Mitragynine pseudoindoxyl

Mitragynine pseudoindoxyl
Names
	IUPAC name Methyl (E)-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)	Interactive image;
ChEMBL	ChEMBL58362;
ChemSpider	23152339;
PubChem CID	44301701;
CompTox Dashboard (EPA)	DTXSID101045678 ;
	InChI 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;
	SMILES CC[C@H](C1)[C@](/C(C(OC)=O)=C\OC)([H])C[C@@](N1CC2)([H])[C@]32NC4=CC=CC(OC)=C4C3=O;
Properties
Chemical formula	C23H30N2O5
Molar mass	414.502 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Mitragynine pseudoindoxyl is a semi-synthetic opioid compound derived from natural mitragynine found in 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]

References

^ 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.
^ 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 (April 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}}: CS1 maint: multiple names: authors list (link)
^ Yamamoto, L. T.; Horie, S.; Takayama, H.; Aimi, N.; Sakai, S.; Yano, S.; Shan, J.; Pang, P. K.; Ponglux, D.; Watanabe, K. (1999). "Opioid receptor agonistic characteristics of mitragynine pseudoindoxyl in comparison with mitragynine derived from Thai medicinal plant Mitragyna speciosa". General pharmacology. 33 (1): 73–81. doi:10.1016/S0306-3623(98)00265-1. PMID 10428019.

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[pmid3419199-1] 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.

[pmid11960505-2] 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 (April 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}}: CS1 maint: multiple names: authors list (link)

[pmid10428019-3] Yamamoto, L. T.; Horie, S.; Takayama, H.; Aimi, N.; Sakai, S.; Yano, S.; Shan, J.; Pang, P. K.; Ponglux, D.; Watanabe, K. (1999). "Opioid receptor agonistic characteristics of mitragynine pseudoindoxyl in comparison with mitragynine derived from Thai medicinal plant Mitragyna speciosa". General pharmacology. 33 (1): 73–81. doi:10.1016/S0306-3623(98)00265-1. PMID 10428019.

[1]

[2]

[3]

Pharmacology

See also

References