Ciclafrine

{{Short description|Chemical compound}}

{{Drugbox

| image = Ciclafrine.svg

| width = 225px

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| CAS_number = 55694-98-9

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 76HZX0GVCD

| ATC_prefix = None

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| PubChem = 193971

| DrugBank =

| ChemSpiderID = 168322

| ChEMBL = 2110798

| synonyms = Go 3026A; W-43026A

| IUPAC_name = 3-(1-Oxa-4-azaspiro[4.6]undec-2-yl)phenol

| C=15 | H=21 | N=1 | O=2

| SMILES = c1cc(cc(c1)O)C2CNC3(O2)CCCCCC3

| StdInChI = 1S/C15H21NO2/c17-13-7-5-6-12(10-13)14-11-16-15(18-14)8-3-1-2-4-9-15/h5-7,10,14,16-17H,1-4,8-9,11H2

| StdInChIKey = AJNAKEPPGKJNKU-UHFFFAOYSA-N

}}

Ciclafrine ({{Abbrlink|INN|International Nonproprietary Name}}; developmental code names Go 3026A, W-43026A) is a sympathomimetic and antihypotensive agent of the phenethylamine family that was never marketed.{{cite book | last=Elks | first=J. | title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies | publisher=Springer US | year=2014 | isbn=978-1-4757-2085-3 | url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA271 | access-date=2024-08-31 | page=271}}{{cite book| vauthors = Ganellin CR, Triggle DJ |title=Dictionary of Pharmacological Agents|url=https://books.google.com/books?id=Z_mfTTIApVEC&pg=PA586|date=21 November 1996|publisher=CRC Press|isbn=978-0-412-46630-4|pages=586–}}{{cite book | last=Milne | first=G.W.A. | title=Drugs: Synonyms and Properties | publisher=Taylor & Francis | series=Routledge Revivals | year=2018 | isbn=978-1-351-78990-5 | url=https://books.google.com/books?id=dloPEAAAQBAJ&pg=PA325 | access-date=31 August 2024 | page=325}}{{cite book| vauthors = Korolkovas A |title=Essentials of medicinal chemistry|url=https://books.google.com/books?id=6hxtAAAAMAAJ|year=1988|publisher=John Wiley & Sons, Incorporated|isbn=978-0-471-88356-2|page=405}}

Chemistry

Ciclafrine is a substituted phenethylamine and belongs to the class of hemiaminal ethers.

=Synthesis=

Ciclafrine can be prepared by the reaction of norfenefrine with cycloheptanone.{{Cite patent|country=DE|number=2336746|pubdate=1975-02-13|title=2-Hydroxyphenyl-1-oxa-4-azaspiro-alkan-Derivate [2-Hydroxyphenyl-1-oxa-4-azaspiro-alkane derivatives]|assign=Gödecke AG|inventor1-last=Satzinger|inventor1-first=Gerhard|inventor2-last=Herrmann|inventor2-first=Manfred}}

:File:Ciclafrine synthesis.svg{{clear-left}}

See also

References