ethanol   

GtoPdb Ligand ID: 2299

Comment: The US FDA granted approval for the use of an injectable formulation of ethanol (alcohol) in dextrose solution, but marketing has been discontinued.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 1
Hydrogen bond donors 1
Rotatable bonds 0
Topological polar surface area 20.23
Molecular weight 46.04
XLogP -0.08
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CCO
Isomeric SMILES CCO
InChI InChI=1S/C2H6O/c1-2-3/h3H,2H2,1H3
InChI Key LFQSCWFLJHTTHZ-UHFFFAOYSA-N
References
1. Aryal P, Dvir H, Choe S, Slesinger PA. (2009)
A discrete alcohol pocket involved in GIRK channel activation.
Nat. Neurosci., 12 (8): 988-95. [PMID:19561601]
2. Downie DL, Hope AG, Belelli D, Lambert JJ, Peters JA, Bentley KR, Steward LJ, Chen CY, Barnes NM. (1995)
The interaction of trichloroethanol with murine recombinant 5-HT3 receptors.
Br. J. Pharmacol., 114 (8): 1641-51. [PMID:7541281]
3. Hayrapetyan V, Jenschke M, Dillon GH, Machu TK. (2005)
Co-expression of the 5-HT(3B) subunit with the 5-HT(3A) receptor reduces alcohol sensitivity.
Brain Res. Mol. Brain Res., 142 (2): 146-50. [PMID:16257471]
4. Hu XQ, Hayrapetyan V, Gadhiya JJ, Rhubottom HE, Lovinger DM, Machu TK. (2006)
Mutations of L293 in transmembrane two of the mouse 5-hydroxytryptamine3A receptor alter gating and alcohol modulatory actions.
Br. J. Pharmacol., 148 (1): 88-101. [PMID:16520747]
5. Kobayashi T, Ikeda K, Kojima H, Niki H, Yano R, Yoshioka T, Kumanishi T. (1999)
Ethanol opens G-protein-activated inwardly rectifying K+ channels.
Nat. Neurosci., 2 (12): 1091-7. [PMID:10570486]
6. Lewohl JM, Wilson WR, Mayfield RD, Brozowski SJ, Morrisett RA, Harris RA. (1999)
G-protein-coupled inwardly rectifying potassium channels are targets of alcohol action.
Nat. Neurosci., 2 (12): 1084-90. [PMID:10570485]
7. Mascia MP, Mihic SJ, Valenzuela CF, Schofield PR, Harris RA. (1996)
A single amino acid determines differences in ethanol actions on strychnine-sensitive glycine receptors.
Mol. Pharmacol., 50 (2): 402-6. [PMID:8700149]
8. Zhou Q, Verdoorn TA, Lovinger DM. (1998)
Alcohols potentiate the function of 5-HT3 receptor-channels on NCB-20 neuroblastoma cells by favouring and stabilizing the open channel state.
J. Physiol. (Lond.), 507 ( Pt 2): 335-52. [PMID:9518697]