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 (JSmol)	Interactive image;
ChEBI	CHEBI:16415 ;
ChEMBL	ChEMBL486179 ;
ChemSpider	4799 ;
ECHA InfoCard	100.004.546
EC Number	204-999-6;
KEGG	C05189 ;
PubChem CID	4970;
UNII	UIW569HT35 ;
CompTox Dashboard (EPA)	DTXSID90156282 ;
	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/cm3
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).

Protopine is an alkaloid occurring in opium poppy,^[2] Corydalis tubers^[3] and other plants of the family papaveraceae, like Fumaria officinalis.^[4] Protopine is metabolically derived from the benzylisoquinoline alkaloid (S)-Reticuline through a progressive series of five enzymatic transformations: 1) berberine bridge enzyme to (S)-Scoulerine; 2) (S)-cheilanthifoline synthase/CYP719A25 to (S)-Cheilanthifoline; 3) (S)-stylopine synthase/CYP719A20 to (S)-Stylopine; 4) (S)-tetrahydroprotoberberine N-methyltransferase to (S)-cis-N-Methylstylopine; and ultimately, 5) N-methylstylopine hydroxylase to protopine.^[5]

It has been found to inhibit histamine H1 receptors and platelet aggregation, and acts as an analgesic.^[6]^[7]

References

^ The Merck Index (9 ed.). New Jersey: Merck & Co. 1976. p. 1023.
^ The Free Dictionary: Protopine
^ 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.
^ 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.
^ Hagel, Jillian M; Morris, Jeremy S; Lee, Eun-Jeong; Desgagne-Penix, Isabel; Bross, Crystal D; Chang, Limei; Chen, Xue; Farrow, Scott C; Zhang, Ye (2015). "Transcriptome analysis of 20 taxonomically related benzylisoquinoline alkaloid-producing plants". BMC Plant Biology. 15: 227. doi:10.1186/s12870-015-0596-0. PMID 26384972.
^ Saeed, SA; Gilani, AH; Majoo, RU; Shah, BH (1997). "Anti-thrombotic and anti-inflammatory activities of protopine". Pharmacological Research. 36 (1): 1–7. doi:10.1006/phrs.1997.0195. PMID 9368908.
^ Protopine at the US National Library of Medicine Medical Subject Headings (MeSH)

[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] Hagel, Jillian M; Morris, Jeremy S; Lee, Eun-Jeong; Desgagne-Penix, Isabel; Bross, Crystal D; Chang, Limei; Chen, Xue; Farrow, Scott C; Zhang, Ye (2015). "Transcriptome analysis of 20 taxonomically related benzylisoquinoline alkaloid-producing plants". BMC Plant Biology. 15: 227. doi:10.1186/s12870-015-0596-0. PMID 26384972.

[6] Saeed, SA; Gilani, AH; Majoo, RU; Shah, BH (1997). "Anti-thrombotic and anti-inflammatory activities of protopine". Pharmacological Research. 36 (1): 1–7. doi:10.1006/phrs.1997.0195. PMID 9368908.

[7] Protopine at the US National Library of Medicine Medical Subject Headings (MeSH)

[1]

[2]

[3]

[4]

[5]

[6]

[7]

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 (JSmol)	Interactive image
ChEBI	CHEBI:16415
ChEMBL	ChEMBL486179
ChemSpider	4799
ECHA InfoCard	100.004.546
EC Number	204-999-6
KEGG	C05189
PubChem CID	4970
UNII	UIW569HT35
CompTox Dashboard (EPA)	DTXSID90156282
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/cm³
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).

Protopine

See also

References