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Details

Stereochemistry ABSOLUTE
Molecular Formula C23H30N2O4
Molecular Weight 398.4953
Optical Activity ( - )
Defined Stereocenters 3 / 3
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of MITRAGYNINE

SMILES

[H][C@@]12C[C@@H]([C@H](CC)CN1CCC3=C2NC4=C3C(OC)=CC=C4)C(=C/OC)\C(=O)OC

InChI

InChIKey=LELBFTMXCIIKKX-QVRQZEMUSA-N
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

HIDE SMILES / InChI

Molecular Formula C23H30N2O4
Molecular Weight 398.4953
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 1
Optical Activity UNSPECIFIED

Mitragynine is the main active alkaloid constituent of the plant Mitragyna speciosa Korth. Mitragyna speciosa Korth. (M. speciosa), from the Rubiaceae family, is a tropical medicinal plant native to Southeast Asia. In Malaysia, M. speciosa leaves are known as Ketum or Biak, and in Thailand as Kratom. M. speciosa has been historically used in Southeast Asia as a stimulant drug and in its traditional context as a remedy for various symptoms. Pharmacological activities are mainly mediated via opioid receptors as well as neuronal Ca2+ channels, expression of cAMP and CREB protein and via descending monoaminergic system. Mitragynine acted as a partial agonist at mu-opioid receptors, in contrast, at kappa-opioid receptors, mitragynine was a competitive antagonist, similarly, mitragynine acted as an antagonist at delta-mu-opioid receptors, but with very low potency. Experimental studies in animals have now shown that mitragynine has an addictive potential, however, only at higher doses. Human users in countries of frequent use with a traditional context report a rather low daily consumption with only mild side effects. Kratom and mitragynine can be instrumentalized to enhance physical work power and endurance. A major reason for Kratom consumption is its reported efficacy to replace opiates in chronic users. This makes the Kratom plant preparation and also the isolated compound mitragynine interesting options to treat opiate addiction. In August 2016, the US Drug Enforcement Administration announced plans to classify kratom and its mitragynine constituents as Schedule 1 controlled substances.

Originator

Sources: Hooper D. Pharm J. 1907;78:453.
Curator's Comment: Mitragynine was isolated from Mitragyne speciosa Korth Reference retrieved from https://www.ncbi.nlm.nih.gov/pubmed/17685530

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
339.0 nM [EC50]
8.5 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Contribution of human esterases to the metabolism of selected drugs of abuse.
2015 Jan 5
Patents

Patents

Sample Use Guides

A comprehensive pharmacokinetic description of mitragynine in rats was provided by Parthasarathy et al. (https://www.ncbi.nlm.nih.gov/pubmed/20454783/) after intravenous (i.v.) and oral administration. The blood concentration peaked at 1.2 h with 2.3 µg/mL followed by biphasic elimination with a half-life of 2.9 h and a clearance of 0.09 L/h/kg after administration of 1.5 mg/kg mitragynine (i.v.). The oral absorption of mitragynine was shown to be lengthy and incomplete, with an absolute oral bioavailability of around 3%. Several studies revealed that after oral application of 20–50 mg/kg mitragynine, a volume distribution of 37–89 L/kg and clearance of 1.6–7 L/h (per kg) was reached, which supports the low bioavailability and poor absorption of mitragynine. Chronic administration of mitragynine at a dose of ≥10 mg/kg (i.p.) may cause addiction-like behaviors in animal models.
Route of Administration: Other
Mitragynine showed concentration-dependent cytototoxicity effects and exert profound antiproliferative efficacy at concentration > 100 μM towards HCT 116 and K 562 cancer cell lines, comparable to those of BA and 5-FU (5-Fluorouracil).
Substance Class Chemical
Created
by admin
on Wed Jul 05 22:55:26 UTC 2023
Edited
by admin
on Wed Jul 05 22:55:26 UTC 2023
Record UNII
EP479K822J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MITRAGYNINE
MI   WHO-DD  
Common Name English
INDOLO(2,3-A)QUINOLIZINE-2-ACETIC ACID, 3-ETHYL-1,2,3,4,6,7,12,12B-OCTAHYDRO-8-METHOXY-.ALPHA.-(METHOXYMETHYLENE)-, METHYL ESTER, (.ALPHA.E,2S,3S,12BS)-
Systematic Name English
9-METHOXYCORYNANTHEIDINE
Common Name English
Mitragynine [WHO-DD]
Common Name English
(-)-MITRAGYNINE
Common Name English
(.ALPHA.E,2S,3S,12.BETA.S)-3-ETHYL-1,2,3,4,6,7,12,12B-OCTAHYDRO-8-METHOXY-.ALPHA.-(METHOXYMETHYLENE)-INDOLO(2,3-A)QUINOLIZINE-2-ACETIC ACID METHYL ESTER
Common Name English
MITRAGYNINE [MI]
Common Name English
MITRAGYNIN
Common Name English
Code System Code Type Description
MERCK INDEX
M7573
Created by admin on Wed Jul 05 22:55:26 UTC 2023 , Edited by admin on Wed Jul 05 22:55:26 UTC 2023
PRIMARY Merck Index
PUBCHEM
3034396
Created by admin on Wed Jul 05 22:55:26 UTC 2023 , Edited by admin on Wed Jul 05 22:55:26 UTC 2023
PRIMARY
MESH
C001801
Created by admin on Wed Jul 05 22:55:26 UTC 2023 , Edited by admin on Wed Jul 05 22:55:26 UTC 2023
PRIMARY
SMS_ID
100000136870
Created by admin on Wed Jul 05 22:55:26 UTC 2023 , Edited by admin on Wed Jul 05 22:55:26 UTC 2023
PRIMARY
CAS
6202-22-8
Created by admin on Wed Jul 05 22:55:26 UTC 2023 , Edited by admin on Wed Jul 05 22:55:26 UTC 2023
SUPERSEDED
EPA CompTox
DTXSID701032140
Created by admin on Wed Jul 05 22:55:26 UTC 2023 , Edited by admin on Wed Jul 05 22:55:26 UTC 2023
PRIMARY
FDA UNII
EP479K822J
Created by admin on Wed Jul 05 22:55:26 UTC 2023 , Edited by admin on Wed Jul 05 22:55:26 UTC 2023
PRIMARY
WIKIPEDIA
MITRAGYNINE
Created by admin on Wed Jul 05 22:55:26 UTC 2023 , Edited by admin on Wed Jul 05 22:55:26 UTC 2023
PRIMARY
EVMPD
SUB75071
Created by admin on Wed Jul 05 22:55:26 UTC 2023 , Edited by admin on Wed Jul 05 22:55:26 UTC 2023
PRIMARY
CAS
4098-40-2
Created by admin on Wed Jul 05 22:55:26 UTC 2023 , Edited by admin on Wed Jul 05 22:55:26 UTC 2023
PRIMARY
HSDB
7901
Created by admin on Wed Jul 05 22:55:26 UTC 2023 , Edited by admin on Wed Jul 05 22:55:26 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> AGONIST
PARENT -> ACTIVE CONSTITUENT ALWAYS PRESENT
60% of alkaloid extractions
WEIGHT PERCENT
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METABOLITE INACTIVE -> PARENT
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URINE
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METABOLITE -> PARENT
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ACTIVE MOIETY