Cyamemazine

Cyamemazine

Clinical data
Trade names	Tercian
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral, IM, IV
ATC code	N05AA06 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	10-70%
Metabolism	Hepatic
Elimination half-life	10 hours
Excretion	Urine
Identifiers
IUPAC name 10-(3-dimethylamino-2-methyl-propyl)phenothiazine-2-carbonitrile
CAS Number	3546-03-0 Y
PubChem CID	62865
IUPHAR/BPS	84
DrugBank	DB09000 N
ChemSpider	56597 Y
UNII	A2JGV5CNU4
KEGG	D07307 Y
ChEMBL	ChEMBL2104153 N
ECHA InfoCard	100.020.541
Chemical and physical data
Formula	C19H21N3S
Molar mass	323.46 g·mol−1
3D model (JSmol)	Interactive image
SMILES N#Cc2cc1N(c3c(Sc1cc2)cccc3)CC(C)CN(C)C
InChI 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 Y Key:SLFGIOIONGJGRT-UHFFFAOYSA-N Y
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Cyamemazine (Tercian), also known as cyamepromazine, is a typical antipsychotic drug of the phenothiazine class which was introduced by Theraplix in France in 1972 and later in Portugal as well.

Medical use

It is used for the treatment of schizophrenia and, especially, for psychosis-associated anxiety, due to its unique anxiolytic efficacy.

It is also used to reduce anxiety associated with benzodiazepine withdrawal syndrome and anxiety in depression with suicidal tendency.

Side effects

Here are some of the most common side effects and related incidence:

• Sedation (20%)
• Vertigo (7.9%)
• Constipation (4%)
• Dyskinesia (4.4%)
• Dryness of mouth (5.9%)
• Hypotension (7.4%)
• Tachycardia (3.2%)

Mechanism

Cyamemazine differs from other phenothiazine neuroleptics in that aside from the usual profile of dopamine, α₁-adrenergic, H₁, and mACh receptor antagonism, it additionally produces potent blockade of several serotonin receptors, including 5-HT_2A, 5-HT_2C, and 5-HT₇. These actions have been implicated in cyamemazine's anxiolytic effects (5-HT_2C) and lack of extrapyramidal side effects (5-HT_2A), and despite being classified as a typical antipsychotic, it actually behaves like an atypical antipsychotic.

Synthesis

Synthesis: Patent:

2-Cyanophenothiazine [38642-74-9] (1) 3-Chloro-2-methylpropyl(dimethyl)amine [23349-86-2] (2)