| Stereochemistry | ACHIRAL |
| Molecular Formula | C6H10N4 |
| Molecular Weight | 138.1704 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C1CCN2N=NN=C2CC1
InChI
InChIKey=CWRVKFFCRWGWCS-UHFFFAOYSA-N
InChI=1S/C6H10N4/c1-2-4-6-7-8-9-10(6)5-3-1/h1-5H2
| Molecular Formula | C6H10N4 |
| Molecular Weight | 138.1704 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Pentetrazol (pentylenetetrazole, BTD-001) is a pharmaceutical agent that displays activity as a central nervous system and respiratory stimulant. It is considered a non-competitive gamma-aminobutyric acid (GABA) antagonist. Pentetrazol (pentylenetetrazole) has been used experimentally to study seizure phenomenon and to identify pharmaceuticals that may control seizure susceptibility. GABA is thought to play a role in promoting sleep and its function is believed to be elevated in idiopathic hypersomnia. By blocking GABA’s function, pentetrazol (pentylenetetrazole, BTD-001) is expected to reduce excessive daytime sleepiness.
CNS Activity
Originator
Approval Year
Doses
AEs
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as victim
Sourcing
PubMed
Sample Use Guides
In rat alpha1/beta2/gamma2 gamma-aminobutyric acid (GABA) type A receptors, pentetrazol inhibited GABA-activated Cl(-) current in a concentration-dependent, voltage-independent manner, with an IC50 of 0.62 +/- 0.13 mM. The mechanism of inhibition appeared competitive with respect to GABA in both rat and human alpha1/beta2/gamma2 receptors. Varying subunit configuration (change or lack of alpha subunit isoform or lack of gamma2 subunit) had modest effects on pentetrazol-induced inhibition, as evidenced by comparable IC50 values (0.6-2.2 mM) in all receptor configurations tested. Using a one-site model for pentetrazol interaction with alpha1/beta2/gamma2 receptors, the association rate (k(+1)) was found to be 1.14 x 10^3 M(-1)s(-1) and the dissociation rate (k(-1)) was 0.476 s(-1), producing a functional Kd of 0.418 mM.
