ALEXIS Biochemicals: N-Oleoyldopamine

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ALX-340-029

Revised 08-Jul-08

Anandamide
SYNONYMS	AEA N-Arachidonoylethanolamine (all-Z)-N-(2-Hydroxyethyl)-5,8,11,14-eicosatetraenamide
PRODUCT LINE	Neurobiology
PRODUCT CATEGORY	Anandamide & Anandamide Analogs

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-340-029-M005		5 mg	51.00 USD

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: K_i=52nm; CB₂: K_i=1930nm [2]) and TRPV1 (K_i=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-340-049

Revised 03-Dec-07

N-Arachidonoyldopamine
SYNONYMS	N-Arachidonoyl-3-hydroxytyramine NADA AA-DA
PRODUCT LINE	Neurobiology
PRODUCT CATEGORY	Endocannabinoids

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-340-049-M001		1 mg	20.00 USD
ALX-340-049-M005		5 mg	35.00 USD

Product Specification

FORMULA:	C₂₈H₄₁NO₃
MW:	439.6
CAS NUMBER:	199875-69-9
PURITY:	≥99% (HPLC)
APPEARANCE:	Lyophilized.
SOLUBILITY:	Soluble in methanol, 100% ethanol or DMSO.
SHIPPING:	SHIPPED ON DRY ICE
LONG TERM STORAGE:	-20°C
HANDLING:	Packaged under inert gas.

Product Description

Endogenous, specific ligand for the CB₁ receptor (CB₁: K_i=250nM; CB₂: K_i=12µM) [1] and TRPV1 [2] (EC₅₀=50nM) found in nervous tissues [3, 4]. Immunosuppressant inhibiting T cell proliferation and phosphorylation of the NF-κB p65 subunit [5]. Potent vasorelaxant [6] and inhibitor of HIV-1 [7].

Product Specific Literature References

[1] N-acyl-dopamines: novel synthetic CB(1) cannabinoid-receptor ligands and inhibitors of anandamide inactivation with cannabimimetic activity in vitro and in vivo: T. Bisogno, et al.; Biochem. J. 351, 817 (2000) Abstract; Full Text
[2] Actions of two naturally occurring saturated N-acyldopamines on transient receptor potential vanilloid 1 (TRPV1) channels: L. De Petrocellis, et al.; Br. J. Pharmacol. 143, 251 (2004) Abstract; Full Text
[3] An endogenous capsaicin-like substance with high potency at recombinant and native vanilloid VR1 receptors: S.M. Huang, et al.; PNAS 99, 8400 (2002) Abstract
[4] Arachidonyl dopamine as a ligand for the vanilloid receptor VR1 of the rat: A. Toth, et al.; Life Sci. 73, 487 (2003) Abstract
[5] Immunosuppressive activity of endovanilloids: N-arachidonoyl-dopamine inhibits activation of the NF-kappa B, NFAT, and activator protein 1 signaling pathways: R. Sancho, et al.; J. Immunol. 172, 2341 (2004) Abstract
[6] Characterisation of the vasorelaxant properties of the novel endocannabinoid N-arachidonoyl-dopamine (NADA): S.E. O'Sullivan, et al.; Br. J. Pharmacol. 141, 803 (2004) Abstract
[7] Mechanisms of HIV-1 inhibition by the lipid mediator N-arachidonoyldopamine: R. Sancho, et al.; J. Immunol. 175, 3990 (2005) Abstract
Synthesis and biological evaluation of novel amides of polyunsaturated fatty acids with dopamine: V. Bezuglov, et al.; Bioorg. Med. Chem. Lett. 11, 447 (2001) 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
Mechanisms of HIV-1 Inhibition by the Lipid Mediator N-Arachidonoyldopamine: R. Sancho, et al.; J. Immunol. 175, 3990 (2005) Abstract

Further Categories Containing This Product:

Endovanilloids • Immunomodulators Other Products

ALX-340-063

Revised 19-Apr-07

N-Arachidonoyl-L-serine
SYNONYMS	N-[(5Z,8Z,11Z,14Z)-1-Oxo-5,8,11,14-eicosatetraenyl)]-L-serine ARA-S
PRODUCT LINE	Neurobiology
PRODUCT CATEGORY	Endocannabinoids

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-340-063-M010		10 mg	90.00 USD

Product Specification

FORMULA:	C₂₃H₃₇NO₄
MW:	391.5
CAS NUMBER:	187224-29-9
PURITY:	≥98%
APPEARANCE:	Waxy solid.
SOLUBILITY:	Soluble in DMSO or dimethyl formamide; sparingly soluble in water.
SHIPPING:	SHIPPED ON DRY ICE
LONG TERM STORAGE:	-80°C

Product Description

Endocannabinoid-like brain constituent with similar biological profile like abnormal cannabidiol. Binds weakly to CB₁ and CB₂ receptors and TRPV1. Produces endothelium-dependent vasodilation. Increases phosphorylation of Akt and mitogen-activated protein kinase (MAPK) in HUVEC.

Product Specific Literature References

N-arachidonoyl L-serine, an endocannabinoid-like brain constituent with vasodilatory properties: G. Milman, et al.; PNAS 103, 2428 (2006) Abstract; Full Text

Further Categories Containing This Product:

MAPK Pathway Activators • Endovanilloids • PI(3)K-Akt-mTOR Pathway Other Products

ALX-340-057

Revised 10-Jul-08

12(S)-HpETE
SYNONYMS	12-(S)-Hydroperoxy-5Z,8Z,10E,14Z-eicosatetraenoic acid
PRODUCT LINE	Inflammation
PRODUCT CATEGORY	Eicosanoids Other Products

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-340-057-C025		25 µg	162.00 USD
ALX-340-057-C050		50 µg	308.00 USD

Product Specification

FORMULA:	C₂₀H₃₂O₄
MW:	336.5
CAS NUMBER:	71774-10-2
PURITY:	≥98%
FORMULATION:	Liquid. Solution in ethanol.
SOLUBILITY:	Soluble in DMSO or dimethyl formamide; slightly soluble in PBS, pH 7.2 (0.8mg/ml) or 0.1M Na₂CO₃ (2mg/ml).
SHIPPING:	SHIPPED ON DRY ICE
LONG TERM STORAGE:	-80°C
USE/STABILITY:	Stable for at least 6 months after receipt when stored at -80°C. Product is highly unstable in aqueous solution. We recommend using aqueous solutions within fifteen minutes.

Product Description

Endogenous TRPV1 agonist (K_i=0.35µM).

Product Specific Literature References

Direct activation of capsaicin receptors by products of lipoxygenases: endogenous capsaicin-like substances: S.W. Hwang, et al.; PNAS 97, 6155 (2000) Abstract
Bradykinin-12-lipoxygenase-VR1 signaling pathway for inflammatory hyperalgesia: J. Shin, et al.; PNAS 99, 10150 (2002) 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:

Fos & Jun Proteins / Related Products • Endovanilloids

ALX-340-058

Revised 10-Jul-08

15(S)-HpETE
SYNONYMS	15S-Hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid
PRODUCT LINE	Inflammation
PRODUCT CATEGORY	Eicosanoids Other Products

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-340-058-C025		25 µg	41.00 USD
ALX-340-058-C050		50 µg	79.00 USD

Product Specification

FORMULA:	C₂₀H₃₂O₄
MW:	336.5
CAS NUMBER:	70981-96-3
PURITY:	≥98%
FORMULATION:	Liquid. Solution in ethanol.
SOLUBILITY:	Soluble in DMSO or dimethyl formamide; slightly soluble in PBS, pH 7.2 (0.8mg/ml) or 0.1M Na₂CO₃ (2mg/ml).
USE/STABILITY:	Stable for at least 1 year after receipt when stored at -80°C. Product is highly unstable in aqueous solution. We recommend using aqueous solutions within 15 minutes.

Product Description

Endogenous TRPV1 agonist.

Product Specific Literature References

Direct activation of capsaicin receptors by products of lipoxygenases: endogenous capsaicin-like substances: S.W. Hwang, et al.; PNAS 97, 6155 (2000) 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:

Fos & Jun Proteins / Related Products • Endovanilloids

ALX-550-398

Revised 10-Jul-08

N-Oleoyldopamine
SYNONYMS	OLDA N-[2-(3,4-Dihydroxyphenyl)ethyl]-9Z-octadecenamide
PRODUCT LINE	Neurobiology
PRODUCT CATEGORY	TRPV1 Agonists and Antagonists / Related Products

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-550-398-M005		5 mg	35.00 USD

Product Specification

FORMULA:	C₂₆H₄₃NO₃
MW:	417.6
CAS NUMBER:	105955-11-1
CONCENTRATION:	50mg/ml
PURITY:	≥98%
FORMULATION:	Liquid. Solution in ethanol.
SOLUBILITY:	20mg/ml soluble in DMSO or dimethyl formamide; 0.5mg/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.
HANDLING:	Protect from light.

Product Description

Endogenous TRPV1 agonist (K_i=36nM, EC₅₀=36nM) with weak affinity for rat CB₁ receptor (K_i=1.6µM). Potent inhibitor of 5-lipoxygenase (IC₅₀=7.5nM) and of early and late events in TCR mediated T cell activation. Inhibits NF-κB dependent transcriptional activity without affecting either degradation of the cytoplasmic NF-κB inhibitory protein, IκBα, or DNA binding activity.

Product Specific Literature References

Inhibition of arachidonate 5-lipoxygenase by phenolic compounds: S. Iwakami, et al.; Chem. Pharm. Bull. 34, 3960 (1986) Abstract
Inhibition of in vitro prostaglandin and leukotriene biosyntheses by cinnamoyl-beta-phenethylamine and N-acyldopamine derivatives: C.F. Tseng, et al.; Chem. Pharm. Bull. 40, 396 (1992) Abstract
N-oleoyldopamine, a novel endogenous capsaicin-like lipid that produces hyperalgesia: C.J. Chu, et al.; J. Biol. Chem. 278, 13633 (2003) Abstract
Direct evidence for activation and desensitization of the capsaicin receptor by N-oleoyldopamine on TRPV1-transfected cell, line in gene deleted mice and in the rat: J. Szolcsanyi, et al.; Neurosci. Lett. 361, 155 (2004) Abstract
Immunosuppressive activity of endovanilloids: N-arachidonoyl-dopamine inhibits activation of the NF-kappa B, NFAT, and activator protein 1 signaling pathways: R. Sancho, et al.; J. Immunol. 172, 2341 (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:

Endovanilloids • Lipoxygenases / Related Products • NF-kB Pathway Inhibitors

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