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Anandamide & Anandamide Analogs
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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-340-029 Revised 08-Jul-08
Anandamide
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SYNONYMS AEA
N-Arachidonoylethanolamine
(all-Z)-N-(2-Hydroxyethyl)-5,8,11,14-eicosatetraenamide
PRODUCT LINE Neurobiology
PRODUCT CATEGORY Anandamide & Anandamide Analogs
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ALX-340-029-M005   5 mg 51.00 USD Add To Cart
Product Specification
FORMULA: C22H37NO2
MW: 347.5
CAS NUMBER: 94421-68-8
MERCK INDEX: 14: 624
RTECS: JX3842500
CONCENTRATION: 50mg/ml 
PURITY: ≥98%
FORMULATION: Liquid. Solution in ethanol.
SOLUBILITY: 10mg/ml soluble in DMSO or dimethyl formamide.
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. Stable for at least 6 months in other organic solvents when stored at -20°C.
HANDLING: Protect from light and oxygen.

Product Description
Endogenous [1] ligand for the CB1 receptor (CB1: Ki=52nm; CB2: Ki=1930nm [2]) and TRPV1 (Ki=5.78µM [3,4]). Inhibits NF-κB activation through direct binding to IKKβ [5] and induces apoptosis independently of cannabinoid or vanilloid receptors [6]. Activates the MAP kinase (MAPK/ERK) signalling pathway [7].
Product Specific Literature References
[1] Isolation and structure of a brain constituent that binds to the cannabinoid receptor: W.A. Devane, et al.; Science 258, 1946 (1992) Abstract
[2] Novel analogues of arachidonylethanolamide (anandamide): affinities for the CB1 and CB2 cannabinoid receptors and metabolic stability: S. Lin, et al.; J. Med. Chem. 41, 5353 (1998) Abstract
[3] Vanilloid receptors on sensory nerves mediate the vasodilator action of anandamide: P.M. Zygmunt, et al.; Nature 400, 452 (1999) Abstract
[4] Structure-activity relationship for the endogenous cannabinoid, anandamide, and certain of its analogues at vanilloid receptors in transfected cells and vas deferens: R.A. Ross, et al.; Br. J. Pharmacol. 132, 631 (2001) Abstract
[5] Anandamide inhibits nuclear factor-kappaB activation through a cannabinoid receptor-independent pathway: R. Sancho, et al.; Mol. Pharmacol. 63, 429 (2003) Abstract
[6] Anandamide induces cell death independently of cannabinoid receptors or vanilloid receptor 1: possible involvement of lipid rafts: K.P. Sarker, et al.; Cell Mol. Life Sci. 60, 1200 (2003) Abstract
[7] The MAP kinase signal transduction pathway is activated by the endogenous cannabinoid anandamide: M. Wartmann, et al.; FEBS Lett. 359, 133 (1995) Abstract
Biochemistry and pharmacology of arachidonylethanolamide, a putative endogenous cannabinoid: C.J. Hillard & W.B. Campbell; J. Lipid Res. 38, 2383 (1997), (Review) Abstract
The endogenous cannabinoid anandamide inhibits human breast cancer cell proliferation: L. De Petrocellis, et al.; PNAS 95, 8375 (1998) Abstract
Cannabinoid receptors and their endogenous agonist, anandamide: J. Axelrod & C.C. Felder; Neurochem. Res. 23, 575 (1998), (Review) Abstract
Endocannabinoids: endogenous cannabinoid receptor ligands with neuromodulatory action: V. Di Marzo, et al.; TINS 21, 521 (1998), (Review) Abstract
Endocannabinoids: a new class of vasoactive substances: M.D. Randall & D.A. Kendall; TIPS 19, 55 (1998), (Review) Abstract
Metabolism of anandamide and 2-arachidonoylglycerol: an historical overview and some recent developments: V. Di Marzo, et al.; Lipids 34, S319 (1999), (Review) Abstract
Anandamide: a candidate neurotransmitter heads for the big leagues: D.W. Self; Nat. Neurosci. 2, 303 (1999), (Review) Abstract
New perspectives on enigmatic vanilloid receptors: A. Szallasi & V. Di Marzo; TINS 23, 491 (2000), (Review) Abstract
Anandamide: some like it hot: V. Di Marzo, et al.; TIPS 22, 346 (2001), (Review) Abstract
Anandamide is an endogenous inhibitor for the migration of tumor cells and T lymphocytes: J. Joseph, et al.; Cancer Immunol. Immunother. 53, 723 (2004) Abstract
Anandamide-induced cell death in primary neuronal cultures: role of calpain and caspase pathways: V.A. Movsesyan, et al.; Cell Death Differ. 11, 1121 (2004) Abstract
Arachidonylethanolamide induces apoptosis of human glioma cells through vanilloid receptor-1: E. Contassot, et al.; J. Neuropathol. Exp. Neurol. 63, 956 (2004) Abstract
Preferred conformations of endogenous cannabinoid ligand anandamide: J.Z. Chen, et al.; Life Sci. 76, 2053 (2005) Abstract
The cardiovascular actions of anandamide: more targets?: M.D. Randall; Br. J. Pharmacol. 145, 565 (2005) Abstract; Full Text
Accumulation of anandamide: Evidence for cellular diversity: C.J. Hillard and A. Jarrahian; Neuropharmacology 48, 1072 (2005) Abstract
Anandamide as an intracellular messenger regulating ion channel activity: M. van der Stelt and V. Di Marzo; Prostaglandins Other Lipid Mediat. 77, 111 (2005) Abstract
Anandamide reduces infarct size in rat isolated hearts subjected to ischaemia-reperfusion by a novel cannabinoid mechanism: N.J. Underdown, et al.; Br. J. Pharmacol. 146, 809 (2005) Abstract
Anandamide inhibits adhesion and migration of breast cancer cells: C. Grimaldi, et al.; Exp. Cell Res. 312, 363 (2006) 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:
Endocannabinoids • MAPK Pathway Activators • Apoptosis Inducers & Inhibitors Other Products • Endovanilloids • NF-kB Pathway Inhibitors
 
 
ALX-340-050 Revised 08-Jul-08
N-Arachidonoyl-γ-aminobutyric acid
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SYNONYMS NAGABA
4-(1-oxo-5Z,8Z,11Z,14Z-Eicosatetraenyl)amino-butanoic acid
PRODUCT LINE Neurobiology
PRODUCT CATEGORY Anandamide & Anandamide Analogs
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ALX-340-050-M005   5 mg 72.00 USD Add To Cart
Product Specification
FORMULA: C24H39NO3
MW: 389.6
CAS NUMBER: 128201-89-8
PURITY: ≥98%
FORMULATION: Liquid. Solution in ethanol.
SOLUBILITY: 20mg/ml soluble in DMSO or dimethyl formamide; also soluble in PBS, pH 7.2 (2mg/ml).
SHIPPING: SHIPPED ON BLUE ICE
LONG TERM STORAGE: -20°C
USE/STABILITY: Stable for at least one year after receipt when stored at -20°C. We do not recommend storing aqueous solutions for more than one day.

Product Specific Literature References
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
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.
 
 
ALX-340-053 Revised 04-Aug-08
Arachidonoyl 2’-chloroethylamide
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SYNONYMS ACEA
N-(2-Chloroethyl)-5Z,8Z,11Z,14Z-eicosatetraenamide
PRODUCT LINE Neurobiology
PRODUCT CATEGORY Anandamide & Anandamide Analogs
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ALX-340-053-M005   5 mg 46.00 USD Add To Cart
Product Specification
FORMULA: C22H36NOCl
MW: 366.0
CAS NUMBER: 220556-69-4
CONCENTRATION: 10mg/ml
PURITY: ≥96%
FORMULATION: Liquid. Solution in methyl acetate.
SOLUBILITY: 20mg/ml soluble in 100% ethanol, DMSO or dimethyl formamide; 250μg/ml soluble in a 1:3 solution of ethanol:PBS (pH 7.2) (dilute the ethanol solution with PBS).
SHIPPING: SHIPPED ON DRY ICE
LONG TERM STORAGE: -80°C
USE/STABILITY: Stable for at least 1 year after receipt when stored at -80°C. We do not recommend storing aqueous solutions for more than one day.

Product Description
Non-pungent, potent and highly selective CB1 receptor agonist (Ki=1.4nM). Displays >1'400-fold selectivity over CB2 receptors (Ki=3.1µM). Active in vivo.
Product Specific Literature References
Synthesis and characterization of potent and selective agonists of the neuronal cannabinoid receptor (CB1): C.J. Hillard, et al.; J. Pharmacol. Exp. Ther. 289, 1427 (1999) Abstract
Arachidonylcyclopropylamide increases microglial cell migration through cannabinoid CB2 and abnormal-cannabidiol-sensitive receptors: A. Franklin, et al.; Eur. J. Pharmacol. 474, 195 (2003) Abstract
Modulation of trigeminal sensory neuron activity by the dual cannabinoid-vanilloid agonists anandamide, N-arachidonoyl-dopamine and arachidonyl-2-chloroethylamide: T.J. Price, et al.; Br. J. Pharmacol. 141, 1118 (2004) Abstract
The cannabinomimetic arachidonyl-2-chloroethylamide (ACEA) acts on capsaicin-sensitive TRPV1 receptors but not cannabinoid receptors in rat joints: C.L. Baker and J.J. McDougall; Br. J. Pharmacol. 142, 1361 (2004) Abstract; Full Text
General Information
BACKGROUND/TECHNICAL INFORMATION To change the solvent, evaporate the methyl acetate under a gentle stream of nitrogen and immediately add the solvent of choice.
Further Categories Containing This Product:
Cannabinoid Receptor Agonists & Antagonists / Related Products
 
 
ALX-340-054 Revised 09-Jul-08
Arachidonoyl cyclopropylamide
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SYNONYMS ACPA
N-Cyclopropyl-5Z,8Z,11Z,14Z-eicosatetraenamide
PRODUCT LINE Neurobiology
PRODUCT CATEGORY Anandamide & Anandamide Analogs
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Product Numbers: Format: Size: Unit Price: Quantity: Add To Cart
ALX-340-054-M005   5 mg 46.00 USD Add To Cart
Product Specification
FORMULA: C23H37NO
MW: 343.6
CAS NUMBER: 229021-64-1
PURITY: ≥98%
FORMULATION: Liquid. Solution in ethanol.
SOLUBILITY: 10mg/ml soluble in 100% ethanol, DMSO or dimethyl formamide; 1mg/ml soluble in a 1:1 solution of in ethanol:PBS (pH 7.2) (dilute the ethanol solution with PBS).
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 CB1 agonist (Ki=2.2nM). Displays 325-fold selectivity over CB2 receptors (Ki=0.7µM). Active in vivo.
Product Specific Literature References
Synthesis and characterization of potent and selective agonists of the neuronal cannabinoid receptor (CB1): C.J. Hillard, et al.; J. Pharmacol. Exp. Ther. 289, 1427 (1999) Abstract
Arachidonylcyclopropylamide increases microglial cell migration through cannabinoid CB2 and abnormal-cannabidiol-sensitive receptors: A. Franklin, et al.; Eur. J. Pharmacol. 474, 195 (2003) Abstract
The interaction of cannabinoids and opioids on pentylenetetrazole-induced seizure threshold in mice: H. Shafaroodi, et al.; Neuropharmacology 47, 390 (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:
Cannabinoid Receptor Agonists & Antagonists / Related Products
 
 
ALX-340-061 Revised 10-Jul-08
Arachidonoyl 2'-fluoroethylamide
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SYNONYMS N-(2-Fluoroethyl)-5Z,8Z,11Z,14Z-eicosatetraenamide
2'-Fluoro AEA
2'-Fluoro anandamide
PRODUCT LINE Neurobiology
PRODUCT CATEGORY Anandamide & Anandamide Analogs
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ALX-340-061-M005   5 mg 63.00 USD Add To Cart
Product Specification
FORMULA: C22H36NOF
MW: 349.5
CAS NUMBER: 166100-37-4
PURITY: ≥98%
FORMULATION: Liquid. Solution in ethanol.
SOLUBILITY: 7mg/ml soluble in DMSO or dimethyl formamide; 8mg/ml soluble in a 1:1 solution of ethanol:PBS (pH 7.2) (dilute the ethanol solution with PBS).
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
CB1 receptor agonist (CB1: Ki=26.7nM; CB2: Ki=908nM).
Product Specific Literature References
Novel analogues of arachidonylethanolamide (anandamide): affinities for the CB1 and CB2 cannabinoid receptors and metabolic stability: S. Lin, et al.; J. Med. Chem. 41, 5353 (1998) 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:
Cannabinoid Receptor Agonists & 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
Ordering Information
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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-340-060 Revised 10-Jul-08
Arachidonoyl serotonin
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SYNONYMS AA-5HT
N-[2-(5-Hydroxy-1H-indol-3-yl)]ethyl-5Z,8Z,11Z,14Z-eicosatetraenamide
PRODUCT LINE Neurobiology
PRODUCT CATEGORY Anandamide & Anandamide Analogs
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ALX-340-060-M005   5 mg 55.00 USD Add To Cart
Product Specification
FORMULA: C30H42N2O2
MW: 462.7
CAS NUMBER: 187947-37-1
PURITY: ≥98%
FORMULATION: Liquid. Solution in methyl acetate.
SOLUBILITY: Soluble in 100% ethanol (15mg/ml), DMSO (30mg/ml), dimethyl formamide (30mg/ml) or PBS, pH 7.2 (290μg/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
Tight binding, competitive inhibitor of fatty acid amide hydrolase (FAAH) (IC50=12µM).
Product Specific Literature References
Arachidonoylserotonin and other novel inhibitors of fatty acid amide hydrolase: T. Bisogno, et al.; BBRC 248, 515 (1998) Abstract
General Information
BACKGROUND/TECHNICAL INFORMATION To change the solvent, evaporate the methyl acetate under a gentle stream of nitrogen and immediately add the solvent of choice.
Further Categories Containing This Product:
Fatty Acid Amide Hydrolase [FAAH] / Related Products
 
 
ALX-340-030 Revised 08-Jul-08
R-1 Methanandamide
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SYNONYMS (R)-(+)-Arachidonyl-1'-hydroxy-2'-propylamide
AM 356
N-(2-Hydroxy-1R-methylethyl)-5Z,8Z,11Z,14Z-eicosatetraenamide
PRODUCT LINE Neurobiology
PRODUCT CATEGORY Anandamide & Anandamide Analogs
Ordering Information
Product Numbers: Format: Size: Unit Price: Quantity: Add To Cart
ALX-340-030-M005   5 mg 63.00 USD Add To Cart
Product Specification
FORMULA: C23H39NO2
MW: 361.6
CAS NUMBER: 157182-49-5
PURITY: ≥98%
FORMULATION: Liquid. Solution in ethanol.
SOLUBILITY: 10mg/ml soluble in DMSO or dimethyl formamide; sparingly soluble in aqueous buffers. To prevent oxidation, the solvent should be purged with an inert gas.
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. Keep aqueous solutions on ice and use within 12 hours.
HANDLING: Protect from light and oxygen.
HAZARD: IRRITANT.

Product Description
Amidase resistant cannabinoid receptor (CB) agonist (CB1: Ki=20nM; CB2: Ki=815nM). The most potent of the series of methyl-anandamides. About 4-fold higher binding affinity for cannabinoid receptor CB1 than anandamide (Prod. No. ALX-340-029) in the presence of PMSF. Does also bind to TRPV1 (Ki=4.67µM).
Product Specific Literature References
(R)-methanandamide: a chiral novel anandamide possessing higher potency and metabolic stability: V. Abadji, et al.; J. Med. Chem. 37, 1889 (1994) Abstract
Head group analogs of arachidonylethanolamide, the endogenous cannabinoid ligand: A.D. Khanolkar, et al.; J. Med. Chem. 39, 4515 (1996) Abstract
Extrapyramidal effects of