187947-37-1,MFCD02179189
Catalog No.:AA002GII

187947-37-1 | 5,8,11,14-Eicosatetraenamide, N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-, (5Z,8Z,11Z,14Z)-

Pack Size
Purity
Availability
Price(USD)
Quantity
  
5mg
≥98%
in stock  
$70.00   $49.00
- +
10mg
≥98%
in stock  
$118.00   $82.00
- +
50mg
≥98%
in stock  
$443.00   $310.00
- +
100mg
≥98%
in stock  
$815.00   $570.00
- +
  • Technical Information
  • Properties
  • Literature
  • Request for Quotation
  • Download SDS
Technical Information
Catalog Number:
AA002GII
Chemical Name:
5,8,11,14-Eicosatetraenamide, N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-, (5Z,8Z,11Z,14Z)-
CAS Number:
187947-37-1
Molecular Formula:
C30H42N2O2
Molecular Weight:
462.6667
MDL Number:
MFCD02179189
SMILES:
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCc1c[nH]c2c1cc(O)cc2
Properties
Computed Properties
 
Complexity:
652  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0  
Defined Bond Stereocenter Count:
4  
Formal Charge:
0  
Heavy Atom Count:
34  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0  
Rotatable Bond Count:
17  
Undefined Atom Stereocenter Count:
0  
Undefined Bond Stereocenter Count:
0  
XLogP3:
7  

Literature

Title: Oxidation of endogenous N-arachidonoylserotonin by human cytochrome P450 2U1.

Journal: The Journal of biological chemistry 20140411

Title: N-arachidonoyl-serotonin in the basolateral amygdala increases anxiolytic behavior in the elevated plus maze.

Journal: Behavioural brain research 20120801

Title: The blockade of the transient receptor potential vanilloid type 1 and fatty acid amide hydrolase decreases symptoms and central sequelae in the medial prefrontal cortex of neuropathic rats.

Journal: Molecular pain 20110101

Title: The dual fatty acid amide hydrolase/TRPV1 blocker, N-arachidonoyl-serotonin, relieves carrageenan-induced inflammation and hyperalgesia in mice.

Journal: Pharmacological research 20100601

Title: Levels of endocannabinoids and palmitoylethanolamide and their pharmacological manipulation in chronic granulomatous inflammation in rats.

Journal: Pharmacological research 20100401

Title: Synthesis and biological evaluation of piperazinyl carbamates and ureas as fatty acid amide hydrolase (FAAH) and transient receptor potential (TRP) channel dual ligands.

Journal: Bioorganic & medicinal chemistry letters 20091201

Title: Altered responses of dopamine D3 receptor null mice to excitotoxic or anxiogenic stimuli: Possible involvement of the endocannabinoid and endovanilloid systems.

Journal: Neurobiology of disease 20091001

Title: Anxiolytic effects in mice of a dual blocker of fatty acid amide hydrolase and transient receptor potential vanilloid type-1 channels.

Journal: Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20090201

Title: The analgesic effect of N-arachidonoyl-serotonin, a FAAH inhibitor and TRPV1 receptor antagonist, associated with changes in rostral ventromedial medulla and locus coeruleus cell activity in rats.

Journal: Neuropharmacology 20081201

Title: Inhibiting parabrachial fatty acid amide hydrolase activity selectively increases the intake of palatable food via cannabinoid CB1 receptors.

Journal: American journal of physiology. Regulatory, integrative and comparative physiology 20081101

Title: Neuronal and glial alterations in the cerebellar cortex of maternally deprived rats: gender differences and modulatory effects of two inhibitors of endocannabinoid inactivation.

Journal: Developmental neurobiology 20081001

Title: Gender-dependent cellular and biochemical effects of maternal deprivation on the hippocampus of neonatal rats: a possible role for the endocannabinoid system.

Journal: Developmental neurobiology 20080915

Title: New N-arachidonoylserotonin analogues with potential 'dual' mechanism of action against pain.

Journal: Journal of medicinal chemistry 20071227

Title: Cannabinoid CB1 receptor stimulation affords neuroprotection in MPTP-induced neurotoxicity by attenuating S100B up-regulation in vitro.

Journal: Journal of molecular medicine (Berlin, Germany) 20071201

Title: Pharmacological enhancement of the endocannabinoid system in the nucleus accumbens shell stimulates food intake and increases c-Fos expression in the hypothalamus.

Journal: British journal of pharmacology 20070801

Title: Analgesic actions of N-arachidonoyl-serotonin, a fatty acid amide hydrolase inhibitor with antagonistic activity at vanilloid TRPV1 receptors.

Journal: British journal of pharmacology 20070301

Title: Endocannabinoids activate transient receptor potential vanilloid 1 receptors to reduce hyperdopaminergia-related hyperactivity: therapeutic implications.

Journal: Biological psychiatry 20060315

Title: Endocannabinoids at the spinal level regulate, but do not mediate, nonopioid stress-induced analgesia.

Journal: Neuropharmacology 20060301

Title: Up-regulation of anandamide levels as an endogenous mechanism and a pharmacological strategy to limit colon inflammation.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20060301

Title: Cisplatin increases brain 2-arachidonoylglycerol (2-AG) and concomitantly reduces intestinal 2-AG and anandamide levels in the least shrew.

Journal: Neuropharmacology 20050901

Title: The endocannabinoid system: drug targets, lead compounds, and potential therapeutic applications.

Journal: Journal of medicinal chemistry 20050811

Title: Effect of repeated systemic administration of selective inhibitors of endocannabinoid inactivation on rat brain endocannabinoid levels.

Journal: Biochemical pharmacology 20050801

Title: A new strategy to block tumor growth by inhibiting endocannabinoid inactivation.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20041001

Title: Inhibition of fatty acid amidohydrolase, the enzyme responsible for the metabolism of the endocannabinoid anandamide, by analogues of arachidonoyl-serotonin.

Journal: Journal of enzyme inhibition and medicinal chemistry 20030601

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Additional Info:
SDS
Historical Records
Tags:187947-37-1 Molecular Formula|187947-37-1 MDL|187947-37-1 SMILES|187947-37-1 5,8,11,14-Eicosatetraenamide, N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-, (5Z,8Z,11Z,14Z)-
Catalog No.: AA002GII
187947-37-1,MFCD02179189
187947-37-1 | 5,8,11,14-Eicosatetraenamide, N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-, (5Z,8Z,11Z,14Z)-
Pack Size: 5mg
Purity: ≥98%
in stock
$70.00 $49.00
Pack Size: 10mg
Purity: ≥98%
in stock
$118.00 $82.00
Pack Size: 50mg
Purity: ≥98%
in stock
$443.00 $310.00
Pack Size: 100mg
Purity: ≥98%
in stock
$815.00 $570.00
Quantity
- +
Add to Card
Order Now
bulk Quotation Request
Technical Information
Catalog Number: AA002GII
Chemical Name: 5,8,11,14-Eicosatetraenamide, N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-, (5Z,8Z,11Z,14Z)-
CAS Number: 187947-37-1
Molecular Formula: C30H42N2O2
Molecular Weight: 462.6667
MDL Number: MFCD02179189
SMILES: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCc1c[nH]c2c1cc(O)cc2
Properties
Complexity: 652  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 0  
Defined Bond Stereocenter Count: 4  
Formal Charge: 0  
Heavy Atom Count: 34  
Hydrogen Bond Acceptor Count: 2  
Hydrogen Bond Donor Count: 3  
Isotope Atom Count: 0  
Rotatable Bond Count: 17  
Undefined Atom Stereocenter Count: 0  
Undefined Bond Stereocenter Count: 0  
XLogP3: 7  
Literature fold

Title: Oxidation of endogenous N-arachidonoylserotonin by human cytochrome P450 2U1.

Journal: The Journal of biological chemistry20140411

Title: N-arachidonoyl-serotonin in the basolateral amygdala increases anxiolytic behavior in the elevated plus maze.

Journal: Behavioural brain research20120801

Title: The blockade of the transient receptor potential vanilloid type 1 and fatty acid amide hydrolase decreases symptoms and central sequelae in the medial prefrontal cortex of neuropathic rats.

Journal: Molecular pain20110101

Title: The dual fatty acid amide hydrolase/TRPV1 blocker, N-arachidonoyl-serotonin, relieves carrageenan-induced inflammation and hyperalgesia in mice.

Journal: Pharmacological research20100601

Title: Levels of endocannabinoids and palmitoylethanolamide and their pharmacological manipulation in chronic granulomatous inflammation in rats.

Journal: Pharmacological research20100401

Title: Synthesis and biological evaluation of piperazinyl carbamates and ureas as fatty acid amide hydrolase (FAAH) and transient receptor potential (TRP) channel dual ligands.

Journal: Bioorganic & medicinal chemistry letters20091201

Title: Altered responses of dopamine D3 receptor null mice to excitotoxic or anxiogenic stimuli: Possible involvement of the endocannabinoid and endovanilloid systems.

Journal: Neurobiology of disease20091001

Title: Anxiolytic effects in mice of a dual blocker of fatty acid amide hydrolase and transient receptor potential vanilloid type-1 channels.

Journal: Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology20090201

Title: The analgesic effect of N-arachidonoyl-serotonin, a FAAH inhibitor and TRPV1 receptor antagonist, associated with changes in rostral ventromedial medulla and locus coeruleus cell activity in rats.

Journal: Neuropharmacology20081201

Title: Inhibiting parabrachial fatty acid amide hydrolase activity selectively increases the intake of palatable food via cannabinoid CB1 receptors.

Journal: American journal of physiology. Regulatory, integrative and comparative physiology20081101

Title: Neuronal and glial alterations in the cerebellar cortex of maternally deprived rats: gender differences and modulatory effects of two inhibitors of endocannabinoid inactivation.

Journal: Developmental neurobiology20081001

Title: Gender-dependent cellular and biochemical effects of maternal deprivation on the hippocampus of neonatal rats: a possible role for the endocannabinoid system.

Journal: Developmental neurobiology20080915

Title: New N-arachidonoylserotonin analogues with potential 'dual' mechanism of action against pain.

Journal: Journal of medicinal chemistry20071227

Title: Cannabinoid CB1 receptor stimulation affords neuroprotection in MPTP-induced neurotoxicity by attenuating S100B up-regulation in vitro.

Journal: Journal of molecular medicine (Berlin, Germany)20071201

Title: Pharmacological enhancement of the endocannabinoid system in the nucleus accumbens shell stimulates food intake and increases c-Fos expression in the hypothalamus.

Journal: British journal of pharmacology20070801

Title: Analgesic actions of N-arachidonoyl-serotonin, a fatty acid amide hydrolase inhibitor with antagonistic activity at vanilloid TRPV1 receptors.

Journal: British journal of pharmacology20070301

Title: Endocannabinoids activate transient receptor potential vanilloid 1 receptors to reduce hyperdopaminergia-related hyperactivity: therapeutic implications.

Journal: Biological psychiatry20060315

Title: Endocannabinoids at the spinal level regulate, but do not mediate, nonopioid stress-induced analgesia.

Journal: Neuropharmacology20060301

Title: Up-regulation of anandamide levels as an endogenous mechanism and a pharmacological strategy to limit colon inflammation.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology20060301

Title: Cisplatin increases brain 2-arachidonoylglycerol (2-AG) and concomitantly reduces intestinal 2-AG and anandamide levels in the least shrew.

Journal: Neuropharmacology20050901

Title: The endocannabinoid system: drug targets, lead compounds, and potential therapeutic applications.

Journal: Journal of medicinal chemistry20050811

Title: Effect of repeated systemic administration of selective inhibitors of endocannabinoid inactivation on rat brain endocannabinoid levels.

Journal: Biochemical pharmacology20050801

Title: A new strategy to block tumor growth by inhibiting endocannabinoid inactivation.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology20041001

Title: Inhibition of fatty acid amidohydrolase, the enzyme responsible for the metabolism of the endocannabinoid anandamide, by analogues of arachidonoyl-serotonin.

Journal: Journal of enzyme inhibition and medicinal chemistry20030601

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