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{{Short description|Antipsychotic medication}}
{{Short description|Antipsychotic medication}}
{{cs1 config |name-list-style=vanc |display-authors=6}}
{{Infobox drug
{{Infobox drug
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| image = Clomacran no stereo.png
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<!--Clinical data-->
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| tradename = Devryl, Olaxin,<ref name="chemicalbook">{{Cite web |title=Clomacran {{!}} 5310-55-4 |url=https://www.chemicalbook.com/ChemicalProductProperty_EN_CB61178346.htm |access-date=2023-08-25 |website=ChemicalBook |language=en}}</ref> Develar<ref name="Elks">{{Cite book |url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA297 |title=Dictionary of Drugs |date=1990 |publisher=Springer US |isbn=978-1-4757-2087-7 |editor-last=Elks |editor-first=J. |location=Boston, MA |pages=297 |language=en |doi=10.1007/978-1-4757-2085-3 |editor-last2=Ganellin |editor-first2=C. R.}}</ref><ref>{{Cite news |date=1986-11-05 |title=Substâncias e remédios sob controle |language=pt-br |trans-title=Substances and drugs under control |pages=14 |work=[[Jornal do Brasil]] |url=https://memoria.bn.br/pdf/030015/per030015_1986_00211.pdf |url-status=live |access-date=2023-08-08 |archive-url=https://web.archive.org/web/20230808230340/https://memoria.bn.br/pdf/030015/per030015_1986_00211.pdf |archive-date=2023-08-08}}</ref>
| tradename = Devryl, Olaxin,<ref name="chemicalbook">{{Cite web |title=Clomacran {{!}} 5310-55-4 |url=https://www.chemicalbook.com/ChemicalProductProperty_EN_CB61178346.htm |access-date=2023-08-25 |website=ChemicalBook |language=en}}</ref> Develar<ref name="Elks">{{Cite book |url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA297 |title=Dictionary of Drugs |date=1990 |publisher=Springer US |isbn=978-1-4757-2087-7 | veditors = Elks J, Ganellin CR |location=Boston, MA |pages=297 |language=en |doi=10.1007/978-1-4757-2085-3 }}</ref><ref>{{Cite news |date=1986-11-05 |title=Substâncias e remédios sob controle |language=pt-br |trans-title=Substances and drugs under control |pages=14 |work=[[Jornal do Brasil]] |url=https://memoria.bn.br/pdf/030015/per030015_1986_00211.pdf |url-status=live |access-date=2023-08-08 |archive-url=https://web.archive.org/web/20230808230340/https://memoria.bn.br/pdf/030015/per030015_1986_00211.pdf |archive-date=2023-08-08}}</ref>
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| legal_UN_comment =
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| legal_status = Withdrawn<ref name="Dixit">{{Cite journal |last=Dixit |first=Nandan |last2=Patel |first2=Chirag |last3=Bhavsar |first3=Mansi |last4=Patel |first4=Saumya |last5=Rawal |first5=Rakesh |last6=Solanki |first6=Hitesh |date=2022-05-02 |title=Quantitative Structure-activity Relationship (QSAR) study of Liver Toxic Drugs |journal=International Association of Biologicals and Computational Digest |pages=63–71 |doi=10.56588/iabcd.v1i1.17 |eissn=2583-3995 |doi-access=free}}</ref>
| legal_UK= Withdrawn<ref name="Dixit">{{Cite journal | vauthors = Dixit N, Patel C, Bhavsar M, Patel S, Rawal R, Solanki H |date=2022-05-02 |title=Quantitative Structure-activity Relationship (QSAR) study of Liver Toxic Drugs |journal=International Association of Biologicals and Computational Digest |volume=1 |pages=63–71 |doi=10.56588/iabcd.v1i1.17 |eissn=2583-3995 |doi-access=free}}</ref>


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'''Clomacran''' is an [[antipsychotic drug]] of the [[acridine]]s class, developed in the 1970s<ref name="Elks"/> by the pharmaceutical company [[Smith, Kline & French]] under the brand names Devryl and Olaxin.<ref name="chemicalbook"/>
'''Clomacran''' is an [[antipsychotic drug]] of the dihydro[[acridine]] class, developed in the 1970s<ref name="Elks"/> by the pharmaceutical company [[Smith, Kline & French]] (now [[GlaxoSmithKline]]) under the brand names Devryl and Olaxin.<ref name="chemicalbook"/>


It was withdrawn from the market in the UK, due to liver toxicity, in 1982.<ref name="Dixit" /><ref name="PubChem">{{Cite web |title=Clomacran |url=https://pubchem.ncbi.nlm.nih.gov/compound/21382 |access-date=2023-08-25 |website=PubChem |language=en}}</ref><ref>{{Cite book |url=https://onlinelibrary.wiley.com/doi/book/10.1002/9781118820186 |title=Mann's Pharmacovigilance |date=2014 |publisher=Wiley |isbn=978-0-470-67104-7 |editor-last=Andrews |editor-first=Elizabeth B. |edition=1 |language=en |doi=10.1002/9781118820186 |editor-last2=Moore |editor-first2=Nicholas}}</ref>
It was used to treat schizophrenia in the 70s.<ref>{{cite journal | vauthors = Pecknold JC, Ban TA, Lehmann HE, Climan M | title = Clomacran in the treatment of schizophrenic patients: a comparison of two assessment methods | journal = International Journal of Clinical Pharmacology and Biopharmacy | volume = 11 | issue = 4 | pages = 299–303 | date = June 1975 | pmid = 1099021 }}</ref> It was withdrawn from the market in the UK, due to liver toxicity, in 1982.<ref name="Dixit" /><ref name="PubChem">{{Cite web |title=Clomacran |url= https://pubchem.ncbi.nlm.nih.gov/compound/21382 |access-date=2023-08-25 | work = PubChem |language=en | publisher = U.S. National Library of Medicine }}</ref><ref>{{Cite book |title=Mann's Pharmacovigilance |date=2014 |publisher=Wiley |isbn=978-0-470-67104-7 | veditors = Andrews EB, Moore N |edition=1st |language=en |doi=10.1002/9781118820186 }}</ref>

==Synthesis==
[[File:Clomacran synthesis.svg|thumb|center|500px|Patents:<ref>Zirkle Charles L, {{US patent|3131190}} (1964 to Smith Kline French Lab).</ref><ref>E Anderson & H Graboyes, {{US patent|3781358}} (1973 to SmithKline Beecham Corp).</ref><ref>Elvin L Anderson & Harold Graboyes, {{US patent|3692834}} (1972 to Smith Kline and French Laboratories Ltd, GlaxoSmithKline LLC SmithKline Beecham Corp).</ref><ref>Elvin L Anderson & Harold Graboyes, {{US patent|3919312}} (1975 to SmithKline Beecham Corp).</ref>]]

The first step involves FGI of 3-chloro-N,N-dimethylpropylamine Fb: [109-54-6] ('''2''') into the Grignard reagent, i.e. (3-(Dimethylamino)propyl)magnesium chloride [19070-16-7] ([154034-91-0]). The Grignard reaction with 2-chloroacridone [7497-52-1] ('''1''') affords the tertiary carbinol ('''3'''). Dehydration by means of acid or simply heat gives the corresponding olefin ('''4'''). Catalytic reduction completes the synthesis of ('''5''').


== References ==
== References ==

Latest revision as of 17:42, 25 June 2024

Clomacran
Clinical data
Trade namesDevryl, Olaxin,[1] Develar[2][3]
ATC code
Legal status
Legal status
Identifiers
  • 3-(2-chloro-9,10-dihydroacridin-9-yl)-N,N-dimethylpropan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H21ClN2
Molar mass300.83 g·mol−1
3D model (JSmol)
Density1.120 g/cm3 [1]
  • CN(C)CCCC1C2=CC=CC=C2NC3=C1C=C(C=C3)Cl
  • InChI=1S/C18H21ClN2/c1-21(2)11-5-7-14-15-6-3-4-8-17(15)20-18-10-9-13(19)12-16(14)18/h3-4,6,8-10,12,14,20H,5,7,11H2,1-2H3 checkY
  • Key:JFRLWWDJCFYFSU-UHFFFAOYSA-N checkY

Clomacran is an antipsychotic drug of the dihydroacridine class, developed in the 1970s[2] by the pharmaceutical company Smith, Kline & French (now GlaxoSmithKline) under the brand names Devryl and Olaxin.[1]

It was used to treat schizophrenia in the 70s.[6] It was withdrawn from the market in the UK, due to liver toxicity, in 1982.[4][7][8]

Synthesis[edit]

Patents:[9][10][11][12]

The first step involves FGI of 3-chloro-N,N-dimethylpropylamine Fb: [109-54-6] (2) into the Grignard reagent, i.e. (3-(Dimethylamino)propyl)magnesium chloride [19070-16-7] ([154034-91-0]). The Grignard reaction with 2-chloroacridone [7497-52-1] (1) affords the tertiary carbinol (3). Dehydration by means of acid or simply heat gives the corresponding olefin (4). Catalytic reduction completes the synthesis of (5).

References[edit]

  1. ^ a b c "Clomacran | 5310-55-4". ChemicalBook. Retrieved 2023-08-25.
  2. ^ a b Elks J, Ganellin CR, eds. (1990). Dictionary of Drugs. Boston, MA: Springer US. p. 297. doi:10.1007/978-1-4757-2085-3. ISBN 978-1-4757-2087-7.
  3. ^ "Substâncias e remédios sob controle" [Substances and drugs under control] (PDF). Jornal do Brasil (in Brazilian Portuguese). 1986-11-05. p. 14. Archived (PDF) from the original on 2023-08-08. Retrieved 2023-08-08.
  4. ^ a b Dixit N, Patel C, Bhavsar M, Patel S, Rawal R, Solanki H (2022-05-02). "Quantitative Structure-activity Relationship (QSAR) study of Liver Toxic Drugs". International Association of Biologicals and Computational Digest. 1: 63–71. doi:10.56588/iabcd.v1i1.17. eISSN 2583-3995.
  5. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-03.
  6. ^ Pecknold JC, Ban TA, Lehmann HE, Climan M (June 1975). "Clomacran in the treatment of schizophrenic patients: a comparison of two assessment methods". International Journal of Clinical Pharmacology and Biopharmacy. 11 (4): 299–303. PMID 1099021.
  7. ^ "Clomacran". PubChem. U.S. National Library of Medicine. Retrieved 2023-08-25.
  8. ^ Andrews EB, Moore N, eds. (2014). Mann's Pharmacovigilance (1st ed.). Wiley. doi:10.1002/9781118820186. ISBN 978-0-470-67104-7.
  9. ^ Zirkle Charles L, U.S. patent 3,131,190 (1964 to Smith Kline French Lab).
  10. ^ E Anderson & H Graboyes, U.S. patent 3,781,358 (1973 to SmithKline Beecham Corp).
  11. ^ Elvin L Anderson & Harold Graboyes, U.S. patent 3,692,834 (1972 to Smith Kline and French Laboratories Ltd, GlaxoSmithKline LLC SmithKline Beecham Corp).
  12. ^ Elvin L Anderson & Harold Graboyes, U.S. patent 3,919,312 (1975 to SmithKline Beecham Corp).
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