Mitragynine

Mitragynine
Clinical data
Routes of
administration		By mouth
Drug classOpioid
ATC code
  • None
Legal status
Legal status
  • AU: S8 (Controlled drug)
  • BR: Class B1 (Psychoactive drugs)[1]
  • CA: Unscheduled
  • DE: NpSG (Industrial and scientific use only)
  • NZ: Unscheduled
  • UK: Under Psychoactive Substances Act
  • US: Unscheduled
  • UN: Unscheduled
  • In general legal for medical and research uses as a research chemical.[2]
Pharmacokinetic data
Bioavailability21%
Metabolites7-Hydroxymitragynine
Elimination half-life7–39 hours
Identifiers
  • methyl (16E)-9,17-dimethoxy-16,17-didehydro-20β-corynan-16-carboxylate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H30N2O4
Molar mass398.503 g·mol−1
3D model (JSmol)
Melting point102–106 °C[3]
  • COC1=CC=CC2=C1C3=C([C@@](C[C@H](/C(C(OC)=O)=C\OC)[C@H](CC)C4)([H])N4CC3)N2
  • InChI=1S/C23H30N2O4/c1-5-14-12-25-10-9-15-21-18(7-6-8-20(21)28-3)24-22(15)19(25)11-16(14)17(13-27-2)23(26)29-4/h6-8,13-14,16,19,24H,5,9-12H2,1-4H3/b17-13+/t14-,16+,19+/m1/s1
  • Key:LELBFTMXCIIKKX-QVRQZEMUSA-N

Mitragynine is an indole-based alkaloid and is one of the main psychoactive constituents in the Southeast Asian plant Mitragyna speciosa, commonly known as kratom.[4] It is an opioid that is typically consumed as a part of kratom for its pain-relieving and euphoric effects. It has also been researched for its use to potentially manage symptoms of opioid withdrawal.

Mitragynine is the most abundant active alkaloid in kratom. In Thai varieties of kratom, mitragynine is the most abundant component (up to 66% of total alkaloids), while 7-hydroxymitragynine (7-OH) is a minor constituent (up to 2% of total alkaloid content). In Malaysian kratom varieties, mitragynine is present at lower concentration (12% of total alkaloids).[5] Total alkaloid concentration in dried leaves ranges from 0.5 to 1.5%. Such preparations are orally consumed and typically involve dried kratom leaves which are brewed into tea[4][5] or ground and placed into capsules.[5]

  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.
  2. ^ "指定薬物一覧" [List of designated drugs] (PDF). 障害福祉のお仕事の世界 (The world of disability welfare work) (in Japanese). Retrieved 5 December 2023.
  3. ^ "Kratom profile (chemistry, effects, other names, origin, mode of use, other names, medical use, control status)". European Monitoring Centre for Drugs and Drug Addiction (EMCDDA).
  4. ^ a b Hassan Z, Muzaimi M, Navaratnam V, Yusoff NH, Suhaimi FW, Vadivelu R, et al. (February 2013). "From Kratom to mitragynine and its derivatives: physiological and behavioural effects related to use, abuse, and addiction". Neuroscience and Biobehavioral Reviews. 37 (2): 138–151. doi:10.1016/j.neubiorev.2012.11.012. PMID 23206666. S2CID 8463133.
  5. ^ a b c Warner ML, Kaufman NC, Grundmann O (January 2016). "The pharmacology and toxicology of kratom: from traditional herb to drug of abuse". International Journal of Legal Medicine. 130 (1): 127–138. doi:10.1007/s00414-015-1279-y. PMID 26511390. S2CID 2009878.