Mitragynine

Mitragynine
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]
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 the most abundant active alkaloid in the Southeast Asian plant Mitragyna speciosa, commonly known as kratom.[4] The total alkaloid concentration in dried leaves ranges from 0.5 to 1.5%. In Thai varieties, mitragynine is the most abundant component (up to 66% of total alkaloids) while 7-hydroxymitragynine 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] 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] Mitragynine consumption for medicinal and recreation purposes dates back centuries, although early use was primarily limited to Southeast Asian countries such as Indonesia and Thailand where the plant grows indigenously.[6] Recently, mitragynine use has spread throughout Europe and the Americas as both a recreational and medicinal drug.[7] While research into the effects of kratom have begun to emerge, investigations on the active compound mitragynine are less common.

  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.
  6. ^ Veltri C, Grundmann O (2019). "Current perspectives on the impact of Kratom use". Substance Abuse and Rehabilitation. 10: 23–31. doi:10.2147/SAR.S164261. PMC 6612999. PMID 31308789.
  7. ^ Prozialeck WC, Jivan JK, Andurkar SV (December 2012). "Pharmacology of kratom: an emerging botanical agent with stimulant, analgesic and opioid-like effects". The Journal of the American Osteopathic Association. 112 (12): 792–799. PMID 23212430.