PHENSERINE
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- CAS-Nr.
- 101246-66-6
- Englisch Name:
- PHENSERINE
- Synonyma:
- PHENSERINE;(-)-Phenserine;(3as-cis)-amate(ester;(-)-Eseroline phenylcarbamate;(-)-N-PHENYLCARBAMOYLESEROLINE;3-b)indol-5-ol,1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-pyrrolo(phenylcarb;1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-pyrrolo[2,3-b]indol-5-ol phenylcarbamate (ester);(3aS,8aR)-1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-ol5-(N-phenylcarbamate);Pyrrolo[2,3-b]indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, 5-(N-phenylcarbamate), (3aS,8aR)-
- CBNumber:
- CB5731231
- Summenformel:
- C20H23N3O2
- Molgewicht:
- 337.42
- MOL-Datei:
- 101246-66-6.mol
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PHENSERINE Eigenschaften
- Schmelzpunkt:
- 151-152 °C
- Siedepunkt:
- 468.7±45.0 °C(Predicted)
- Dichte
- 1.228±0.06 g/cm3(Predicted)
- storage temp.
- 2-8°C
- L?slichkeit
- H2O: <2mg/mL
- pka
- 13.05±0.70(Predicted)
- Aggregatzustand
- solid
- Farbe
- off-white
- Wasserl?slichkeit
- H2O: <2mg/mL
DMSO: >5mg/mL
- InChI
- InChI=1S/C20H23N3O2/c1-20-11-12-22(2)18(20)23(3)17-10-9-15(13-16(17)20)25-19(24)21-14-7-5-4-6-8-14/h4-10,13,18H,11-12H2,1-3H3,(H,21,24)/t18-,20+/m1/s1
- InChIKey
- PBHFNBQPZCRWQP-QUCCMNQESA-N
- SMILES
- N1(C)C2=C(C=C(OC(=O)NC3=CC=CC=C3)C=C2)[C@]2(C)CCN(C)[C@]12[H]
Sicherheit
- Risiko- und Sicherheitserkl?rung
- Gefahreninformationscode (GHS)
| Kennzeichnung gef?hrlicher |
Xi |
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| R-S?tze: |
36/37/38 |
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| S-S?tze: |
26 |
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| WGK Germany |
3 |
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| RTECS-Nr. |
UY8586000 |
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| Speicherklasse |
11 - Combustible Solids |
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| Hazard Classifications |
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
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| Bildanzeige (GHS) |
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| Alarmwort |
Warnung
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| Gefahrenhinweise |
| Code |
Gefahrenhinweise |
Gefahrenklasse |
Abteilung |
Alarmwort |
Symbol |
P-Code |
| H315 |
Verursacht Hautreizungen. |
Hautreizung |
Kategorie 2 |
Warnung |
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P264, P280, P302+P352, P321,P332+P313, P362 |
| H319 |
Verursacht schwere Augenreizung. |
Schwere Augenreizung |
Kategorie 2 |
Warnung |
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P264, P280, P305+P351+P338,P337+P313P |
| H335 |
Kann die Atemwege reizen. |
Spezifische Zielorgan-Toxizit?t (einmalige Exposition) |
Kategorie 3 (Atemwegsreizung) |
Warnung |
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| Sicherheit |
| P261 |
Einatmen von Staub vermeiden. |
| P264 |
Nach Gebrauch gründlich waschen. |
| P264 |
Nach Gebrauch gründlich waschen. |
| P271 |
Nur im Freien oder in gut belüfteten R?umen verwenden. |
| P280 |
Schutzhandschuhe/Schutzkleidung/Augenschutz tragen. |
| P302+P352 |
BEI BERüHRUNG MIT DER HAUT: Mit viel Wasser/... (Hersteller kann, falls zweckm??ig, ein Reinigungsmittel angeben oder, wenn Wasser eindeutig ungeeignet ist, ein alternatives Mittel empfehlen) waschen. |
| P305+P351+P338 |
BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach M?glichkeit entfernen. Weiter spülen. |
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PHENSERINE Chemische Eigenschaften,Einsatz,Produktion Methoden
Verwenden
Phenserine is inhibitor of amyloid precursor protein (APP). Used in Alzheimer’s treatments.
Biologische Aktivit?t
Physostigmine analog that inhibits acetylcholinesterase. Inhibits production of amyloid precursor protein (APP) and A β . Improves morris water maze performance of scopolamine-treated rats.
Enzyminhibitor
This long-acting AChE inhibitor and A42-lowering agent (FW = 337,42
g/mol; CAS 101246-66-6), also known as (–) -N-phenylcarbamoyl eseroline,
is a carbamate analogue of eserine (or physostigmine) that inhibits
acetylcholinesterase and is under active investigation for its potential in
cholinomimetic therapy to reduce cognitive impairments associated with
aging and Alzheimer's Disease. Phenserine is a potent and highly selective
AChE inhibitor (IC50 = 22 nM), displaying 70x greater inhibitory action
than observed with butyrylcholinesterase, or BChE (IC50 = 1560 nM), both
in vitro and in clinical trials for treatment of Alzheimer's disease (1-5).
Compared to physostigmine and tacrine, phenserine appears to be less toxic
and robustly enhances cognition in animal models. In rats, phenserine
achieves maximum acetylcholinesterase inhibition of 73.5% at 5 min,
maintaining high and relatively constant inhibition for >8 hours.
Phenserine decreased the levels of secreted b-amyloid precursor protein (b-
APP) in the cerebrospinal fluid (CSF) of forebrain cholinergic system-
lesioned rats, whereas DFP, a relatively non-specific cholinesterase
inhibitor, failed to affect CSF levels of secreted b-APP. Such findings
suggest that phenserine alters the induction of cortical b-APP mRNAs and
increased levels of secreted b-APP in the CSF. Phenserine reduces Ab
levels by regulating b-APP translation via a recently described iron
regulatory element in the 5'-untranslated region of b-APP mRNA that was
previously shown to be up-regulated in the presence of interleukin-1.
Other dual AChE/A42 inhibitors include: rivastigmine, ladostigil,
asenapine, phenserine, amitriptyline, clomipramine, doxepin and
desipramine. Posiphen, the better-tolerated (+) -enantiomer of phenserine, is
devoid of anticholinesterase action, but represses translation of neural α-
synuclein, a druggable target in the treatment of Parkinson Disease.
PHENSERINE Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
PHENSERINE Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.
Global( 50)Lieferanten
101246-66-6()Verwandte Suche:
- (3as-cis)-amate(ester
- 3-b)indol-5-ol,1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-pyrrolo(phenylcarb
- (-)-N-PHENYLCARBAMOYLESEROLINE
- PHENSERINE
- (3aS,8aR)-1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-ol5-(N-phenylcarbamate)
- 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-pyrrolo[2,3-b]indol-5-ol phenylcarbamate (ester)
- (-)-Eseroline phenylcarbamate
- Pyrrolo[2,3-b]indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, 5-(N-phenylcarbamate), (3aS,8aR)-
- (-)-Phenserine
- 101246-66-6
