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 rearrangement product of 7-hydroxymitragynine.^[1] It is an ananlgesic being more potent than morphine and about as potent as enkephalin.^[2]^[3]

Pharmacology

Mitragynine pseudoindoxyl is a μ opioid receptor agonist and δ opioid receptor antagonist and acts as a G-Protein biased agonist at μ opioid receptors and possesses a favourable side effect profile compared to conventional opioids.^[4]

^ 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.
^ 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.
^ Váradi A, Marrone GF, Palmer TC, Narayan A, Szabó MR, Le Rouzic V, Grinnell SG, Subrath JJ, Warner E, Kalra S, Hunkele A, Pagirsky J, Eans SO, Medina JM, Xu J, Pan YX, Borics A, Pasternak GW, McLaughlin JP, Majumdar S (2016). "Mitragynine/Corynantheidine Pseudoindoxyls As Opioid Analgesics with Mu Agonism and Delta Antagonism, Which Do Not Recruit β-Arrestin-2". J. Med. Chem. 59 (18): 8381–97. doi:10.1021/acs.jmedchem.6b00748. PMID 27556704.

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