Dapiprazole

Modify Date: 2025-08-21 16:44:07

Dapiprazole Structure
Dapiprazole structure
Common Name Dapiprazole
CAS Number 72822-12-9 Molecular Weight 325.451
Density 1.2±0.1 g/cm3 Boiling Point 538.9±60.0 °C at 760 mmHg
Molecular Formula C19H27N5 Melting Point N/A
MSDS N/A Flash Point 279.7±32.9 °C

 Use of Dapiprazole


Dapiprazole is a potent, selective and orally active alpha-1 adrenoceptor antagonist. Dapiprazole suppresses the opioid withdrawal symptoms. Dapiprazole is also used as eye drops for reversing mydriasis[1][2][3].

 Names

Name dapiprazole
Synonym More Synonyms

 Dapiprazole Biological Activity

Description Dapiprazole is a potent, selective and orally active alpha-1 adrenoceptor antagonist. Dapiprazole suppresses the opioid withdrawal symptoms. Dapiprazole is also used as eye drops for reversing mydriasis[1][2][3].
Related Catalog
Target

α1-adrenergic receptor

In Vivo Dapiprazole hydrochloride (0-10 mg/kg or 0-3 mg/mice; i.p. or i.c.v.; once) reduces the overall severity of the opiate withdrawal symptoms in mice[1]. Animal Model: Swiss Albino male CD-1 mice weighing 20 -25 g, acute dependence model (mice were injected i.p. with morphine (25 mg/kg) and 2 h later with naloxone (12.5 mg/kg))[1] Dosage: 5, 7.5 and 10 mg/kg (i.p.) or 0.5, 1 and 3 mg/mice (i.c.v.), once Administration: Intraperitoneal injection or intracerebroventricular administration, once Result: Decreased jumping behavior, head shakes and paw shakes when administered just before naloxone. Resulted in a notable suppression of morphine withdrawal symptoms in a dose-related fashion when injected i.c.v..
References

[1]. Valeri P, et al. Effects of dapiprazole, clonidine and yohimbine on the development of dependence and withdrawal behaviour in mice. Drug Alcohol Depend. 1989 Jan;23(1):73-7.

[2]. Allinson RW, et al. Reversal of mydriasis by dapiprazole. Ann Ophthalmol. 1990 Apr;22(4):131-3, 138.

[3]. Hou RH, et al. Arousal and the pupil: why diazepam-induced sedation is not accompanied by miosis. Psychopharmacology (Berl). 2007 Nov;195(1):41-59.

 Chemical & Physical Properties

Density 1.2±0.1 g/cm3
Boiling Point 538.9±60.0 °C at 760 mmHg
Molecular Formula C19H27N5
Molecular Weight 325.451
Flash Point 279.7±32.9 °C
Exact Mass 325.226654
PSA 37.19000
LogP 2.44
Vapour Pressure 0.0±1.4 mmHg at 25°C
Index of Refraction 1.658
InChIKey RFWZESUMWJKKRN-UHFFFAOYSA-N
SMILES Cc1ccccc1N1CCN(CCc2nnc3n2CCCC3)CC1

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
XZ5625000
CHEMICAL NAME :
s-Triazolo(4,3-a)pyridine, 5,6,7,8-tetrahydro-3-(2-(4-(o-tolyl)-1-piperazinyl)et hyl)-, hydrochloride
CAS REGISTRY NUMBER :
72822-12-9
LAST UPDATED :
199009
DATA ITEMS CITED :
1
MOLECULAR FORMULA :
C19-H27-N5.Cl-H
MOLECULAR WEIGHT :
361.97
WISWESSER LINE NOTATION :
T56 AN CNN&TJ B2- AT6N DNTJ DR B1 &GH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
260 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - miosis (pupillary constriction) Behavioral - changes in motor activity (specific assay) Behavioral - ataxia
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 32,668,1982

 DapiprazoleBioassay

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Name: DRUGMATRIX: Opiate delta1 (OP1, DOP) radioligand binding (ligand: [3H] Naltrindole)
Source: ChEMBL
Target: Delta-type opioid receptor
External Id: CHEMBL1909180
Name: Binding affinity towards human GABRA1 in an in vitro assay with cellular components m...
Source: ChEMBL
Target: Gamma-aminobutyric acid receptor subunit gamma-2
External Id: CHEMBL5291799
Name: DRUGMATRIX: Nitric Oxide Synthase, Inducible (iNOS) enzyme inhibition (substrate: L-A...
Source: ChEMBL
Target: Nitric oxide synthase, inducible
External Id: CHEMBL1909179
Name: DRUGMATRIX: Opiate mu (OP3, MOP) radioligand binding (ligand: [3H] Diprenorphine)
Source: ChEMBL
Target: Mu-type opioid receptor
External Id: CHEMBL1909182
Name: DRUGMATRIX: Opiate kappa (OP2, KOP) radioligand binding (ligand: [3H] Diprenorphine)
Source: ChEMBL
Target: Kappa-type opioid receptor
External Id: CHEMBL1909181
Name: DRUGMATRIX: Phosphodiesterase PDE3 enzyme inhibition (substrate: [3H]cAMP + cAMP)
Source: ChEMBL
Target: N/A
External Id: CHEMBL1909184
Name: DRUGMATRIX: Phorbol Ester radioligand binding (ligand: [3H] PDBu)
Source: ChEMBL
Target: N/A
External Id: CHEMBL1909183
Name: DRUGMATRIX: Phosphodiesterase PDE5 enzyme inhibition (substrate: [3H]cGMP + cGMP)
Source: ChEMBL
Target: cGMP-specific 3',5'-cyclic phosphodiesterase
External Id: CHEMBL1909186
Name: DRUGMATRIX: Phosphodiesterase PDE4 enzyme inhibition (substrate: [3H]cAMP + cAMP)
Source: ChEMBL
Target: N/A
External Id: CHEMBL1909185
Name: Binding affinity towards human ESR1 in an in vitro cell free assay (CRO assay) measur...
Source: ChEMBL
Target: Estrogen receptor
External Id: CHEMBL5291792
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 Synonyms

Rev-Eyes
3-[2-[4-(2-methylphenyl)piperazin-1-yl]ethyl]-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine
5,6,7,8-Tetrahydro-3-[2-[4-(2-methylphenyl)-1-piperazinyl]ethyl]-1,2,4-triazolo[4,3-a]pyridine
Dapiprazole
Dapiprazol [German]
Dapirazol
Glamidolo
3-{2-[4-(2-Methylphenyl)piperazin-1-yl]ethyl}-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine
3-[2-(4-o-tolyl-piperazin-1-yl)-ethyl]-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine
3-{2-[4-(2-Methylphenyl)-1-piperazinyl]ethyl}-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine
5,6,7,8-Tetrahydro-3-[2-(4-o-tolyl-1-piperazinyl)ethyl]-s-triazolo[4,3-a]pyridine
5,6,7,8-tetrahydro-3-[2-(4-o-tolyl-1-piperazin)ethyl]-1,2,4-triazolo[4,3-a]pyridine
Reversil
Dapiprazole [INN]
Dapiprazol
dapiprazolum
Dapirazolum
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