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Pentylenetetrazol
Chemical compound
Chemical compound
| Field | Value | |
|---|---|---|
| Verifiedfields | changed | |
| Watchedfields | changed | |
| INN | Pentetrazol | |
| verifiedrevid | 415933541 | |
| IUPAC_name | 6,7,8,9-Tetrahydro-5*H*-tetrazolo(1,5-*a*)azepine | |
| image | Pentylenetetrazol.svg | |
| image_class | skin-invert-image | |
| width | 150 | |
| image2 | File:Pentylenetetrazol ball-and-stick model.png | |
| image_class2 | bg-transparent | |
| <!--Clinical data--> | tradename | Metrazol, others |
| pregnancy_AU | ||
| pregnancy_US | ||
| legal_AU | ||
| legal_UK | ||
| legal_US | ||
| routes_of_administration | ||
| excretion | ||
| CAS_number_Ref | ||
| CAS_number | 54-95-5 | |
| ATC_prefix | R07 | |
| ATC_suffix | AB03 | |
| PubChem | 5917 | |
| DrugBank_Ref | ||
| ChemSpiderID_Ref | ||
| ChemSpiderID | 5704 | |
| UNII_Ref | ||
| UNII | WM5Z385K7T | |
| ChEBI_Ref | ||
| ChEBI | 34910 | |
| ChEMBL_Ref | ||
| ChEMBL | 116943 | |
| KEGG_Ref | ||
| KEGG | D07409 | |
| synonyms | Pentylenetetrazole; pentetrazol; pentamethylenetetrazol | |
| <!--Chemical data--> | C | 6 |
| H | 10 | |
| N | 4 | |
| smiles | C1CCc2nnnn2CC1 | |
| StdInChI_Ref | ||
| StdInChI | 1S/C6H10N4/c1-2-4-6-7-8-9-10(6)5-3-1/h1-5H2 | |
| StdInChIKey_Ref | ||
| StdInChIKey | CWRVKFFCRWGWCS-UHFFFAOYSA-N |
| elimination_half-life =
Pentylenetetrazol (PTZ), also known as pentylenetetrazole, pentetrazol (INN), and pentamethylenetetrazol, is a drug formerly used as a circulatory and respiratory stimulant. High doses cause convulsions, as discovered by Hungarian-American neurologist and psychiatrist Ladislas J. Meduna in 1934. It has been used in convulsive therapy, and was found to be effective in treating depression, but side effects, such as uncontrolled seizures, were difficult to avoid. In 1939, pentylenetetrazol was replaced by electroconvulsive therapy, which is easier to administer, as the preferred method for inducing seizures in England's mental hospitals. In the US, pentylenetetrazol’s approval by the Food and Drug Administration (FDA) was revoked in 1982. It is used in Italy as a cardio-respiratory stimulant in combination with dihydrocodeine in a cough suppressant drug.
Side effects
Pentylenetetrazol is anxiogenic and has been known to induce severe anxiety in humans.
Mechanism of action
The mechanism of pentylenetetrazol is not well understood, and it may have multiple mechanisms of action. In 1984, Squires et al. published a report analyzing pentylenetetrazol and several structurally related convulsant drugs. They found that in vivo convulsant potency was strongly correlated to in vitro affinity to the picrotoxin binding site on the GABAA receptor complex. Many GABAA receptor ligands, such as diazepam and phenobarbital, are effective anticonvulsants, but pentylenetetrazol presumably has the opposite effect when it binds to the GABAA receptor.
Several studies have focused on the way pentylenetetrazol influences neuronal ion channels. A 1987 study found that pentylenetetrazol increases calcium influx and sodium influx, both of which depolarize the neuron. Because these effects were antagonized by calcium channel blockers, pentylenetetrazol apparently acts at calcium channels, and it causes them to lose selectivity and conduct sodium ions, as well.
Research
Pentylenetetrazol has been used experimentally to study seizure phenomena and to identify pharmaceuticals that may control seizure susceptibility. For instance, researchers can induce status epilepticus in animal models. Pentylenetetrazol is also a prototypical anxiogenic drug and has been extensively used in animal models of anxiety. Pentylenetetrazol produces a reliable discriminative stimulus, which is largely mediated by the GABAA receptor. Several classes of compounds can modulate the pentylenetetrazol discriminative stimulus, including 5-HT1A, 5-HT3, NMDA, glycine, and L-type calcium channel ligands.
Pentylenetetrazol is being studied as a wakefulness-promoting agent in the treatment of idiopathic hypersomnia and narcolepsy.
References
References
- (1940). "Consequences of metrazol shock therapy". American Journal of Psychiatry.
- Minkel JR. (February 25, 2007). "Drug May Counteract Down Syndrome". Scientific American.
- "Cardiazol-Paracodina". Agenzia Italiana del Farmaco.
- (2009). "Current Topics in Behavioral Neurosciences". Springer Berlin Heidelberg.
- (October 1984). "Convulsant potencies of tetrazoles are highly correlated with actions on GABA/benzodiazepine/picrotoxin receptor complexes in brain". Life Sciences.
- (1987). "The ionic mechanism of the pentylenetetrazol convulsions". Acta Biologica Hungarica.
- (June 2002). "The discriminative stimulus effects of pentylenetetrazol as a model of anxiety: recent developments". Neuroscience and Biobehavioral Reviews.
- (28 June 2020). "Pentylenetetrazole - Balance Therapeutics". Springer Nature Switzerland AG.
- (3 October 2018). "Advances in pharmaceutical treatment options for narcolepsy". Expert Opinion on Orphan Drugs.
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