Pukateine

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Pukateine
Clinical data
Other names(R)-11-hydroxy-1,2-methylenedioxyaporphine
ATC code
  • none
Identifiers
  • (7aR)-7-methyl-6,7,7a,8-tetrahydro-5H-benzo[g][1,3]benzodioxolo[6,5,4-de]quinolin-12-ol
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H17NO3
Molar mass295.332 g/mol g·mol−1
3D model (JSmol)
  • CN1CCC2=CC3=C(C4=C2[C@H]1CC5=C4C(=CC=C5)O)OCO3
  • InChI=1S/C18H17NO3/c1-19-6-5-11-8-14-18(22-9-21-14)17-15(11)12(19)7-10-3-2-4-13(20)16(10)17/h2-4,8,12,20H,5-7,9H2,1H3/t12-/m1/s1 ☒N
  • Key:IKMXUUHNYQWZBC-GFCCVEGCSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Pukateine is an alkaloid found in the bark of the New Zealand tree Laurelia novae-zelandiae ("Pukatea"). An extract from pukatea is used in traditional Māori herbal medicine as an analgesic,[1][2] and it is thought pukateine is the active component,[3] as it is similar in both structure and activity to alkaloids such as glaucine and tetrahydropalmatine which are found in Chinese medicinal herbs used as analgesics. Pukateine has multiple mechanisms of action, with the most prominent effects being as an agonist at the D2 dopamine receptor and antagonist at the α1-adrenergic receptor.[4][5]

Bernard Cracroft Aston studied the physical and chemical characteristics of the compound, and presented a paper with his findings to the Royal Society of New Zealand on May 11, 1909. [6]


See also

References

  1. ^ Pukatea. Te Ara: The Encyclopedia of New Zealand
  2. ^ Pukatea. University of Otago Pharmacy Dept. Template:Wayback
  3. ^ Fogg WS. The Pharmacological Action of Pukateine. Journal of Pharmacology and Experimental Therapeutics. 1935 Jun;54(2):167-187.
  4. ^ Dajas-Bailador FA, Asencio M, Bonilla C, Scorza MC, Echeverry C, Reyes-Parada M, Silveira R, Protais P, Russell G, Cassels BK, Dajas F. Dopaminergic pharmacology and antioxidant properties of pukateine, a natural product lead for the design of agents increasing dopamine neurotransmission. General Pharmacology. 1999 Mar;32(3):373-9. PMID 10211594
  5. ^ Valiente M, D'Ocon P, Noguera MA, Cassels BK, Lugnier C, Ivorra MD. Vascular activity of (−)-anonaine, (−)-roemerine and (−)-pukateine, three natural 6a(R)-1,2-methylenedioxyaporphines with different affinities for alpha1-adrenoceptor subtypes. Planta Medica. 2004 Jul;70(7):603-9. PMID 15254852
  6. ^ Aston, Bernard Cracroft (1909). "The Alkaloids of the Pukatea". Transactions of the Royal Society of New Zealand. 42. Retrieved October 20, 2015.