Allocryptopine
Names
Preferred IUPAC name
3,4-Dimethoxy-6-methyl-5,7,8,15-tetrahydro-11H-[1,3]benzodioxolo[5,6-e][2]benzazecin-14(6H)-one
Other names
Thalictrimine; allo-Cryptopine; α-Fagarine; Fagarine I; α-Allocryptopine; β-Homochelidonine
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.006.933 Edit this at Wikidata
EC Number
  • 207-626-5
KEGG
UNII
  • InChI=1S/C21H23NO5/c1-22-7-6-14-9-19-20(27-12-26-19)10-15(14)17(23)8-13-4-5-18(24-2)21(25-3)16(13)11-22/h4-5,9-10H,6-8,11-12H2,1-3H3
    Key: HYBRYAPKQCZIAE-UHFFFAOYSA-N
  • CN1CCC2=CC3=C(C=C2C(=O)CC4=C(C1)C(=C(C=C4)OC)OC)OCO3
Properties
C21H23NO5
Molar mass 369.417 g·mol−1
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 H302 (100%): Harmful if swallowed, acute toxicity[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Allocryptopine is a bioactive alkaloid found in plants of the Papaveraceae family, including Glaucium arabicum,[2] Argemone mexicana, Eschscholtzia, Corydalis, Fumaria, Chelidonium, Hunnemannia fumariifolia, Eschscholzia lobbii[3] and other Papaveraceae plants.[4][5]

See also

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References

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  1. ^ "Allocryptopine". PubChem: Open Chemistry Database. PubChem. Retrieved 24 May 2018.
  2. ^ Abu-Ghalyun, Y.; Masalmeh, A.; al-Khalil, S. (October 1997). "Effects of allocryptopine, an alkaloid isolated from Glaucium arabicum on rat isolated ileum and urinary bladder". General Pharmacology. 29 (4): 621–623. doi:10.1016/s0306-3623(96)00562-9. ISSN 0306-3623. PMID 9352312.
  3. ^ "Pflanzeninhaltsstoffe sortiert nach Namen: GIFTPFLANZEN.COMpendium - www.giftpflanzen.com". www.giftpflanzen.com. Retrieved 6 June 2023.
  4. ^ "Kalifornischer Goldmohn (Eschscholzia californica) im GIFTPFLANZEN.COMpendium - www.giftpflanzen.com". www.giftpflanzen.com. Retrieved 6 June 2023.
  5. ^ Brahmachari, Goutam; Gorai, Dilip; Roy, Rajiv (1 May 2013). "Argemone mexicana: Chemical and pharmacological aspects". Revista Brasileira de Farmacognosia. 23 (3): 559–575. doi:10.1590/S0102-695X2013005000021. ISSN 0102-695X.


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Fumaria officinalis

plant contains isoquinoline alkaloids protopine and allocryptopine. Both protopine and allocryptopine increased CYP1A1 and CYP1A2 mRNA levels in human hepatocyte

Chelidonium majus

alkaloids present include methyl 2'-(7,8-dihydrosanguinarine-8-yl)acetate, allocryptopine, stylopine, protopine, cryptopine, hemochelidonine, homochelidonine

Eschscholzia californica

disorders in humans. E. californica contains californidine (N+(CH3)2), allocryptopine, eschscholtzine N-CH3 (californidine), and other similar (Papaveraceae)

Aegle marmelos

a number of essential oils; and, among its alkaloids, á-fargarine(=allocryptopine), O-isopentenylhalfordinol, O-methylhafordinol. Aegeline

Argemone mexicana

argenaxine, Argemexicaines A and B (protopine type), coptisine, cryptopine, allocryptopine and chelerythrine have also been found in this plant. The seed pods

C21H23NO5

C21H23NO5 (molar mass: 369.41 g/mol, exact mass: 369.1576 u) may refer to: Allocryptopine Cryptopine Heroin, or diacetylmorphine This set index page lists chemical

Methyltetrahydroprotoberberine 14-monooxygenase

allocryptopine + NADP+ + H2O The 4 substrates of this enzyme are (S)-N-methylcanadine, NADPH, H+, and O2, whereas its 3 products are allocryptopine,

Eomecon

sanguinarine. Other alkaloids include chelerythrine, protopine and alpha-allocryptopine. Zhang, Mingli; Grey-Wilson, Christopher. "Eomecon". Flora of China