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

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

MedKoo CAT#: 540313

CAS#: 82752-99-6 (HCl)

Description: 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)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 540313
Name: Nefazodone HCl
CAS#: 82752-99-6 (HCl)
Chemical Formula: C25H33Cl2N5O2
Exact Mass: 505.20
Molecular Weight: 506.472
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	2 weeks
2g	USD 450	2 weeks
5g	USD 850	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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:

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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/

Solubility Data

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

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:	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.
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.

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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.

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Nefazodone HCl featured