Adinazolam

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Adinazolam
Adinazolam.svg
Adinazolam3d.png
Clinical data
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • CA: Schedule IV
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class C
Pharmacokinetic data
MetabolismHepatic
Elimination half-life< 3 hours
ExcretionRenal
Identifiers
IUPAC name
  • 1-(8-Chloro-6-phenyl-4H-[1,2,4]triazolo[4,5-a][1,4]benzodiazepin-1-yl)-N,N-dimethylmethanamine
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H18ClN5
Molar mass351.8 g·mol−1
3D model (JSmol)
SMILES
  • Clc3cc2\C(=N/Cc1nnc(n1c2cc3)CN(C)C)c4ccccc4
InChI
  • InChI=1S/C19H18ClN5/c1-24(2)12-18-23-22-17-11-21-19(13-6-4-3-5-7-13)15-10-14(20)8-9-16(15)25(17)18/h3-10H,11-12H2,1-2H3 checkY
  • Key:GJSLOMWRLALDCT-UHFFFAOYSA-N checkY
  

Adinazolam[1] (marketed under the brand name Deracyn) is a tranquilizer of the triazolobenzodiazepine (TBZD) class, which are benzodiazepines (BZDs) fused with a triazole ring. It possesses anxiolytic,[2] anticonvulsant, sedative, and antidepressant[3][4] properties. Adinazolam was developed by Dr. Jackson B. Hester, who was seeking to enhance the antidepressant properties of alprazolam, which he also developed.[5] Adinazolam was never FDA approved and never made available to the public market, however it has been sold as a designer drug.[6]

Side effects[]

Overdose may include muscle weakness, ataxia, dysarthria and particularly in children paradoxical excitement, as well as diminished reflexes, confusion and coma may ensue in more severe cases.[7]

A human study comparing the subjective effects and abuse potential of adinazolam (30 mg and 50 mg) with diazepam, lorazepam and a placebo showed that adinazolam causes the most "mental and physical sedation" and the greatest "mental unpleasantness".[8]

Pharmacodynamics and pharmacokinetics[]

Adinazolam binds to peripheral-type benzodiazepine receptors that interact allosterically with GABA receptors as an agonist to produce inhibitory effects.

Metabolism[]

Adinazolam was reported to have active metabolites in the August 1984 issue of The Journal of Pharmacy and Pharmacology.[9] The main metabolite is N-desmethyladinazolam.[10] NDMAD has an approximately 25-fold high affinity for benzodiazepine receptors as compared to its precursor, accounting for the benzodiazepine-like effects after oral administration.[1] Multiple N-dealkylations lead to the removal of the dimethylaminomethyl side chain, leading to the difference in its potency.[10] The other two metabolites are alpha-hydroxyalprazolam and estazolam.[11] In the August 1986 issue of that same journal, Sethy, Francis and Day reported that proadifen inhibited the formation of N-desmethyladinazolam.[12]

See also[]

References[]

  1. ^ a b FR Patent 2248050
  2. ^ Karthik Venkatakrishnan; Lisa L. Von Moltke; Su Xiang Duan; Joseph C. Fleishaker; Richard I. Shader; David J. Greenblat (March 1998). "Kinetic Characterization and Identification of the Enzymes Responsible for the Hepatic Biotransformation of Adinazolam and N-Desmethyladinazolam in Man". Journal of Pharmacy and Pharmacology. 50 (3): 265–274. doi:10.1111/j.2042-7158.1998.tb06859.x. PMID 9600717. S2CID 33656240.
  3. ^ Dunner D, Myers J, Khan A, Avery D, Ishiki D, Pyke R (June 1998). "Adinazolam-A New Antidepressant: Findings of a Placebo-Controlled, Double-Blind Study in Outpatients with Major Depression". Journal of Clinical Psychopharmacology. 7 (3): 170–172. doi:10.1097/00004714-198706000-00010. PMID 3298327.
  4. ^ Lahti, Robert A.; Vimala H. Sethy; Craig Barsuhn; Jackson B. Hester (November 1983). "Pharmacological profile of the antidepressant adinazolam, a triazolobenzodiazepine". Neuropharmacology. 22 (11): 1277–82. doi:10.1016/0028-3908(83)90200-9. PMID 6320036. S2CID 667962.
  5. ^ "Discovers Award 2004" (PDF). Special Publications. Pharmaceutical Research and Manufacturers of America. April 2004. p. 39. Archived from the original (PDF) on August 24, 2006. Retrieved August 18, 2006.
  6. ^ Moosmann, Bjoern; Bisel, Philippe; Franz, Florian; Huppertz, Laura M.; Auwärter, Volker (2016). "Characterization and in vitro phase I microsomal metabolism of designer benzodiazepines – an update comprising adinazolam, cloniprazepam, fonazepam, 3-hydroxyphenazepam, metizolam, and nitrazolam". Journal of Mass Spectrometry. 51 (11): 1080–1089. doi:10.1002/jms.3840. ISSN 1096-9888. PMID 27535017.
  7. ^ "Adinazolam". DrugBank.
  8. ^ M. Bird; D. Katz; M. Orzack; L. Friedman; E. Dessain; B. Beake; J. McEachern; J. Cole (1987). "The Abuse Potential of Adinazolam: A Comparison with Diazepam, Lorazepam and Placebo" (PDF). NIDA Research Monograph No. 81. Archived from the original (PDF) on 2016-12-22. Retrieved 2015-12-17.
  9. ^ Sethy, Vimala H.; R. J. Collins; E. G. Daniels (August 1984). "Determination of biological activity of adinazolam and its metabolites". Journal of Pharmacy and Pharmacology. 36 (8): 546–8. doi:10.1111/j.2042-7158.1984.tb04449.x. PMID 6148400. S2CID 21094654.
  10. ^ a b Peng, G. W. (August 1984). "Assay of adinazolam in plasma by liquid chromatography". Journal of Pharmaceutical Sciences. 73 (8): 1173–5. doi:10.1002/jps.2600730840. PMID 6491930.
  11. ^ Fraser, A. D.; A. F. Isner; W. Bryan (November–December 1993). "Urinary screening for adinazolam and its major metabolites by the Emit d.a.u. and FPIA benzodiazepine assays with confirmation by HPLC". Journal of Analytical Toxicology. 17 (7): 427–31. doi:10.1093/jat/17.7.427. PMID 8309217.
  12. ^ Sethy, Vimala H.; Jonathan W. Francis; J. S. Day (August 1986). "The effect of proadifen on the metabolism of adinazolam". Journal of Pharmacy and Pharmacology. 38 (8): 631–2. doi:10.1111/j.2042-7158.1986.tb03099.x. PMID 2876087. S2CID 9394686.
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