Protopine

Protopine^[1]

Names
IUPAC name 7-Methyl-6,8,9,16-tetrahydrobis[1,3]benzodioxolo[4,5-c:5′,6′-g]azecin-15(7H)-one
Identifiers
CAS Number	130-86-9
3D model (Jmol)	Interactive image
ChEBI	CHEBI:16415
ChEMBL	ChEMBL486179
ChemSpider	4799
ECHA InfoCard	100.004.546
EC Number	204-999-6
KEGG	C05189
PubChem	4970
InChI InChI=1S/C20H19NO5/c1-21-5-4-13-7-18-19(25-10-24-18)8-14(13)16(22)6-12-2-3-17-20(15(12)9-21)26-11-23-17/h2-3,7-8H,4-6,9-11H2,1H3 Key: GPTFURBXHJWNHR-UHFFFAOYSA-N InChI=1/C20H19NO5/c1-21-5-4-13-7-18-19(25-10-24-18)8-14(13)16(22)6-12-2-3-17-20(15(12)9-21)26-11-23-17/h2-3,7-8H,4-6,9-11H2,1H3 Key: GPTFURBXHJWNHR-UHFFFAOYAW
SMILES c15cc3OCOc3cc5CCN(C)Cc2c(CC1=O)ccc4c2OCO4
Properties
Chemical formula	C20H19NO5
Molar mass	353.369 g/mol
Appearance	white crystals
Density	1.399 g/cm^3
Melting point	208 °C (406 °F; 481 K)
Solubility in water	practically insoluble
Solubility in chloroform	1:15
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Protopine is a benzylisoquinoline alkaloid occurring in opium poppy,^[2] Corydalis tubers^[3] and other plants of the family papaveraceae, like Fumaria officinalis.^[4] It has been found to inhibit histamine H1 receptors and platelet aggregation, and acts as an analgesic.^[5][6]

See also

• Protopine 6-monooxygenase

References

1. The Merck Index (9 ed.). New Jersey: Merck & Co. 1976. p. 1023.
2. The Free Dictionary: Protopine
3. Jiang, B; Cao, K; Wang, R (2004). "Inhibitory effect of protopine on K(ATP) channel subunits expressed in HEK-293 cells.". European Journal of Pharmacology. 506 (2): 93–100. doi:10.1016/j.ejphar.2004.11.004. PMID 15588728.
4. Vrba, J.; Vrublova, E.; Modriansky, M.; Ulrichova, J. (2011). "Protopine and allocryptopine increase mRNA levels of cytochromes P450 1A in human hepatocytes and HepG2 cells independently of AhR". Toxicology Letters. 203 (2): 135–141. doi:10.1016/j.toxlet.2011.03.015. PMID 21419197.
5. Saeed, SA; Gilani, AH; Majoo, RU; Shah, BH (1997). "Anti-thrombotic and anti-inflammatory activities of protopine.". Pharmacological research : the official journal of the Italian Pharmacological Society. 36 (1): 1–7. doi:10.1006/phrs.1997.0195. PMID 9368908.
6. Protopine at the US National Library of Medicine Medical Subject Headings (MeSH)