Erythravine

Erythravine
Names
	IUPAC name 15,16-Dimethoxy-1,2,6,7-tetradehydroerythrinan-3β-ol
	Systematic IUPAC name (9bS,11R)-7,8-Dimethoxy-4,5,10,11-tetrahydro-2H-indolo[7a,1-a]isoquinolin-11-ol
Identifiers
CAS Number	19373-79-6 ;
3D model (JSmol)	Interactive image;
ChemSpider	9406901 ;
PubChem CID	11231853;
UNII	HMX9ZLU64X ;
CompTox Dashboard (EPA)	DTXSID301027523 DTXSID80726716, DTXSID301027523 ;
	InChI InChI=1S/C18H21NO3/c1-21-16-9-12-5-7-19-8-6-13-3-4-14(20)11-18(13,19)15(12)10-17(16)22-2/h3-4,6,9-10,14,20H,5,7-8,11H2,1-2H3/t14-,18-/m0/s1 Key: JEBFJSHKHYDVNP-KSSFIOAISA-N ;
	SMILES COC1=C(C=C2C(=C1)CCN3[C@]24C[C@H](C=CC4=CC3)O)OC;
Properties
Chemical formula	C18H21NO3
Molar mass	299.370 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Erythravine is a tetrahydroisoquinoline alkaloid found in the plant Erythrina mulungu and other species of the genus Erythrina.

Biological activity

Some laboratory research has investigated the biological activity of erythravine, but the relevance to effects in humans is unknown.

Nicotinic acetylcholine receptor

It has been shown to be a potent nicotinic receptor antagonist in animal models with an IC50 of 6μM at the α7 site and 13 nM for the α4β2 receptor.^[1]

Anxiolytic

It appears to have anxiolytic effects in animal models of anxiety. Further studies suggest that the anxiolytic effects are only reproducible with the whole extract of Erythrina mulungu but not with the pure alkaloids.^[2]^[3]

Anticonvulsant

Erythravine inhibited seizures evoked by bicuculline, pentylenetetrazole, and kainic acid as well as increasing the latency of seizures induced by NMDA. Treatment with erythravine prevented death in all the animals tested with the four convulsants except a few of those treated with kainic acid.^[4]

References

^ Setti-Perdigão, Pedro; Serrano, Maria A. R.; Flausino, Otávio A.; Bolzani, Vanderlan S.; Guimarães, Marília Z. P.; Castro, Newton G. (2013-01-01). "Erythrina mulungu alkaloids are potent inhibitors of neuronal nicotinic receptor currents in mammalian cells". PLOS ONE. 8 (12): e82726. Bibcode:2013PLoSO...882726S. doi:10.1371/journal.pone.0082726. ISSN 1932-6203. PMC 3862643. PMID 24349349.
^ Flausino Jr, O; Santos Lde, A; Verli, H; Pereira, AM; Bolzani Vda, S; Nunes-De-Souza, RL (2007). "Anxiolytic effects of erythrinian alkaloids from Erythrina mulungu". Journal of Natural Products. 70 (1): 48–53. doi:10.1021/np060254j. PMID 17253849.
^ Flausino Jr, OA; Pereira, AM; Da Silva Bolzani, V; Nunes-De-Souza, RL (2007). "Effects of erythrinian alkaloids isolated from Erythrina mulungu (Papilionaceae) in mice submitted to animal models of anxiety". Biological & Pharmaceutical Bulletin. 30 (2): 375–8. doi:10.1248/bpb.30.375. hdl:11449/34195. PMID 17268084.
^ Faggion, Silmara Aparecida; Cunha, Alexandra Olimpio Siqueira; Fachim, Helene Aparecida; Gavin, Amanda Salomão; dos Santos, Wagner Ferreira; Pereira, Ana Maria Soares; Beleboni, Renê Oliveira (2011-03-01). "Anticonvulsant profile of the alkaloids (+)-erythravine and (+)-11-α-hydroxy-erythravine isolated from the flowers of Erythrina mulungu Mart ex Benth (Leguminosae-Papilionaceae)". Epilepsy & Behavior. 20 (3): 441–446. doi:10.1016/j.yebeh.2010.12.037. ISSN 1525-5069. PMID 21277832.

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[1] Setti-Perdigão, Pedro; Serrano, Maria A. R.; Flausino, Otávio A.; Bolzani, Vanderlan S.; Guimarães, Marília Z. P.; Castro, Newton G. (2013-01-01). "Erythrina mulungu alkaloids are potent inhibitors of neuronal nicotinic receptor currents in mammalian cells". PLOS ONE. 8 (12): e82726. Bibcode:2013PLoSO...882726S. doi:10.1371/journal.pone.0082726. ISSN 1932-6203. PMC 3862643. PMID 24349349.

[2] Flausino Jr, O; Santos Lde, A; Verli, H; Pereira, AM; Bolzani Vda, S; Nunes-De-Souza, RL (2007). "Anxiolytic effects of erythrinian alkaloids from Erythrina mulungu". Journal of Natural Products. 70 (1): 48–53. doi:10.1021/np060254j. PMID 17253849.

[3] Flausino Jr, OA; Pereira, AM; Da Silva Bolzani, V; Nunes-De-Souza, RL (2007). "Effects of erythrinian alkaloids isolated from Erythrina mulungu (Papilionaceae) in mice submitted to animal models of anxiety". Biological & Pharmaceutical Bulletin. 30 (2): 375–8. doi:10.1248/bpb.30.375. hdl:11449/34195. PMID 17268084.

[4] Faggion, Silmara Aparecida; Cunha, Alexandra Olimpio Siqueira; Fachim, Helene Aparecida; Gavin, Amanda Salomão; dos Santos, Wagner Ferreira; Pereira, Ana Maria Soares; Beleboni, Renê Oliveira (2011-03-01). "Anticonvulsant profile of the alkaloids (+)-erythravine and (+)-11-α-hydroxy-erythravine isolated from the flowers of Erythrina mulungu Mart ex Benth (Leguminosae-Papilionaceae)". Epilepsy & Behavior. 20 (3): 441–446. doi:10.1016/j.yebeh.2010.12.037. ISSN 1525-5069. PMID 21277832.

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