# Cyamemazine

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> Markdown URL: https://mediated.wiki/source/Cyamemazine.md
> Source: https://en.wikipedia.org/wiki/Cyamemazine
> Source revision: 1329180046
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{{Short description|Antipsychotic medication}}
{{cs1 config|name-list-style=vanc}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 444653764
| IUPAC_name = 10-(3-dimethylamino-2-methyl-propyl)phenothiazine-2-carbonitrile
| image = Cyamemazine.svg
| image_class = skin-invert-image

<!--Clinical data-->
| tradename = Tercian
| Drugs.com = {{drugs.com|international|cyamemazine}}
| pregnancy_category =  
| legal_status = Rx-Only
| routes_of_administration = Oral, IM, IV

<!--Pharmacokinetic data-->
| bioavailability = 10-70%
| protein_bound =  
| metabolism = Hepatic
| elimination_half-life = 10 hours
| excretion = Urine

<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 3546-03-0
| ATC_prefix = N05
| ATC_suffix = AA06
| PubChem = 62865
| IUPHAR_ligand = 84
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank = DB09000
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 2104153
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 56597
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = A2JGV5CNU4
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07307

<!--Chemical data-->
| C=19 | H=21 | N=3 | S=1
| smiles = N#Cc2cc1N(c3c(Sc1cc2)cccc3)CC(C)CN(C)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = SLFGIOIONGJGRT-UHFFFAOYSA-N
}}

'''Cyamemazine''' ('''Tercian'''), also known as '''cyamepromazine''', is a [typical antipsychotic](/source/typical_antipsychotic) [drug](/source/drug) of the [phenothiazine](/source/phenothiazine) [class](/source/chemical_class) which was introduced by [Theraplix](/source/Theraplix) in [France](/source/France) in 1972 and later in [Portugal](/source/Portugal) as well.<ref name="urlIndex nominum, international drug ... - Google Books">{{cite book | url = https://books.google.com/books?id=5GpcTQD_L2oC&q=cyamemazine%20tercian&pg=PA280 | title = Index Nominum, International Drug | publisher = Taylor & Francis | isbn = 978-3-88763-075-1 | year = 2000 }}</ref><ref name="isbn0-412-46630-9">{{cite book | vauthors = Triggle DJ | title = Dictionary of Pharmacological Agents | publisher = Chapman & Hall/CRC | location = Boca Raton | year = 1996 | page = 534 | isbn = 0-412-46630-9 | url = https://books.google.com/books?id=DeX7jgInYFMC&pg=RA1-PA534}}</ref><ref name="urlPharmaceutical manufacturing ... - Google Books">{{cite book | url = https://books.google.com/books?id=X2EyLsG4bcUC&q=cyamemazine%20introduced&pg=PA397 | title = Pharmaceutical manufacturing ... - Google Books | isbn = 9780815511441 | vauthors = Sittig M | date = January 1988 | publisher = Noyes Publications }}</ref><ref name="pmid19393381">{{cite journal | vauthors = Bret P, Bret MC, Queuille E | title = [Prescribing patterns of antipsychotics in 13 French psychiatric hospitals] | language = fr | journal = L'Encephale | volume = 35 | issue = 2 | pages = 129–138 | date = April 2009 | pmid = 19393381 | doi = 10.1016/j.encep.2008.03.007 | url = http://www.masson.fr/masson/S0013-7006(08)00103-6 | url-status = dead | archive-url = https://archive.today/20130213173522/http://www.masson.fr/masson/S0013-7006(08)00103-6 | archive-date = 2013-02-13 | url-access = subscription }}</ref>

==Medical use==
It is used for the treatment of [schizophrenia](/source/schizophrenia) and, especially, for [psychosis](/source/psychosis)-associated [anxiety](/source/anxiety), due to its unique [anxiolytic](/source/anxiolytic) efficacy.<ref name="urlStahls Essential Psychopharmacology - Cambridge University Press">{{cite book | chapter-url = http://stahlonline.cambridge.org/prescribers_drug.jsf?page=0521683505c20_p115-120.html.therapeutics&name=Cyamemazine | chapter = Cyamemazine | title = Stahl's Essential Psychopharmacology | publisher = Cambridge University Press }}</ref><ref name="pmid11423169">{{cite journal | vauthors = Bourin M, Claude Colombel M, Dib M, Hascoët M | title = Cyamemazine as an anxiolytic drug on the elevated plus maze and light/dark paradigm in mice | journal = Behavioural Brain Research | volume = 124 | issue = 1 | pages = 87–95 | date = September 2001 | pmid = 11423169 | doi = 10.1016/S0166-4328(01)00238-8 | s2cid = 43312295 }}</ref>

It is also used to reduce anxiety associated with [benzodiazepine withdrawal syndrome](/source/benzodiazepine_withdrawal_syndrome) and anxiety in depression with suicidal tendency.<ref name="Benyamina Naassila Bourin 2012 pp. 307–312">{{cite journal | vauthors = Benyamina A, Naassila M, Bourin M | title = Potential role of cortical 5-HT(2A) receptors in the anxiolytic action of cyamemazine in benzodiazepine withdrawal | journal = Psychiatry Research | volume = 198 | issue = 2 | pages = 307–312 | date = July 2012 | pmid = 22421069 | doi = 10.1016/j.psychres.2012.01.009 | publisher = Elsevier BV | s2cid = 34830082 }}</ref>

==Side effects==
Here are some of the most common side effects and related incidence:<ref name="Bourin Dailly Hascöet pp. 219–229">{{cite journal | vauthors = Bourin M, Dailly E, Hascöet M | title = Preclinical and clinical pharmacology of cyamemazine: anxiolytic effects and prevention of alcohol and benzodiazepine withdrawal syndrome | journal = CNS Drug Reviews | volume = 10 | issue = 3 | pages = 219–229 | date = 2006-06-07 | pmid = 15492772 | pmc = 6741725 | doi = 10.1111/j.1527-3458.2004.tb00023.x | publisher = Wiley }}</ref>
* [Sedation](/source/Sedation) (20%)
* [Vertigo](/source/Vertigo) (7.9%)
* [Constipation](/source/Constipation) (4%)
* [Dyskinesia](/source/Dyskinesia) (4.4%)
* Dryness of mouth (5.9%)
* [Hypotension](/source/Hypotension) (7.4%)
* [Tachycardia](/source/Tachycardia) (3.2%)

==Mechanism==
Cyamemazine differs from other phenothiazine neuroleptics in that aside from the usual profile of [dopamine](/source/dopamine_receptor), [α<sub>1</sub>-adrenergic](/source/Alpha-1_adrenergic_receptor), [H<sub>1</sub>](/source/H1_receptor), and [mACh receptor](/source/muscarinic_acetylcholine_receptor) [antagonism](/source/receptor_antagonist),<ref name="pmid12527336">{{cite journal | vauthors = Hameg A, Bayle F, Nuss P, Dupuis P, Garay RP, Dib M | title = Affinity of cyamemazine, an anxiolytic antipsychotic drug, for human recombinant dopamine vs. serotonin receptor subtypes | journal = Biochemical Pharmacology | volume = 65 | issue = 3 | pages = 435–440 | date = February 2003 | pmid = 12527336 | doi = 10.1016/S0006-2952(02)01515-0 }}</ref> it additionally produces potent blockade of several [serotonin receptor](/source/serotonin_receptor)s, including [5-HT<sub>2A</sub>](/source/5-HT2A_receptor), [5-HT<sub>2C</sub>](/source/5-HT2C_receptor), and [5-HT<sub>7</sub>](/source/5-HT7_receptor).<ref name="pmid12527336"/><ref name="pmid10672635">{{cite journal | vauthors = Alvarez-Guerra M, d'Alché-Birée F, Wolf WA, Vargas F, Dib M, Garay RP | title = 5-HT3- and 5-HT2C-antagonist properties of cyamemazine: significance for its clinical anxiolytic activity | journal = Psychopharmacology | volume = 147 | issue = 4 | pages = 412–417 | date = January 2000 | pmid = 10672635 | doi = 10.1007/s002130050010 | url = http://link.springer.de/link/service/journals/00213/bibs/0147004/01470412.htm | access-date = 2010-02-11 | url-status = dead | s2cid = 25162849 | archive-url = https://web.archive.org/web/20020112021448/http://link.springer.de/link/service/journals/00213/bibs/0147004/01470412.htm | archive-date = 2002-01-12 | url-access = subscription }}</ref><ref name="pmid12421652">{{cite journal | vauthors = Alvarez-Guerra M, Hameg A, Bayle F, Dib M, Garay RP | title = 5-HT2A receptor antagonist properties of cyamemazine in rat and guinea pig smooth muscle | journal = European Journal of Pharmacology | volume = 454 | issue = 2–3 | pages = 235–239 | date = November 2002 | pmid = 12421652 | doi = 10.1016/S0014-2999(02)02489-5 }}</ref><ref name="pmid17936750">{{cite journal | vauthors = Benyamina A, Arbus C, Nuss P, Garay RP, Neliat G, Hameg A | title = Affinity of cyamemazine metabolites for serotonin, histamine and dopamine receptor subtypes | journal = European Journal of Pharmacology | volume = 578 | issue = 2–3 | pages = 142–147 | date = January 2008 | pmid = 17936750 | doi = 10.1016/j.ejphar.2007.09.025 }}</ref> These actions have been implicated in cyamemazine's anxiolytic effects (5-HT<sub>2C</sub>) and lack of [extrapyramidal](/source/extrapyramidal_symptom) [side effect](/source/side_effect)s (5-HT<sub>2A</sub>),<ref name="pmid12527336"/><ref name="pmid10672635"/> and despite being classified as a [typical antipsychotic](/source/typical_antipsychotic), it actually behaves like an [atypical antipsychotic](/source/atypical_antipsychotic).<ref name="pmid12595954">{{cite journal | vauthors = Peinado J, Hameg A, Garay RP, Bayle F, Nuss P, Dib M | title = Reduction of extracellular dopamine and metabolite concentrations in rat striatum by low doses of acute cyamemazine | journal = Naunyn-Schmiedeberg's Archives of Pharmacology | volume = 367 | issue = 2 | pages = 134–139 | date = February 2003 | pmid = 12595954 | doi = 10.1007/s00210-002-0665-4 | s2cid = 682064 }}</ref>
{| class="wikitable sortable floatright" style="font-size:small;"
!Site
!K<sub>i</sub> (nM)
!Species
!Ref
|-
|[H<sub>1</sub>](/source/Histamine_H1_receptor)
|9.3
|Guinea pig
|<ref name=":0">{{cite journal | vauthors = Hameg A, Bayle F, Nuss P, Dupuis P, Garay RP, Dib M | title = Affinity of cyamemazine, an anxiolytic antipsychotic drug, for human recombinant dopamine vs. serotonin receptor subtypes | journal = Biochemical Pharmacology | volume = 65 | issue = 3 | pages = 435–440 | date = February 2003 | pmid = 12527336 | doi = 10.1016/s0006-2952(02)01515-0 }}</ref>
|-
|[H<sub>2</sub>](/source/Histamine_H2_receptor)
|351
|Guinea pig
|<ref name=":0" />
|-
|[H<sub>3</sub>](/source/Histamine_H3_receptor)
|10000+
|Rat
|<ref name=":0" />
|-
|[M<sub>1</sub>](/source/Muscarinic_acetylcholine_receptor_M1)
|13
|Human
|<ref name=":0" />
|-
|[M<sub>2</sub>](/source/Muscarinic_acetylcholine_receptor_M2)
|42
|Human
|<ref name=":0" />
|-
|[M<sub>3</sub>](/source/Muscarinic_acetylcholine_receptor_M3)
|32
|Human
|<ref name=":0" />
|-
|[M<sub>4</sub>](/source/Muscarinic_acetylcholine_receptor_M4)
|12
|Human
|<ref name=":0" />
|-
|[M<sub>5</sub>](/source/Muscarinic_acetylcholine_receptor_M5)
|35
|Human
|<ref name=":0" />
|-
|[5-HT<sub>1A</sub>](/source/5-HT1A_receptor)
|517
|Human
|<ref name=":0" />
|-
|[5-HT<sub>2A</sub>](/source/5-HT2A_receptor)
|1.5
|Human
|<ref name=":0" />
|-
|[5-HT<sub>2C</sub>](/source/5-HT2C_receptor)
|12
|Human
|<ref name=":0" />
|-
|[5-HT<sub>3</sub>](/source/5-HT3_receptor)
|2943
|Human
|<ref name=":0" />
|-
|[5-HT<sub>7</sub>](/source/5-HT7_receptor)
|22
|Human
|<ref name=":0" />
|-
|[D<sub>1</sub>](/source/Dopamine_D1_receptor)
|3.8
|Human
|<ref name=":0" />
|-
|[D<sub>2</sub>](/source/Dopamine_D2_receptor)
|5.8
|Human
|<ref name=":0" />
|-
|[D<sub>3</sub>](/source/Dopamine_D3_receptor)
|2.5
|Human
|<ref name=":0" />
|-
|[D<sub>4</sub>](/source/Dopamine_receptor_D4)
|5.3
|Human
|<ref name=":0" />
|-
|[α<sub>1</sub>](/source/Alpha-1_adrenergic_receptor)
|2.3
|Rat
|<ref name=":0" />
|-
|[α<sub>2</sub>](/source/Alpha-2_adrenergic_receptor)
|1320
|Rat
|<ref name=":0" />
|-
|[GABA<sub>A</sub>](/source/GABAA_receptor)
|10000+
|Rat
|<ref name=":0" />
|-
|[GABA<sub>B</sub>](/source/GABAB_receptor)
|10000+
|Rat
|<ref name=":0" />
|- class="sortbottom"
| colspan="4" |Values are K<sub>i</sub> (nM). The smaller the value, the more strongly the drug binds to the site.
|}

==Synthesis==
thumb|center|500px|class=skin-invert-image|Synthesis:<ref>{{cite journal | vauthors = Craig PN, Gordon M, Lafferty JJ, Lester BM, Saggiomo AJ, Zirkle CL | title = Synthesis of Phenothiazines. VI. Certain 2-Substituted Phenothiazines and Their 10-Aminoalkyl Derivatives | journal = The Journal of Organic Chemistry | date = 1961 | volume = 26 | issue = 4 | pages = 1138–1143 | doi = 10.1021/jo01063a040 }}</ref> Patent:<ref>{{cite patent | country = US | number = 2877224 | inventor = Jacob RM, Georges RJ gdate = 1959 | assign1 = Rhone Poulenc Sa }}</ref>
2-Cyanophenothiazine [38642-74-9] ('''1''')
3-Chloro-2-methylpropyl(dimethyl)amine [23349-86-2] ('''2''')

== References ==
{{Reflist|30em}}

{{Antipsychotics}}
{{Navboxes
| title = [Pharmacodynamics](/source/Pharmacodynamics)
| titlestyle = background:#ccccff
| list1 = 
{{Adrenergic receptor modulators}}
{{Dopamine receptor modulators}}
{{Histamine receptor modulators}}
{{Muscarinic acetylcholine receptor modulators}}
{{Serotonin receptor modulators}}
}}
{{Tricyclics}}

Category:Alpha-1 blockers
Category:Dimethylamino compounds
Category:Dopamine antagonists
Category:H1 receptor antagonists
Category:M1 receptor antagonists
Category:M2 receptor antagonists
Category:M3 receptor antagonists
Category:M4 receptor antagonists
Category:M5 receptor antagonists
Category:Nitriles
Category:Phenothiazines
Category:Serotonin receptor antagonists
Category:Typical antipsychotics

---
Adapted from the Wikipedia article [Cyamemazine](https://en.wikipedia.org/wiki/Cyamemazine) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Cyamemazine?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.