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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H26N2O3
Molecular Weight 354.4427
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CORYNANTHINE

SMILES

[H][C@@]12CC[C@H](O)[C@@H](C(=O)OC)[C@@]1([H])C[C@]3([H])N(CCC4=C3NC5=CC=CC=C45)C2

InChI

InChIKey=BLGXFZZNTVWLAY-DKJBZYCGSA-N
InChI=1S/C21H26N2O3/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/h2-5,12,15,17-19,22,24H,6-11H2,1H3/t12-,15-,17-,18-,19-/m0/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

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
Stimulation of an alpha1-adrenergic receptor downregulates ecto-5' nucleotidase activity on the apical membrane of RPE cells.
2006 Sep
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 Sat Dec 16 06:34:49 UTC 2023
Edited
by admin
on Sat Dec 16 06:34:49 UTC 2023
Record UNII
F5Z7C9RK8U
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CORYNANTHINE
MI   WHO-DD  
Common Name English
NSC-407306
Code English
RAUHIMBIN
Common Name English
YOHIMBAN-16.BETA.-CARBOXYLIC ACID, 17.ALPHA.-HYDROXY-, METHYL ESTER
Common Name English
RAUHIMBINE
Common Name English
YOHIMBAN-16-CARBOXYLIC ACID, 17-HYDROXY-, METHYL ESTER, (16.BETA.,17.ALPHA.)-
Common Name English
Corynanthine [WHO-DD]
Common Name English
CORYNANTHINE [MI]
Common Name English
METHYL (16.BETA.,17.ALPHA.)-17-HYDROXYYOHIMBAN-16-CARBOXYLATE
Common Name English
YOHIMBINE HYDROCHLORIDE IMPURITY C [EP IMPURITY]
Common Name English
CORYNANTHIN
Common Name English
Code System Code Type Description
EVMPD
SUB13474MIG
Created by admin on Sat Dec 16 06:34:49 UTC 2023 , Edited by admin on Sat Dec 16 06:34:49 UTC 2023
PRIMARY
MERCK INDEX
m3805
Created by admin on Sat Dec 16 06:34:49 UTC 2023 , Edited by admin on Sat Dec 16 06:34:49 UTC 2023
PRIMARY Merck Index
NSC
407306
Created by admin on Sat Dec 16 06:34:49 UTC 2023 , Edited by admin on Sat Dec 16 06:34:49 UTC 2023
PRIMARY
PUBCHEM
92766
Created by admin on Sat Dec 16 06:34:49 UTC 2023 , Edited by admin on Sat Dec 16 06:34:49 UTC 2023
PRIMARY
SMS_ID
100000079831
Created by admin on Sat Dec 16 06:34:49 UTC 2023 , Edited by admin on Sat Dec 16 06:34:49 UTC 2023
PRIMARY
FDA UNII
F5Z7C9RK8U
Created by admin on Sat Dec 16 06:34:49 UTC 2023 , Edited by admin on Sat Dec 16 06:34:49 UTC 2023
PRIMARY
EPA CompTox
DTXSID401317915
Created by admin on Sat Dec 16 06:34:49 UTC 2023 , Edited by admin on Sat Dec 16 06:34:49 UTC 2023
PRIMARY
ECHA (EC/EINECS)
207-590-0
Created by admin on Sat Dec 16 06:34:49 UTC 2023 , Edited by admin on Sat Dec 16 06:34:49 UTC 2023
PRIMARY
WIKIPEDIA
Corynanthine
Created by admin on Sat Dec 16 06:34:49 UTC 2023 , Edited by admin on Sat Dec 16 06:34:49 UTC 2023
PRIMARY
CAS
483-10-3
Created by admin on Sat Dec 16 06:34:49 UTC 2023 , Edited by admin on Sat Dec 16 06:34:49 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY