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Mitragynine pseudoindoxyl

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Mitragynine pseudoindoxyl
Names
IUPAC name
(E)-methyl 2-((1'S,6'S,7'S,8a'S)-6'-ethyl-4-methoxy-3-oxo-3',5',6',7',8',8a'-hexahydro-2'H-spiro[indoline-2,1'-indolizin]-7'-yl)-3-methoxyacrylate
Other names
spiro[2H-indole-2,1'(5'H)-indolizine]-7'-acetic acid, 6'-ethyl-1,2',3,3',6',7',8',8'a-octahydro-4-methoxy-α-(methoxymethylene)-3-oxo-, methyl ester, (αE,2S,6'S,7'S,8'aS)
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C23H30N2O5 c1-5-14-12-25-10-9-23(19(25)11-15(14)16(13-28-2)22(27)30-4)21(26)20-17(24-23)7-6-8-18(20)29-3/h6-8,13-15,19,24H,5,9-12H2,1-4H3/b16-13+/t14-,15+,19+,23+/m1/s1
    Key: BAEJBRCYKACTAA-WGUOAFTMSA-N
  • CC[C@H](C1)[C@](/C(C(OC)=O)=C\OC)([H])C[C@@](N1CC2)([H])[C@]32NC4=CC=CC(OC)=C4C3=O
Properties
C23H30N2O5
Molar mass 414.49
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Mitragynine pseudoindoxyl is an indole alkaloid present in the the plant Mitragyna speciosa, commonly known as Kratom.[1]

Pharmacology

Mitragynine pseudoindoxyl itself acts primarily via mu and delta opioid receptors, being more potent than morphine and about as potent as enkephalin. [2][3]

See also

References

  1. ^ Jansen KL, Prast CJ (1988). "Ethnopharmacology of kratom and the Mitragyna alkaloids". J Ethnopharmacol. 23 (1): 115–9. doi:10.1016/0378-8741(88)90121-3. PMID 3419199.
  2. ^ Takayama H, Ishikawa H, Kurihara M, Kitajima M, Aimi N, Ponglux D, Koyama F, Matsumoto K, Moriyama T, Yamamoto LT, Watanabe K, Murayama T, Horie S (2002). "Studies on the synthesis and opioid agonistic activities of mitragynine-related indole alkaloids: discovery of opioid agonists structurally different from other opioid ligands". J. Med. Chem. 45 (9): 1949–56. doi:10.1021/jm010576e. PMID 11960505. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  3. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 10428019, please use {{cite journal}} with |pmid=10428019 instead.

Further reading