Nefazodone HCl | CAS#82752-99-6 | 5-HT2 receptors inhibitor | SERT inhibitor | NET inhibitor | hERG K+

MedKoo Cat#: 540313 | Name: Nefazodone HCl

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Description:

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

Nefazodone HCl is an inhibitor of 5-HT2 receptors, SERT, NET, and hERG K+ channels used to treat mood disorders. It decreases immobility time in the forced swim test.

Chemical Structure

Nefazodone HCl

CAS#82752-99-6 (HCl)

Theoretical Analysis

MedKoo Cat#: 540313

Name: Nefazodone HCl

CAS#: 82752-99-6 (HCl)

Chemical Formula: C25H33Cl2N5O2

Exact Mass: 0.0000

Molecular Weight: 506.47

Elemental Analysis: C, 59.29; H, 6.57; Cl, 14.00; N, 13.83; O, 6.32

Price and Availability

Size	Price	Availability
1g	USD 285.00	2 weeks
2g	USD 450.00	2 weeks
5g	USD 850.00	2 Weeks

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Related CAS #

82752-99-6 (HCl) 83366-66-9 (free base)

Synonym

BMY 13754; BMY13754; BMY-13754; Dutonin; Nefazodone HCl; Rulivan; MJ 13754 1; MJ-13754-1; MJ137541

IUPAC/Chemical Name

2-(3-(4-(3-chlorophenyl)piperazin-1-yl)propyl)-5-ethyl-4-(2-phenoxyethyl)-2,4-dihydro-3H-1,2,4-triazol-3-one hydrochloride

InChi Key

DYCKFEBIOUQECE-UHFFFAOYSA-N

InChi Code

InChI=1S/C25H32ClN5O2.ClH/c1-2-24-27-31(25(32)30(24)18-19-33-23-10-4-3-5-11-23)13-7-12-28-14-16-29(17-15-28)22-9-6-8-21(26)20-22;/h3-6,8-11,20H,2,7,12-19H2,1H3;1H

SMILES Code

O=C1N(CCCN2CCN(C3=CC=CC(Cl)=C3)CC2)N=C(CC)N1CCOC4=CC=CC=C4.[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

>2 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

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Nefazodone hydrochloride (BMY-13754) is a potent and selective 5HT2A (Ki=5.8 nM) antagonist.

In vitro activity:

In glucose-containing medium, nefazodone-induced ATP depletion from Huh7 cells was biphasic. Huh7 cells in glucose-free medium were more sensitive to nefazodone than those in glucose-containing medium, losing the biphasic inhibition. Nefazodone-induced ATP depletion in primary cultured mouse hepatocytes, mainly dependent on oxidative phosphorylation, was monophasic. At lower extracellular concentrations, nefazodone inhibited the oxygen consumption of Huh7 cells, whereas at higher extracellular concentrations, it also inhibited the extracellular acidification. Reference: J Pharmacol Exp Ther. 2020 Nov;375(2):239-246. https://pubmed.ncbi.nlm.nih.gov/32848075/

In vivo activity:

Six common marmosets developed parkinsonism following administration of MPTP, after which they were treated chronically with L-DOPA to induce stable dyskinesia and PLBs. In behavioural experiments, nefazodone (0.01, 0.1 and 1 mg/kg) or vehicle was administered in combination with L-DOPA and its effects on dyskinesia, PLBs and parkinsonian disability were assessed. The addition of nefazodone 0.01, 0.1 and 1 mg/kg to L-DOPA reduced the severity of peak dose dyskinesia by ≈ 21%, ≈ 39% and ≈ 42% (all P < 0.05), while it did not have any significant effect on PLBs, when compared to L-DOPA/vehicle. Reference: Naunyn Schmiedebergs Arch Pharmacol. 2018 Dec;391(12):1339-1345. https://pubmed.ncbi.nlm.nih.gov/30088028/

	Solvent	mg/mL	mM
Solubility
	DMSO	36.0	71.08
	Water	2.0	3.95

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 506.47 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

Formulation protocol:

1. Krajnc E, Visentin M, Gai Z, Stieger B, Samodelov SL, Häusler S, Kullak-Ublick GA. Untargeted Metabolomics Reveals Anaerobic Glycolysis as a Novel Target of the Hepatotoxic Antidepressant Nefazodone. J Pharmacol Exp Ther. 2020 Nov;375(2):239-246. doi: 10.1124/jpet.120.000120. Epub 2020 Aug 26. PMID: 32848075. 2. Ren Z, Chen S, Zhang J, Doshi U, Li AP, Guo L. Endoplasmic Reticulum Stress Induction and ERK1/2 Activation Contribute to Nefazodone-Induced Toxicity in Hepatic Cells. Toxicol Sci. 2016 Dec;154(2):368-380. doi: 10.1093/toxsci/kfw173. Epub 2016 Sep 9. PMID: 27613715; PMCID: PMC5727583. 3. Hamadjida A, Nuara SG, Bédard D, Frouni I, Kwan C, Gourdon JC, Huot P. Nefazodone reduces dyskinesia, but not psychosis-like behaviours, in the parkinsonian marmoset. Naunyn Schmiedebergs Arch Pharmacol. 2018 Dec;391(12):1339-1345. doi: 10.1007/s00210-018-1549-6. Epub 2018 Aug 7. PMID: 30088028. 4. Nakada N, Kawamura A, Kamimura H, Sato K, Kazuki Y, Kakuni M, Ohbuchi M, Kato K, Tateno C, Oshimura M, Usui T. Murine Cyp3a knockout chimeric mice with humanized liver: prediction of the metabolic profile of nefazodone in humans. Biopharm Drug Dispos. 2016 Jan;37(1):3-14. doi: 10.1002/bdd.1990. PMID: 26352195.

In vitro protocol:

In vivo protocol:

1. Hamadjida A, Nuara SG, Bédard D, Frouni I, Kwan C, Gourdon JC, Huot P. Nefazodone reduces dyskinesia, but not psychosis-like behaviours, in the parkinsonian marmoset. Naunyn Schmiedebergs Arch Pharmacol. 2018 Dec;391(12):1339-1345. doi: 10.1007/s00210-018-1549-6. Epub 2018 Aug 7. PMID: 30088028. 2. Nakada N, Kawamura A, Kamimura H, Sato K, Kazuki Y, Kakuni M, Ohbuchi M, Kato K, Tateno C, Oshimura M, Usui T. Murine Cyp3a knockout chimeric mice with humanized liver: prediction of the metabolic profile of nefazodone in humans. Biopharm Drug Dispos. 2016 Jan;37(1):3-14. doi: 10.1002/bdd.1990. PMID: 26352195.

1: Owens MJ, Ieni JR, Knight DL, Winders K, Nemeroff CB. The serotonergic antidepressant nefazodone inhibits the serotonin transporter: in vivo and ex vivo studies. Life Sci. 1995;57(24):PL373-80. PubMed PMID: 7475971. 2: Sreenivas Rao D, Geetha S, Srinivasu MK, Om Reddy G. LC determination and purity evaluation of nefazodone HCl in bulk drug and pharmaceutical formulations. J Pharm Biomed Anal. 2001 Nov;26(4):629-36. PubMed PMID: 11516915. 3: Dursun SM, Bird D, Ronson KE. Nefazodone treatment of dysthymic disorder an open, long-term, prospective pilot study. Prog Neuropsychopharmacol Biol Psychiatry. 2002 May;26(4):671-6. PubMed PMID: 12188098. 4: Marathe PH, Salazar DE, Greene DS, Brennan J, Shukla UA, Barbhaiya RH. Absorption and presystemic metabolism of nefazodone administered at different regions in the gastrointestinal tract of humans. Pharm Res. 1995 Nov;12(11):1716-21. PubMed PMID: 8592675.