Mitragynine pseudoindoxyl

Mitragynine pseudoindoxyl
Clinical data
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-alpha-(methoxymethylene)-3-oxo-, methyl ester, (alphaE,1'S,6'S,7'S,8'as)-
Identifiers
	IUPAC name methyl (E)-2-[(2S,6'S,7'S,8'aS)-6'-ethyl-4-methoxy-3-oxospiro[1H-indole-2,1'-3,5,6,7,8,8a-hexahydro-2H-indolizine]-7'-yl]-3-methoxyprop-2-enoate;
CAS Number	2035457-43-1;
PubChem CID	44301701;
ChemSpider	23152339;
ChEMBL	ChEMBL58362;
CompTox Dashboard (EPA)	DTXSID101045678 ;
Chemical and physical data
Formula	C23H30N2O5
Molar mass	414.502 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC[C@H](C1)[C@](/C(C(OC)=O)=C\OC)([H])C[C@@](N1CC2)([H])[C@]32NC4=CC=CC(OC)=C4C3=O;
	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;

Mitragynine pseudoindoxyl is a rearrangement product of 7-hydroxymitragynine.^[1] It is an analgesic being more potent than morphine.^[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. PMC 5344672. PMID 27556704.

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