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Anandamide Uptake Inhibitors
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Items 14 of 14
ALX-340-064 Revised 10-Jul-08
AM 1172
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SYNONYMS N-5Z,8Z,11Z,14Z-Eicosatetraenyl-4-hydroxy-benzamide
PRODUCT LINE Neurobiology
PRODUCT CATEGORY Anandamide Uptake Inhibitors
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ALX-340-064-M001   1 mg 57.00 USD Add To Cart
ALX-340-064-M005   5 mg 254.00 USD Add To Cart
Product Specification
FORMULA: C27H39NO2
MW: 409.6
CAS NUMBER: 251908-92-6
PURITY: ≥98%
FORMULATION: Liquid. Solution in ethanol.
SOLUBILITY: 30mg/ml soluble in DMSO or dimethyl formamide; sparingly soluble in PBS, pH 7.2 (0.15mg/ml).
SHIPPING: SHIPPED ON BLUE ICE
LONG TERM STORAGE: -20°C
USE/STABILITY: Stable for at least 1 year after receipt when stored at -20°C. We do not recommend storing aqueous solutions for more than one day.

Product Description
Potent and selective inhibitor of anandamide uptake, resistant to fatty acid amide hydrolase (FAAH) hydrolysis. Metabolically stable “reversed” isomer of AM 404 (Prod. No. ALX-340-032).
Product Specific Literature References
Anandamide transport is independent of fatty-acid amide hydrolase activity and is blocked by the hydrolysis-resistant inhibitor AM1172: D. Fegley, et al.; PNAS 101, 8756 (2004) Abstract; Full Text
General Information
BACKGROUND/TECHNICAL INFORMATION To change the solvent, evaporate the ethanol under a gentle stream of nitrogen and immediately add the solvent of choice.
Related Products
 
 
ALX-340-032 Revised 04-Jul-08
AM 404
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SYNONYMS N-(4-Hydroxyphenyl)-5Z,8Z,11Z-eicosatetraenamide
N-(4-Hydroxyphenyl)arachidonoylamide
PRODUCT LINE Neurobiology
PRODUCT CATEGORY Anandamide & Anandamide Analogs
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ALX-340-032-M005   5 mg 40.00 USD Add To Cart
Product Specification
FORMULA: C26H37NO2
MW: 395.6
CAS NUMBER: 198022-70-7
PURITY: ≥98%
APPEARANCE: Waxy solid.
SOLUBILITY: Soluble in DMSO or 100% ethanol (>25mg/ml).
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C
USE/STABILITY: Stable for up to one year after receipt when stored at -20°C. Solutions are stable for up to 3 months when stored at -20°C under an inert atmosphere of nitrogen or argon.
HANDLING: Protect from air.

Product Description
Analog of anandamide (Prod. No. ALX-340-029). Potentiates the activity of endogenous anandamide by blocking its re-uptake into presynaptic membranes. Activates TRPV1 (EC50=0.04µM) at concentrations lower than those required to inhibit anandamide transport into the cell (neuronal (C6 glioma cells): IC50=10µM; non-neuronal (rat RBL-2H3 cells): IC50=11µM). Low affinity to FAAH (IC50=5.9µM), to CB1 receptor (IC50=1.76µM) and to CB2 receptor (IC50>1µM).
Product Specific Literature References
Potentiation of anandamide hypotension by the transport inhibitor, AM404: A. Calignano, et al.; Eur. J. Pharmacol. 337, R1 (1997) Abstract
Functional role of high-affinity anandamide transport, as revealed by selective inhibition: M. Beltramo, et al.; Science 277, 1094 (1997) Abstract
Structural determinants for recognition and translocation by the anandamide transporter: D. Piomelli, et al.; PNAS 96, 5802 (1999) Abstract
The anandamide transport inhibitor AM404 activates vanilloid receptors: P.M. Zygmunt, et al.; Eur. J. Pharmacol. 396, 39 (2000) Abstract
Overlap between the ligand recognition properties of the anandamide transporter and the VR1 vanilloid receptor: inhibitors of anandamide uptake with negligible capsaicin-like activity: L. De Petrocellis, et al.; FEBS Lett. 483, 52 (2000) Abstract
Experimental parkinsonism alters anandamide precursor synthesis, and functional deficits are improved by AM404: a modulator of endocannabinoid function: E. Fernandez-Espejo, et al.; Neuropsychopharmacology 29, 1134 (2004) Abstract
Anandamide transport inhibitor AM404 and structurally related compounds inhibit synaptic transmission between rat hippocampal neurons in culture independent of cannabinoid CB1 receptors: B.G. Kelley and S.A. Thayer; Eur. J. Pharmacol. 496, 33 (2004) Abstract
AM404, an inhibitor of anandamide uptake, prevents pain behaviour and modulates cytokine and apoptotic pathways in a rat model of neuropathic pain: B. Costa, et al.; Br. J. Pharmacol. 148, 1022 (2006) Abstract
Modulation of neuropathic and inflammatory pain by the endocannabinoid transport inhibitor AM404 [N-(4-hydroxyphenyl)-eicosa-5,8,11,14-tetraenamide]: G. La Rana, et al.; J. Pharmacol. Exp. Ther. 317, 1365 (2006) Abstract
Further Categories Containing This Product:
NOS Inhibitors (NOS Induction & Enzyme Activity) • Anandamide Uptake Inhibitors • TRPV1 Agonists and Antagonists / Related Products
 
 
ALX-340-055 Revised 21-Jul-08
N-Arachidonoyl glycine
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SYNONYMS NAGly
N-[1-Oxo-5Z,8Z,11Z,14Z-Eicosatetraenyl]-glycine
PRODUCT LINE Neurobiology
PRODUCT CATEGORY Anandamide & Anandamide Analogs
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ALX-340-055-M005   5 mg 55.00 USD Add To Cart
Product Specification
FORMULA: C22H35NO3
MW: 361.5
CAS NUMBER: 179113-91-8
CONCENTRATION: 50mg/ml
PURITY: ≥98%
FORMULATION: Liquid. Solution in ethanol.
SOLUBILITY: 15mg/ml soluble in DMSO or dimethyl formamide; 2mg/ml soluble in PBS (pH 7.2).
SHIPPING: SHIPPED ON BLUE ICE
LONG TERM STORAGE: -20°C
USE/STABILITY: Stable for at least 2 years after receipt when stored at -20°C. We do not recommend storing aqueous solutions for more than one day.

Product Description
Endogenous anandamide-like compound. Lacks affinity for CB1 receptors (Ki>10µM), TRPV1 (EC50>10µM) and anandamide uptake (IC50>50µM), but inhibits fatty acid amide hydrolase (FAAH) (IC50=8.5µM-50µM, depending on cell type and species).
Product Specific Literature References
Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptor: T. Sheskin, et al.; J. Med. Chem. 40, 659 (1997) Abstract
Identification of a new class of molecules, the arachidonyl amino acids, and characterization of one member that inhibits pain: S.M. Huang, et al.; J. Biol. Chem. 276, 42639 (2001) Abstract
A structure-activity relationship study on N-arachidonoyl-amino acids as possible endogenous inhibitors of fatty acid amide hydrolase: M. Grazia Cascio, et al.; BBRC 314, 192 (2004) Abstract
General Information
BACKGROUND/TECHNICAL INFORMATION To change the solvent, evaporate the ethanol under a gentle stream of nitrogen and immediately add the solvent of choice.
Further Categories Containing This Product:
Anandamide Uptake Inhibitors • Fatty Acid Amide Hydrolase [FAAH] / Related Products
 
 
ALX-340-042 Revised 07-Jan-06
Arvanil
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SYNONYMS N-[(4-Hydroxy-3-methoxyphenyl)methyl]-5Z,8Z,11Z,14Z-eicosatetraenamide
PRODUCT LINE Neurobiology
PRODUCT CATEGORY Cannabinoid Receptor Agonists & Antagonists / Related Products
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ALX-340-042-M005   5 mg 25.00 USD Add To Cart
Product Specification
FORMULA: C28H41NO3
MW: 439.6
CAS NUMBER: 128007-31-8
PURITY: ≥98%
SHIPPING: SHIPPED ON BLUE ICE
LONG TERM STORAGE: -20°C
HANDLING: Protect from light. Keep cool and dry.

Product Description
"Hybrid" activator of CB1 receptor (CB1: Ki=0.5µM; CB2: Ki=>15µM) and TRPV1 (Ki=0.3µM). Also inhibits anandamide uptake (IC50=3.6µM) and fatty acid amide hydrolase (FAAH) (IC50=3µM). Analgesic, vasodilatory and anti-inflammatory in vivo. Apoptosis inducer.
Product Specific Literature References
Unsaturated long-chain N-acyl-vanillyl-amides (N-AVAMs): vanilloid receptor ligands that inhibit anandamide-facilitated transport and bind to CB1 cannabinoid receptors: D. Melck, et al.; BBRC 262, 275 (1999) Abstract
Neurobehavioral activity in mice of N-vanillyl-arachidonyl-amide: V. Di Marzo, et al.; Eur. J. Pharmacol. 406, 363 (2000) Abstract
A structure/activity relationship study on arvanil, an endocannabinoid and vanilloid hybrid: V. Di Marzo, et al.; J. Pharmacol. Exp. Ther. 300, 984 (2002) Abstract
The CB1/VR1 agonist arvanil induces apoptosis through an FADD/caspase-8-dependent pathway: R. Sancho, et al.; Br. J. Pharmacol. 140, 1035 (2003) Abstract
Evidence against the presence of an anandamide transporter: S.T. Glaser, et al.; PNAS 100, 4269 (2003) Abstract
Arvanil, a hybrid endocannabinoid and vanilloid compound, behaves as an antihyperkinetic agent in a rat model of Huntington's disease: E. de Lago, et al.; Brain Res. 1050, 210 (2005) Abstract
Arvanil inhibits T lymphocyte activation and ameliorates autoimmune encephalomyelitis: A.M. Malfitano, et al.; J. Neuroimmunol. 171, 110 (2006) Abstract
Further Categories Containing This Product:
Anandamide Uptake Inhibitors • Apoptosis Inducers & Inhibitors Other Products • TRPV1 Agonists and Antagonists / Related Products • Analgesic / Anti-nociceptive Agents / Related Products • Fatty Acid Amide Hydrolase [FAAH] / Related Products • Anti-inflammatory Agents Other Products
 
 
ALX-430-152 Revised 03-Apr-08
Cannabidiol
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SYNONYMS CBD
2-[(1R,6R)-3-Methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-5-pentyl-1,3-benzenediol
PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Natural Products for Neurological Research
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ALX-430-152-M001   1 mg Inquire
ALX-430-152-M005   5 mg Inquire
Product Specification
FORMULA: C21H30O2
MW: 314.5
CAS NUMBER: 13956-29-1
MERCK INDEX: 14: 1747
RTECS: VH1600000
SOURCE/HOST: Natural product.
PURITY: ≥98% (HPLC)
APPEARANCE: White to pale yellow powder.
SOLUBILITY: Soluble in DMSO, 100% ethanol or methanol; insoluble in water.
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C

Product Description
Non-psychotropic, anticonvulsive and neuroprotective in vivo. Shown to be a weak CB1 receptor antagonist and inhibitor of anandamide uptake (IC50=3.35mM and 27.5mM, respectively). Weak agonist of TRPV1 (EC50=3.5mM).
Product Specific Literature References
Cannabidiol and (-)Delta9-tetrahydrocannabinol are neuroprotective antioxidants: A.J. Hampson, et al.; PNAS 95, 8268 (1998) Abstract; Full Text
The nonpsychoactive cannabis constituent cannabidiol is an oral anti-arthritic therapeutic in murine collagen-induced arthritis: A.M. Malfait, et al.; PNAS 97, 9561 (2000) Abstract; Full Text
Neuroprotective effect of (-)Delta9-tetrahydrocannabinol and cannabidiol in N-methyl-D-aspartate-induced retinal neurotoxicity: involvement of peroxynitrite: A.B. El-Remessy, et al.; Am. J. Pathol. 163, 1997 (2003) Abstract; Full Text
Antitumor effects of cannabidiol, a nonpsychoactive cannabinoid, on human glioma cell lines: P. Massi, et al.; J. Pharmacol. Exp. Ther. 308, 838 (2004) Abstract; Full Text
Effects of cannabidiol (CBD) on regional cerebral blood flow: J.A. Crippa, et al.; Neuropsychopharmacology 29, 417 (2004) Abstract; Full Text
Inhibition of an equilibrative nucleoside transporter by cannabidiol: a mechanism of cannabinoid immunosuppression: E.J. Carrier, et al.; PNAS 103, 7895 (2006) Abstract; Full Text
Cannabidiol, unlike synthetic cannabinoids, triggers activation of RBL-2H3 mast cells: E. Del Giudice, et al.; J. Leukoc. Biol. 81, 1512 (2007) Abstract; Full Text
Further Categories Containing This Product:
Anandamide Uptake Inhibitors • Cannabinoid Receptor Agonists & Antagonists / Related Products • TRPV1 Agonists and Antagonists / Related Products • Natural Products - Antioxidants
 
 
ALX-340-044 Revised 04-Feb-05
Linvanil
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PRODUCT LINE Neurobiology
PRODUCT CATEGORY TRPV1 Agonists and Antagonists / Related Products
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ALX-340-044-M005   5 mg 130.00 USD Add To Cart
Product Specification
FORMULA: C26H39NO3
MW: 413.6
PURITY: ≥92%
SHIPPING: SHIPPED ON BLUE ICE
LONG TERM STORAGE: -20°C
HANDLING: Keep under inert gas. Protect from light.

Product Description
Ligand of TRPV1 with low affinity to CB1 receptor (Ki=3.4µM). Also inhibits anandamide uptake (IC50=8.0µM).
Product Specific Literature References
Unsaturated long-chain N-acyl-vanillyl-amides (N-AVAMs): vanilloid receptor ligands that inhibit anandamide-facilitated transport and bind to CB1 cannabinoid receptors: D. Melck, et al.; BBRC 262, 275 (1999) Abstract
Anandamide uptake by human endothelial cells and its regulation by nitric oxide: M. Maccarrone, et al.; J. Biol. Chem. 275, 13484 (2000) Abstract; Full Text
Overlap between the ligand recognition properties of the anandamide transporter and the VR1 vanilloid receptor: inhibitors of anandamide uptake with negligible capsaicin-like activity: L. De Petrocellis, et al.; FEBS Lett. 483, 52 (2000) Abstract
Hypolocomotor effects in rats of capsaicin and two long chain capsaicin homologues: V. Di Marzo, et al.; Eur. J. Pharmacol. 420, 123 (2001) Abstract
The uptake by cells of 2-arachidonoylglycerol, an endogenous agonist of cannabinoid receptors: T. Bisogno, et al.; Eur. J. Biochem. 268, 1982 (2001) Abstract
Further Categories Containing This Product:
Cannabinoid Receptor Agonists & Antagonists / Related Products • Anandamide Uptake Inhibitors
 
 
ALX-550-411 Revised 11-Apr-07
LY2183240
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SYNONYMS 5-Biphenyl-4-ylmethyltetrazole-1-carboxylic acid dimethylamide
PRODUCT LINE Neurobiology
PRODUCT CATEGORY Anandamide Uptake Inhibitors
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ALX-550-411-M010   10 mg 60.00 USD Add To Cart
ALX-550-411-M050   50 mg 240.00 USD Add To Cart
Product Specification
FORMULA: C17H17N5O
MW: 307.4
CAS NUMBER: 874902-19-9
PURITY: ≥98% (TLC)
APPEARANCE: White to off-white solid.
SOLUBILITY: Soluble in DMSO or dimethyl formamide.
SHIPPING: SHIPPED ON BLUE ICE
LONG TERM STORAGE: -20°C

Product Description
Initially described as potent, competitive small molecule inhibitor of anandamide uptake. Has recently been shown to inhibit fatty acid amide hydrolase (FAAH) and several additional serine hydrolases.
Product Specific Literature References
Identification of a high-affinity binding site involved in the transport of endocannabinoids: S.A. Moore, et al.; PNAS 102, 17852 (2005) Abstract; Full Text
Toward an anandamide transporter: R. Mechoulam and D.G. Deutsch; PNAS 102, 17541 (2005) Abstract
The putative endocannabinoid transport blocker LY2183240 is a potent inhibitor of FAAH and several other brain serine hydrolases: J.P. Alexander and B.F. Cravatt; JACS 128, 9699 (2006) Abstract
Pharmacological characterization of endocannabinoid transport and fatty acid amide hydrolase inhibitors: A.K. Dickason-Chesterfield, et al.; Cell. Mol. Neurobiol. 26, 407 (2006) Abstract
Further Categories Containing This Product:
Fatty Acid Amide Hydrolase [FAAH] / Related Products
 
 
ALX-340-041 Revised 11-Dec-07
Olvanil
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SYNONYMS NE-19550
N-Vanillyloleoylamide
PRODUCT LINE Neurobiology
PRODUCT CATEGORY TRPV1 Agonists and Antagonists / Related Products
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ALX-340-041-M005   5 mg 30.00 USD Add To Cart
ALX-340-041-M010   10 mg 48.00 USD Add To Cart
Product Specification
FORMULA: C26H43NO3
MW: 417.6
CAS NUMBER: 58493-49-5
PURITY: ≥98%
APPEARANCE: White to off-white solid.
SOLUBILITY: Soluble in 100% ethanol, chloroform, dimethyl formamide or DMSO.
SHIPPING: SHIPPED ON BLUE ICE
LONG TERM STORAGE: -20°C
HANDLING: Protect from light.

Product Description
"Hybrid" activator of CB1 receptor (CB1: Ki=1.6µM; CB2: Ki=15µM) and TRPV1 (Ki=0.4µM; EC50=33nM (human); EC50=6.71nM (rat)). Also inhibits anandamide uptake (IC50=9µM, Ki=14.1µM) and fatty acid amide hydrolase (FAAH) (IC50=20µM).
Product Specific Literature References
NE-19550: a novel, orally active anti-inflammatory analgesic: L. Brand, et al.; Drugs Exp. Clin. Res. 13, 259 (1987) Abstract
The antinociceptive effect and pharmacokinetics of olvanil following oral and subcutaneous dosing in the mouse: W.K. Sietsema, et al.; Life Sci. 43, 1385 (1988) Abstract
Olvanil: more potent than capsaicin at stimulating the efferent function of sensory nerves: S.R. Hughes, et al.; Eur. J. Pharmacol. 219, 481 (1992) Abstract
Interactions between synthetic vanilloids and the endogenous cannabinoid system: V. Di Marzo, et al.; FEBS Lett. 436, 449 (1998) Abstract
Anandamide transport inhibition by the vanilloid agonist olvanil: M. Beltramo & D. Piomelli; Eur. J. Pharmacol. 364, 75 (1999) Abstract
Unsaturated long-chain N-acyl-vanillyl-amides (N-AVAMs): vanilloid receptor ligands that inhibit anandamide-facilitated transport and bind to CB1 cannabinoid receptors: D. Melck, et al.; BBRC 262, 275 (1999) Abstract
Vanilloid receptors on sensory nerves mediate the vasodilator action of anandamide: P.M. Zygmunt, et al.; Nature 400, 452 (1999) Abstract
Overlap between the ligand recognition properties of the anandamide transporter and the VR1 vanilloid receptor: inhibitors of anandamide uptake with negligible capsaicin-like activity: L. De Petrocellis, et al.; FEBS Lett. 483, 52 (2000) Abstract
Characterization using FLIPR of rat vanilloid receptor (rVR1) pharmacology: J.C. Jerman, et al.; Br. J. Pharmacol. 130, 916 (2000) Abstract
Evidence against the presence of an anandamide transporter: S.T. Glaser, et al.; PNAS 100, 4269 (2003) Abstract
Identification of species-specific determinants of the action of the antagonist capsazepine and the agonist PPAHV on TRPV1: E. Phillips, et al.; J. Biol. Chem. 279, 17165 (2004) Abstract
Effects of the vanilloid agonist olvanil and antagonist capsazepine on rat behaviors: J.W. Kasckow, et al.; Prog. Neuropsychopharmacol. Biol. Psychiatry 28, 291 (2004) Abstract
Further Categories Containing This Product:
Anandamide Uptake Inhibitors • Cannabinoid Receptor Agonists & Antagonists / Related Products • Fatty Acid Amide Hydrolase [FAAH] / Related Products
 
 
ALX-550-386 Revised 29-Jan-05
OMDM-1
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SYNONYMS (S)-N-Oleyl tyrosinol
(S)-N-(1-(4-Hydroxyphenyl)-2-hydroxyethyl)oleamide
PRODUCT LINE Neurobiology
PRODUCT CATEGORY Anandamide Uptake Inhibitors
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ALX-550-386-M005   5 mg 85.00 USD Add To Cart
Product Specification
FORMULA: C27H45NO3
MW: 431.7
PURITY: ≥98%
APPEARANCE: White to off-white crystalline solid.
SOLUBILITY: Soluble in 100% ethanol, dimethyl formamide or DMSO; also soluble in a 1:1 solution of ethanol:PBS.
SHIPPING: SHIPPED ON BLUE ICE
LONG TERM STORAGE: -20°C
USE/STABILITY: Stable for at least 2 years after receipt when stored at -20°C. We do not recommend storing the aqueous solution for more than one day.

Product Description
Metabolically stable, potent inhibitor of cellular anandamide uptake (neuronal (C6 glioma cells): IC50=2.6µM; non-neuronal (rat RBL-2H3 cells): IC50>20µM) with negligible effects on CB1 receptor (CB1: Ki=12.1µM; CB2: Ki>10µM), TRPV1 (EC50>10µM) and FAAH (IC50>100µM).
Product Specific Literature References
Novel selective and metabolically stable inhibitors of anandamide cellular uptake: G. Ortar, et al.; Biochem. Pharmacol. 65, 1473 (2003) Abstract
Selective inhibition of anandamide cellular uptake versus enzymatic hydrolysis--a difficult issue to handle: C.J. Fowler, et al.; Eur. J. Pharmacol. 492, 1 (2004) Abstract
Further evidence for the existence of a specific process for the membrane transport of anandamide: A. Ligresti, et al.; Biochem. J. 380, 265 (2004) Abstract
In vivo pharmacological actions of two novel inhibitors of anandamide cellular uptake: E. de Lago, et al.; Eur. J. Pharmacol. 484, 249 (2004) Abstract
 
 
ALX-550-387 Revised 04-Mar-05
OMDM-2