ChemicalBook CAS DataBase List 1356447-90-9

1356447-90-9

Name	3-[(2R,6S)-2,6-Bis[2-(4-methoxyphenyl)ethyl]-1-piperidinyl]-(2R)-1,2-propanediol hydrochloride
CAS	1356447-90-9
Molecular Formula	C26H38ClNO4
MDL Number	MFCD27952933
Molecular Weight	464.04
MOL File	1356447-90-9.mol

Chemical Properties

storage temp.	2-8°C
solubility	H2O: soluble3mg/mL, clear
form	powder
color	white to beige
Water Solubility	H2O: 3mg/mL, clear
InChIKey	FLFFCQKGCYZDOI-SJUVJREQSA-N
SMILES	Cl.N1([C@H](CCC[C@H]1CCc3ccc(cc3)OC)CCc2ccc(cc2)OC)C[C@@H](O)CO

Safety Data

Hazard Codes	N
Risk Statements	50/53 less more
Safety Statements	60-61 less more
RIDADR	UN 3077 9 / PGIII
WGK Germany	3
Storage Class	11 - Combustible Solids
Hazard Classifications	Aquatic Acute 1 Aquatic Chronic 1

Hazard Information

Uses

GZ-793A is an orally active and selective vesicular monoamine transporter-2 (VMAT2) inhibitor, with an Ki of 0.029 μM. GZ-793A inhibits the neurochemical effects of methamphetamine (METH)-induced dopamine release. GZ-793A can be used for research of METH addiction[1][2][3].

Biological Activity

GZ-793A is a selective inhibitor of vesicular monoamine transporter 2 (VMAT2)which transports the monoamine neurotransmitters from cellular cytosol into synaptic vesicles. GZ-793A is 50-fold selective for VM at over the serotonin or dopamine transporters. VMAT2 has recently been considered a target for the treatment of methamphetamine abuse. In r at studiesGZ-793A decreased self-administration of methamphetamine with no development of tolerance.

in vivo

GZ-793A (30, 60, 120 or 240 mg/kg; p.o.; once) decreases the number of METH infusions self-administered across each time interval evaluats in a dose-dependent manner^[1].
GZ-793A (1-100 μM; 90 min) inhibits METH (5 μM)-evoked fractional dopamine releases^[2].

Animal Model:	Adult male Sprague-Dawley rats^[1].
Dosage:	30, 60, 120 or 240 mg/kg
Administration:	Oral administration; once.
Result:	Decreased the number of METH infusions self-administered in a dose-dependent manner, and with an ~85% reduction at the highest dose (240 mg/kg). Decreased the METH self-administration produced by lasted at least 180 min.

Animal Model:	Male Sprague-Dawley rats (250–275 g; 9-week-old; 0.5 mm thick rats coronal striatal slices are used)^[2].
Dosage:	1-100 μM
Administration:	90 min
Result:	Inhibited methamphetamine-evoked dopamine released in a concentration-dependent manner.

References

[1] Wilmouth CE, et al. Oral administration of GZ-793A, a VMAT2 inhibitor, decreases methamphetamine self-administration in rats. Pharmacol Biochem Behav. 2013 Nov;112:29-33. DOI:10.1016/j.pbb.2013.09.006
[2] Nickell JR, et al. GZ-793A inhibits the neurochemical effects of methamphetamine via a selective interaction with the vesicular monoamine transporter-2. Eur J Pharmacol. 2017 Jan 15;795:143-149. DOI:10.1016/j.ejphar.2016.12.016
[3] Nickell JR, et al. The vesicular monoamine transporter-2: an important pharmacological target for the discovery of novel therapeutics to treat methamphetamine abuse. Adv Pharmacol. 2014;69:71-106. DOI:10.1016/B978-0-12-420118-7.00002-0

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