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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
The effect of adrenergic compounds on neurogenic dural vasodilatation.
2001 Jul 13
Small molecules targeting severe acute respiratory syndrome human coronavirus.
2004 Jul 6
Histamine receptors that influence blockage of the normal human nasal airway.
2005 Mar
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 GMT 2023
Edited
by admin
on Sat Dec 16 06:34:49 GMT 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 GMT 2023 , Edited by admin on Sat Dec 16 06:34:49 GMT 2023
PRIMARY
MERCK INDEX
m3805
Created by admin on Sat Dec 16 06:34:49 GMT 2023 , Edited by admin on Sat Dec 16 06:34:49 GMT 2023
PRIMARY Merck Index
NSC
407306
Created by admin on Sat Dec 16 06:34:49 GMT 2023 , Edited by admin on Sat Dec 16 06:34:49 GMT 2023
PRIMARY
PUBCHEM
92766
Created by admin on Sat Dec 16 06:34:49 GMT 2023 , Edited by admin on Sat Dec 16 06:34:49 GMT 2023
PRIMARY
SMS_ID
100000079831
Created by admin on Sat Dec 16 06:34:49 GMT 2023 , Edited by admin on Sat Dec 16 06:34:49 GMT 2023
PRIMARY
FDA UNII
F5Z7C9RK8U
Created by admin on Sat Dec 16 06:34:49 GMT 2023 , Edited by admin on Sat Dec 16 06:34:49 GMT 2023
PRIMARY
EPA CompTox
DTXSID401317915
Created by admin on Sat Dec 16 06:34:49 GMT 2023 , Edited by admin on Sat Dec 16 06:34:49 GMT 2023
PRIMARY
ECHA (EC/EINECS)
207-590-0
Created by admin on Sat Dec 16 06:34:49 GMT 2023 , Edited by admin on Sat Dec 16 06:34:49 GMT 2023
PRIMARY
WIKIPEDIA
Corynanthine
Created by admin on Sat Dec 16 06:34:49 GMT 2023 , Edited by admin on Sat Dec 16 06:34:49 GMT 2023
PRIMARY
CAS
483-10-3
Created by admin on Sat Dec 16 06:34:49 GMT 2023 , Edited by admin on Sat Dec 16 06:34:49 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY