Pukateine

Pukateine
Systematic (IUPAC) name
	(7aR)-7-methyl-6,7,7a,8-tetrahydro-5H-benzo[g][1,3]benzodioxolo[6,5,4-de]quinolin-12-ol
Identifiers
CAS Number	81-67-4
ATC code	none
PubChem	CID: 442340
ChemSpider	390793
ChEMBL	CHEMBL258370
Synonyms	(R)-11-hydroxy-1,2-methylenedioxyaporphine
Chemical data
Formula	C18H17NO3
Molecular mass	295.332 g/mol
	SMILES CN1CCC2=CC3=C(C4=C2[C@H]1CC5=C4C(=CC=C5)O)OCO3 ;
	InChI 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 ; Key:IKMXUUHNYQWZBC-GFCCVEGCSA-N ;
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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]

References

↑ Pukatea. Te Ara: The Encyclopedia of New Zealand
↑ Pukatea. University of Otago Pharmacy Dept.^{[dead link]}
↑ Fogg WS. The Pharmacological Action of Pukateine. Journal of Pharmacology and Experimental Therapeutics. 1935 Jun;54(2):167-187.
↑ 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
↑ 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
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