Aporphine

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Aporphine
Chemical structure of aporphine
Names
Preferred IUPAC name
6-Methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline
Identifiers
3D model (JSmol)
192257
ChEBI
ChemSpider
  • 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 checkY
    Key: BZKUYNBAFQJRDM-UHFFFAOYSA-N checkY
  • 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
  • c12c(cccc1)CC4c3c(cccc23)CCN4C
Properties
C17H17N
Molar mass 235.330 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N  (what is checkY☒N ?)
Infobox references

Aporphine is an alkaloid with the chemical formula C17H17N. It is the core chemical substructure of the aporphine alkaloids, a subclass of quinoline alkaloids. It can exist in either of two enantiomeric forms, (R)-aporphine and (S)-aporphine.

Derivatives[]

Many different derivatives have been isolated from plants.[1] For example, many water-lilies (Nymphaea species) produce aporphine alkaloids such as , , , α- and β-.[2]

In vitro tests of some aporphine derivatives isolated from Cassytha filiformis, namely , , and dicentrine, showed antiparasitic activity against Trypanosoma brucei. Investigation of possible mechanisms revealed that the compounds bind to DNA and act as intercalating agents, besides inhibiting topoisomerase activity.[3]

Pharmacology[]

(R)-Aporphine is a dopamine receptor D1 antagonist with a Ki of 717 nM[4] and a dopamine receptor D2 antagonist with a Ki of 527 nM.[5] Aporphine and its related alkaloids bulbocapnine, boldine, glaucine, and are antipsychotic, exert naloxone-reversible antinociceptive activity, and with the exception of corytuberine are anticonvulsant.[6] 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.[7]

Pharmacokinetics[]

Aporphine is hydroxylated in the body to form apomorphine.[8]

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. doi:10.2174/1568011053174864. hdl:2078.1/10136. PMID 15777224.
  2. ^ Oliver-Bever, B. (1983). "Medicinal plants in tropical West Africa II. Plants acting on the nervous system". Journal of Ethnopharmacology. 7 (1): 1–93. doi:10.1016/0378-8741(83)90082-X. PMID 6132025.
  3. ^ Hoet, S.; Stévigny, C.; Block, S.; Opperdoes, F.; Colson, P.; Baldeyrou, B.; Lansiaux, A.; Bailly, C.; Quetin-Leclercq, J. (2004). "Alkaloids from Cassytha filiformis and Related Aporphines: Antitrypanosomal Activity, Cytotoxicity, and Interaction with DNA and Topoisomerases". Planta Medica. 70 (5): 407–13. doi:10.1055/s-2004-818967. PMID 15124084.
  4. ^ Hedberg, M. H.; Linnanen, T.; Jansen, J. M.; 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): 3503–3513. doi:10.1021/jm960189i. PMID 8784448.
  5. ^ 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.
  6. ^ 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: 255–281. PMID 2907279.
  7. ^ Baldessarini, R. J.; Campbell, A.; Ben-Jonathan, N.; Ellingboe, J.; Zong, R.; Neumeyer, J. L. (1994). "Effects of aporphine isomers on rat prolactin". Neuroscience Letters. 176 (2): 269–271. doi:10.1016/0304-3940(94)90098-1. PMID 7830962. S2CID 38264784.
  8. ^ Bertol, Elisabetta; Fineschi, Vittorio; Karch, Steven B.; Mari, Francesco; Riezzo, Irene (2004). "Nymphaea Cults in Ancient Egypt and the New World: A Lesson in Empirical Pharmacology". Journal of the Royal Society of Medicine. 97 (2): 84–85. doi:10.1177/014107680409700214. PMC 1079300. PMID 14749409.
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