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Aporphine

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Title: Aporphine  
Author: World Heritage Encyclopedia
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Subject: Apomorphine, Nelumbo nucifera, Entheogen, Glaucine, Solanaceae
Collection: Alkaloids, Dibenzoquinolines
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Aporphine

Aporphine
Chemical structure of aporphine
Names
IUPAC name
6-Methyl-5,6,6a,7-tetrahydro-4H-dibenzo(de,g)quinoline
Identifiers
 N
ChEBI  Y
ChemSpider  Y
Jmol-3D images Image
Properties
C17H17N
Molar mass 235.324 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N  (: Y/N?)

Aporphine is one of a class of quinoline alkaloids. Many different relatives of this compound have been purified from plants.[1] One commonly used aporphine derivative is apomorphine, although it does not occur naturally.

Aporphine is a 5-HT1a partial agonist with a ki of 80nM and a 5-HT7 antagonist with a ki of 88nM.[2] Aporphine is a Dopamine D1 antagonist with a ki of 717nM[3] and a dopamine D2 antagonist with a ki of 527nM.[4] Aporphine and its related alkaloids bulbocapnine, boldine, glaucine and corytuberine are antipsychotic, exert naloxone-reversible antinociceptive activity and with the exception of corytuberine are anticonvulsant.[5] Some derivatives of aporphine such as S(+)-N-propylnorapomorphine have potential as low side effect profile antipsychotics. S(+)-N-propylnorapomorphine is highly selective for meso-limbic dopaminergic tracts and function as efficacious partial agonists, with no elevation in prolactin.[6]

See also

References

  1. ^ Stévigny, C.; Bailly, C.; Quetin-Leclercq, J. (2005). "Cytotoxic and antitumor potentialities of aporphinoid alkaloids". Current medicinal chemistry. Anti-cancer agents 5 (2): 173–182.  
  2. ^ Leopoldo M, Lacivita E, Berardi F, Perrone R, Hedlund PB (February 2011). "Serotonin 5-HT7 receptor agents: Structure-activity relationships and potential therapeutic applications in central nervous system disorders". Pharmacology & Therapeutics 129 (2): 120–48.  
  3. ^ Hedberg MH, Linnanen T, Jansen JM; et al. (August 1996). "11-substituted (R)-aporphines: synthesis, pharmacology, and modeling of D2A and 5-HT1A receptor interactions". Journal of Medicinal Chemistry 39 (18): 3503–13.  
  4. ^ Linnanen T, Brisander M, Unelius L; et al. (April 2001). "Atropisomeric derivatives of 2',6'-disubstituted (R)-11-phenylaporphine: selective serotonin 5-HT(7) receptor antagonists". Journal of Medicinal Chemistry 44 (9): 1337–40.  
  5. ^ Zetler G (1988). "Neuroleptic-like, anticonvulsant and antinociceptive effects of aporphine alkaloids: bulbocapnine, corytuberine, boldine and glaucine". Archives Internationales De Pharmacodynamie Et De Thérapie 296: 255–81.  
  6. ^ Baldessarini RJ, Campbell A, Ben-Jonathan N, Ellingboe J, Zong R, Neumeyer JL (August 1994). "Effects of aporphine isomers on rat prolactin". Neuroscience Letters 176 (2): 269–71.  


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