Diclazepam

Strukturformel
Allgemeines
Freiname	Diclazepam
Andere Namen	Chlordiazepam; 2′-Chlordiazepam; 7-Chlor-5-(2-chlorphenyl)-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-on;
Summenformel	C16H12Cl2N2O
Kurzbeschreibung	weißer Feststoff[1]
Externe Identifikatoren/Datenbanken
PubChem	76168
Wikidata	Q15408412
Arzneistoffangaben
Wirkstoffklasse	Anxiolytikum; Benzodiazepin;
Eigenschaften
Molare Masse	318,03 g·mol−1
Aggregatzustand	fest[1]
Schmelzpunkt	217–219 °C[1]
Löslichkeit	löslich in Wasser (20,5 mg/l bei 25 °C)[1]
Sicherheitshinweise
GHS-Gefahrstoffkennzeichnung [2] Achtung
H- und P-Sätze	H: 302
	P: 264‐270‐301+312‐330‐501 [2]
	Soweit möglich und gebräuchlich, werden SI-Einheiten verwendet. Wenn nicht anders vermerkt, gelten die angegebenen Daten bei Standardbedingungen.

Diclazepam (2′-Chlordiazepam) ist eine chemische Verbindung aus der Gruppe der Benzodiazepine und wirkt analog zu Diazepam.

Entdeckung

Diclazepam wurde erstmals 1960 von einem Kollektiv um Leo Sternbach bei Hoffmann-La Roche synthetisiert.[3] Die Wirkung ähnelt dem anderer Benzodiazepine: es wirkt angstlösend, krampflösend, hypnotisch, beruhigend, muskelrelaxierend und amnestisch.[4]

Man schätzt, dass die Wirkung von 1 mg Diclazepam etwa der von 5–10 mg Diazepam entspricht.[5][6]

Rechtslage

In Deutschland wurde Diclazepam mit der 30. Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften vom 11. November 2015 dem BtMG in der Anlage II als verkehrs-, aber nicht verschreibungsfähige Substanz unterstellt.[7]

Siehe auch

Schädlicher Gebrauch von Benzodiazepinen

Literatur

Bjoern Moosmann, Philippe Bisel, Volker Auwärter: Characterization of the designer benzodiazepine diclazepam and preliminary data on its metabolism and pharmacokinetics. In: Drug Testing and Analysis, 2014, doi:10.1002/dta.1628
Lauren C. O’Connor, Hazel J. Torrance, Denise A. McKeown: ELISA Detection of Phenazepam, Etizolam, Pyrazolam, Flubromazepam, Diclazepam and Delorazepam in Blood Using Immunalysis® Benzodiazepine Kit. In: Journal of Analytical Toxicology, S. bkv122, doi:10.1093/jat/bkv122.

Einzelnachweise

WHO Expert Committee on Drug Dependence: forty-third report. World Health Organization, 2021, ISBN 978-92-4002302-4, S. 187 (books.google.com).
Diclazepam (CAS 2894-68-0). In: caymanchem.com. Abgerufen am 20. Januar 2022 (englisch).
US Patent 3136815 – Amino substituted benzophenone oximes and derivatives thereof.
Yakubovs'ka et al.: Dopovidi Akademii Nauk Ukrains'koi. RSR, Seriya B: Geologichni, Khimichni ta Biologichni Nauki, 1977, S. 819.
M. Babbini, M. Gaiardi, M. Bartoletti: Anxiolytic versus sedative properties in the benzodiazepines series: Differencies in structure - activity relationships. In: Life Sciences. 25, 1979, S. 15, doi:10.1016/0024-3205(79)90484-3.
„Regarding the potency of this new drug, only limited data can be found in the literature. One study conducted by Babbini et al. showed that diclazepam is approximately 4–8 times more potent than diazepam in terms of reducing motor activity and conflict behavior in rats and studies carried out by Sternbach et al. found diclazepam to be approximately equally potent as diazepam with regard to muscle relaxant and sedative effects in mice and twice as potent than diazepam investigating the same effects in cats. The Ki value at recombinant wild-type α1β2γ2 γ-aminobutyric acid (GABAA) receptors demonstrated a 30 times higher binding affinity for diclazepam than for diazepam. However, Bradley et al. found that diclazepam given in the same doses as diazepam showed no differences in effects on the behavioral activity of monkeys.“
- Bjoern Moosmann, Philippe Bisel, Volker Auwärter: Characterization of the designer benzodiazepine diclazepam and preliminary data on its metabolism and pharmacokinetics. In: Drug Testing and Analysis. 6, 2014, S. 757, doi:10.1002/dta.1628.
Dreißigste Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften Drucksache 399/15 (PDF)

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[WHO-1] WHO Expert Committee on Drug Dependence: forty-third report. World Health Organization, 2021, ISBN 978-92-4002302-4, S. 187 (books.google.com).

[cayman-2] Diclazepam (CAS 2894-68-0). In: caymanchem.com. Abgerufen am 20. Januar 2022 (englisch).

[3] US Patent 3136815 – Amino substituted benzophenone oximes and derivatives thereof.

[4] Yakubovs'ka et al.: Dopovidi Akademii Nauk Ukrains'koi. RSR, Seriya B: Geologichni, Khimichni ta Biologichni Nauki, 1977, S. 819.

[DOI10.1016/0024-3205(79)90484-3-5] M. Babbini, M. Gaiardi, M. Bartoletti: Anxiolytic versus sedative properties in the benzodiazepines series: Differencies in structure - activity relationships. In: Life Sciences. 25, 1979, S. 15, doi:10.1016/0024-3205(79)90484-3.

[DOI10.1002/dta.1628-6] „Regarding the potency of this new drug, only limited data can be found in the literature. One study conducted by Babbini et al. showed that diclazepam is approximately 4–8 times more potent than diazepam in terms of reducing motor activity and conflict behavior in rats and studies carried out by Sternbach et al. found diclazepam to be approximately equally potent as diazepam with regard to muscle relaxant and sedative effects in mice and twice as potent than diazepam investigating the same effects in cats. The Ki value at recombinant wild-type α1β2γ2 γ-aminobutyric acid (GABAA) receptors demonstrated a 30 times higher binding affinity for diclazepam than for diazepam. However, Bradley et al. found that diclazepam given in the same doses as diazepam showed no differences in effects on the behavioral activity of monkeys.“
Bjoern Moosmann, Philippe Bisel, Volker Auwärter: Characterization of the designer benzodiazepine diclazepam and preliminary data on its metabolism and pharmacokinetics. In: Drug Testing and Analysis. 6, 2014, S. 757, doi:10.1002/dta.1628.

[7] Bjoern Moosmann, Philippe Bisel, Volker Auwärter: Characterization of the designer benzodiazepine diclazepam and preliminary data on its metabolism and pharmacokinetics. In: Drug Testing and Analysis. 6, 2014, S. 757, doi:10.1002/dta.1628.

[7] Dreißigste Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften Drucksache 399/15 (PDF)