ChemicalBook--->CAS DataBase List--->139290-65-6

139290-65-6

139290-65-6 Structure

139290-65-6 Structure
IdentificationBack Directory
[Name]

(R)-(+)-ALPHA-(2,3-DIMETHOXYPHENYL)-1-[2-(4-FLUORO-PHENYL)ETHYL]-4-PIPERIDINE METHANOL
[CAS]

139290-65-6
[Synonyms]

M 100907
MDL100907
VOLINANSERIN
R-MDL 100907
MDL100907-L-tartrate
MDL100907 tartrate salt
MDL-100907(Volinanserin)
Volinanserin Hydrochloride Salt
(R)-(2,3-dimethoxyphenyl)(1-(4-fluorophenethyl)piperidin-4-yl)methanol
(+)-a-(2,3-Dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol
(aR)-a-(2,3-Dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol
(R)-(+)-a-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-pipidinemethanol
4-Piperidinemethanol, 1-[2-(4-fluorophenyl)ethyl]-(-(2,3-dimethoxyphenyl)-, ((R)
4-piperidinemethanol, a-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-, (ar)-
(R)-(+)-(-(2,3-Dimethoxyphenyl)-1-[2-(4-fluoro-phenyl)ethyl]-4-piperidine methanol
(R)-(+)-ALPHA-(2,3-DIMETHOXYPHENYL)-1-[2-(4-FLUORO-PHENYL)ETHYL]-4-PIPERIDINE METHANOL
4-PIPERIDINEMETHANOL, 1-[2-(4-FLUOROPHENYL)ETHYL]-ALPHA-(2,3-DIMETHOXYPHENYL)-, (ALPHAR)
(+)-a-(2,3-Dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol Hydrochloride
(+)-α-(2,3-DiMethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidineMethanol Hydrochloride
(αR)-α-(2,3-DiMethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidineMethanol Hydrochloride
(aR)-a-(2,3-Dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol Hydrochloride
4-Piperidinemethanol, 1-[2-(4-fluorophenyl)ethyl]-(-(2,3-dimethoxyphenyl)-, ((R), (R,R)-tartrate
(R)-(+)-(-(2,3-Dimethoxyphenyl)-1-[2-(4-fluoro-phenyl)ethyl]-4-piperidine methanol (R,R)-tartrate
[Molecular Formula]

C22H28FNO3
[MDL Number]

MFCD00909060
[MOL File]

139290-65-6.mol
[Molecular Weight]

373.46
Chemical PropertiesBack Directory
[Appearance]

Colourless solid
[Melting point ]

89-91°C
[Boiling point ]

499.4±45.0 °C(Predicted)
[density ]

1.150±0.06 g/cm3(Predicted)
[storage temp. ]

-20°C Freezer
[solubility ]

DMSO: ≥20mg/mL
[form ]

powder
[pka]

13.93±0.20(Predicted)
[color ]

off-white to light brown
[InChI]

1S/C22H28FNO3/c1-26-20-5-3-4-19(22(20)27-2)21(25)17-11-14-24(15-12-17)13-10-16-6-8-18(23)9-7-16/h3-9,17,21,25H,10-15H2,1-2H3/t21-/m1/s1
[InChIKey]

HXTGXYRHXAGCFP-OAQYLSRUSA-N
[SMILES]

COc1cccc([C@H](O)C2CCN(CC2)CCc3ccc(F)cc3)c1OC
Hazard InformationBack Directory
[Chemical Properties]

Colourless solid
[Uses]

A serotonin 5-HT2A receptor antagonist. Used as potential controls in various biological studies
[Description]

Volinanserin is a potent and selective antagonist of the serotonin receptor 5-HT2A (Ki = 0.36-0.85 nM). It weakly binds 5-HT2C, α1-adrenergic, and sigma receptors (Ki = 88, 128, and 87 nM) and much less effectively associates with other serotonin, dopamine, adrenergic, muscarinic acetylcholine receptors and monoamine transporters. Volinanserin displays antipsychotic activity, attenuates impulsivity, and augments antidepressant effects in vivo.
[General Description]

M100907 blocks the serotonin 2A (5-HT2A) receptors and imposes antidepressant-like effects. It may be used for treating dopaminergic anomalies.
[Biochem/physiol Actions]

M100907 is a selective 5-HT2A Antagonist.
[storage]

+4°C
[References]

[1] S M SORENSEN. Characterization of the 5-HT2 receptor antagonist MDL 100907 as a putative atypical antipsychotic: behavioral, electrophysiological and neurochemical studies.[J]. Journal of Pharmacology and Experimental Therapeutics, 1993, 266 2: 684-691.
[2] J H KEHNE. Preclinical characterization of the potential of the putative atypical antipsychotic MDL 100,907 as a potent 5-HT2A antagonist with a favorable CNS safety profile.[J]. Journal of Pharmacology and Experimental Therapeutics, 1996, 277 2: 968-981.
[3] ELIZABETH A PEHEK. Evidence for the Preferential Involvement of 5-HT2A Serotonin Receptors in Stress- and Drug-Induced Dopamine Release in the Rat Medial Prefrontal Cortex[J]. Neuropsychopharmacology, 2005, 31 2: 265-277. DOI: 10.1038/sj.npp.1300819
[4] PAUL A ARDAYFIO. The 5-hydroxytryptamine2A receptor antagonist R-(+)-alpha-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl-4-piperidinemethanol (M100907) attenuates impulsivity after both drug-induced disruption (dizocilpine) and enhancement (antidepressant drugs) of differential-reinforcement-of-low-rate 72-s behavior in the rat.[J]. Journal of Pharmacology and Experimental Therapeutics, 2008, 327 3: 891-897. DOI: 10.1124/jpet.108.143370
[5] LAURA J. BOOTHMAN  Trevor S  Stephen N Mitchell. Investigation of the SSRI augmentation properties of 5-HT2 receptor antagonists using in vivo microdialysis[J]. Neuropharmacology, 2006, 50 6: Pages 726-732. DOI: 10.1016/j.neuropharm.2005.11.020
[6] VERN LEWIS. A non-hallucinogenic LSD analog with therapeutic potential for mood disorders.[J]. Cell reports, 2023, 42 3: 112203. DOI: 10.1016/j.celrep.2023.112203
Safety DataBack Directory
[Hazard Codes ]

N
[Risk Statements ]

50
[Safety Statements ]

61
[RIDADR ]

UN 3077 9 / PGIII
[WGK Germany ]

3
[Storage Class]

11 - Combustible Solids
Spectrum DetailBack Directory
[Spectrum Detail]

(R)-(+)-ALPHA-(2,3-DIMETHOXYPHENYL)-1-[2-(4-FLUORO-PHENYL)ETHYL]-4-PIPERIDINE METHANOL(139290-65-6)1HNMR
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