Pukateine

Pukateine
Clinical data
Other names	(R)-11-hydroxy-1,2-methylenedioxyaporphine
ATC code	none;
Identifiers
	IUPAC name (7aR)-7-methyl-6,7,7a,8-tetrahydro-5H-benzo[g][1,3]benzodioxolo[6,5,4-de]quinolin-12-ol;
CAS Number	81-67-4 ;
PubChem CID	442340;
ChemSpider	390793 ;
UNII	Z9Y5O2QUPA;
ChEMBL	ChEMBL258370 ;
CompTox Dashboard (EPA)	DTXSID00331801 ;
Chemical and physical data
Formula	C18H17NO3
Molar mass	295.338 g·mol−1
3D model (JSmol)	Interactive image;
	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 ;
	(what is this?) (verify)

Pukateine is an alkaloid found in the bark of the New Zealand tree Laurelia novae-zelandiae ("Pukatea"), as well as some South American plants.[1] An extract from pukatea is used in traditional Māori herbal medicine as an analgesic.[2][3]

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.[4]

References

Quiroz-Carreño S, Pastene-Navarrete E, Espinoza-Pinochet C, Muñoz-Núñez E, Devotto-Moreno L, Céspedes-Acuña CL, Alarcón-Enos J. Assessment of Insecticidal Activity of Benzylisoquinoline Alkaloids from Chilean Rhamnaceae Plants against Fruit-Fly Drosophila melanogaster and the Lepidopteran Crop Pest Cydia pomonella. Molecules. 2020 Nov 3;25(21):5094. doi:10.3390/molecules25215094 PMID 33153001
Dajas-Bailador FA, Asencio M, Bonilla C, Scorza MC, Echeverry C, Reyes-Parada M, et al. (March 1999). "Dopaminergic pharmacology and antioxidant properties of pukateine, a natural product lead for the design of agents increasing dopamine neurotransmission". General Pharmacology. 32 (3): 373–9. doi:10.1016/s0306-3623(98)00210-9. PMID 10211594.
Valiente M, D'Ocon P, Noguera MA, Cassels BK, Lugnier C, Ivorra MD (July 2004). "Vascular activity of (-)-anonaine, (-)-roemerine and (-)-pukateine, three natural 6a(R)-1,2-methylenedioxyaporphines with different affinities for alpha1-adrenoceptor subtypes". Planta Medica. 70 (7): 603–9. doi:10.1055/s-2004-827181. PMID 15254852.
Aston BC (1909). "The Alkaloids of the Pukatea". Transactions of the Royal Society of New Zealand. 42. Retrieved October 20, 2015.

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[1] Quiroz-Carreño S, Pastene-Navarrete E, Espinoza-Pinochet C, Muñoz-Núñez E, Devotto-Moreno L, Céspedes-Acuña CL, Alarcón-Enos J. Assessment of Insecticidal Activity of Benzylisoquinoline Alkaloids from Chilean Rhamnaceae Plants against Fruit-Fly Drosophila melanogaster and the Lepidopteran Crop Pest Cydia pomonella. Molecules. 2020 Nov 3;25(21):5094. doi:10.3390/molecules25215094 PMID 33153001

[2] Dajas-Bailador FA, Asencio M, Bonilla C, Scorza MC, Echeverry C, Reyes-Parada M, et al. (March 1999). "Dopaminergic pharmacology and antioxidant properties of pukateine, a natural product lead for the design of agents increasing dopamine neurotransmission". General Pharmacology. 32 (3): 373–9. doi:10.1016/s0306-3623(98)00210-9. PMID 10211594.

[3] Valiente M, D'Ocon P, Noguera MA, Cassels BK, Lugnier C, Ivorra MD (July 2004). "Vascular activity of (-)-anonaine, (-)-roemerine and (-)-pukateine, three natural 6a(R)-1,2-methylenedioxyaporphines with different affinities for alpha1-adrenoceptor subtypes". Planta Medica. 70 (7): 603–9. doi:10.1055/s-2004-827181. PMID 15254852.

[4] Aston BC (1909). "The Alkaloids of the Pukatea". Transactions of the Royal Society of New Zealand. 42. Retrieved October 20, 2015.

Pukateine

See also

References