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MedKoo Cat#: 317181 | Name: Amisulpride free base
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Description:

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

Amisulpride is an atypical antipsychotic used to treat psychosis in schizophrenia and episodes of mania in bipolar disorder. In Italy, it is also used as a treatment for dysthymia. It was introduced by Sanofi-Aventis in the 1990s. Its patent had expired by 2008 and hence generic formulations are now available.Amisulpride function primarily as a D2 and D3 receptor antagonist. It has high affinity for these receptors with dissociation constants of 2.2 nM and 2.4 nM, respectively. Although standard doses used to treat psychosis inhibit dopaminergic neurotransmission, low doses preferentially block inhibitory pre-synaptic autoreceptors.

Chemical Structure

Amisulpride free base
Amisulpride free base
CAS#71675-85-9 (free base)

Theoretical Analysis

MedKoo Cat#: 317181

Name: Amisulpride free base

CAS#: 71675-85-9 (free base)

Chemical Formula: C17H27N3O4S

Exact Mass: 369.1722

Molecular Weight: 369.48

Elemental Analysis: C, 55.26; H, 7.37; N, 11.37; O, 17.32; S, 8.68

Price and Availability

Size Price Availability Quantity
100mg USD 350.00 2 Weeks
1g USD 1,250.00 2 Weeks
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Related CAS #
81342-13-4 (HCl) 71675-85-9 (free base) 71675-92-8 (S-isomer) 71675-90-6 (R-isomer) 2129505-46-8 ( R-isomer HCl)
Synonym
Solian; Aminosultopride; Deniban; Amisulprida; Amazeo; Amipride; Amival; Soltus; Sulpitac; Sulprix
IUPAC/Chemical Name
4-amino-N-[(1-ethylpyrrolidin-2-yl)methyl]-5-ethylsulfonyl-2-methoxybenzamide
InChi Key
NTJOBXMMWNYJFB-UHFFFAOYSA-N
InChi Code
InChI=1S/C17H27N3O4S/c1-4-20-8-6-7-12(20)11-19-17(21)13-9-16(25(22,23)5-2)14(18)10-15(13)24-3/h9-10,12H,4-8,11,18H2,1-3H3,(H,19,21)
SMILES Code
CCN1CCCC1CNC(=O)C2=CC(=C(C=C2OC)N)S(=O)(=O)CC
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, not in water
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
View handling instruction
Biological target:
Amisulpride is a dopamine D2/D3 receptor antagonist with Kis of 2.8 and 3.2 nM for human dopamine D2 and D3, respectively.
In vitro activity:
TBD
In vivo activity:
As depicted in fig. (3), UCMS induced a significant reduction in sucrose preference starting from the end of the 3rd week till the end of the experiment compared to control rats (P < 0.001). AMI (Amisulpride) significantly (P < 0.05) reversed UCMS-induced effects on sucrose preference at the end of the 6th week compared to UCMS vehicle-treated group. Repeated measures ANOVA revealed a significant effect of time (F(6,6) = 108.4, P < 0.001), treatment (F(1,6) = 23, P < 0.001), stress (F(1,6) = 434, P < 0.001), time with treatment (F(6,6) = 2.706, P = 0.0141), time with stress (F(6,6) = 80.86, P < 0.001) and treatment with stress (F(1,6) = 4.018, P = 0.0459). Reference: Eur J Pharmacol. 2020 Oct 15;885:173411. https://pubmed.ncbi.nlm.nih.gov/32800810/
Solvent mg/mL mM
Solubility
DMSO 39.4 106.56
DMF 15.0 40.60
DMF:PBS (pH 7.2) (1:1) 0.5 1.35
Ethanol 37.5 101.49
Water 0.2 0.54
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 369.48 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. Mohamed AM, Habib MZ, Ebeid MA, Abdelraouf SM, El Faramawy Y, Aboul-Fotouh S, Magdy Y. Amisulpride alleviates chronic mild stress-induced cognitive deficits: Role of prefrontal cortex microglia and Wnt/β-catenin pathway. Eur J Pharmacol. 2020 Oct 15;885:173411. doi: 10.1016/j.ejphar.2020.173411. Epub 2020 Aug 13. PMID: 32800810. 2. Donahue TJ, Hillhouse TM, Webster KA, Young R, De Oliveira EO, Porter JH. (S)-amisulpride as a discriminative stimulus in C57BL/6 mice and its comparison to the stimulus effects of typical and atypical antipsychotics. Eur J Pharmacol. 2014 Jul 5;734:15-22. doi: 10.1016/j.ejphar.2014.03.047. Epub 2014 Apr 12. PMID: 24726559.
In vitro protocol:
TBD
In vivo protocol:
1. Mohamed AM, Habib MZ, Ebeid MA, Abdelraouf SM, El Faramawy Y, Aboul-Fotouh S, Magdy Y. Amisulpride alleviates chronic mild stress-induced cognitive deficits: Role of prefrontal cortex microglia and Wnt/β-catenin pathway. Eur J Pharmacol. 2020 Oct 15;885:173411. doi: 10.1016/j.ejphar.2020.173411. Epub 2020 Aug 13. PMID: 32800810. 2. Donahue TJ, Hillhouse TM, Webster KA, Young R, De Oliveira EO, Porter JH. (S)-amisulpride as a discriminative stimulus in C57BL/6 mice and its comparison to the stimulus effects of typical and atypical antipsychotics. Eur J Pharmacol. 2014 Jul 5;734:15-22. doi: 10.1016/j.ejphar.2014.03.047. Epub 2014 Apr 12. PMID: 24726559.
1: Bonnet U, Taazimi B, Montag M, Ronge R, Gespers H, Kuhlmann R, Grabbe D, Jahn J. Severe acute pancreatitis, neuroleptic malignant syndrome and grand mal seizures associated with elevated amisulpride and low clozapine serum levels. Psychiatr Danub. 2015 Dec;27(4):424-5. PubMed PMID: 26609657. 2: Vinkers CH, Sommer IE. [Amisulpride: a treatment option for psychotic disorders soon to be available in the Netherlands]. Tijdschr Psychiatr. 2015;57(11):830-4. Dutch. PubMed PMID: 26552930. 3: Arora M, Banal R, Praharaj SK, Mahajan V. Amisulpride Augmentation in Acute Catatonia. Am J Ther. 2015 Aug 11. [Epub ahead of print] PubMed PMID: 26270797. 4: Liang Y, Su YA, Zhao ZG, Gao N, Huang JZ, Tang MQ, Li KQ, Yang FD, Yu X, Si TM. Acute Effects of Haloperidol, Amisulpride, and Quetiapine on Bone Turnover Markers in Patients With Schizophrenia. J Clin Psychopharmacol. 2015 Oct;35(5):583-6. doi: 10.1097/JCP.0000000000000379. PubMed PMID: 26270200. 5: Deepak TS, Raveesh BN, Parashivamurthy BM, Kumar MN, Majgi SM, Nagesh HN. Clinical Assessment of Weight Gain with Atypical Antipsychotics - Blonanserin vs Amisulpride. J Clin Diagn Res. 2015 Jun;9(6):FC07-10. doi: 10.7860/JCDR/2015/13007.6066. Epub 2015 Jun 1. PubMed PMID: 26266134; PubMed Central PMCID: PMC4525523. 6: Metzger CD, Wiegers M, Walter M, Abler B, Graf H. Local and Global Resting State Activity in the Noradrenergic and Dopaminergic Pathway Modulated by Reboxetine and Amisulpride in Healthy Subjects. Int J Neuropsychopharmacol. 2015 Jul 25. pii: pyv080. doi: 10.1093/ijnp/pyv080. [Epub ahead of print] PubMed PMID: 26209860. 7: Gros M, Williams M, Llorca M, Rodriguez-Mozaz S, Barceló D, Kookana RS. Photolysis of the antidepressants amisulpride and desipramine in wastewaters: Identification of transformation products formed and their fate. Sci Total Environ. 2015 Oct 15;530-531:434-44. doi: 10.1016/j.scitotenv.2015.05.135. Epub 2015 Jun 8. PubMed PMID: 26068227. 8: Laoutidis ZG, Konstantinidis A, Grohmann R, Luckhaus C, Mobascher J, Cordes J. Reversible Amisulpride-induced Elevation of Creatine Kinase (CK): A Case Series from the German AMSP Pharmacovigilance Project. Pharmacopsychiatry. 2015 Jul;48(4-5):178-81. doi: 10.1055/s-0035-1549997. Epub 2015 May 18. PubMed PMID: 25984709. 9: Bogorni F, Moreira FF, Pimentel EM, Grohs GE, Diaz AP. Amisulpride augmentation for clozapine-refractory positive symptoms: additional benefit in reducing hypersialorrhea. Case Rep Psychiatry. 2015;2015:408179. doi: 10.1155/2015/408179. Epub 2015 Mar 9. PubMed PMID: 25838958; PubMed Central PMCID: PMC4370110. 10: Hong CC, Chen CK, Yeh TC, Chu CS, Chen TY. Amisulpride monotherapy may be a choice of maintenance treatment for patients with both bipolar I disorder and metabolic syndrome. Aust N Z J Psychiatry. 2015 Aug;49(8):757-8. doi: 10.1177/0004867415577438. Epub 2015 Mar 18. PubMed PMID: 25788497.