Synonym
R 5808; R-5808; R5808; AMI-193; AMI 193; AMI193
IUPAC/Chemical Name
8-(3-(4-fluorophenoxy)propyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one
InChi Key
FJUKDAZEABGEIH-UHFFFAOYSA-N
InChi Code
InChI=1S/C22H26FN3O2/c23-18-7-9-20(10-8-18)28-16-4-13-25-14-11-22(12-15-25)21(27)24-17-26(22)19-5-2-1-3-6-19/h1-3,5-10H,4,11-17H2,(H,24,27)
SMILES Code
O=C1NCN(C2=CC=CC=C2)C13CCN(CCCOC4=CC=C(F)C=C4)CC3
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
2934.99.03.00
Biological target:
Spiramide is an antagonist of 5-HT2 and dopamine D2 receptor, with Kis of 2 nM and 3 nM, respectively. Spiramide has >2000-fold selectivity for 5-HT2 versus 5-HT1C (Ki=4300 nM) receptors.
In vivo activity:
In squirrel monkeys trained under a fixed-interval (FI) schedule of stimulus termination, spiramide reduced response rate under a fixed-interval schedule and attenuated cocaine's discriminative-stimulus effects. When combined with cocaine or dopamine uptake inhibitors, spiramide's effects were reversed, suggesting its D(2)-antagonist effects play a prominent role in its behavioral pharmacology.
Reference: Pharmacol Biochem Behav. 2000 Oct;67(2):257-64. https://pubmed.ncbi.nlm.nih.gov/11124389/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMSO |
20.0 |
52.16 |
|
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
383.46
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. Zanganeh F, Zendehdel M, Panahi N, Asghari A. Interconnection between Adrenergic and Dopaminergic Systems in Feeding Behavior in Neonatal Chicks. Arch Razi Inst. 2021 Jul;76(2):345-358. doi: 10.22092/ari.2020.341240.1425. Epub 2021 Jul 1. PMID: 34223733; PMCID: PMC8410192.
2. Czoty PW, Howell LL. Behavioral effects of AMI-193, a 5-HT(2A)- and dopamine D(2)-receptor antagonist, in the squirrel monkey. Pharmacol Biochem Behav. 2000 Oct;67(2):257-64. doi: 10.1016/s0091-3057(00)00321-x. PMID: 11124389.
In vivo protocol:
1. Zanganeh F, Zendehdel M, Panahi N, Asghari A. Interconnection between Adrenergic and Dopaminergic Systems in Feeding Behavior in Neonatal Chicks. Arch Razi Inst. 2021 Jul;76(2):345-358. doi: 10.22092/ari.2020.341240.1425. Epub 2021 Jul 1. PMID: 34223733; PMCID: PMC8410192.
2. Czoty PW, Howell LL. Behavioral effects of AMI-193, a 5-HT(2A)- and dopamine D(2)-receptor antagonist, in the squirrel monkey. Pharmacol Biochem Behav. 2000 Oct;67(2):257-64. doi: 10.1016/s0091-3057(00)00321-x. PMID: 11124389.
1: Kjellberg B, Randrup A. Partial restoration by a neuroleptic (spiramide) of items of grooming behaviour suppressed by amphetamine. Arch Int Pharmacodyn Ther. 1974 Jul;210(1):61-6. PubMed PMID: 4474849.
2: Nielsen EB, Lyon M. Drinking behaviour and brain dopamine: antagonistic effect of two neuroleptic drugs (pimozide and spiramide) upon amphetamine-or apomorphine-induced hypodipsia. Psychopharmacologia. 1973 Dec 20;33(4):299-308. PubMed PMID: 4776656.
3: Platica M, Doody J, Mandeli JP, Hollander VP. Role of prolactin in growth of the rat mammary tumor MTW9. Int J Cancer. 1991 Apr 22;48(1):109-12. PubMed PMID: 2019452.
4: Rasbach KA, Funk JA, Jayavelu T, Green PT, Schnellmann RG. 5-hydroxytryptamine receptor stimulation of mitochondrial biogenesis. J Pharmacol Exp Ther. 2010 Feb;332(2):632-9. doi: 10.1124/jpet.109.159947. Epub 2009 Oct 29. PubMed PMID: 19875674; PubMed Central PMCID: PMC2812119.
5: He HP, Shen YM, Zhang JX, Zuo GY, Hao XJ. New diterpene alkaloids from the roots of Spiraea japonica. J Nat Prod. 2001 Mar;64(3):379-80. PubMed PMID: 11277763.
6: Czoty PW, Howell LL. Behavioral effects of AMI-193, a 5-HT(2A)- and dopamine D(2)-receptor antagonist, in the squirrel monkey. Pharmacol Biochem Behav. 2000 Oct;67(2):257-64. PubMed PMID: 11124389.
7: Hansen HC, Olsson R, Croston G, Andersson CM. Multistep solution-phase parallel synthesis of spiperone analogues. Bioorg Med Chem Lett. 2000 Nov 6;10(21):2435-9. PubMed PMID: 11078195.
8: Hamada K, Yoshida M, Isayama H, Yagi Y, Kanazashi S, Kashihara Y, Takeuchi K, Yamaguchi I. Possible involvement of endogenous 5-HT in aggravation of cerulein-induced acute pancreatitis in mice. J Pharmacol Sci. 2007 Nov;105(3):240-50. Epub 2007 Oct 27. PubMed PMID: 17965538.
9: Li S, Song JH, Kim TI, Yoo WG, Won MH, Dai F, Hong SJ. Chemotactic migration of newly excysted juvenile Clonorchis sinensis is suppressed by neuro-antagonists. PLoS Negl Trop Dis. 2019 Aug 13;13(8):e0007573. doi: 10.1371/journal.pntd.0007573. PMID: 31408466; PMCID: PMC6691982.
10: Ghashghayi E, Zendehdel M, Khodadadi M, Rahmani B. Central dopaminergic, serotoninergic, as well as GABAergic systems mediate NMU-induced hypophagia in newborn chicken. Int J Neurosci. 2024 Apr;134(4):353-363. doi: 10.1080/00207454.2022.2102980. Epub 2022 Jul 28. PMID: 35901030.
