Cyamemazine

Names

[ Name ]:
Cyamemazine

[Synonym ]:
Kyamepromazin
Kyamepromazine
10H-Phenothiazine-2-carbonitrile, 10-[3-(dimethylamino)-2-methylpropyl]-
7204 R.E.
Ciamatil
Cyamemazine
10-[3-(Dimethylamino)-2-methylpropyl]-10H-phenothiazine-2-carbonitrile
2-Cyano-10-(3-dimethylamino-2-methylpropyl)phenothiazine
Tercian
10-[3-(dimethylamino)-2-methylpropyl]phenothiazine-2-carbonitrile

Biological Activity

[Description]:

Cyamemazine is a neuroleptic agent that contains the phenothiazine chromophore. Cyamemazine is often used as an anxiolytic. Cyamemazine is a potent 5-HT3 (Ki of 12 nM), 5-HT2A (Ki = 1.5 nM) and 5-HT2C (Ki of 75 nM) receptors antagonist with antipsychotic activity[1][2].

[Related Catalog]:

Research Areas >> Neurological Disease

Signaling Pathways >> GPCR/G Protein >> 5-HT Receptor

Signaling Pathways >> Neuronal Signaling >> 5-HT Receptor

[Target]

5-HT2A Receptor:1.5 nM (Ki)

5-HT2C Receptor:12 nM (Ki)

5-HT3 Receptor:75 nM (Ki)

[In Vitro]

Cyamemazine exhibits a high affinity for dopamine receptors, which is consistent with its antipsychotic activity. The antagonist activity of Cyamemazine at muscarinic receptors is consistent with its affinity for M1 (Ki = 13 nM), M2 (Ki = 42 nM), M3 (Ki = 321 nM), M4 (Ki = 12 nM), and M5 (Ki = 35 nM) receptors[1].

[In Vivo]

Cyamemazine behaves as an antagonist at the 5-HT3, 5-HT2C, and 5-HT2A receptors in 5-HT3-dependent contraction of isolated guinea pig ileum and bradycardic responses in rats, in 5-HT2C-dependent phospholipase C stimulation in the rat brain membrane, and in 5-HT2A-dependent contraction of isolated rat aorta rings and isolated guinea pig trachea. Cyamemazine antagonizes 5-HT3 and 5-HT2C receptors and that this effect is partially involved in its therapeutic activity in anxiety disorders. Acute administration of low doses of Cyamemazine can reduces extracellular dopamine and metabolite concentrations in rat striatum[1].

[References]

[1]. Bourin M, et al. Preclinical and clinical pharmacology of cyamemazine: anxiolytic effects and prevention of alcohol and benzodiazepine withdrawal syndrome. CNS Drug Rev. 2004 Fall;10(3):219-29.

[2]. Vendrell-Criado V, et al. Photobehavior of the antipsychotic drug cyamemazine in a supramolecular gel protective environment. J Photochem Photobiol B. 2020 Jan;202:111686.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
479.0±45.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₉H₂₁N₃S

[ Molecular Weight ]:
323.455

[ Flash Point ]:
243.5±28.7 °C

[ Exact Mass ]:
323.145630

[ PSA ]:
55.57000

[ LogP ]:
4.62

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.655

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: SN6950000

CHEMICAL NAME :: Phenothiazine-2-carbonitrile, 10-(3-(dimethylamino)-2-methylpropyl)-

CAS REGISTRY NUMBER :: 3546-03-0

BEILSTEIN REFERENCE NO. :: 0093261

LAST UPDATED :: 199703

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C19-H21-N3-S

MOLECULAR WEIGHT :: 323.49

WISWESSER LINE NOTATION :: T C666 BN ISJ B1Y1&1N1&1 ECN

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration into the eye

SPECIES OBSERVED :: Rodent - rabbit

REFERENCE :: FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 20,573,1982

TYPE OF TEST :: Rinsed with water

ROUTE OF EXPOSURE :: Administration into the eye

SPECIES OBSERVED :: Rodent - rabbit

REFERENCE :: FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 20,573,1982 ** ACUTE TOXICITY DATA **

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 107 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JATOD3 Journal of Analytical Toxicology. (Preston Pub. Inc., POB 48312, Niles, IL 60648) V.1- 1977- Volume(issue)/page/year: 17,386,1993

Safety Information

[ Symbol ]:

GHS09

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H410

[ Precautionary Statements ]:
P273-P501

[ Hazard Codes ]:
Xi

[ RIDADR ]:
UN 3077 9 / PGIII

[ HS Code ]:
2934300000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2934300000

[ Summary ]:
2934300000. other compounds containing in the structure a phenothiazine ring-system (whether or not hydrogenated), not further fused. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Identification and quantification of 35 psychotropic drugs and metabolites in hair by LC-MS/MS: application in forensic toxicology.

Int. J. Legal Med. 129(2) , 259-68, (2015)

Despite a non-invasive sampling, hair samples are generally collected in limited amounts for an obvious esthetic reason. In order to reduce the required quantity of samples, a multianalytes method all...

Fatal intoxication with milnacipran

J. Forensic Leg. Med. 15(6) , 388-90, (2008)

The antidepressant milnacipran is a double serotonin/noradrenalin reuptake inhibitor. The low reported incidence of intoxication indicates excellent tolerance in comparison with tricyclic and second g...

Prise en charge médicamenteuse de l’anxiété chez le patient souffrant de schizophrénie

Encephale 37 Suppl 1 , S83-9, (2011)

L’anxiété est un symptôme fréquent et majeur de la schizophrénie. Elle est un symptôme clinique dominant dans la phase prodromique [indice de progression vers la « décompensation psychotique »] et acc...