GZ-793A | CAS#1356447-90-9 | VMAT2 inhibitor

MedKoo Cat#: 558410 | Name: GZ-793A

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

GZ-793A inhibits dopamine uptake at the vesicular monoamine transporter-2 (VMAT2. A lobelane analog, GZ-793A interacts with the vesicular monoamine transporter-2 to inhibit the effect of methamphetamine.

Chemical Structure

GZ-793A

CAS#1356447-90-9

Theoretical Analysis

MedKoo Cat#: 558410

Name: GZ-793A

CAS#: 1356447-90-9

Chemical Formula: C26H38ClNO4

Exact Mass: 463.2500

Molecular Weight: 464.04

Elemental Analysis: C, 67.30; H, 8.25; Cl, 7.64; N, 3.02; O, 13.79

Price and Availability

Size	Price	Availability	Quantity
25mg	USD 850.00	2 Weeks

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Related CAS #

No Data

Synonym

GZ-793A; GZ 793A; GZ793A;

IUPAC/Chemical Name

(R)-3-[2,6-cis-Di(4-methoxyphenethyl)piperidin-1-yl]propane-1,2-diol hydrochloride

InChi Key

FLFFCQKGCYZDOI-SJUVJREQSA-N

InChi Code

InChI=1S/C26H37NO4.ClH/c1-30-25-14-8-20(9-15-25)6-12-22-4-3-5-23(27(22)18-24(29)19-28)13-7-21-10-16-26(31-2)17-11-21;/h8-11,14-17,22-24,28-29H,3-7,12-13,18-19H2,1-2H3;1H/t22-,23+,24-;/m1./s1

SMILES Code

OC[C@H](O)CN1[C@H](CCC2=CC=C(OC)C=C2)CCC[C@@H]1CCC3=CC=C(OC)C=C3.[H]Cl

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 464.04 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Penthala NR, Ponugoti PR, Nickell JR, Deaciuc AG, Dwoskin LP, Crooks PA. Pyrrolidine analogs of GZ-793A: synthesis and evaluation as inhibitors of the vesicular monoamine transporter-2 (VMAT2). Bioorg Med Chem Lett. 2013 Jun 1;23(11):3342-5. doi: 10.1016/j.bmcl.2013.03.092. Epub 2013 Apr 2. PubMed PMID: 23597792; PubMed Central PMCID: PMC3725993. 2: Horton DB, Nickell JR, Zheng G, Crooks PA, Dwoskin LP. GZ-793A, a lobelane analog, interacts with the vesicular monoamine transporter-2 to inhibit the effect of methamphetamine. J Neurochem. 2013 Oct;127(2):177-86. doi: 10.1111/jnc.12371. Epub 2013 Aug 19. PubMed PMID: 23875622; PubMed Central PMCID: PMC3822038. 3: Meyer AC, Neugebauer NM, Zheng G, Crooks PA, Dwoskin LP, Bardo MT. Effects of VMAT2 inhibitors lobeline and GZ-793A on methamphetamine-induced changes in dopamine release, metabolism and synthesis in vivo. J Neurochem. 2013 Oct;127(2):187-98. doi: 10.1111/jnc.12373. Epub 2013 Aug 20. PubMed PMID: 23875705; PubMed Central PMCID: PMC3795981. 4: Wilmouth CE, Zheng G, Crooks PA, Dwoskin LP, Bardo MT. 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. Epub 2013 Sep 26. PubMed PMID: 24075974; PubMed Central PMCID: PMC3842023. 5: Alvers KM, Beckmann JS, Zheng G, Crooks PA, Dwoskin LP, Bardo MT. The effect of VMAT2 inhibitor GZ-793A on the reinstatement of methamphetamine-seeking in rats. Psychopharmacology (Berl). 2012 Nov;224(2):255-62. doi: 10.1007/s00213-012-2748-3. Epub 2012 May 26. PubMed PMID: 22638813; PubMed Central PMCID: PMC3680349. 6: Beckmann JS, Denehy ED, Zheng G, Crooks PA, Dwoskin LP, Bardo MT. The effect of a novel VMAT2 inhibitor, GZ-793A, on methamphetamine reward in rats. Psychopharmacology (Berl). 2012 Mar;220(2):395-403. doi: 10.1007/s00213-011-2488-9. Epub 2011 Sep 21. PubMed PMID: 21938414; PubMed Central PMCID: PMC3390966. 7: Joolakanti SR, Nickell JR, Janganati V, Zheng G, Dwoskin LP, Crooks PA. Lobelane analogues containing 4-hydroxy and 4-(2-fluoroethoxy) aromatic substituents: Potent and selective inhibitors of [(3)H]dopamine uptake at the vesicular monoamine transporter-2. Bioorg Med Chem Lett. 2016 May 15;26(10):2422-2427. doi: 10.1016/j.bmcl.2016.03.119. Epub 2016 Apr 1. PubMed PMID: 27080180; PubMed Central PMCID: PMC4977194. 8: Horton DB, Siripurapu KB, Zheng G, Crooks PA, Dwoskin LP. Novel N-1,2-dihydroxypropyl analogs of lobelane inhibit vesicular monoamine transporter-2 function and methamphetamine-evoked dopamine release. J Pharmacol Exp Ther. 2011 Oct;339(1):286-97. doi: 10.1124/jpet.111.184770. Epub 2011 Jul 21. PubMed PMID: 21778282; PubMed Central PMCID: PMC3186287. 9: Nickell JR, Siripurapu KB, Horton DB, Zheng G, Crooks PA, Dwoskin LP. 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. Epub 2016 Dec 13. PubMed PMID: 27986625. 10: Nickell JR, Siripurapu KB, Vartak A, Crooks PA, Dwoskin LP. 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. Review. PubMed PMID: 24484975; PubMed Central PMCID: PMC4084610.