in cyclic pyranose form.		2.0610D-glucuronic acidalgal metabolite
sr141716
[no description available]		2.4820amidopiperidine;
carbohydrazide;
dichlorobenzene;
monochlorobenzenes;
pyrazoles		anti-obesity agent;
appetite depressant;
CB1 receptor antagonist
cp-55,940
[no description available]		2.0810
1,1-dimethylheptyl-11-hydroxytetrahydrocannabinol
HU 211: structure given in first source; HU 211 is active & HU 210 is inactive as canibinoids; functional N-methyl-D-aspartate receptor blocker; RN given is for (6aS-trans)-isomer		2.3110
3-(2-hydroxy-4-(1,1-dimethylheptylphenyl)cyclohexan-1-ol)
CP 47497: cannabimimetic agent; structure given in first source		3.620alkylbenzene;
ring assembly
6-hydroxyindole
6-hydroxyindole: structure in first source		2.0810
3-(2-hydroxy-4-(1,1-dimethylheptyl)phenyl)-4-(3-hydroxypropyl)cyclohexanol
3-(2-hydroxy-4-(1,1-dimethylheptyl)phenyl)-4-(3-hydroxypropyl)cyclohexanol: (-)-CP-55,940 and (+)-CP-56,667 are enantiomers; RN refers to CP-55,940		2.520alkylbenzene;
ring assembly
heroin
Heroin: A narcotic analgesic that may be habit-forming. It is a controlled substance (opium derivative) listed in the U.S. Code of Federal Regulations, Title 21 Parts 329.1, 1308.11 (1987). Sale is forbidden in the United States by Federal statute. (Merck Index, 11th ed). heroin : A morphinane alkaloid that is morphine bearing two acetyl substituents on the O-3 and O-6 positions. As with other opioids, heroin is used as both an analgesic and a recreational drug. Frequent and regular administration is associated with tolerance and physical dependence, which may develop into addiction. Its use includes treatment for acute pain, such as in severe physical trauma, myocardial infarction, post-surgical pain, and chronic pain, including end-stage cancer and other terminal illnesses.		2.3110morphinane alkaloidmu-opioid receptor agonist;
opioid analgesic;
prodrug
hexarelin
hexarelin: a synthetic growth hormone releasing peptide; structurally similar to GHRP-6, with the substitution of D-Trp with its 2-methyl derivative; more potent & stable and less toxic than GHRP-6		2.1710
am 694
1-(5-fluoropentyl)-3-(2-iodobenzoyl)indole : A member of the class of indoles that is 1H-indole which is substituted at position 1 by a 5-fluoropentyl group and a position 3 by an o-fluorobenzoyl group. It is a selective agonist for the CB1 cannabinoid receptor; Ki values for the CB1 and CB2 receptors are 0.08 and 1.44 nM, respectively.		2.0810aromatic ketone;
indoles;
organofluorine compound;
organoiodine compound;
synthetic cannabinoid		cannabinoid receptor agonist
jwh 018
1-pentyl-3-(1-naphthoyl)indole: structure in first source		6.51320indolecarboxamide
piperidines
Piperidines: A family of hexahydropyridines.		2.0710
jwh-122
(4-methyl-1-naphthyl)-(1-pentylindol-3-yl)methanone: structure in first source		2.8130
ur-144
(1-pentyl-1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone: structure in first source		2.5320
jwh-210
4-ethylnaphthalen-1-yl-(1-pentylindol-3-yl)methanone: a cannabimimetic; structure in first source		2.830indolecarboxamide
jwh 019
(1-hexyl-1H-indol-3-yl)-1-naphthalenylmethanone: a synthetic cannabinoid; structure in first source		2.7830
AM2201
1-(5-fluoropentyl)-3-(1-naphthoyl)indole: a cannabimimetic; structure in first source		9.1440indolecarboxamide
AKB48
N-(1-adamantyl)-1-pentylindazole-3-carboxamide: a synthetic cannabinoid; structure in first source		2.1510aromatic amide;
indazoles
xlr-11
XLR-11: synthetic cannabinoid; structure in first source		2.1510
n-(1-amino-3,3-dimethyl-1-oxobutan-2-yl)-1-pentyl-1h-indazole-3-carboxamide
N-(1-amino-3,3-dimethyl-1-oxobutan-2-yl)-1-pentyl-1H-indazole-3-carboxamide: a synthetic cannabinoid known as black mamba		2.1110
ConditionIndicatedRelationship StrengthStudiesTrials
Alcohol Abuse
[description not available]		02.0810
Alcoholism
A primary, chronic disease with genetic, psychosocial, and environmental factors influencing its development and manifestations. The disease is often progressive and fatal. It is characterized by impaired control over drinking, preoccupation with the drug alcohol, use of alcohol despite adverse consequences, and distortions in thinking, most notably denial. Each of these symptoms may be continuous or periodic. (Morse & Flavin for the Joint Commission of the National Council on Alcoholism and Drug Dependence and the American Society of Addiction Medicine to Study the Definition and Criteria for the Diagnosis of Alcoholism: in JAMA 1992;268:1012-4)		02.0810
Congenital Zika Syndrome
[description not available]		02.2510
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.5820
Zika Virus Infection
A viral disease transmitted by the bite of AEDES mosquitoes infected with ZIKA VIRUS. Its mild DENGUE-like symptoms include fever, rash, headaches and ARTHRALGIA. The viral infection during pregnancy, in rare cases, is associated with congenital brain and ocular abnormalities, called Congenital Zika Syndrome, including MICROCEPHALY and may also lead to GUILLAIN-BARRE SYNDROME.		02.2510
Chemical Dependence
[description not available]		03.7230
Hypothermia, Accidental
[description not available]		03.9540
Ache
[description not available]		02.0810
Hypothermia
Lower than normal body temperature, especially in warm-blooded animals.		08.9540
Pain
An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.		07.0810
Substance-Related Disorders
Disorders related to substance use or abuse.		03.7230
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		02.7830
Ambulation Disorders, Neurologic
[description not available]		02.1310
Nervous System Disorders
[description not available]		02.1310
Nervous System Diseases
Diseases of the central and peripheral nervous system. This includes disorders of the brain, spinal cord, cranial nerves, peripheral nerves, nerve roots, autonomic nervous system, neuromuscular junction, and muscle.		02.1310
Behavior Disorders
[description not available]		03.0610
Absence Seizure
[description not available]		03.0610
Drug Withdrawal Symptoms
[description not available]		03.4220
Mental Disorders
Psychiatric illness or diseases manifested by breakdowns in the adaptational process expressed primarily as abnormalities of thought, feeling, and behavior producing either distress or impairment of function.		03.0610
Seizures
Clinical or subclinical disturbances of cortical function due to a sudden, abnormal, excessive, and disorganized discharge of brain cells. Clinical manifestations include abnormal motor, sensory and psychic phenomena. Recurrent seizures are usually referred to as EPILEPSY or seizure disorder.		03.0610
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.		03.4220
Cannabis Abuse
[description not available]		02.4820
Marijuana Abuse
Use of marijuana associated with abnormal psychological, social, and or occupational functioning.		02.4820