Isoquinoline

Isoquinoline
Isoquinoline molecule
C=black, H=white, N=blue
Isoquinoline molecule
C=black, H=white, N=blue
Names
Preferred IUPAC name
Isoquinoline[1]
Other names
Benzo[c]pyridine
2-benzazine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.947 Edit this at Wikidata
EC Number
  • 204-341-8
UNII
  • InChI=1S/C9H7N/c1-2-4-9-7-10-6-5-8(9)3-1/h1-7H checkY
    Key: AWJUIBRHMBBTKR-UHFFFAOYSA-N checkY
  • InChI=1/C9H7N/c1-2-4-9-7-10-6-5-8(9)3-1/h1-7H
    Key: AWJUIBRHMBBTKR-UHFFFAOYAX
  • C1(C=NC=C2)=C2C=CC=C1
Properties
C9H7N
Molar mass 129.162 g·mol−1
Appearance Colorless oily liquid; hygroscopic platelets when solid
Density 1.099 g/cm3
Melting point 26–28 °C (79–82 °F; 299–301 K)
Boiling point 242 °C (468 °F; 515 K)
Acidity (pKa) pKBH+ = 5.14[2]
−83.9·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Isoquinoline is an individual chemical specimen - a heterocyclic aromatic organic compound - as well as the name of a family of many thousands of natural plant alkaloids, any one of which might be referred to as "an isoquinoline". It is a structural isomer of quinoline. Isoquinoline and quinoline are benzopyridines, which are composed of a benzene ring fused to a pyridine ring. In a broader sense, the term isoquinoline is used to make reference to isoquinoline derivatives. 1-Benzylisoquinoline is the structural backbone in many naturally occurring alkaloids such as papaverine. The isoquinoline ring in these natural compound derives from the aromatic amino acid tyrosine.[3][4][5][6][7][8]

  1. ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 212. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  2. ^ Brown, H.C., et al., in Baude, E.A. and Nachod, F.C., Determination of Organic Structures by Physical Methods, Academic Press, New York, 1955.
  3. ^ Gilchrist, T.L. (1997). Heterocyclic Chemistry (3rd ed.). Essex, UK: Addison Wesley Longman.
  4. ^ Harris, J.; Pope, W.J. "isoQuinoline and the isoQuinoline-Reds" Journal of the Chemical Society (1922) volume 121, pp. 1029–1033.
  5. ^ Katritsky, A.R.; Pozharskii, A.F. (2000). Handbook of Heterocyclic Chemistry (2nd ed.). Oxford, UK: Elsevier.
  6. ^ Katritsky, A.R.; Rees, C.W.; Scriven, E.F. (Eds.). (1996). Comprehensive Heterocyclic Chemistry II: A Review of the Literature 1982–1995 (Vol. 5). Tarrytown, NY: Elsevier.
  7. ^ Nagatsu, T. "Isoquinoline neurotoxins in the brain and Parkinson's disease" Neuroscience Research (1997) volume 29, pp. 99–111.
  8. ^ O'Neil, Maryadele J. (Ed.). (2001). The Merck Index (13th ed.). Whitehouse Station, NJ: Merck.