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Details

Stereochemistry ACHIRAL
Molecular Formula C14H16ClN3S
Molecular Weight 293.815
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 6-[(4-Chlorophenyl)methyl]-5,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepin-2-amine

SMILES

NC1=NC2=C(CCN(CC3=CC=C(Cl)C=C3)CC2)S1

InChI

InChIKey=QHNGFZZXGOFXPN-UHFFFAOYSA-N
InChI=1S/C14H16ClN3S/c15-11-3-1-10(2-4-11)9-18-7-5-12-13(6-8-18)19-14(16)17-12/h1-4H,5-9H2,(H2,16,17)

HIDE SMILES / InChI

Molecular Formula C14H16ClN3S
Molecular Weight 293.815
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/6126817 | https://www.ncbi.nlm.nih.gov/pubmed/3006858

B-HT 958 (2-amino-6-(p-chlorobenzyl)-4H-5,6,7,8-tetrahydrothiazolo[5,4-d]az epine), a compound chemically related to clonidine-like drugs of the azepine type, exerts a strong agonistic effect on brain dopamine autoreceptors. B-HT 958 is a partial agonist at peripheral alpha 2-adrenoceptors. In doses of about 1 mg/kg and with low frequency sympathetic stimulation (less than 6.4 Hz) it acts presynaptically as agonist; in this dose the drug acts postsynaptically mainly as antagonist.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
B-HT 958 lowers blood pressure and heart rate in the rat through stimulation of dopamine receptors.
1986-02
B-HT 958--an antagonist at alpha 2-adrenoceptors and an agonist at dopamine autoreceptors in the brain.
1984-11-13
B-HT 958 stimulates dopamine autoreceptors but blocks noradrenaline autoreceptors in the brain.
1984-11
Patents

Sample Use Guides

Rats: B-HT 958 350 mg/kg i.v. caused significant falls in blood pressure and heart rate which were maximal 5 min after dosing
Route of Administration: Intravenous
In Vitro Use Guide
Curator's Comment: Slices from nucleus accumbens of the rat were preincubated with 3H-dopamine and superfused at 23 degrees C or 37 degrees C. Electrical field stimulation was applied using frequencies of 0.5 or 5 Hz.
B-HT 958 (0.1-10 umol/l) reduced electrically induced overflow of tritium at 37 degrees C/5 Hz, had no effect at 23 degrees C/0.5 Hz, and facilitated tritium overflow at 23 degrees C/5 Hz.
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:01:13 GMT 2025
Edited
by admin
on Mon Mar 31 19:01:13 GMT 2025
Record UNII
BG8CY57KCH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
B-HT-958
Preferred Name English
6-[(4-Chlorophenyl)methyl]-5,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepin-2-amine
Systematic Name English
4H-Thiazolo[4,5-d]azepin-2-amine, 6-[(4-chlorophenyl)methyl]-5,6,7,8-tetrahydro-
Systematic Name English
2-Amino-6-(p-chlorobenzyl)-4H-5,6,7,8-tetrahydrothiazolo(5,4-d)azepine
Systematic Name English
Code System Code Type Description
PUBCHEM
134342
Created by admin on Mon Mar 31 19:01:13 GMT 2025 , Edited by admin on Mon Mar 31 19:01:13 GMT 2025
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FDA UNII
BG8CY57KCH
Created by admin on Mon Mar 31 19:01:13 GMT 2025 , Edited by admin on Mon Mar 31 19:01:13 GMT 2025
PRIMARY
EPA CompTox
DTXSID501003725
Created by admin on Mon Mar 31 19:01:13 GMT 2025 , Edited by admin on Mon Mar 31 19:01:13 GMT 2025
PRIMARY
CAS
83718-64-3
Created by admin on Mon Mar 31 19:01:13 GMT 2025 , Edited by admin on Mon Mar 31 19:01:13 GMT 2025
PRIMARY