CORYNANTHINE TARTRATE

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2862619 | https://www.ncbi.nlm.nih.gov/pubmed/6270312 | https://www.ncbi.nlm.nih.gov/pubmed/1356570 |

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

Primary Target	Pharmacology	Potency
Alpha-1A adrenergic receptor 19 Target ID: P35348\|\|\|B0ZBD9\|\|\|Q6RUJ8 Gene ID: 148.0 Gene Symbol: ADRA1A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/2862619 \| https://www.ncbi.nlm.nih.gov/pubmed/6144048 \| https://www.ncbi.nlm.nih.gov/pubmed/6270312	Antagonist 2778	562.0 nM [Kd]
Alpha-2A adrenergic receptor 26 Target ID: P08913 Gene ID: 150.0 Gene Symbol: ADRA2A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/6144048 \| https://www.ncbi.nlm.nih.gov/pubmed/6270312 \| https://www.ncbi.nlm.nih.gov/pubmed/7870186	Antagonist 2778	5.1 null [pKd]
Alpha-2C adrenergic receptor 11 Target ID: P22086 Gene ID: 24175.0 Gene Symbol: Adra2c Target Organism: Rattus norvegicus (Rat) Sources: https://www.ncbi.nlm.nih.gov/pubmed/1356570	Antagonist 2778	232.0 nM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Intra ocular hypertension 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2862619	Primary		Not Provided 504	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Influence of prazosin and clonidine on morphine analgesia, tolerance and withdrawal in mice.	2003 Jan 24	12559372
Pharmacological characterization of unique prazosin-binding sites in human kidney.	2003 Jul	12827214
Ocular hypotensive effects of melatonin receptor agonists in the rabbit: further evidence for an MT3 receptor.	2003 Mar	12642384
Presynaptic alpha1 adrenergic receptors differentially regulate synaptic glutamate and GABA release to hypothalamic presympathetic neurons.	2006 Feb	16249372
[Effect of the endogenous catecholamines synthesized by lymphocytes on T cell proliferation].	2009 Feb	21186623

Patents

Sample Use Guides

In Vivo Use Guide

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 UTC 2023` Edited by `admin` on `Fri Dec 15 15:16:35 UTC 2023`
Record UNII	7359P0A2QF
Record Status	`Validated (UNII)`
Record Version

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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