Synonym
AC-90179; AC 90179; AC90179; AC-90179 HCl; AC-90179 hydrochloride
IUPAC/Chemical Name
2-(4-methoxyphenyl)-N-[(4-methylphenyl)methyl]-N-(1-methylpiperidin-4-yl)acetamide hydrochloride
InChi Key
JFSJPTRVYLBFQC-UHFFFAOYSA-N
InChi Code
InChI=1S/C23H30N2O2.ClH/c1-18-4-6-20(7-5-18)17-25(21-12-14-24(2)15-13-21)23(26)16-19-8-10-22(27-3)11-9-19;/h4-11,21H,12-17H2,1-3H3;1H
SMILES Code
O=C(N(CC1=CC=C(C)C=C1)C2CCN(C)CC2)CC3=CC=C(OC)C=C3.[H]Cl
Appearance
White to off-white 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
Biological target:
AC-90179 hydrochloride is a selective serotonin (5-HT2A) receptor inverse agonist.
In vitro activity:
Like all atypical antipsychotics, AC-90179 shows high potency as an inverse agonist and competitive antagonist at 5HT2A receptors. In addition, AC-90179 exhibits antagonism at 5HT2C receptors. In contrast, AC-90179 does not have significant potency for D2 and H1 receptors that have been implicated in the dose-limiting side effects of other antipsychotic drugs.
Reference: J Pharmacol Exp Ther. 2004 Sep;310(3):943-51. https://jpet.aspetjournals.org/content/310/3/943.long
In vivo activity:
The ability of AC-90179 to block 5-HT2A receptor signaling in vivo was demonstrated by its blockade of the rate-decreasing effects of the 5-HT2A agonist, (+/-)-2,5-dimethoxy-4-iodoamphetamine hydrochloride, under a fixed ratio schedule of reinforcement. Similar to clozapine and haloperidol, AC-90179 attenuated phencyclidine-induced hyperactivity.
Reference: J Pharmacol Exp Ther. 2004 Sep;310(3):943-51. https://jpet.aspetjournals.org/content/310/3/943.long
Preparing Stock Solutions
The following data is based on the
product
molecular weight
402.96
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. Ruderman MA, Powell SB, Geyer MA. A Kappa Opioid Model of Atypical Altered Consciousness and Psychosis: U50488, DOI, AC90179 Effects on Prepulse Inhibition and Locomotion in Mice. J Young Investig. 2009 Jul 1;19(13):1-7. PMID: 25346645; PMCID: PMC4208663.
2. Vanover KE, Harvey SC, Son T, Bradley SR, Kold H, Makhay M, Veinbergs I, Spalding TA, Weiner DM, Andersson CM, Tolf BR, Brann MR, Hacksell U, Davis RE. Pharmacological characterization of AC-90179 [2-(4-methoxyphenyl)-N-(4-methyl-benzyl)-N-(1-methyl-piperidin-4-yl)-acetamide hydrochloride]: a selective serotonin 2A receptor inverse agonist. J Pharmacol Exp Ther. 2004 Sep;310(3):943-51. doi: 10.1124/jpet.104.066688. Epub 2004 Apr 21. PMID: 15102927.
In vitro protocol:
1. Vanover KE, Harvey SC, Son T, Bradley SR, Kold H, Makhay M, Veinbergs I, Spalding TA, Weiner DM, Andersson CM, Tolf BR, Brann MR, Hacksell U, Davis RE. Pharmacological characterization of AC-90179 [2-(4-methoxyphenyl)-N-(4-methyl-benzyl)-N-(1-methyl-piperidin-4-yl)-acetamide hydrochloride]: a selective serotonin 2A receptor inverse agonist. J Pharmacol Exp Ther. 2004 Sep;310(3):943-51. doi: 10.1124/jpet.104.066688. Epub 2004 Apr 21. PMID: 15102927.
In vivo protocol:
1. Ruderman MA, Powell SB, Geyer MA. A Kappa Opioid Model of Atypical Altered Consciousness and Psychosis: U50488, DOI, AC90179 Effects on Prepulse Inhibition and Locomotion in Mice. J Young Investig. 2009 Jul 1;19(13):1-7. PMID: 25346645; PMCID: PMC4208663.
2. Vanover KE, Harvey SC, Son T, Bradley SR, Kold H, Makhay M, Veinbergs I, Spalding TA, Weiner DM, Andersson CM, Tolf BR, Brann MR, Hacksell U, Davis RE. Pharmacological characterization of AC-90179 [2-(4-methoxyphenyl)-N-(4-methyl-benzyl)-N-(1-methyl-piperidin-4-yl)-acetamide hydrochloride]: a selective serotonin 2A receptor inverse agonist. J Pharmacol Exp Ther. 2004 Sep;310(3):943-51. doi: 10.1124/jpet.104.066688. Epub 2004 Apr 21. PMID: 15102927.
1: Vanover KE, Harvey SC, Son T, Bradley SR, Kold H, Makhay M, Veinbergs I, Spalding TA, Weiner DM, Andersson CM, Tolf BR, Brann MR, Hacksell U, Davis RE. Pharmacological characterization of AC-90179 [2-(4-methoxyphenyl)-N-(4-methyl-benzyl)-N-(1-methyl-piperidin-4-yl)-acetamide hydrochloride]: a selective serotonin 2A receptor inverse agonist. J Pharmacol Exp Ther. 2004 Sep;310(3):943-51. Epub 2004 Apr 21. PubMed PMID: 15102927.
2: Ruderman MA, Powell SB, Geyer MA. A Kappa Opioid Model of Atypical Altered Consciousness and Psychosis: U50488, DOI, AC90179 Effects on Prepulse Inhibition and Locomotion in Mice. J Young Investig. 2009 Jul 1;19(13):1-7. PubMed PMID: 25346645; PubMed Central PMCID: PMC4208663.
3: Blessing WW, Seaman B. 5-hydroxytryptamine(2A) receptors regulate sympathetic nerves constricting the cutaneous vascular bed in rabbits and rats. Neuroscience. 2003;117(4):939-48. PubMed PMID: 12654345.
4: Weiner DM, Burstein ES, Nash N, Croston GE, Currier EA, Vanover KE, Harvey SC, Donohue E, Hansen HC, Andersson CM, Spalding TA, Gibson DF, Krebs-Thomson K, Powell SB, Geyer MA, Hacksell U, Brann MR. 5-hydroxytryptamine2A receptor inverse agonists as antipsychotics. J Pharmacol Exp Ther. 2001 Oct;299(1):268-76. PubMed PMID: 11561089.
