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Q1004

Sigma-Aldrich

Quipazine maleate salt

Synonym(s):

2-(1-Piperazinyl)quinoline maleate salt

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About This Item

Empirical Formula (Hill Notation):
C13H15N3 · C4H4O4
CAS Number:
5786-68-5
Molecular Weight:
329.35
EC Number:
227-314-2
MDL number:
MFCD00133796
UNSPSC Code:
12352200
PubChem Substance ID:
24278122
NACRES:
NA.77

solubility

H2O: soluble
alcohol: soluble
dilute aqueous acid: soluble

Quality Level

200

storage temp.

2-8°C

SMILES string

OC(=O)\C=C/C(O)=O.C1CN(CCN1)c2ccc3ccccc3n2

InChI

1S/C13H15N3.C4H4O4/c1-2-4-12-11(3-1)5-6-13(15-12)16-9-7-14-8-10-16;5-3(6)1-2-4(7)8/h1-6,14H,7-10H2;1-2H,(H,5,6)(H,7,8)/b;2-1-

InChI key

QYJJDHZHSCTBII-BTJKTKAUSA-N

Gene Information

human ... HTR1A(3350) , HTR1B(3351) , HTR1D(3352) , HTR1E(3354) , HTR1F(3355) , HTR2A(3356) , HTR2B(3357) , HTR2C(3358) , HTR3A(3359) , HTR3B(9177) , HTR3C(170572) , HTR3D(200909) , HTR3E(285242) , HTR4(3360) , HTR5A(3361) , HTR5B(645694) , HTR6(3362) , HTR7(3363)

Application

Quipazine maleate salt has been used as a serotonin receptor agonist to study its effects on mouse models with spinal cord injury. It has also been used as a serotonin receptor agonist to study its effects on the locomotion of zebrafish.

Biochem/physiol Actions

Quipazine belongs to the class of psychedelics and acts as a serotonin/5-hydroxytryptamine-2A/C receptor agonist. It also acts as an inhibitor of prolactin.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Precautionary Statements

P301 + P310 + P330

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Grégoire Courtine et al.
Nature neuroscience, 12(10), 1333-1342 (2009-09-22)
After complete spinal cord transections that removed all supraspinal inputs in adult rats, combinations of serotonergic agonists and epidural electrical stimulation were able to acutely transform spinal networks from nonfunctional to highly functional and adaptive states as early as 1
I D Knowles et al.
British journal of pharmacology, 128(3), 530-542 (1999-10-12)
1. The effects of injections i.c.v. of quipazine, (2 micromol kg-1) and 1-(2,5-di-methoxy-4-iodophenyl)-2-aminopropane (DOI; 2 micromol kg-1) on renal sympathetic and phrenic nerve activity, mean arterial blood pressure (MAP) and heart rate were investigated in alpha-chloralose anaesthetized rats pretreated with
Dilip Kumar Pandey et al.
Pharmacology, biochemistry, and behavior, 94(3), 363-373 (2009-10-06)
Collective evidence suggests that inhibition of neuronal 5-hydroxytryptamine type 2A (5-HT(2A)) receptors contributes to the assuagement of depression-like behaviour in rodents. The present study evaluated the antidepressant-like effect of the 5-((4-benzo [alpha] isothiazol-3-yl) piperazin-1-yl) methyl)-6-chloroindolin-2-one (BIP-1), a compound having affinity
Mario de la Fuente Revenga et al.
ACS chemical neuroscience, 12(5), 831-844 (2021-01-06)
Known classic psychedelic serotonin 2A receptor (5-HT2AR) agonists retain a tryptamine or phenethylamine at their structural core. However, activation of the 5-HT2AR can be elicited by drugs lacking these fundamental scaffolds. Such is the case of the N-substituted piperazine quipazine.
Sabine Rehm et al.
Birth defects research. Part B, Developmental and reproductive toxicology, 80(3), 253-257 (2007-06-16)
Observations associated with drug-induced hyper- or hypoprolactinemia in rat toxicology studies may be similar and include increased ovarian weight due to increased presence of corpora lutea. Hyperprolactinemia may be distinguished if mammary gland hyperplasia with secretion and/or vaginal mucification is
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