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Homotaurine

Names
IUPAC name 3-Aminopropane-1-sulfonic acid
Other names Tramiprosate; Alzhemed; 3-APS
Identifiers
CAS Number	3687-18-1
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL149082
ChemSpider	1584
ECHA InfoCard	100.020.889
KEGG	D06202
PubChem CID	1646
CompTox Dashboard (EPA)	DTXSID80190352
InChI InChI=1S/C3H9NO3S/c4-2-1-3-8(5,6)7/h1-4H2,(H,5,6,7)Key: SNKZJIOFVMKAOJ-UHFFFAOYSA-N InChI=1/C3H9NO3S/c4-2-1-3-8(5,6)7/h1-4H2,(H,5,6,7)Key: SNKZJIOFVMKAOJ-UHFFFAOYAT
SMILES O=S(=O)(O)CCCN
Properties
Chemical formula	C3H9NO3S
Molar mass	139.17 g·mol
Melting point	293 °C (559 °F; 566 K) (decomposition)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is  ?) Infobox references

Homotaurine (3-amino-1-propanesulfonic acid (3-APS) or tramiprosate (INN)) is a synthetic organic compound. It is analogous to taurine, but with an extra carbon in its chain. Because of its similarity in structure to the neurotransmitter gamma-aminobutyric acid (GABA), it has GABAergic effects and may be useful as an anticonvulsant.

Homotaurine has also been investigated as a potential treatment for Alzheimer's disease. It binds to soluble amyloid beta and inhibits the formation of neurotoxic aggregates that lead to amyloid plaque deposition in the brain. However, clinical trials failed to show improvement compared to placebo.

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Homotaurine is a GABA_A Partial Receptor Agonist. and a GABA_B receptor low efficacy partial agonist becoming antagonist and reversed the catatonia induced by baclofen in rats. Moreover, Homotaurine suppress ethanol-stimulated dopamine release, ethanol intake and preference in rats similar to acamprosate (Acetylated homotaurine analogue) .

Acamprosate, enhance NMDA currents but inhibited GABA_B receptor too.

B)Jytdog

It is a GABA antagonist, apparently by mimicking GABA, which is it resembles. Homotaurine has shown activity in animal models of alcoholism, and acamprosate, the N-acetyl derivative of homotaurine, was approved by the FDA in 2004 to treat alcohol dependence.

Homotaurine is a zwitterion at neutral pH.

See also

• Acamprosate

References

1. Homotaurine at Sigma-Aldrich
2. Fariello RG, Golden GT, Pisa M; Golden; Pisa (1982). "Homotaurine (3 aminopropanesulfonic acid; 3APS) protects from the convulsant and cytotoxic effect of systemically administered kainic acid". Neurology. 32 (3): 241–5. doi:10.1212/wnl.32.3.241. PMID 7199633.{{cite journal}}: CS1 maint: multiple names: authors list (link)
3. Gauthier, S; Aisen, P. S.; Ferris, S. H.; Saumier, D; Duong, A; Haine, D; Garceau, D; Suhy, J; Oh, J; Lau, W; Sampalis, J (2009). "Effect of tramiprosate in patients with mild-to-moderate Alzheimer's disease: Exploratory analyses of the MRI sub-group of the Alphase study". The journal of nutrition, health & aging. 13 (6): 550–7. PMID 19536424.
4. Aisen PS, Gauthier S, Vellas B (2007). "Alzhemed: a potential treatment for Alzheimer's disease". Curr Alzheimer Res. 4 (4): 473–8. doi:10.2174/156720507781788882. PMID 17908052. {{cite journal}}: Unknown parameter |displayauthors= ignored (|display-authors= suggested) (help)CS1 maint: multiple names: authors list (link)
5. "Tramiprosate in mild-to-moderate Alzheimer's disease – a randomized, double-blind, placebo-controlled, multi-centre study (the Alphase Study)". Arch Med Sci. Pubmed Link.
6. Reyes-Haro D1, Cabrera-Ruíz E, Estrada-Mondragón A, Miledi R, Martínez-Torres A. "Modulation of GABA-A receptors of astrocytes and STC-1 cells by taurine structural analogs". PMID 25119985. {{cite journal}}: Cite journal requires |journal= (help)CS1 maint: multiple names: authors list (link) CS1 maint: numeric names: authors list (link)
7. Giotti A, Luzzi S, Spagnesi S, Zilletti L. "Homotaurine: a GABAB antagonist in guinea-pig ileum". PMID 6652358. {{cite journal}}: Cite journal requires |journal= (help)CS1 maint: multiple names: authors list (link)
8. Serrano MI1, Serrano JS, Fernández A, Asadi I, Serrano-Martino MC. "GABA(B) receptors and opioid mechanisms involved in homotaurine-induced analgesia". PMID 9510095. {{cite journal}}: Cite journal requires |journal= (help)CS1 maint: multiple names: authors list (link) CS1 maint: numeric names: authors list (link)
9. Serrano MI1, Serrano JS, Asadi I, Fernández A, Serrano-Martino MC. "Role of K+ -channels in homotaurine-induced analgesia". PMID 11468027. {{cite journal}}: Cite journal requires |journal= (help)CS1 maint: multiple names: authors list (link) CS1 maint: numeric names: authors list (link)
10. Mehta AK1, Ticku MK. "Baclofen induces catatonia in rats". PMID 2823166. {{cite journal}}: Cite journal requires |journal= (help)CS1 maint: numeric names: authors list (link)
11. Olive MF, Nannini MA, Ou CJ, Koenig HN, Hodge CW. "Effects of acute acamprosate and homotaurine on ethanol intake and ethanol-stimulated mesolimbic dopamine release". PMID 11864639. {{cite journal}}: Cite journal requires |journal= (help)CS1 maint: multiple names: authors list (link)
12. Berton F, et al. Alcohol Clin Exp Res. 1998. . "Acamprosate reduces ethanol drinking behaviors and alters the metabolite profile in mice lacking ENT1". PMID 21172405. {{cite journal}}: Cite journal requires |journal= (help); line feed character in |author= at position 45 (help)CS1 maint: numeric names: authors list (link)
13. Olive MF, Nannini MA, Ou CJ, Koenig HN, Hodge CW. "Acamprosate enhances N-methyl-D-apartate receptor-mediated neurotransmission but inhibits presynaptic GABA(B) receptors in nucleus accumbens neurons". PMID 9514305. {{cite journal}}: Cite journal requires |journal= (help)CS1 maint: multiple names: authors list (link)
14. ^ Daniel Lednicer, The Organic Chemistry of Drug Synthesis. John Wiley & Sons, 2007 ISBN 9780470180662. Page 15

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