Morphinan

Not to be confused with 3-Methoxymorphinan.
Morphinan
Structural formula of morphinan
Ball-and-stick model of morphinan
Names
IUPAC name
Morphinan[1]
Systematic IUPAC name
(4aR,10R,10aR)-1,3,4,9,10,10a-Hexahydro-2H-10,4a-(azanoethano)phenanthrene
Identifiers
3D model (JSmol)
1375527
ChEBI
ChemSpider
UNII
  • InChI=1S/C16H21N/c1-2-6-13-12(5-1)11-15-14-7-3-4-8-16(13,14)9-10-17-15/h1-2,5-6,14-15,17H,3-4,7-11H2/t14-,15-,16+/m0/s1
    Key: INAXVFBXDYWQFN-HRCADAONSA-N
  • c12c(cccc1)C[C@H]3NCC[C@]24[C@H]3CCCC4
Properties
C16H21N
Molar mass 227.351 g·mol−1
Density 1.58 g/cm3
Boiling point 115±0.05 °C (liquid oil)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Morphinan is the prototype chemical structure of a large chemical class of psychoactive drugs, consisting of opiate analgesics, cough suppressants, and dissociative hallucinogens, among others. Typical examples include compounds such as morphine, codeine, and dextromethorphan (DXM). Despite related molecular structures, the pharmacological profiles and mechanisms of action between the various types of morphinan substances can vary substantially. They tend to function either as μ-opioid receptor agonists (analgesics), or NMDA receptor antagonists (dissociatives).[2]

  1. ^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 1522. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  2. ^ Schmidt, Roland; Griesbaum, Karl; Behr, Arno; Biedenkapp, Dieter; Voges, Heinz-Werner; Garbe, Dorothea; Paetz, Christian; Collin, Gerd; Mayer, Dieter; Höke, Hartmut (2014). "Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–74. doi:10.1002/14356007.a13_227.pub3. ISBN 978-3-527-30673-2.