ANANDAMIDE

Bezeichnung:ANANDAMIDE

CAS-Nr94421-68-8

Englisch Name:ANANDAMIDE

CBNumberCB7168648

SummenformelC22H37NO2

Molgewicht347.53

MOL-Datei94421-68-8.mol

ANANDAMIDE physikalisch-chemischer Eigenschaften

Siedepunkt	522.3±50.0 °C(Predicted)
Dichte	0.92 g/mL at 25 °C (lit.)
Flammpunkt	14 °C
storage temp.	-20°C
Löslichkeit	ethanol: soluble
Aggregatzustand	oil
pka	14.48±0.10(Predicted)
Farbe	light yellow
Wasserlöslichkeit	413ug/L(25 ºC)
Stabilität	Stable for 1 year from date of purchase as supplied. Subject to oxidation – protect from air. Solutions in degassed DMSO or ethanol may be stored under nitrogen or argon at -80°C for up to 1 month.

Sicherheit

Kennzeichnung gefährlicher	F
R-Sätze:	11
S-Sätze:	24/25-16-7
RIDADR	UN 1170 3/PG 2
WGK Germany	3
RTECS-Nr.	JX3842500

Gefahreninformationscode (GHS)

ANANDAMIDE Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R11:Leichtentzündlich.
S-Sätze Betriebsanweisung:
S24/25:Berührung mit den Augen und der Haut vermeiden.
S16:Von Zündquellen fernhalten - Nicht rauchen.
S7:Behälter dicht geschlossen halten.
Beschreibung
Anandamide (94421-68-8) is an endogenous cannabinoid receptor agonist.1-3?Ki=89 nM for CB1?and 371 nM for CB2?receptors.
Verwenden
Anandamide is an endogenous cannabinoid and TRPV1 receptor agonist. Findings suggest that endocannabinoids such as anandamide may help cause runner’s high, the feeling of euphoria, reduced anxiety and lessened ability to feel pain associated with exercise.
Definition
ChEBI: An N-(polyunsaturated fatty acyl)ethanolamine resulting from the formal condensation of carboxy group of arachidonic acid with amino group of ethanolamine.
Hazard
A reproductive hazard.
Biologische Aktivität
Endogenous cannabinoid and vanilloid receptor agonist, in water-soluble emulsion (for details see TocrisolveTM 100). K i values are 89 and 371 nM for CB 1 and CB 2 receptors respectively; EC 50 values are 18, 31 and 27 nM at GPR55, CB 1 and CB 2 respectively; pK i = 5.68 for rVR1. Also blocks TNF- α -induced NF-kB activation via direct inhibition of IKK. Also available as the pure oil dissolved in ethanol (N-(2-Hydroxyethyl)-5Z,8Z,11Z,14Z-eicosatetraenamide ).
Biochem/physiol Actions
An arachidonic acid derivative that is an endogenous ligand for the CB cannabinoid receptor and for the VR1 vanilloid receptor. Inhibits calcium currents in neuroblastomas and neurons. Activates the MAP kinase signaling pathway. Inhibits proliferation and induces apoptosis of lymphocytes and human breast cancer cells.
Enzyminhibitor
This lipid neurotransmitter and endocannabinoid receptor ligand (FW = 347.54 g/mol; CAS 94421-68-8), also known as arachidonylethanolamide, inhibits calcium ion currents and activates the MAP kinase signaling pathway. Anandamide is a naturally occurring effector of central and peripheral nervous systems, as mediated by CB1 and CB2 cannabinoid receptors, respectively. (These receptors were originally characterized as binding Δ9 -tetrahydrocannabinol, or THC, marijuana’s major psychoactive ingredient.) Anandamide, 2-arachidonoylglycerol, and congeners (N- oleoylethanolamide and N-palmitoylethanolamide) are lipophilic signalling molecules with multiple physiological roles in learning and memory, neuroinflammation, oxidative stress, neuroprotection and neurogenesis. Anandamide likewise plays a role in regulating uterine implantation of the early-stage embryo (blastocyst). Anandamide synthesis occurs from N- acetylphosphatidylethanolamine by multiple pathways that include phospholipase A2, phospholipase C, and NAPE-hydrolyzing phospholipase D (or NAPE-PLD). Target(s): adenylate cyclase; Na + channels; a7-nicotinic acetylcholine receptor; 5 HT3 receptors; Ca 2+ channels; K+ channels, voltage-gated; acylglycerol lipase, or monoacylglycerol lipase.
Lager
Store at -20°C
Einzelnachweise
1) Devane?et al. (1992),?Isolation and structure of a brain constituent that binds to the cannabinoid receptor; Science,258?1946 2) Devane?et al. (1994),?New dawn of cannabinoid pharmacology; Trends Pharmacol.Sci.,?15?40 3) Hillard?et al. (1997),?Biochemistry and pharmacology of arachidonoylethanolamide, a putative endogenous cannabinoid; J. Lipid Res.,?38?2383

ANANDAMIDE Upstream-Materialien And Downstream Produkte

ANANDAMIDE Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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