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85798-08-9 molecular structure
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(4aR,8aR)-5-propyl-2H,4H,4aH,5H,6H,7H,8H,8aH,9H-pyrido[2,3-f]indazole hydrochloride

ChemBase ID: 134069
Molecular Formular: C13H22ClN3
Molecular Mass: 255.78688
Monoisotopic Mass: 255.1502254
SMILES and InChIs

SMILES:
CCCN1CCC[C@H]2[C@H]1Cc1c[nH]nc1C2.Cl
Canonical SMILES:
CCCN1CCC[C@H]2[C@H]1Cc1c[nH]nc1C2.Cl
InChI:
InChI=1S/C13H21N3.ClH/c1-2-5-16-6-3-4-10-7-12-11(8-13(10)16)9-14-15-12;/h9-10,13H,2-8H2,1H3,(H,14,15);1H/t10-,13-;/m1./s1
InChIKey:
HJHVRVJTYPKTHX-HTMVYDOJSA-N

Cite this record

CBID:134069 http://www.chembase.cn/molecule-134069.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(4aR,8aR)-5-propyl-2H,4H,4aH,5H,6H,7H,8H,8aH,9H-pyrido[2,3-f]indazole hydrochloride
IUPAC Traditional name
(4aR,8aR)-5-propyl-2H,4H,4aH,6H,7H,8H,8aH,9H-pyrido[2,3-f]indazole hydrochloride
Synonyms
(–)-Quinpirole monohydrochloride
trans-(–)-(4aR)-4,4a,5,6,7,8,8a,9-Octahydro-5-propyl-1H-pyrazolo[3,4-g]quinoline monohydrochloride
LY-171,555
(-)-Quinpirole hydrochloride
CAS Number
85798-08-9
MDL Number
MFCD00069336
PubChem SID
24277929
162228346
PubChem CID
55397

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Sigma Aldrich
Q102 external link Add to cart Please log in.
Data Source Data ID
PubChem 55397 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Lipinski's Rule of Five true  Acid pKa 16.111439 
H Acceptors H Donor
LogD (pH = 5.5) -1.3089768  LogD (pH = 7.4) -0.31849062 
Log P 2.140967  Molar Refractivity 66.8137 cm3
Polarizability 25.464058 Å3 Polar Surface Area 31.92 Å2
Rotatable Bonds

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
0.1 M HCl: soluble23 mg/mL expand Show data source
H2O: soluble7.3 mg/mL expand Show data source
Apperance
white solid expand Show data source
Optical Rotation
[α]25/D -124.5°, c = 0.4 in H2O(lit.) expand Show data source
RTECS
UR0809270 expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
-20°C expand Show data source
Gene Information
human ... DRD2(1813), DRD3(1814) expand Show data source
Purity
≥98% (HPLC) expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - Q102 external link
Legal Information
Manufactured and sold with the permission of Eli Lilly and Company.
Biochem/physiol Actions
The putative D2 dopamine receptor agonist quinpirole (LY 171,555) is the most widely used D2 agonist in in vivo and in vitro studies Active enantiomer of (±)-quinpirole. Quinpirole is a dopamine agonist with high affinity for the D2 and D3 dopamine receptor subtypes. Specific [3H]quinpirole binding in rat brain was saturable, and dependent on temperature, membrane concentration, sodium concentration and guanine nucleotides. Saturation analysis revealed high affinity binding characteristics (KD = 2.3 +/- 0.3 nM) which were confirmed by association-dissociation kinetics. The regional distribution of [3H]quinpirole binding sites roughly paralleled the distribution of [3H]spiperone binding sites, with greatest densities present in the striatum, nucleus accumbens and olfactory tubercles. A variety of drugs, most notably monoamine oxidase inhibitors (MAOls), inhibit the binding of [3H]quinpirole, but not [3H]spiperone or [3H](-)N-n-Propylnorapomorphine, in rat striatal membranes by a mechanism that does not appear to involve the enzymatic activity of MAO. Clinically antidepressant MAOIs exhibited selectivity between sites labeled by [3H]quinpirole and [3H]spiperone as did a number of structurally related propargylamines and N-acylethylenediamine derivatives and other drugs such as debrisoquin and phenylbiguanide. The MAOIs clorgyline and Ro 41-1049 were the most potent. MAOIs interact with a novel binding site that is labeled by [3H]quinpirole or that modulates [3H]quinpirole binding. This site may be associated with D2-like dopamine receptors.

REFERENCES

REFERENCES

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PATENTS

PATENTS

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