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'''Homotaurine''' ('''3-amino-1-propanesulfonic acid''' ('''3-APS''') or '''tramiprosate''' (])) is a synthetic ]. It is analogous to ], but with an extra carbon in its chain. Because of its similarity in structure to the ] ] (GABA), it has ] effects and may be useful as an anticonvulsant.<ref>{{cite journal |author=Fariello RG, Golden GT, Pisa M |title=Homotaurine (3 aminopropanesulfonic acid; 3APS) protects from the convulsant and cytotoxic effect of systemically administered kainic acid |journal=Neurology |volume=32 |issue=3 |pages=241–5 |year=1982 |pmid=7199633 |doi=10.1212/wnl.32.3.241|last2=Golden |last3=Pisa }}</ref> '''Homotaurine''' ('''3-amino-1-propanesulfonic acid''' ('''3-APS''') or '''tramiprosate''' (])) is a synthetic ]. It is analogous to ], but with an extra carbon in its chain. Because of its similarity in structure to the ] ] (GABA), it has ] effects and may be useful as an anticonvulsant.<ref>{{cite journal |author=Fariello RG, Golden GT, Pisa M |title=Homotaurine (3 aminopropanesulfonic acid; 3APS) protects from the convulsant and cytotoxic effect of systemically administered kainic acid |journal=Neurology |volume=32 |issue=3 |pages=241–5 |year=1982 |pmid=7199633 |doi=10.1212/wnl.32.3.241|last2=Golden |last3=Pisa }}</ref>

It is a ] receptor antagonist <ref>{{cite journal|title=Homotaurine: a GABAB antagonist in guinea-pig ileum.|pmid=6652358|author=Giotti A, Luzzi S, Spagnesi S, Zilletti L.}}</ref> and reversed the catatonia induced by baclofen in rats. <ref>{{cite journal|title=Baclofen induces catatonia in rats.|pmid=2823166|author=Mehta AK1, Ticku MK.}}</ref>Moreover, Homotaurine suppress ethanol-stimulated dopamine release, ethanol intake and preference in rats similar to ] (Acetylated homotaurine analogue) <ref>{{cite journal|title=Effects of acute acamprosate and homotaurine on ethanol intake and ethanol-stimulated mesolimbic dopamine release.|pmid=11864639|author=Olive MF, Nannini MA, Ou CJ, Koenig HN, Hodge CW.}}</ref>.


Homotaurine is a ] at neutral ]. Homotaurine is a ] at neutral ].

Revision as of 21:20, 9 March 2016

Homotaurine
Skeletal formula
Ball-and-stick model
Names
IUPAC name 3-Aminopropane-1-sulfonic acid
Other names Tramiprosate; Alzhemed; 3-APS
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.020.889 Edit this at Wikidata
KEGG
PubChem CID
CompTox Dashboard (EPA)
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). checkY verify (what is  ?) Infobox references
Chemical compound

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.

It is a GABAB receptor 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) .

Homotaurine is a zwitterion at neutral pH.

Skeletal formulaBall-and-stick modelThe zwitterionic form of homotaurine

See also

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. 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)
  4. 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)
  5. 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)


Anticonvulsants (N03)
GABAergics
GABAAR PAMs
GABA-T inhibitors
Others
Channel
modulators
Sodium blockers
Calcium blockers
Potassium openers
Others
CA inhibitors
Others
GABA receptor modulators
Ionotropic
GABAATooltip γ-Aminobutyric acid A receptor
GABAA-ρTooltip γ-Aminobutyric acid A-rho receptor
Metabotropic
GABABTooltip γ-Aminobutyric acid B receptor
See also
Receptor/signaling modulators
GABAA receptor positive modulators
GABA metabolism/transport modulators


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