Adinazolam

Adinazolam
Clinical data
Trade names	Deracyn
Routes of; administration	Oral
ATC code	N05BA07 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class B1 (Psychoactive drugs); CA: Schedule IV; DE: NpSG (Industrial and scientific use only); UK: Class C; US: Unscheduled (Not FDA approved); UN: Unscheduled;
Pharmacokinetic data
Metabolism	Hepatic
Metabolites	N-desmethyladinazolam N, N-didesmethyladinazolam estazolam alpha-hydroxy-alprazolam
Elimination half-life	< 3 hours
Excretion	Renal
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	37115-32-5 ;
PubChem CID	37632;
DrugBank	DB00546 ;
ChemSpider	34519 ;
UNII	KN08449444;
KEGG	D02770 ;
ChEBI	CHEBI:251412 ;
ChEMBL	ChEMBL328250 ;
CompTox Dashboard (EPA)	DTXSID40190611 ;
Chemical and physical data
Formula	C19H18ClN5
Molar mass	351.84 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	171–172.5 °C (339.8–342.5 °F)
Solubility in water	LogP: 4.16 Soluble in dichloromethane and methanol Salt (mesylate) soluble in water mg/mL (20 °C)
	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 ; Key:GJSLOMWRLALDCT-UHFFFAOYSA-N ;
	(verify)

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 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]

^ FR 2248050, "4,5-dihydro-4h-s-triazolo (4,3-a) (1,4) benzodiazepine - cns depressants, anti-convulsants, anti-aggressives and somatic reflex in", issued 21 January 1977, assigned to Ciba-Geigy AG and Novartis AG.
^ Venkatakrishnan K, von Moltke LL, Duan SX, Fleishaker JC, Shader RI, Greenblatt DJ (March 1998). "Kinetic characterization and identification of the enzymes responsible for the hepatic biotransformation of adinazolam and N-desmethyladinazolam in man". The Journal of Pharmacy and Pharmacology. 50 (3): 265–274. doi:10.1111/j.2042-7158.1998.tb06859.x. PMID 9600717. S2CID 33656240.
^ Dunner D, Myers J, Khan A, Avery D, Ishiki D, Pyke R (June 1987). "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.
^ Lahti RA, Sethy VH, Barsuhn C, Hester JB (November 1983). "Pharmacological profile of the antidepressant adinazolam, a triazolobenzodiazepine". Neuropharmacology. 22 (11): 1277–1282. doi:10.1016/0028-3908(83)90200-9. PMID 6320036. S2CID 667962.
^ "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.
^ Moosmann B, Bisel P, Franz F, Huppertz LM, Auwärter V (November 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. Bibcode:2016JMSp...51.1080M. doi:10.1002/jms.3840. PMID 27535017.

[FR-1] FR 2248050, "4,5-dihydro-4h-s-triazolo (4,3-a) (1,4) benzodiazepine - cns depressants, anti-convulsants, anti-aggressives and somatic reflex in", issued 21 January 1977, assigned to Ciba-Geigy AG and Novartis AG.

[Venkatakrishnan_1998-2] Venkatakrishnan K, von Moltke LL, Duan SX, Fleishaker JC, Shader RI, Greenblatt DJ (March 1998). "Kinetic characterization and identification of the enzymes responsible for the hepatic biotransformation of adinazolam and N-desmethyladinazolam in man". The 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 1987). "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.

[antidepressant-4] Lahti RA, Sethy VH, Barsuhn C, Hester JB (November 1983). "Pharmacological profile of the antidepressant adinazolam, a triazolobenzodiazepine". Neuropharmacology. 22 (11): 1277–1282. doi:10.1016/0028-3908(83)90200-9. PMID 6320036. S2CID 667962.

[Jackson_B_Hester-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.

[Moosmann_2016-6] Moosmann B, Bisel P, Franz F, Huppertz LM, Auwärter V (November 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. Bibcode:2016JMSp...51.1080M. doi:10.1002/jms.3840. PMID 27535017.

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