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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H26N2O3.C4H6O6
Molecular Weight 504.5296
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CORYNANTHINE TARTRATE

SMILES

O[C@H]([C@@H](O)C(O)=O)C(O)=O.[H][C@@]12CC[C@H](O)[C@@H](C(=O)OC)[C@@]1([H])C[C@]3([H])N(CCC4=C3NC5=C4C=CC=C5)C2

InChI

InChIKey=HMEXTTWSBUBIOL-URXSSEHMSA-N
InChI=1S/C21H26N2O3.C4H6O6/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24;5-1(3(7)8)2(6)4(9)10/h2-5,12,15,17-19,22,24H,6-11H2,1H3;1-2,5-6H,(H,7,8)(H,9,10)/t12-,15-,17-,18-,19-;1-,2-/m01/s1

HIDE SMILES / InChI

Molecular Formula C21H26N2O3
Molecular Weight 354.4427
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C4H6O6
Molecular Weight 150.0868
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Corynanthine is one of the two diastereomers of yohimbine (the other is alpha-yohimbine). Corynanthine is an antagonist of the alpha-1, alpha-2A and alpha-2C adrenergic receptors showing greater selectivity for the alpha-1 adrenergic receptor. Corynanthine was tested as the active ingredient of eye drops in a small clinical trial for Ocular hypertension where formulations of 2% and 5% demonstrated relief of symptoms.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P35348|||B0ZBD9|||Q6RUJ8
Gene ID: 148.0
Gene Symbol: ADRA1A
Target Organism: Homo sapiens (Human)
562.0 nM [Kd]
5.1 null [pKd]
Target ID: P22086
Gene ID: 24175.0
Gene Symbol: Adra2c
Target Organism: Rattus norvegicus (Rat)
232.0 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

10 symmetrically ocular hypertensive patients were treated with a single drop of 1%, 2% and 5% corynanthine solution. The 1% solution showed no effect while the 2% solution reduced IOP for at least 8 hours and the 5% solution showed a significant reduction in IOP in both eyes.
Route of Administration: Topical
In Vitro Use Guide
The binding constants obtained for 26 compounds (including, corynanthine) were determined by the 3-curve approach. Of these compounds WB4101, corynanthine, rauwolscine, yohimbine, ARC 239 and prazosin were found to be clearly alpha2C-selective; their electivites ranging from 16 to 30 fold (Kd for corynanthine = 232 nM). Radioligand binding was performed in 150 uL of 1 mM EDTA, 100 uM Gpp(NH)p (guanyl-5'-yl-imido-diphos-phate), 140 mM NaCl, 33 mM Tris-Cl, pH 7.5 with [3H]-MK912 and drugs for 1 h at 25°C and then filtering and washing on Whatman GF/C filters.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:16:35 GMT 2023
Edited
by admin
on Fri Dec 15 15:16:35 GMT 2023
Record UNII
7359P0A2QF
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CORYNANTHINE TARTRATE
Common Name English
NSC-274278
Code English
YOHIMBAN-16-CARBOXYLIC ACID, 17-HYDROXY-, METHYL ESTER, (16.BETA.,17.ALPHA.)-, (R-(R*,R*))-2,3-DIHYDROXYBUTANEDIOATE (1:1) (SALT)
Common Name English
YOHIMBAN-16-CARBOXYLIC ACID, 17-HYDROXY-, METHYL ESTER, (16.BETA.,17.ALPHA.)-, (2R,3R)-2,3-DIHYDROXYBUTANEDIOATE (1:1) (SALT)
Common Name English
Code System Code Type Description
NSC
274278
Created by admin on Fri Dec 15 15:16:35 GMT 2023 , Edited by admin on Fri Dec 15 15:16:35 GMT 2023
PRIMARY
PUBCHEM
24721101
Created by admin on Fri Dec 15 15:16:35 GMT 2023 , Edited by admin on Fri Dec 15 15:16:35 GMT 2023
PRIMARY
CAS
92634-48-5
Created by admin on Fri Dec 15 15:16:35 GMT 2023 , Edited by admin on Fri Dec 15 15:16:35 GMT 2023
NON-SPECIFIC STOICHIOMETRY
CAS
63989-78-6
Created by admin on Fri Dec 15 15:16:35 GMT 2023 , Edited by admin on Fri Dec 15 15:16:35 GMT 2023
PRIMARY
EPA CompTox
DTXSID90981713
Created by admin on Fri Dec 15 15:16:35 GMT 2023 , Edited by admin on Fri Dec 15 15:16:35 GMT 2023
PRIMARY
FDA UNII
7359P0A2QF
Created by admin on Fri Dec 15 15:16:35 GMT 2023 , Edited by admin on Fri Dec 15 15:16:35 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY