Aporphine

Aporphine

Names
IUPAC name 6-Methyl-5,6,6a,7-tetrahydro-4H-dibenzo(de,g)quinoline
Identifiers
CAS Number	478-57-9
3D model (Jmol)	Interactive image
ChEBI	CHEBI:35643
ChemSpider	102860
InChI InChI=1S/C17H17N/c1-18-10-9-12-6-4-8-15-14-7-3-2-5-13(14)11-16(18)17(12)15/h2-8,16H,9-11H2,1H3 Key: BZKUYNBAFQJRDM-UHFFFAOYSA-N InChI=1/C17H17N/c1-18-10-9-12-6-4-8-15-14-7-3-2-5-13(14)11-16(18)17(12)15/h2-8,16H,9-11H2,1H3 Key: BZKUYNBAFQJRDM-UHFFFAOYAP
SMILES c12c(cccc1)CC4c3c(cccc23)CCN4C
Properties
Chemical formula	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).
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Infobox references

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, which can be found in Nymphaea caerulea.

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

• Apomorphine
• Anonaine
• Boldine
• Bulbocapnine
• Liriodenine
• Magnoflorine
• Nuciferine
• Nantenine
• List of entheogens

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. doi:10.2174/1568011053174864. PMID 15777224.
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. doi:10.1016/j.pharmthera.2010.08.013. PMC 3031120. PMID 20923682.
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. doi:10.1021/jm960189i. PMID 8784448.
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. doi:10.1021/jm0108505. PMID 11311055.
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. PMID 2907279.
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. doi:10.1016/0304-3940(94)90098-1. PMID 7830962.