7-Hydroxymitragynine

{{Short description|Opioid analgesic compound}}{{Drugbox

| drug_name = 7-Hydroxymitragynine

| IUPAC_name = Methyl (2E)-2-[(2S,3S,7aS,12bS)-3-ethyl-7a-hydroxy-8-methoxy-1,2,3,4,6,7,7a,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate

| image = 7-hydroxymitragynine2DACS.svg

| image2 = 7-OH-mitragynine.png

| legal_BR = F1

| legal_US = Unscheduled

| routes_of_administration = By mouth; inhalation

| metabolites = Mitragynine pseudoindoxyl

| CAS_number = 174418-82-7

| CAS_number_Ref = {{cascite|changed|??}}

| ATC_prefix = None

| PubChem = 44301524

| ChemSpiderID = 23152144

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| UNII = 2T3TWA75R0

| UNII_Ref = {{fdacite|changed|FDA}}

| ChEMBL = 61630

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| synonyms = 7α-Hydroxy-7H-mitragynine;Chemical Abstracts Service: Columbus, OH, 2004; RN 174418-82-7 (accessed via SciFinder Scholar, version 2007.3; November 30, 2011)

9-Methoxycorynantheidine hydroxyindolenine

| C = 23

| H = 30

| N = 2

| O = 5

| SMILES = CC[C@@H]1CN2CC[C@@]3(O)C(=Nc4cccc(OC)c34)[C@@H]2C[C@@H]1\C(=C/OC)C(=O)OC

| StdInChI = 1S/C23H30N2O5/c1-5-14-12-25-10-9-23(27)20-17(7-6-8-19(20)29-3)24-21(23)18(25)11-15(14)16(13-28-2)22(26)30-4/h6-8,13-15,18,27H,5,9-12H2,1-4H3/b16-13+/t14-,15+,18+,23+/m1/s1

| StdInChIKey = RYENLSMHLCNXJT-CYXFISRXSA-N

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| class = Opioid

| SMILES2 = CC[C@@H]1CN2CC[C@@]3(O)C(=NC4=CC=CC(OC)=C34)[C@@H]2C[C@@H]1\C(=C/OC)C(=O)OC

}}{{cs1 config|name-list-style=vanc}}

7-Hydroxymitragynine (7-OH-MIT) is a terpenoid indole alkaloid present in the plant Mitragyna speciosa, commonly known as kratom.{{cite journal | vauthors = Matsumoto K, Horie S, Ishikawa H, Takayama H, Aimi N, Ponglux D, Watanabe K | title = Antinociceptive effect of 7-hydroxymitragynine in mice: Discovery of an orally active opioid analgesic from the Thai medicinal herb Mitragyna speciosa | journal = Life Sciences | volume = 74 | issue = 17 | pages = 2143–2155 | date = March 2004 | pmid = 14969718 | doi = 10.1016/j.lfs.2003.09.054 }} It was first described in 1994.{{cite journal | vauthors = Ponglux D, Wongseripipatana S, Takayama H, Kikuchi M, Kurihara M, Kitajima M, Aimi N, Sakai S | display-authors = 6 | title = A New Indole Alkaloid, 7 alpha-Hydroxy-7H-mitragynine, from Mitragyna speciosa in Thailand | journal = Planta Medica | volume = 60 | issue = 6 | pages = 580–581 | date = December 1994 | pmid = 17236085 | doi = 10.1055/s-2006-959578 | bibcode = 1994PlMed..60..580P | s2cid = 260252538 }} In humans, it is produced as an active metabolite of mitragynine via hepatic oxidation.{{Cite journal |last=Ganasan |first=Jegathiswary |last2=Karunakaran |first2=Thiruventhan |last3=Marimuthu |first3=Yathindra |last4=Rusmadi |first4=Nurul Najwa |last5=Firouz |first5=Noor Syarafana |last6=Jenis |first6=Janar |last7=Kumar |first7=U. Seeta Uthaya |date=2024-10-10 |title=Chemistry and toxicity of 7-hydroxymitragynine (7-OHMG): an updated review on the oxidized derivative of mitragynine |url=https://doi.org/10.1007/s11101-024-10029-x |journal=Phytochemistry Reviews |language=en |doi=10.1007/s11101-024-10029-x |issn=1572-980X}} 7-OH-MIT exhibits greater binding affinity to mu-opioid receptors (MOR) than mitragynine.