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MedKoo Cat#: 562557 | Name: ICI-199441 HCl
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Description:

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

ICI-199441 HCl is a highly potent κ agonist. ICI 199441 was found to strongly inhibit the activity of cytochrome P450 2D6 (CYP2D6) (1: CYP2D6 IC50=26 nM).

Chemical Structure

ICI-199441 HCl
ICI-199441 HCl
CAS#115199-84-3 (HCl)

Theoretical Analysis

MedKoo Cat#: 562557

Name: ICI-199441 HCl

CAS#: 115199-84-3 (HCl)

Chemical Formula: C21H25Cl3N2O

Exact Mass: 0.0000

Molecular Weight: 427.79

Elemental Analysis: C, 58.96; H, 5.89; Cl, 24.86; N, 6.55; O, 3.74

Price and Availability

Size Price Availability Quantity
5mg USD 90.00 Ready to ship
10mg USD 150.00 Ready to ship
25mg USD 300.00 Ready to ship
50mg USD 500.00 Ready to ship
100mg USD 850.00 Ready to ship
200mg USD 1,450.00 Ready to ship
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Related CAS #
116508-24-8 (free base) 115199-84-3 (HCl) 136328-89-7 (R-isomer) 159531-32-5 (racemic)
Synonym
ICI-199441 HCl; ICI 199441 HCl; ICI199441 HCl; ICI-199441 Hydrochloride; ICI 199441 Hydrochloride; ICI199441 Hydrochloride;
IUPAC/Chemical Name
2-(3,4-Dichlorophenyl)-N-methyl-N-[(1S)-1-phenyl-2-(1-pyrrolidinyl)ethyl]acetamide hydrochloride
InChi Key
VFLWVWZSDBTGQJ-VEIFNGETSA-N
InChi Code
InChI=1S/C21H24Cl2N2O.ClH/c1-24(21(26)14-16-9-10-18(22)19(23)13-16)20(15-25-11-5-6-12-25)17-7-3-2-4-8-17;/h2-4,7-10,13,20H,5-6,11-12,14-15H2,1H3;1H/t20-;/m1./s1
SMILES Code
O=C(N(C)[C@@H](C1=CC=CC=C1)CN2CCCC2)CC3=CC=C(Cl)C(Cl)=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
>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
Biological target:
ICI-199441 HCl is a highly potent κ agonist.
In vitro activity:
Whole-cell recordings of TTX-r sodium currents were performed on cultured adult rat DRGs. Structurally diverse kappa-ORAs were studied for their abilities to inhibit TTX-r sodium channels. Structurally related kappa-ORAs, such as BRL 52537 and ICI 199,441 also inhibited TTX-r sodium currents. Reference: Anesth Analg. 2009 Aug;109(2):632-40. https://pubmed.ncbi.nlm.nih.gov/19608841/
In vivo activity:
The opioid κ receptor agonists (−)-U-50,488 and ICI 199.441 induced bradycardia in rats during reperfusion that was not eliminated by pretreatment with naltrexone, naloxone methiodide, nor-binaltorphimine (Table 1b). Reference: Physiol Res. 2021 Aug 31;70(4):523-531. https://pubmed.ncbi.nlm.nih.gov/34062075/
Solvent mg/mL mM
Solubility
DMSO 42.8 100.00
Ethanol 21.4 50.00
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 427.79 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.

Recalculate based on batch purity %
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. Su X, Castle NA, Antonio B, Roeloffs R, Thomas JB, Krafte DS, Chapman ML. The effect of kappa-opioid receptor agonists on tetrodotoxin-resistant sodium channels in primary sensory neurons. Anesth Analg. 2009 Aug;109(2):632-40. doi: 10.1213/ane.0b013e3181a909a4. PMID: 19608841. 2. Le Bourdonnec B, Ajello CW, Seida PR, Susnow RG, Cassel JA, Belanger S, Stabley GJ, DeHaven RN, DeHaven-Hudkins DL, Dolle RE. Arylacetamide kappa opioid receptor agonists with reduced cytochrome P450 2D6 inhibitory activity. Bioorg Med Chem Lett. 2005 May 16;15(10):2647-52. doi: 10.1016/j.bmcl.2005.03.020. PMID: 15863335. 3. Popov SV, Mukhomedzyanov AV, Tsibulnikov SY, Khaliuli I, Oeltgen PR, Prasad NR, Maslov LN. Activation of Peripheral Opioid Kappa1 Receptor Prevents Cardiac Reperfusion Injury. Physiol Res. 2021 Aug 31;70(4):523-531. doi: 10.33549/physiolres.934646. Epub 2021 Jun 1. PMID: 34062075; PMCID: PMC8820547. 4. Tsibulnikov SY, Maslov LN, Mukhomedzyanov AV, Krylatov AV, Tsibulnikova MR, Lishmanov YB. Prospects of Using of κ-Opioid Receptor Agonists U-50,488 and ICI 199,441 for Improving Heart Resistance to Ischemia/Reperfusion. Bull Exp Biol Med. 2015 Oct;159(6):718-21. doi: 10.1007/s10517-015-3057-8. Epub 2015 Oct 31. PMID: 26519268.
In vitro protocol:
1. Su X, Castle NA, Antonio B, Roeloffs R, Thomas JB, Krafte DS, Chapman ML. The effect of kappa-opioid receptor agonists on tetrodotoxin-resistant sodium channels in primary sensory neurons. Anesth Analg. 2009 Aug;109(2):632-40. doi: 10.1213/ane.0b013e3181a909a4. PMID: 19608841. 2. Le Bourdonnec B, Ajello CW, Seida PR, Susnow RG, Cassel JA, Belanger S, Stabley GJ, DeHaven RN, DeHaven-Hudkins DL, Dolle RE. Arylacetamide kappa opioid receptor agonists with reduced cytochrome P450 2D6 inhibitory activity. Bioorg Med Chem Lett. 2005 May 16;15(10):2647-52. doi: 10.1016/j.bmcl.2005.03.020. PMID: 15863335.
In vivo protocol:
1. Popov SV, Mukhomedzyanov AV, Tsibulnikov SY, Khaliuli I, Oeltgen PR, Prasad NR, Maslov LN. Activation of Peripheral Opioid Kappa1 Receptor Prevents Cardiac Reperfusion Injury. Physiol Res. 2021 Aug 31;70(4):523-531. doi: 10.33549/physiolres.934646. Epub 2021 Jun 1. PMID: 34062075; PMCID: PMC8820547. 2. Tsibulnikov SY, Maslov LN, Mukhomedzyanov AV, Krylatov AV, Tsibulnikova MR, Lishmanov YB. Prospects of Using of κ-Opioid Receptor Agonists U-50,488 and ICI 199,441 for Improving Heart Resistance to Ischemia/Reperfusion. Bull Exp Biol Med. 2015 Oct;159(6):718-21. doi: 10.1007/s10517-015-3057-8. Epub 2015 Oct 31. PMID: 26519268.
1: Popov SV, Mukhomedzyanov AV, Tsibulnikov SY, Khaliuli I, Oeltgen PR, Prasad NR, Maslov LN. Activation of Peripheral Opioid Kappa1 Receptor Prevents Cardiac Reperfusion Injury. Physiol Res. 2021 Aug 31;70(4):523-531. doi: 10.33549/physiolres.934646. Epub 2021 Jun 1. PMID: 34062075; PMCID: PMC8820547. 2: Jacobs BA, Pando MM, Jennings E, Chavera TA, Clarke WP, Berg KA. Allosterism within δ Opioid-κ Opioid Receptor Heteromers in Peripheral Sensory Neurons: Regulation of κ Opioid Agonist Efficacy. Mol Pharmacol. 2018 Apr;93(4):376-386. doi: 10.1124/mol.117.109975. Epub 2018 Feb 7. PMID: 29436492; PMCID: PMC5832326. 3: Tsibulnikov SY, Maslov LN, Mukhomedzyanov AV, Krylatov AV, Tsibulnikova MR, Lishmanov YB. Prospects of Using of κ-Opioid Receptor Agonists U-50,488 and ICI 199,441 for Improving Heart Resistance to Ischemia/Reperfusion. Bull Exp Biol Med. 2015 Oct;159(6):718-21. doi: 10.1007/s10517-015-3057-8. Epub 2015 Oct 31. PMID: 26519268. 4: Nascimento AI, Ferreira HS, Saraiva RM, Almeida TS, Fregoneze JB. Central kappa opioid receptors modulate salt appetite in rats. Physiol Behav. 2012 Jun 25;106(4):506-14. doi: 10.1016/j.physbeh.2012.03.028. Epub 2012 Mar 29. PMID: 22484111. 5: Su X, Castle NA, Antonio B, Roeloffs R, Thomas JB, Krafte DS, Chapman ML. The effect of kappa-opioid receptor agonists on tetrodotoxin-resistant sodium channels in primary sensory neurons. Anesth Analg. 2009 Aug;109(2):632-40. doi: 10.1213/ane.0b013e3181a909a4. PMID: 19608841. 6: Zhang J, Liu G, Tang Y. Chemical function-based pharmacophore generation of selective kappa-opioid receptor agonists by catalyst and phase. J Mol Model. 2009 Sep;15(9):1027-41. doi: 10.1007/s00894-008-0418-5. Epub 2009 Feb 11. PMID: 19205759. 7: Tao YM, Li QL, Zhang CF, Xu XJ, Chen J, Ju YW, Chi ZQ, Long YQ, Liu JG. LPK-26, a novel kappa-opioid receptor agonist with potent antinociceptive effects and low dependence potential. Eur J Pharmacol. 2008 Apr 28;584(2-3):306-11. doi: 10.1016/j.ejphar.2008.02.028. Epub 2008 Feb 19. PMID: 18353307. 8: Page AJ, O'Donnell TA, Blackshaw LA. Opioid modulation of ferret vagal afferent mechanosensitivity. Am J Physiol Gastrointest Liver Physiol. 2008 Apr;294(4):G963-70. doi: 10.1152/ajpgi.00562.2007. Epub 2008 Feb 7. PMID: 18258789. 9: Terner JM, Lomas LM, Lewis JW, Husbands SM, Picker MJ. Effects of the long- lasting kappa opioid 2-(3,4-dichlorophenyl)-N-methyl-N-[(1S)-1-(3-isothiocyanato phenyl)-2-(1-pyrrolidinyl) ethyl] acetamide in a drug discrimination and warm water tail-withdrawal procedure. Behav Pharmacol. 2005 Dec;16(8):665-70. doi: 10.1097/00008877-200512000-00010. PMID: 16286819. 10: Narita M, Kaneko C, Miyoshi K, Nagumo Y, Kuzumaki N, Nakajima M, Nanjo K, Matsuzawa K, Yamazaki M, Suzuki T. Chronic pain induces anxiety with concomitant changes in opioidergic function in the amygdala. Neuropsychopharmacology. 2006 Apr;31(4):739-50. doi: 10.1038/sj.npp.1300858. PMID: 16123756. 11: Le Bourdonnec B, Ajello CW, Seida PR, Susnow RG, Cassel JA, Belanger S, Stabley GJ, DeHaven RN, DeHaven-Hudkins DL, Dolle RE. Arylacetamide kappa opioid receptor agonists with reduced cytochrome P450 2D6 inhibitory activity. Bioorg Med Chem Lett. 2005 May 16;15(10):2647-52. doi: 10.1016/j.bmcl.2005.03.020. PMID: 15863335. 12: Daniels DJ, Kulkarni A, Xie Z, Bhushan RG, Portoghese PS. A bivalent ligand (KDAN-18) containing delta-antagonist and kappa-agonist pharmacophores bridges delta2 and kappa1 opioid receptor phenotypes. J Med Chem. 2005 Mar 24;48(6):1713-6. doi: 10.1021/jm034234f. PMID: 15771416. 13: Tuthill PA, Seida PR, Barker W, Cassel JA, Belanger S, DeHaven RN, Koblish M, Gottshall SL, Little PJ, DeHaven-Hudkins DL, Dolle RE. Azepinone as a conformational constraint in the design of kappa-opioid receptor agonists. Bioorg Med Chem Lett. 2004 Nov 15;14(22):5693-7. doi: 10.1016/j.bmcl.2004.08.041. PMID: 15482950. 14: Mori T, Nomura M, Yoshizawa K, Nagase H, Narita M, Suzuki T. Differential properties between TRK-820 and U-50,488H on the discriminative stimulus effects in rats. Life Sci. 2004 Oct 1;75(20):2473-82. doi: 10.1016/j.lfs.2004.05.017. PMID: 15350822. 15: Suzuki T, Izumimoto N, Takezawa Y, Fujimura M, Togashi Y, Nagase H, Tanaka T, Endoh T. Effect of repeated administration of TRK-820, a kappa-opioid receptor agonist, on tolerance to its antinociceptive and sedative actions. Brain Res. 2004 Jan 9;995(2):167-75. doi: 10.1016/j.brainres.2003.09.057. PMID: 14672806. 16: Nakae Y, Fujita S, Namiki A. Modulation of myofilament Ca2+ densitivity by delta- and kappa-opioid agonists in intact guinea pig hearts. Anesth Analg. 2003 Mar;96(3):733-739. doi: 10.1213/01.ANE.0000050281.16556.33. PMID: 12598254. 17: Kumar V, Marella MA, Cortes-Burgos L, Chang AC, Cassel JA, Daubert JD, DeHaven RN, DeHaven-Hudkins DL, Gottshall SL, Mansson E, Maycock AL. Arylacetamides as peripherally restricted kappa opioid receptor agonists. Bioorg Med Chem Lett. 2000 Nov 20;10(22):2567-70. doi: 10.1016/s0960-894x(00)00519-9. PMID: 11086731. 18: Perez JM, Wilhelm EJ, Sucholeiki I. The use of power ultrasound coupled with magnetic separation for the solid phase synthesis of compound libraries. Bioorg Med Chem Lett. 2000 Jan 17;10(2):171-4. doi: 10.1016/s0960-894x(99)00651-4. PMID: 10673104. 19: Endoh T, Tajima A, Suzuki T, Kamei J, Narita M, Tseng L, Nagase H. Characterization of the antinociceptive effects of TRK-820 in the rat. Eur J Pharmacol. 2000 Jan 10;387(2):133-40. doi: 10.1016/s0014-2999(99)00815-8. PMID: 10650153. 20: Chang AC, Cowan A, Takemori AE, Portoghese PS. Aspartic acid conjugates of 2-(3,4-dichlorophenyl)-N-methyl-N-[(1S)-1(3-aminophenyl)-2-(1-pyrrolidi nyl) ethyl]acetamide: kappa opioid receptor agonists with limited access to the central nervous system. J Med Chem. 1996 Oct 25;39(22):4478-82. doi: 10.1021/jm960459x. PMID: 8893842.