Page last updated: 2024-12-11

am-356

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Description

methanandamide: structure given in first source; RN given refers to (all-Z)-(+-)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID6321351
CHEMBL ID120526
CHEBI ID167729
SCHEMBL ID338871
MeSH IDM0233338

Synonyms (46)

Synonym
bdbm50054472
(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoic acid ((r)-2-hydroxy-1-methyl-ethyl)-amide
CHEBI:167729
BRD-K97602563-001-02-7
BSPBIO_001285
IDI1_033755
BCBCMAP01_000201
methanandamide
r(+)-methanandamide, 5 mg/ml in absolute ethanol, >=96% (hplc)
n-(1r-methyl-2-hydroxy-ethyl)-5z,8z,11z,14z-eicosatetraenoyl amine
n-(1r-methyl-2-hydroxy-ethyl) arachidonoyl amine
LMFA08020040
n-(1r-methyl-2-hydroxy-ethyl)arachidonoylamide
NCGC00161309-02
NCGC00161309-03
NCGC00161309-01
NCGC00161309-04
(5z,8z,11z,14z)-n-[(2r)-1-hydroxypropan-2-yl]icosa-5,8,11,14-tetraenamide
gtpl2506
r-(+)-methanandamide
am-356
HMS1989A07
CHEMBL120526 ,
BML2-C03
HMS1791A07
HMS1361A07
r(+)-methanandamide
SCHEMBL338871
AKOS024456397
(r)-n-(2-hydroxy-1-methylethyl)-5z,8z,11z,14z-eicosatetraenamide
(r)-(+)-methanandamide
SQKRUBZPTNJQEM-FQPARAGTSA-N
(r)-(+)-arachidonyl-1\\\\ffffff92-hydroxy-2\\\\ffffff92-propylamide
(r)-(+)-methanandamide (in tocrisolvetrade mark 100)
HMS3649D09
HMS3402A07
5,8,11,14-eicosatetraenamide,n-[(1r)-2-hydroxy-1-methylethyl]-,(5z,8z,11z,14z)-
J-009387
(5z,8z,11z,14z)-n-((r)-1-hydroxypropan-2-yl)icosa-5,8,11,14-tetraenamide
SR-01000946643-1
sr-01000946643
Q6553887
(5z,8z,11z, 14z)-n-((2r)-1-hydroxypropan-2-yl)eicosa-5,8,11,14-tetraenamide
F4U8EF3PBH ,
5,8,11,14-eicosatetraenamide, n-((1r)-2-hydroxy-1-methylethyl)-, (5z,8z,11z,14z)-
unii-f4u8ef3pbh

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"The generation of hyperpolarising vasorelaxant endothelial cytochrome P450 epoxygenase (CYP)-derived metabolites of arachidonic may provide beneficial effects for the treatment of cardiovascular diseases in which the bioavailability of NO is impaired."( Cytochrome P450 pathway contributes to methanandamide-induced vasorelaxation in rat aorta.
Alsasua, A; Dannert, MT; Herradón, E; López-Miranda, V; Martín, MI, 2010
)
0.36

Dosage Studied

ExcerptRelevanceReference
" Following training, substitution tests using a cumulative dosing procedure revealed that anandamide (0."( (R)-methanandamide, but not anandamide, substitutes for delta 9-THC in a drug-discrimination procedure.
Burkey, RT; Nation, JR, 1997
)
0.3
"We examined the effects of Delta 9-tetrahydrocannabinol (Delta 9-THC), (R)-(+)-arachidonyl-1'-hydroxy-2'-propylamide ((R)-methanandamide, AM 356), SR 141716, and d-amphetamine on fixed-ratio (FR) responding maintained by food in rats before and during daily dosing with Delta 9-THC."( Effects of Delta 9-tetrahydrocannabinol, (R)-methanandamide, SR 141716,and d-amphetamine before and during daily Delta 9-tetrahydrocannabinol dosing.
Goutopoulos, A; Järbe, TU; Lamb, RJ; Lin, S; Makriyannis, A, 2000
)
0.31
"3 and 1 mg/kg) produced rightward shifts in the Delta9-THC dose-response curve for Delta9-THC-appropriate responding and for (R)-methanandamide-appropriate responding (surmountable antagonism)."( (R)-methanandamide and Delta 9-THC as discriminative stimuli in rats: tests with the cannabinoid antagonist SR-141716 and the endogenous ligand anandamide.
Järbe, TU; Lamb, RJ; Lin, S; Makriyannis, A, 2001
)
0.31
"As in many of our earlier studies with the same dosage regimen we found in the behavioural part both development of sensitization to methamphetamine stimulatory effects after repeated treatment and cross-sensitization to them by pre-treatment with cannabinoid receptor CB1 agonist methanandamide."( Altered dopamine D1 and D2 receptor mRNA expression in mesencephalon from mice exposed to repeated treatments with methamphetamine and cannabinoid CB1 agonist methanandamide.
Jurajda, M; Landa, L; Sulcova, A, 2012
)
0.38
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
fatty amideA monocarboxylic acid amide derived from a fatty acid.
[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 (16)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency39.81070.003245.467312,589.2998AID2517
Chain A, TYROSYL-DNA PHOSPHODIESTERASEHomo sapiens (human)Potency28.18380.004023.8416100.0000AID485290
Chain A, Ferritin light chainEquus caballus (horse)Potency28.18385.623417.292931.6228AID485281
phosphopantetheinyl transferaseBacillus subtilisPotency22.38720.141337.9142100.0000AID1490
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency7.07950.011212.4002100.0000AID1030
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency2.51190.035520.977089.1251AID504332
Bloom syndrome protein isoform 1Homo sapiens (human)Potency31.62280.540617.639296.1227AID2528
vitamin D3 receptor isoform VDRAHomo sapiens (human)Potency35.48130.354828.065989.1251AID504847
thyroid hormone receptor beta isoform aHomo sapiens (human)Potency50.11870.010039.53711,122.0200AID1469
DNA polymerase kappa isoform 1Homo sapiens (human)Potency39.81070.031622.3146100.0000AID588579
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Potassium channel subfamily K member 3Homo sapiens (human)IC50 (µMol)0.10000.00700.89855.1000AID1525567
Cannabinoid receptor 1Rattus norvegicus (Norway rat)Ki0.02160.00020.566510.0000AID49140; AID49141; AID49664; AID49674
Cannabinoid receptor 2 Homo sapiens (human)Ki0.22000.00000.415610.0000AID1386799
Cannabinoid receptor 2Mus musculus (house mouse)Ki1.00000.00020.07970.7943AID1386798
Cannabinoid receptor 2Rattus norvegicus (Norway rat)Ki0.02400.02000.22060.9120AID49140; AID49141
[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)
Fatty-acid amide hydrolase 1Rattus norvegicus (Norway rat)Km33.00002.34002.56002.7800AID38666
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (23)

Processvia Protein(s)Taxonomy
potassium ion transportPotassium channel subfamily K member 3Homo sapiens (human)
chemical synaptic transmissionPotassium channel subfamily K member 3Homo sapiens (human)
response to xenobiotic stimulusPotassium channel subfamily K member 3Homo sapiens (human)
monoatomic ion transmembrane transportPotassium channel subfamily K member 3Homo sapiens (human)
negative regulation of cytosolic calcium ion concentrationPotassium channel subfamily K member 3Homo sapiens (human)
regulation of resting membrane potentialPotassium channel subfamily K member 3Homo sapiens (human)
cellular response to zinc ionPotassium channel subfamily K member 3Homo sapiens (human)
cellular response to hypoxiaPotassium channel subfamily K member 3Homo sapiens (human)
cochlea developmentPotassium channel subfamily K member 3Homo sapiens (human)
potassium ion transmembrane transportPotassium channel subfamily K member 3Homo sapiens (human)
stabilization of membrane potentialPotassium channel subfamily K member 3Homo sapiens (human)
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 (8)

Processvia Protein(s)Taxonomy
monoatomic ion channel activityPotassium channel subfamily K member 3Homo sapiens (human)
open rectifier potassium channel activityPotassium channel subfamily K member 3Homo sapiens (human)
potassium channel activityPotassium channel subfamily K member 3Homo sapiens (human)
potassium ion leak channel activityPotassium channel subfamily K member 3Homo sapiens (human)
S100 protein bindingPotassium channel subfamily K member 3Homo sapiens (human)
outward rectifier potassium channel activityPotassium channel subfamily K member 3Homo sapiens (human)
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 (7)

Processvia Protein(s)Taxonomy
plasma membranePotassium channel subfamily K member 3Homo sapiens (human)
synapsePotassium channel subfamily K member 3Homo sapiens (human)
plasma membranePotassium channel subfamily K member 3Homo sapiens (human)
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 (60)

Assay IDTitleYearJournalArticle
AID1386814Antiallodynic activity in CD1 mouse model of CFA-induced inflammatory pain assessed as increase in CFA-reduced mechanical paw withdrawal threshold at 20 mg/kg, ip measured at 60 mins post injection2018Journal of medicinal chemistry, 10-11, Volume: 61, Issue:19
( R)- N-(1-Methyl-2-hydroxyethyl)-13-( S)-methyl-arachidonamide (AMG315): A Novel Chiral Potent Endocannabinoid Ligand with Stability to Metabolizing Enzymes.
AID132852Tested for potency towards inhibition of the twitch response in mouse vas deferens1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
(R)-methanandamide: a chiral novel anandamide possessing higher potency and metabolic stability.
AID49659Binding affinity towards cannabinoid receptor 1 from rat forebrain membranes in the presence of phenylmethanesulfonylfluoride (PMSF) using 0.8 nM [3H]CP-55940 as radioligand1998Journal of medicinal chemistry, Dec-31, Volume: 41, Issue:27
Novel analogues of arachidonylethanolamide (anandamide): affinities for the CB1 and CB2 cannabinoid receptors and metabolic stability.
AID38666Km value for hydrolysis by rat brain microsomal anandamide amidohydrolase (AAH).1999Journal of medicinal chemistry, Mar-11, Volume: 42, Issue:5
Substrate specificity and stereoselectivity of rat brain microsomal anandamide amidohydrolase.
AID346383Stimulation of MMP2 activity in CB1 receptor knockout HUVEC assessed as increase in enzyme activity at 1 uM relative to control2009Journal of medicinal chemistry, Feb-26, Volume: 52, Issue:4
Total synthesis of photoactivatable or fluorescent anandamide probes: novel bioactive compounds with angiogenic activity.
AID20504Mean percentage time spend immobile on ring between 5 and 10 min at 1.5625 (mg/kg) intravenous dose in 6 mice1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
(R)-methanandamide: a chiral novel anandamide possessing higher potency and metabolic stability.
AID20506Mean percentage time spend immobile on ring between 5 and 10 min at 3.125 (mg/kg) intravenous dose in 6 mice1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
(R)-methanandamide: a chiral novel anandamide possessing higher potency and metabolic stability.
AID346379Stimulation of MMP2 activity in CB1 receptor knockout HUVEC assessed as increase in enzyme activity at 10 nM relative to control2009Journal of medicinal chemistry, Feb-26, Volume: 52, Issue:4
Total synthesis of photoactivatable or fluorescent anandamide probes: novel bioactive compounds with angiogenic activity.
AID346377Stimulation of MMP2 activity in HUVEC assessed as increase in enzyme activity at 1 uM relative to control2009Journal of medicinal chemistry, Feb-26, Volume: 52, Issue:4
Total synthesis of photoactivatable or fluorescent anandamide probes: novel bioactive compounds with angiogenic activity.
AID19734Mean number of squares entered(counts) over a 5 min period after placement in the center of a walled arena marked out in 16 squares of equal size at 3.125 (mg/kg) intravenous dose in 6 mice1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
(R)-methanandamide: a chiral novel anandamide possessing higher potency and metabolic stability.
AID22954Mean difference between tail flick latency measured at -30 min and tail flick latency measured at 12 min calculated as percent maximum possible effect at 3.125 (mg/kg) intravenous dose in 6 mice1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
(R)-methanandamide: a chiral novel anandamide possessing higher potency and metabolic stability.
AID49140Binding affinity for the cannabinoid receptor in the absence of phenylmethanesulfonyl fluoride (PMSF) was determined in rat fore brain membranes1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
(R)-methanandamide: a chiral novel anandamide possessing higher potency and metabolic stability.
AID1386813Antiallodynic activity in CD1 mouse model of CFA-induced inflammatory pain assessed as increase in CFA-reduced mechanical paw withdrawal threshold at 20 mg/kg, ip measured up to 30 mins post injection2018Journal of medicinal chemistry, 10-11, Volume: 61, Issue:19
( R)- N-(1-Methyl-2-hydroxyethyl)-13-( S)-methyl-arachidonamide (AMG315): A Novel Chiral Potent Endocannabinoid Ligand with Stability to Metabolizing Enzymes.
AID109901Effective concentration that causes twitch inhibition in a mouse vas deferens assay1997Journal of medicinal chemistry, Oct-24, Volume: 40, Issue:22
Synthesis and pharmacological comparison of dimethylheptyl and pentyl analogs of anandamide.
AID195417Effective concentration required for stimulation of [35S]GTP-gamma-S, binding in rat microsomal membranes1998Journal of medicinal chemistry, Dec-31, Volume: 41, Issue:27
Novel analogues of arachidonylethanolamide (anandamide): affinities for the CB1 and CB2 cannabinoid receptors and metabolic stability.
AID38685Tested for hydrolysis by rat brain microsomal anandamide amidohydrolase (AAH).1999Journal of medicinal chemistry, Mar-11, Volume: 42, Issue:5
Substrate specificity and stereoselectivity of rat brain microsomal anandamide amidohydrolase.
AID1127510Selectivity ratio of Ki for CB2 receptor of mouse spleen to Ki for human CB1 receptor2013Journal of medicinal chemistry, Nov-14, Volume: 56, Issue:21
Therapeutic utility of cannabinoid receptor type 2 (CB(2)) selective agonists.
AID346569Stimulation of MMP9 activity in CB1 receptor knockout HUVEC assessed as increase in enzyme activity at 1 uM relative to control2009Journal of medicinal chemistry, Feb-26, Volume: 52, Issue:4
Total synthesis of photoactivatable or fluorescent anandamide probes: novel bioactive compounds with angiogenic activity.
AID49857Compound was evaluated for its binding affinity for mouse spleen Cannabinoid receptor 21996Journal of medicinal chemistry, Oct-25, Volume: 39, Issue:22
Head group analogs of arachidonylethanolamide, the endogenous cannabinoid ligand.
AID232843Ratio of Vmax value and Km value of the compound.1999Journal of medicinal chemistry, Mar-11, Volume: 42, Issue:5
Substrate specificity and stereoselectivity of rat brain microsomal anandamide amidohydrolase.
AID1127486Binding affinity to mouse spleen CB2 receptor2013Journal of medicinal chemistry, Nov-14, Volume: 56, Issue:21
Therapeutic utility of cannabinoid receptor type 2 (CB(2)) selective agonists.
AID346375Stimulation of MMP2 activity in HUVEC assessed as increase in enzyme activity at 100 nM relative to control2009Journal of medicinal chemistry, Feb-26, Volume: 52, Issue:4
Total synthesis of photoactivatable or fluorescent anandamide probes: novel bioactive compounds with angiogenic activity.
AID1386796Displacement of [3H]CP-55,940 from CB1 receptor in rat brain membranes in absence of FAAH inhibitor PMSF by radioligand binding assay2018Journal of medicinal chemistry, 10-11, Volume: 61, Issue:19
( R)- N-(1-Methyl-2-hydroxyethyl)-13-( S)-methyl-arachidonamide (AMG315): A Novel Chiral Potent Endocannabinoid Ligand with Stability to Metabolizing Enzymes.
AID346381Stimulation of MMP2 activity in CB1 receptor knockout HUVEC assessed as increase in enzyme activity at 100 nM relative to control2009Journal of medicinal chemistry, Feb-26, Volume: 52, Issue:4
Total synthesis of photoactivatable or fluorescent anandamide probes: novel bioactive compounds with angiogenic activity.
AID1386797Displacement of [3H]CP-55,940 from CB1 receptor in rat brain membranes in presence of FAAH inhibitor PMSF by radioligand binding assay2018Journal of medicinal chemistry, 10-11, Volume: 61, Issue:19
( R)- N-(1-Methyl-2-hydroxyethyl)-13-( S)-methyl-arachidonamide (AMG315): A Novel Chiral Potent Endocannabinoid Ligand with Stability to Metabolizing Enzymes.
AID195418Concentration required for stimulation of [35S]GTP-gamma-S, binding in rat microsomal membranes expressed as Emax1998Journal of medicinal chemistry, Dec-31, Volume: 41, Issue:27
Novel analogues of arachidonylethanolamide (anandamide): affinities for the CB1 and CB2 cannabinoid receptors and metabolic stability.
AID49854Binding affinity towards Cannabinoid receptor 2 from mouse spleen membranes using 0.8 nM [3H]CP-55940 as radioligand1998Journal of medicinal chemistry, Dec-31, Volume: 41, Issue:27
Novel analogues of arachidonylethanolamide (anandamide): affinities for the CB1 and CB2 cannabinoid receptors and metabolic stability.
AID49141Binding affinity for the cannabinoid receptor in the presence of phenylmethanesulfonyl fluoride (PMSF) was determined in rat fore brain membranes1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
(R)-methanandamide: a chiral novel anandamide possessing higher potency and metabolic stability.
AID1386816Antiallodynic activity in CD1 mouse model of CFA-induced inflammatory pain assessed as increase in CFA-reduced mechanical paw withdrawal threshold at 20 mg/kg, ip measured at 120 mins post injection2018Journal of medicinal chemistry, 10-11, Volume: 61, Issue:19
( R)- N-(1-Methyl-2-hydroxyethyl)-13-( S)-methyl-arachidonamide (AMG315): A Novel Chiral Potent Endocannabinoid Ligand with Stability to Metabolizing Enzymes.
AID19733Mean number of squares entered(counts) over a 5 min period after placement in the center of a walled arena marked out in 16 squares of equal size at 1.5625 (mg/kg) intravenous dose in 6 mice1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
(R)-methanandamide: a chiral novel anandamide possessing higher potency and metabolic stability.
AID15317Mean difference between rectal temperature measured at time zero and rectal temperature measured at 10 min at 1.5625 (mg/kg) intravenous dose in 6 mice1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
(R)-methanandamide: a chiral novel anandamide possessing higher potency and metabolic stability.
AID1386799Displacement of [3H]CP-55,940 from human CB2 receptor expressed in HEK293 cell membranes in absence of FAAH inhibitor PMSF by radioligand binding assay2018Journal of medicinal chemistry, 10-11, Volume: 61, Issue:19
( R)- N-(1-Methyl-2-hydroxyethyl)-13-( S)-methyl-arachidonamide (AMG315): A Novel Chiral Potent Endocannabinoid Ligand with Stability to Metabolizing Enzymes.
AID38682Tested for hydrolysis by rat brain microsomal anandamide amidohydrolase (AAH).1999Journal of medicinal chemistry, Mar-11, Volume: 42, Issue:5
Substrate specificity and stereoselectivity of rat brain microsomal anandamide amidohydrolase.
AID49142Binding affinity towards cannabinoid receptor using [3H]CP-55940 as radioligand in rat brain membrane1997Journal of medicinal chemistry, Oct-24, Volume: 40, Issue:22
Synthesis and pharmacological comparison of dimethylheptyl and pentyl analogs of anandamide.
AID49674Tested for binding affinity to Cannabinoid receptor 11999Journal of medicinal chemistry, Mar-11, Volume: 42, Issue:5
Substrate specificity and stereoselectivity of rat brain microsomal anandamide amidohydrolase.
AID346378Stimulation of MMP9 activity in HUVEC assessed as increase in enzyme activity at 1 uM relative to control2009Journal of medicinal chemistry, Feb-26, Volume: 52, Issue:4
Total synthesis of photoactivatable or fluorescent anandamide probes: novel bioactive compounds with angiogenic activity.
AID346376Stimulation of MMP9 activity in HUVEC assessed as increase in enzyme activity at 100 nM relative to control2009Journal of medicinal chemistry, Feb-26, Volume: 52, Issue:4
Total synthesis of photoactivatable or fluorescent anandamide probes: novel bioactive compounds with angiogenic activity.
AID346373Stimulation of MMP2 activity in HUVEC assessed as increase in enzyme activity at 10 nM relative to control2009Journal of medicinal chemistry, Feb-26, Volume: 52, Issue:4
Total synthesis of photoactivatable or fluorescent anandamide probes: novel bioactive compounds with angiogenic activity.
AID38683V max value for hydrolysis by rat brain microsomal anandamide amidohydrolase (AAH).1999Journal of medicinal chemistry, Mar-11, Volume: 42, Issue:5
Substrate specificity and stereoselectivity of rat brain microsomal anandamide amidohydrolase.
AID1386809Antiallodynic activity in CD1 mouse model of CFA-induced inflammatory pain assessed as increase in CFA-reduced mechanical paw withdrawal threshold at 20 mg/kg, ip measured at 10 mins post injection2018Journal of medicinal chemistry, 10-11, Volume: 61, Issue:19
( R)- N-(1-Methyl-2-hydroxyethyl)-13-( S)-methyl-arachidonamide (AMG315): A Novel Chiral Potent Endocannabinoid Ligand with Stability to Metabolizing Enzymes.
AID15319Mean difference between rectal temperature measured at time zero and rectal temperature measured at 10 min at 3.125 (mg/kg) intravenous dose in 6 mice1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
(R)-methanandamide: a chiral novel anandamide possessing higher potency and metabolic stability.
AID49664Displacement of [3H]CP-55940 from Cannabinoid receptor 1 of rat forebrain membranes1996Journal of medicinal chemistry, Oct-25, Volume: 39, Issue:22
Head group analogs of arachidonylethanolamide, the endogenous cannabinoid ligand.
AID113393Maximal degree of inhibition of electrically evoked contractions in a mouse vas deferens assay1997Journal of medicinal chemistry, Oct-24, Volume: 40, Issue:22
Synthesis and pharmacological comparison of dimethylheptyl and pentyl analogs of anandamide.
AID1525567Inhibition of human TASK1 expressed in African green monkey COS cells by whole cell patch clamp assay2019Journal of medicinal chemistry, 11-27, Volume: 62, Issue:22
TASK Channels Pharmacology: New Challenges in Drug Design.
AID346382Stimulation of MMP9 activity in CB1 receptor knockout HUVEC assessed as increase in enzyme activity at 100 nM relative to control2009Journal of medicinal chemistry, Feb-26, Volume: 52, Issue:4
Total synthesis of photoactivatable or fluorescent anandamide probes: novel bioactive compounds with angiogenic activity.
AID410014Displacement of [3H]CP-55940 from cannabinoid CB2 receptor in mouse spleen membrane2008Bioorganic & medicinal chemistry letters, Nov-15, Volume: 18, Issue:22
Development of novel tail-modified anandamide analogs.
AID346374Stimulation of MMP9 activity in HUVEC assessed as increase in enzyme activity at 10 nM relative to control2009Journal of medicinal chemistry, Feb-26, Volume: 52, Issue:4
Total synthesis of photoactivatable or fluorescent anandamide probes: novel bioactive compounds with angiogenic activity.
AID1127512Displacement of [3H]-CP55940 from CB1 receptor of rat cerebellar membranes by liquid scintillation counting in presence of serine protease inhibitor PMSF2013Journal of medicinal chemistry, Nov-14, Volume: 56, Issue:21
Therapeutic utility of cannabinoid receptor type 2 (CB(2)) selective agonists.
AID22952Mean difference between tail flick latency measured at -30 min and tail flick latency measured at 12 min calculated as percent maximum possible effect at 1.5625 (mg/kg) intravenous dose in 6 mice1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
(R)-methanandamide: a chiral novel anandamide possessing higher potency and metabolic stability.
AID409742Displacement of [3H]CP-55940 from cannabinoid CB1 receptor in rat brain membrane in presence of phenylmethanesulfonyl fluoride2008Bioorganic & medicinal chemistry letters, Nov-15, Volume: 18, Issue:22
Development of novel tail-modified anandamide analogs.
AID49143Binding affinity towards cannabinoid receptor using [3H]SR-141,716A as radioligand in rat brain membrane1997Journal of medicinal chemistry, Oct-24, Volume: 40, Issue:22
Synthesis and pharmacological comparison of dimethylheptyl and pentyl analogs of anandamide.
AID195419Effective concentration required for stimulation of [35S]GTP-gamma-S, binding in rat microsomal membranes expressed as log EC501998Journal of medicinal chemistry, Dec-31, Volume: 41, Issue:27
Novel analogues of arachidonylethanolamide (anandamide): affinities for the CB1 and CB2 cannabinoid receptors and metabolic stability.
AID49658Binding affinity towards cannabinoid receptor 1 from rat forebrain membranes in the absence of phenylmethanesulfonylfluoride (PMSF) using 0.8 nM [3H]CP-55940 as radioligand1998Journal of medicinal chemistry, Dec-31, Volume: 41, Issue:27
Novel analogues of arachidonylethanolamide (anandamide): affinities for the CB1 and CB2 cannabinoid receptors and metabolic stability.
AID346380Stimulation of MMP9 activity in CB1 receptor knockout HUVEC assessed as increase in enzyme activity at 10 nM relative to control2009Journal of medicinal chemistry, Feb-26, Volume: 52, Issue:4
Total synthesis of photoactivatable or fluorescent anandamide probes: novel bioactive compounds with angiogenic activity.
AID1386798Displacement of [3H]CP-55,940 from mouse CB2 receptor expressed in HEK293 cell membranes in absence of FAAH inhibitor PMSF by radioligand binding assay2018Journal of medicinal chemistry, 10-11, Volume: 61, Issue:19
( R)- N-(1-Methyl-2-hydroxyethyl)-13-( S)-methyl-arachidonamide (AMG315): A Novel Chiral Potent Endocannabinoid Ligand with Stability to Metabolizing Enzymes.
AID1346669Human K2P9.1 (Two P domain potassium channels)2000The Journal of biological chemistry, Jun-02, Volume: 275, Issue:22
TASK-3, a novel tandem pore domain acid-sensitive K+ channel. An extracellular histiding as pH sensor.
AID1346753Rat CB1 receptor (Cannabinoid receptors)1996Journal of medicinal chemistry, Oct-25, Volume: 39, Issue:22
Head group analogs of arachidonylethanolamide, the endogenous cannabinoid ligand.
AID1346602Human K2P3.1 (Two P domain potassium channels)2001The EMBO journal, Jan-15, Volume: 20, Issue:1-2
The endocannabinoid anandamide is a direct and selective blocker of the background K(+) channel TASK-1.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (211)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's32 (15.17)18.2507
2000's128 (60.66)29.6817
2010's44 (20.85)24.3611
2020's7 (3.32)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 33.10

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

MetricThis Compound (vs All)
Research Demand Index33.10 (24.57)
Research Supply Index5.38 (2.92)
Research Growth Index4.71 (4.65)
Search Engine Demand Index47.56 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (33.10)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (0.93%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other214 (99.07%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]