Quinisocaine

In today's world, Quinisocaine has gained great relevance in society. Its impact has extended to different areas, generating discussions, debates and reflections around its importance and repercussions. From the political to the cultural sphere, Quinisocaine has become a topic of general interest that leaves no one indifferent. In this article, we will explore the many facets of Quinisocaine, analyzing its evolution over time and its influence on people's daily lives. Additionally, we will examine the different perspectives that exist around Quinisocaine, offering a complete overview of its impact on today's society.

Quinisocaine
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • 2-(3-Butylisoquinolin-1-yl)oxy-N,N-dimethyl-ethanamine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.001.546 Edit this at Wikidata
Chemical and physical data
FormulaC17H24N2O
Molar mass272.392 g·mol−1
3D model (JSmol)
  • O(c2nc(cc1ccccc12)CCCC)CCN(C)C
  • InChI=1S/C17H24N2O/c1-4-5-9-15-13-14-8-6-7-10-16(14)17(18-15)20-12-11-19(2)3/h6-8,10,13H,4-5,9,11-12H2,1-3H3 checkY
  • Key:XNMYNYSCEJBRPZ-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Quinisocaine (INN) or dimethisoquin (BAN and USAN) is a topical anesthetic used as an antipruritic.[1]

Synthesis

Thieme Synthesis:[2][3] Patent:[4][5]

The Henry reaction between phthalaldehydic acid (2-Formylbenzoic acid) (1) and 1-nitropentane occurs by a mechanism that involves a hydroxy acid (2). Expulsion of water then gives (3). Reduction of the nitro group via catalytic hydrogenation leads to the amine, CID:158569430 (4). Treatment of that amine with sodium hydroxide leads to ring opening of the lactone ring to the intermediary amino acid (5). This cyclises spontaneously to the lactam so that the product isolated from the reaction mixture is in fact the isoquinoline derivative, CID:154188092 (7). Dehydration by means of strong acid gives 3-Butylisocarbostyril (8). Phosphorus oxychloride converts the oxygen function to the corresponding chloride via the enol forms 3-butyl-1-chloroisoquinoline (9). Displacement of halogen with the sodium salt from 2-dimethylaminoethanol (10) affords dimethisoquin (11).

References

  1. ^ Elks J (1990). "Dimethisoquin". The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Dordrecht: Springer. p. 430. ISBN 978-1-4757-2085-3.
  2. ^ Eloy, F. et al, Chim. Ther., 1969, 4, 469.
  3. ^ Wilson, James W.; Dawson, Norman D.; Brooks, Walter.; Ullyot, Glenn E. (1949). "Local Anesthetics. Aminoalkoxyisoquinoline Derivatives". Journal of the American Chemical Society 71 (3): 937–938. doi:10.1021/ja01171a047.
  4. ^ Anon., GB 681358  (1952 to Smith Kline and French International Co).
  5. ^ Ullyot, U.S. patent 2,612,503 (1952 to SK & F).


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