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SML0321

Sigma-Aldrich

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
EC Number:
222-594-2
MDL number:
MFCD00868180
UNSPSC Code:
12352200
PubChem Substance ID:
329825326
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

light yellow to yellow-green

solubility

DMSO: ≥5 mg/mL

storage temp.

2-8°C

SMILES string

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

InChI key

SLFGIOIONGJGRT-UHFFFAOYSA-N

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

pictograms

Environment
GHS09

signalword

Warning

hcodes

H410

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Bernard Marc et al.
Presse medicale (Paris, France : 1983), 36(10 Pt 1), 1399-1403 (2007-06-15)
The toxic effects of Datura stramonium most often include visual and auditory hallucinations, confusion and agitation. Severe and even fatal complications (coma, respiratory distress or death in more than 5% of cases) are not rare since the lethal concentration of
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.
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
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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