U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C10H12ClN3.HNO3
Molecular Weight 272.688
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TOLONIDINE NITRATE

SMILES

O[N+]([O-])=O.CC1=CC(Cl)=C(NC2=NCCN2)C=C1

InChI

InChIKey=SEIGDXGATKHXKR-UHFFFAOYSA-N
InChI=1S/C10H12ClN3.HNO3/c1-7-2-3-9(8(11)6-7)14-10-12-4-5-13-10;2-1(3)4/h2-3,6H,4-5H2,1H3,(H2,12,13,14);(H,2,3,4)

HIDE SMILES / InChI

Molecular Formula HNO3
Molecular Weight 63.0128
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C10H12ClN3
Molecular Weight 209.675
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Tolonidine, 2(2-chloro-p-toluidino)-2-imidazoline-nitrate, is a substance chemically related to clonidine. In the anesthetized dog, tolonidine administered i.v. decreased the amplitude of ventricular contractions, reduced aortic blood flow and increased peripheral vascular resistances. In the bivagotomized pithed rat, tolonidine induced a long-lasting increase in blood pressure with no secondary hypotension, thus suggesting peripheral sympathomimetic properties, however, contractions of seminal vesicles in vitro were not obtained. The product proved to have no peripheral sympatholytic or parasympatholytic properties.

CNS Activity

Curator's Comment: In the central nervous system, tolonidine produced a sedation which first appeared at doses having an antihypertensive effect but which was only fully apparent with increased doses.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Pharmacological properties of 2-(2-chloro-p-toluidino)-2-imidazoline-nitrate (tolonidine), a new antihypertensive agent. II. Action on cardiac contraction, circulatory parameters, autonomic receptors and diuresis.
1975-11
Pharmacological properties of 2-(2-chloro-p-toluidino)-2-imidazoline-nitrate (Tolonidine), a new antihypertensive agent. I. Action on blood pressure and heart rate.
1975-10
Pharmacological properties of 2-(2-chloro-p-toluidino)-2-imidazoline-nitrate (tolonidine), a new antihypertensive agent. III. Action on the secretions of the digestive tract and on the central nervous system, acute toxicity.
1975
Patents

Sample Use Guides

The rats: systemic administration of tolonidine in rats (0.05-5.0 umol/Kg) produced behavioural and electrocortical slow-wave sleep lasting between 35 and 200 min depending on the dose. In addition, a dose-dependent fall in deep body temperature was observed. Similar effects were evoked by infusing tolonidine (5-80 nmol) into the third cerebral ventricle.
Route of Administration: Intraperitoneal
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:53:17 GMT 2025
Edited
by admin
on Mon Mar 31 18:53:17 GMT 2025
Record UNII
75W1B0GTHA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TOLONIDINE NITRATE
MART.   MI   WHO-DD  
Common Name English
2-(2-CHLORO-P-TOLUIDINO)-2-IMIDAZOLINE NITRATE
Preferred Name English
TOLONIDINE NITRATE [MI]
Common Name English
TOLONIDINE NITRATE [MART.]
Common Name English
Tolonidine nitrate [WHO-DD]
Common Name English
Code System Code Type Description
ECHA (EC/EINECS)
260-785-2
Created by admin on Mon Mar 31 18:53:17 GMT 2025 , Edited by admin on Mon Mar 31 18:53:17 GMT 2025
PRIMARY
EVMPD
SUB04910MIG
Created by admin on Mon Mar 31 18:53:17 GMT 2025 , Edited by admin on Mon Mar 31 18:53:17 GMT 2025
PRIMARY
SMS_ID
100000084636
Created by admin on Mon Mar 31 18:53:17 GMT 2025 , Edited by admin on Mon Mar 31 18:53:17 GMT 2025
PRIMARY
MERCK INDEX
m971
Created by admin on Mon Mar 31 18:53:17 GMT 2025 , Edited by admin on Mon Mar 31 18:53:17 GMT 2025
PRIMARY Merck Index
PUBCHEM
198360
Created by admin on Mon Mar 31 18:53:17 GMT 2025 , Edited by admin on Mon Mar 31 18:53:17 GMT 2025
PRIMARY
FDA UNII
75W1B0GTHA
Created by admin on Mon Mar 31 18:53:17 GMT 2025 , Edited by admin on Mon Mar 31 18:53:17 GMT 2025
PRIMARY
CAS
57524-15-9
Created by admin on Mon Mar 31 18:53:17 GMT 2025 , Edited by admin on Mon Mar 31 18:53:17 GMT 2025
PRIMARY
EPA CompTox
DTXSID101350514
Created by admin on Mon Mar 31 18:53:17 GMT 2025 , Edited by admin on Mon Mar 31 18:53:17 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY