DIPPA HCl | CAS# 155512-52-0 | κ-opioid receptor antagonist

MedKoo Cat#: 574349 | Name: DIPPA HCl

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Description:

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

DIPPA HCl is a selective κ-opioid receptor antagonist with potential anti-depressant effects.

Chemical Structure

DIPPA HCl

CAS#155512-52-0

Theoretical Analysis

MedKoo Cat#: 574349

Name: DIPPA HCl

CAS#: 155512-52-0

Chemical Formula: C22H24Cl3N3OS

Exact Mass: 0.0000

Molecular Weight: 484.86

Elemental Analysis: C, 54.50; H, 4.99; Cl, 21.93; N, 8.67; O, 3.30; S, 6.61

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 550.00	2 Weeks
50mg	USD 1,660.00	2 Weeks

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Related CAS #

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Synonym

DIPPA HCl; DIPPA hydrochloride

IUPAC/Chemical Name

(S)-2-(3,4-dichlorophenyl)-N-(1-(3-isothiocyanatophenyl)-2-(pyrrolidin-1-yl)ethyl)-N-methylacetamide hydrochloride

InChi Key

BNWYENYHNOESCX-ZMBIFBSDSA-N

InChi Code

InChI=1S/C22H23Cl2N3OS.ClH/c1-26(22(28)12-16-7-8-19(23)20(24)11-16)21(14-27-9-2-3-10-27)17-5-4-6-18(13-17)25-15-29;/h4-8,11,13,21H,2-3,9-10,12,14H2,1H3;1H/t21-;/m1./s1

SMILES Code

S=C=NC1=CC([C@@H](CN2CCCC2)N(C)C(CC3=CC(Cl)=C(Cl)C=C3)=O)=CC=C1.[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

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

DIPPA (hydrochloride) is an irreversible, long-lasting, selective and high affinity κ-opioid receptor antagonist.

In vitro activity:

In smooth muscle preparations, the non-electrophilic parent compound (+)-S-2 and the affinity labels 3-6 behaved as kappa agonists in that they were potently antagonized by norbinaltorphimine (norBNI). In addition to the high binding affinity and selectivity of the 3-isothiocyanate 3 (DIPPA) to kappa opioid receptors, wash studies have suggested that this involves covalent binding. Reference: J Med Chem. 1994 Dec 23;37(26):4490-8. https://pubmed.ncbi.nlm.nih.gov/7799399/

In vivo activity:

DIPPA (5 mg/kg) decreased burying in both strains compared to the within-strain control groups (Fig. 2b). Immobility time (Fig. 2c) also showed significant effects of strain (F(1, 79)=13.45, p<0.001) and drug treatment (F(2, 79)=4.06, p=0.021). Saline-treated WKY rats spent more time immobile than saline-treated SD rats. DIPPA (5 mg/kg) increased immobility in SD rats compared to the saline-treated strain control group but not in WKY rats (Fig. 2c). Reference: Psychopharmacology (Berl). 2010 Jun;210(2):295-302. https://pubmed.ncbi.nlm.nih.gov/20369354/

	Solvent	mg/mL	mM
Solubility
	DMSO	24.2	49.99
	Ethanol	14.6	30.01

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 484.86 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. Chang AC, Takemori AE, Ojala WH, Gleason WB, Portoghese PS. kappa Opioid receptor selective affinity labels: electrophilic benzeneacetamides as kappa-selective opioid antagonists. J Med Chem. 1994 Dec 23;37(26):4490-8. doi: 10.1021/jm00052a008. PMID: 7799399. 2. Hughes EM, Thornton AM, Kerr DM, Smith K, Sanchez C, Kelly JP, Finn DP, Roche M. Kappa Opioid Receptor-mediated Modulation of Social Responding in Adolescent Rats and in Rats Prenatally Exposed to Valproic Acid. Neuroscience. 2020 Sep 15;444:9-18. doi: 10.1016/j.neuroscience.2020.07.055. Epub 2020 Aug 5. PMID: 32763285. 3. Carr GV, Lucki I. Comparison of the kappa-opioid receptor antagonist DIPPA in tests of anxiety-like behavior between Wistar Kyoto and Sprague Dawley rats. Psychopharmacology (Berl). 2010 Jun;210(2):295-302. doi: 10.1007/s00213-010-1832-9. Epub 2010 Apr 6. PMID: 20369354; PMCID: PMC3370387.

In vitro protocol:

In vivo protocol:

1. Hughes EM, Thornton AM, Kerr DM, Smith K, Sanchez C, Kelly JP, Finn DP, Roche M. Kappa Opioid Receptor-mediated Modulation of Social Responding in Adolescent Rats and in Rats Prenatally Exposed to Valproic Acid. Neuroscience. 2020 Sep 15;444:9-18. doi: 10.1016/j.neuroscience.2020.07.055. Epub 2020 Aug 5. PMID: 32763285. 2. Carr GV, Lucki I. Comparison of the kappa-opioid receptor antagonist DIPPA in tests of anxiety-like behavior between Wistar Kyoto and Sprague Dawley rats. Psychopharmacology (Berl). 2010 Jun;210(2):295-302. doi: 10.1007/s00213-010-1832-9. Epub 2010 Apr 6. PMID: 20369354; PMCID: PMC3370387.

Carr, G. et al.: Neuropsychopharm., 35, 752 (2010)