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Merck
CN

SML0321

Cyamemazine

≥98% (HPLC)

Synonym(s):

10-[3-(Dimethylamino)-2-methylpropyl]-10H-phenothiazine-2-carbonitrile, 7204 R. E., 7204 RP, Ciamatil, Cianatil, Cyamemazin, R.P. 7204, TH 2602

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About This Item

Empirical Formula (Hill Notation):
C19H21N3S
CAS Number:
3546-03-0
Molecular Weight:
323.46
NACRES:
NA.77
PubChem Substance ID:
329825326
UNSPSC Code:
12352200
EC Number:
222-594-2
MDL number:
MFCD00868180
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100

Key Documents

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form

powder

InChI key

SLFGIOIONGJGRT-UHFFFAOYSA-N

InChI

1S/C19H21N3S/c1-14(12-21(2)3)13-22-16-6-4-5-7-18(16)23-19-9-8-15(11-20)10-17(19)22/h4-10,14H,12-13H2,1-3H3

SMILES string

CC(CN(C)C)CN1c2ccccc2Sc3ccc(cc13)C#N

assay

≥98% (HPLC)

color

light yellow to yellow-green

solubility

DMSO: ≥5 mg/mL

storage temp.

2-8°C

Quality Level

100

Application

Cyamemazine has been used as an internal standard and antipsychotic drug to spike plasma samples in mass spectrometry studies. It has also been used as an analytical standard in gas chromatography-tandem mass spectroscopic (GC-MS/MS) analysis.

Biochem/physiol Actions

Cyamemazine is a potent antagonist of 5-HT2C and 5-HT3 receptors with antipsychotic and anxiolytic properties.
Cyamemazine is a potent antagonist of 5-HT2C and 5-HT3 receptors.
Cyamemazine belongs to the class of phenothiazine drugs. It is known to treat severe depression, schizophrenia and bipolar disorder.

pictograms

Environment
GHS09

signalword

Warning

hcodes

H410

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000415892
0000415892
0000140357
0000140355
0000138151

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Yann Hodé et al.
Psychopharmacology, 217(3), 315-321 (2011-04-12)
Cyamemazine (Tercian®) is an antipsychotic agent blocking central dopamine D(2) receptors, which induces few extrapyramidal adverse effects, due to a potent antagonistic action at serotonin 5-HT(2A) receptors. In vitro studies showed that the desmethyl metabolite of cyamemazine (N-desmethyl cyamemazine) has
F-J Baylé et al.
L'Encephale, 37 Suppl 1, S83-S89 (2011-05-28)
Anxiety is a major and frequent symptom of schizophrenia, which is associated with an increased risk of relapse, impaired functioning, lower quality of life and increased incidence of suicide attempts. Despite its clinical relevance, anxiety in schizophrenia remains poorly understood.
Seth H Walters et al.
Schizophrenia bulletin, 46(3), 643-649 (2019-07-30)
Many psychiatric drugs are weak bases that accumulate in and are released from synaptic vesicles, but the functional impact of vesicular drug release is largely unknown. Here, we examine the effect of vesicular release of the anxiolytic antipsychotic drug cyamemazine
Christophe Arbus et al.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 32(4-5), 357-366 (2007-10-24)
Recombinant human liver microsomal enzymes of the cytochrome P450 family (CYP1A2, CYP2A6, CYP3A4, CYP2B6, CYP2C8, CYP2C9, CYP2C19, CYP2D6, CYP2E1) were used to determine the metabolic fate of the antipsychotic anxiolytic agent cyamemazine. An LC/MS-MS tandem methodology was developed specifically for
Michel Bourin et al.
CNS drug reviews, 10(3), 219-229 (2004-10-20)
Several studies have suggested that the antipsychotic compound, cyamemazine, possesses anxiolytic properties in humans. The original pharmacological profile of cyamemazine (D(2), 5-HT(2A), 5-HT(2C), and 5-HT(3) receptor antagonist), which was established by binding, microdialysis and behavioral studies, is consistent with these
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