WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 577955
CAS#: 102392-05-2 (free base)
Description: NAN-190 is a mixed antagonist and partial agonist of the serotonin (5-HT) receptor subtype 5-HT1A. NAN-190 potentiates the circadian response to light and speeds re-entrainment to advanced light cycles. NAN-190 potentiates the impairment of retention produced by swim stress. NAN-190 is a possible antagonist for methamphetamine.
MedKoo Cat#: 577955
Name: NAN190 free base
CAS#: 102392-05-2 (free base)
Chemical Formula: C23H27N3O3
Exact Mass: 393.2052
Molecular Weight: 393.487
Elemental Analysis: C, 70.21; H, 6.92; N, 10.68; O, 12.20
Related CAS #: 102392-05-2 (free base) 115338-32-4 (HBr)
Synonym: NAN190 free base; NAN-190; NAN 190; NAN190
IUPAC/Chemical Name: 1H-Isoindole-1,3(2H)-dione, 2-(4-(4-(2-methoxyphenyl)-1-piperazinyl)butyl)-
InChi Key: SJDOMIRMMUGQQK-UHFFFAOYSA-N
InChi Code: 1S/C23H27N3O3/c1-29-21-11-5-4-10-20(21)25-16-14-24(15-17-25)12-6-7-13-26-22(27)18-8-2-3-9-19(18)23(26)28/h2-5,8-11H,6-7,12-17H2,1H3
SMILES Code: O=C1N(C(C2=C1C=CC=C2)=O)CCCCN3CCN(CC3)C4=CC=CC=C4OC
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: To be determined
Shelf Life: >2 years if stored properly
Drug Formulation: To be determined
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
| Biological target: | NAN-190 is a mixed antagonist and partial agonist of the serotonin (5-HT) receptor subtype 5-HT1A. |
| In vitro activity: | Nan-190 was identified as an inhibitor of Nav1.7 sodium channels and animal experiments showed that NAN-190 significantly alleviated CFA-induced inflammatory pain. Mechanism studies demonstrated that NAN-190 was a state-dependent Nav1.7 blocker with IC50 value on the inactivated state ten-fold more potent than that on the rest state. NAN-190 leftward-shifted the fast and slow inactivation curves about 9.07 mV and 38.56 mV, respectively, but had no effects on channel activation. Reference: Life Sci. 2023 Apr 15;319:121520. https://pubmed.ncbi.nlm.nih.gov/36828129/ |
| In vivo activity: | The adult prenatally stressed OVX female offspring were chronically (during 14 days) treated by 5-HT(1A)-receptors antagonist--NAN-190 (0.1 mg/kg, s. c.) or 5-HT(2A/2C)-receptors antagonist--ketanserine (0.1 mg/kg, i. p.) alone, or in a combination with its preparartions a low dose of 17β-estradiol (5.0 μg/rat, s. c.). Treatment with NAN-190 alone induced marked depressant-like effect, while NAN-190 administered in a combination with a low dose of 17β-estradiol resulted in an antidepressant-like effect in the FST in the prenatally stressed OVX females as compared to the control prenatally stressed female offspring. Administration of NAN-190 plus 17β-estradiol led to decreased frequency of rearing, exploratory and grooming behavior in prenatally stressed OVX female offspring in the OFT. Reference: Ross Fiziol Zh Im I M Sechenova. 2015 Jan;101(1):35-43. https://pubmed.ncbi.nlm.nih.gov/25868324/ |
The following data is based on the product molecular weight 393.487 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. Li S, Jin Y, Li M, Yu H. NAN-190, a 5-HT1A antagonist, alleviates inflammatory pain by targeting Nav1.7 sodium channels. Life Sci. 2023 Apr 15;319:121520. doi: 10.1016/j.lfs.2023.121520. Epub 2023 Feb 22. PMID: 36828129. 2. Terada K, Murata A, Toki E, Goto S, Yamakawa H, Setoguchi S, Watase D, Koga M, Takata J, Matsunaga K, Karube Y. Atypical Antipsychotic Drug Ziprasidone Protects against Rotenone-Induced Neurotoxicity: An In Vitro Study. Molecules. 2020 Sep 14;25(18):4206. doi: 10.3390/molecules25184206. PMID: 32937854; PMCID: PMC7570562. 3. Goitia B, Rivero-Echeto MC, Weisstaub NV, Gingrich JA, Garcia-Rill E, Bisagno V, Urbano FJ. Modulation of GABA release from the thalamic reticular nucleus by cocaine and caffeine: role of serotonin receptors. J Neurochem. 2016 Feb;136(3):526-35. doi: 10.1111/jnc.13398. Epub 2015 Nov 12. PMID: 26484945; PMCID: PMC5367149. 4. Fedotova IuO, Pivina SG, Akulova VK, Ordian NÉ. [Pecularities for action of combined administration of NAN-190 and ketanserine with low dose of 17β-estradiol on depression-like behavior in prenatally stressed ovariectomized rats]. Ross Fiziol Zh Im I M Sechenova. 2015 Jan;101(1):35-43. Russian. PMID: 25868324. |
| In vitro protocol: | 1. Li S, Jin Y, Li M, Yu H. NAN-190, a 5-HT1A antagonist, alleviates inflammatory pain by targeting Nav1.7 sodium channels. Life Sci. 2023 Apr 15;319:121520. doi: 10.1016/j.lfs.2023.121520. Epub 2023 Feb 22. PMID: 36828129. 2. Terada K, Murata A, Toki E, Goto S, Yamakawa H, Setoguchi S, Watase D, Koga M, Takata J, Matsunaga K, Karube Y. Atypical Antipsychotic Drug Ziprasidone Protects against Rotenone-Induced Neurotoxicity: An In Vitro Study. Molecules. 2020 Sep 14;25(18):4206. doi: 10.3390/molecules25184206. PMID: 32937854; PMCID: PMC7570562. |
| In vivo protocol: | 1. Goitia B, Rivero-Echeto MC, Weisstaub NV, Gingrich JA, Garcia-Rill E, Bisagno V, Urbano FJ. Modulation of GABA release from the thalamic reticular nucleus by cocaine and caffeine: role of serotonin receptors. J Neurochem. 2016 Feb;136(3):526-35. doi: 10.1111/jnc.13398. Epub 2015 Nov 12. PMID: 26484945; PMCID: PMC5367149. 2. Fedotova IuO, Pivina SG, Akulova VK, Ordian NÉ. [Pecularities for action of combined administration of NAN-190 and ketanserine with low dose of 17β-estradiol on depression-like behavior in prenatally stressed ovariectomized rats]. Ross Fiziol Zh Im I M Sechenova. 2015 Jan;101(1):35-43. Russian. PMID: 25868324. |
1: Fedotova IuO, Pivina SG, Akulova VK, Ordian NÉ. [Pecularities for action of combined administration of NAN-190 and ketanserine with low dose of 17β-estradiol on depression-like behavior in prenatally stressed ovariectomized rats]. Ross Fiziol Zh Im I M Sechenova. 2015 Jan;101(1):35-43. Russian. PMID: 25868324.
2: Fedotova IuO, Sapronov NS. [Co-administration of NAN-190 with low dose of testosterone propionate improves passive avoidance performance in rats with androgen deficiency]. Eksp Klin Farmakol. 2013;76(12):15-9. Russian. PMID: 24605422.
3: Fedotova IuO, Pivina SG, Ordian NÉ. [Analysis of 8-OH-DPAT and NAN-190 effects in young prenatally stressed rats under experimental estrogen deficiency conditions]. Eksp Klin Farmakol. 2012;75(7):11-4. Russian. PMID: 23025046.
4: Kowalski P, Jaśkowska J. An efficient synthesis of aripiprazole, buspirone and NAN-190 by the reductive alkylation of amines procedure. Arch Pharm (Weinheim). 2012 Jan;345(1):81-5. doi: 10.1002/ardp.201100112. Epub 2011 Oct 5. PMID: 22234973.
5: Fedotova YO, Ordyan NE. Effects of 8-OH-DPAT and NAN-190 on anxious- depressive-like behavior of female rats during the estrous cycle. Bull Exp Biol Med. 2010 Dec;150(2):165-7. English, Russian. doi: 10.1007/s10517-010-1094-x. PMID: 21246079.
6: Foong JP, Bornstein JC. 5-HT antagonists NAN-190 and SB 269970 block alpha2-adrenoceptors in the guinea pig. Neuroreport. 2009 Feb 18;20(3):325-30. doi: 10.1097/WNR.0b013e3283232caa. PMID: 19190523.
7: Kessler EJ, Sprouse J, Harrington ME. NAN-190 potentiates the circadian response to light and speeds re-entrainment to advanced light cycles. Neuroscience. 2008 Jul 17;154(4):1187-94. doi: 10.1016/j.neuroscience.2008.04.054. Epub 2008 May 6. PMID: 18538936; PMCID: PMC2637398.
8: Sterniczuk R, Stepkowski A, Jones M, Antle MC. Enhancement of photic shifts with the 5-HT1A mixed agonist/antagonist NAN-190: intra-suprachiasmatic nucleus pathway. Neuroscience. 2008 May 15;153(3):571-80. doi: 10.1016/j.neuroscience.2008.02.062. Epub 2008 Mar 6. PMID: 18406538.
9: Schneider AM, Simson PE. NAN-190 potentiates the impairment of retention produced by swim stress. Pharmacol Biochem Behav. 2007 May;87(1):73-80. doi: 10.1016/j.pbb.2007.04.002. Epub 2007 Apr 11. PMID: 17490739.
10: Sapronov NS, Fedotova YO, Losev NA. Combined administration of NAN-190 and 17beta-estradiol abolishes the amnesic effect of scopolamine in middle-aged ovariectomized rats. Bull Exp Biol Med. 2006 Jul;142(1):80-2. English, Russian. doi: 10.1007/s10517-006-0297-7. PMID: 17369909.
11: Paluchowska MH, Bugno R, Charakchieva-Minol S, Bojarski AJ, Tatarczyńska E, Chojnacka-Wójcik E. Conformational restriction in novel NAN-190 and MP3022 analogs and their 5-HT(1A) receptor activity. Arch Pharm (Weinheim). 2006 Sep;339(9):498-506. doi: 10.1002/ardp.200600009. PMID: 16941730.
12: Djavadian RL, Wielkopolska E, Turlejski K. Postnatal treatment with NAN-190 but not with 5-HT1A receptor agonists retards growth of the rat brain. Int J Dev Neurosci. 2005 Aug;23(5):485-93. doi: 10.1016/j.ijdevneu.2005.02.001. PMID: 16026684.
13: Ginawi OT, Al-Majed AA, Al-Suwailem AK. NAN-190, a possible specific antagonist for methamphetamine. Regul Toxicol Pharmacol. 2005 Mar;41(2):122-7. doi: 10.1016/j.yrtph.2004.10.005. Epub 2004 Dec 19. PMID: 15698535.
14: Wesołowska A, Borycz J, Paluchowska MH, Chojnacka-Wójcik E. Pharmacological analysis of the hypothermic effects of NAN-190 and its analogs, postsynaptic 5-HT1A receptor antagonists, in mice. Pol J Pharmacol. 2002 Jul-Aug;54(4):391-9. PMID: 12523493.
15: Paluchowska MH, Mokrosz MJ, Bojarski A, Wesołowska A, Borycz J, Charakchieva-Minol S, Chojnacka-Wójcik E. On the bioactive conformation of NAN-190 (1) and MP3022 (2), 5-HT(1A) receptor antagonists. J Med Chem. 1999 Dec 2;42(24):4952-60. doi: 10.1021/jm991045h. PMID: 10585205.
16: Cao BJ, Rodgers RJ. Influence of 5-HT1A receptor antagonism on plus-maze behaviour in mice. II. WAY 100635, SDZ 216-525 and NAN-190. Pharmacol Biochem Behav. 1997 Oct;58(2):593-603. doi: 10.1016/s0091-3057(97)00279-7. PMID: 9300624.
17: Belcheva I, Belcheva S, Petkov VV, Hadjiivanova C, Petkov VD. Behavorial responses to the 5-HT1A receptor antagonist NAN190 injected into rat CA1 hippocampal area. Gen Pharmacol. 1997 Mar;28(3):435-41. doi: 10.1016/s0306-3623(96)00185-1. PMID: 9068987.
18: Sharp T, Umbers V, Hjorth S. The role of 5-HT1A autoreceptors and alpha 1-adrenoceptors in the inhibition of 5-HT release--II NAN-190 and SDZ 216-525. Neuropharmacology. 1996 Jun;35(6):735-41. doi: 10.1016/0028-3908(96)84645-4. PMID: 8887982.
19: Dalpiaz A, Ferretti V, Gilli P, Bertolasi V. Stereochemistry of serotonin receptor ligands from crystallographic data. Crystal structures of NAN-190.HBr, 1-phenylbiguanide, MDL 72222 and mianserin.HCl and selectivity criteria towards 5-HT1, 5-HT2, and 5-HT3 receptor subtypes. Acta Crystallogr B. 1996 Jun 1;52 ( Pt 3):509-18. doi: 10.1107/s0108768195014765. PMID: 8767764.
20: Neckelmann D, Bjørkum AA, Bjorvatn B, Ursin R. Sleep and EEG power spectrum effects of the 5-HT1A antagonist NAN-190 alone and in combination with citalopram. Behav Brain Res. 1996 Feb;75(1-2):159-68. doi: 10.1016/0166-4328(96)00204-5. PMID: 8800653.
