Corynantheidine: Chemical And Structural Characterization

Corynantheidine: Chemical & Structural Characterization

Chemical Classification

Corynantheidine is an indolo[2,3-a]quinolizine (Corynanthe-type) plant alkaloid reported from Mitragyna speciosa (kratom) and related Naucleeae taxa.

Data Sources

Core chemical identity and registry information are taken from:

CAS Common Chemistry
NCATS Inxight Drugs
PubChem
ChEBI

Analytical Characterization

Analytical characterization is drawn from peer-reviewed LC–MS/MS method papers and reviews listed in the References.

Identity and Identifiers

Field	Value
Preferred name	Corynantheidine [1]
CAS Registry Number	23407-35-4 [2]
PubChem CID	3000341 [3]
FDA UNII	QMP2RF3L41 [4]
ChEBI ID	CHEBI:70073 [5]
EPA CompTox (DSSTox)	DTXSID801106946 [6]
InChIKey	NMLUOJBSAYAYEM-QALMDFCDSA-N [7]
Synonyms (selected)	(–)-Corynantheidine; Isocorynantheidine (stereoisomer); 9-Demethoxymitragynine (catalog synonym)

Composition And Stereochemistry

Property	Value
Molecular formula	C₂₂H₂₈N₂O₃ [8]
Formula (relative) mass	368.47 g/mol [9]
IUPAC name (one representation)	methyl (E)-2-[(2S,3S,12bS)-3-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo [2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate [10]
Stereochemistry	3 defined tetrahedral centers (2S,3S,12bS); one E/Z double bond defined as E [11]

Solid-state and basic physicochemical data

Property	Value	Notes
Melting point (literature)	152–153 °C	free base; when reported [12]
Computed properties	XLogP3, tPSA, HBD/HBA, rotatable bonds	from “Computed Properties” panel [13]

Spectroscopic/structural characterization in the literature

Peer-reviewed method papers confirm identity/purity using HRMS and (when reported) NMR before quantitative work [14]. If primary NMR/IR/UV numeric assignments specific to corynantheidine are located in isolation/synthesis papers, include them with solvent/field and cite directly; if not located, mark “not available in primary literature found.”

Analytical Detection and Quantification

Plant/Product QC Panel

UPLC–MS/MS for ten kratom alkaloids (includes corynantheidine). Validated for plant materials and commercial products. Positive-mode ESI, MRM; LLOQ in low ng/mL; run time ~22.5 min to separate all targets [15].

Single-Analyte Plasma Bioanalysis

UPLC–MS/MS specific to corynantheidine for rat plasma PK: Waters BEH C18 (2.1 × 50 mm), gradient with ammonium acetate (pH 3.5)/acetonitrile; 3.0 min run; ESI+ MRM m/z 369.2→144.0 and 369.2→226.1; linear range 1–500 ng/mL; protein precipitation, 25 µL plasma [16].

Multi-Analyte Plasma PK

Validated LC–MS/MS for 11 alkaloids in rat plasma applied to kratom tea/liquid shot studies (includes corynantheidine) [17].

Use-case	Matrix	Run time	Calibration range (ng/mL)	Notes
Single-analyte PK	Rat plasma	3.0	1–500	MRM 369.2→144.0, 369.2→226.1; 25 µL; protein precipitation
10-analyte QC	Leaf/extract/product	~22.5	1–200 (typical)	UPLC–MS/MS separation of ten kratom alkaloids
11-analyte PK	Rat plasma	method-specific	validated	Applied to oral kratom matrices

Occurrence

Minor Component in Surveys

Validated LC–MS/MS surveys report corynantheidine as a minor component (levels vary by material/batch). Use the ten-alkaloid QC method for product-level quantitation; report batch-specific values with method and internal standard details [18].

Structural Context

Reviews treat corynantheidine as a demethoxy analogue of mitragynine within the same scaffold [19].

Structure relationships

Structural Analogue

Corynantheidine is the 9-demethoxy analogue of mitragynine within the Corynanthe scaffold; see structural set comparisons in kratom-alkaloid cheminformatics and receptor-binding panels for context (structure only here; no pharmacology) [20].

Purity assessment, related substances, stability

Purity / Identity for Standards

Confirm by HRMS (±5 ppm), retention time in a validated LC–MS/MS method, and orthogonal evidence (e.g., NMR) where available [21].

Related Substances in Plant QC

Monitor co-eluting indole alkaloids per the ten-analyte panel [22].

Stability

Include only if primary sources report stress-testing or storage data; otherwise, state “no peer-reviewed stability data located.”

Summary

Overview

Corynantheidine (CAS 23407-35-4; C₂₂H₂₈N₂O₃; 368.47 g/mol) is an indolo[2,3-a]quinolizine alkaloid with defined stereochemistry (2S,3S,12bS; E). Identity and registry data are consistent across CAS [23], Inxight [24], PubChem [25], and ChEBI [26]. Validated UPLC–MS/MS methods exist for plant/product QC [27] and , for single-analyte plasma PK with short runtime and documented MRM transitions [28]; multi-analyte PK assays also include corynantheidine [29].