3-APPA

3-APPA
Identifiers
	IUPAC name 3-aminopropylphosphinic acid;
CAS Number	103680-47-3 ;
PubChem CID	121956;
IUPHAR/BPS	1081;
ChemSpider	10462431;
UNII	QMT5SS3QRE;
ChEMBL	ChEMBL112203;
CompTox Dashboard (EPA)	DTXSID201336775 ;
Chemical and physical data
Formula	C3H10NO2P
Molar mass	123.092 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C(CN)CP(=O)O;
	InChI InChI=1S/C3H10NO2P/c4-2-1-3-7(5)6/h7H,1-4H2,(H,5,6); Key:ZTHNRNOOZGJLRR-UHFFFAOYSA-N;

3-Aminopropylphosphinic acid, also known in the literature as 3-APPA or CGP 27492,^[1] is a compound used in scientific research which acts as an agonist at the GABA_B receptor. It is part of a class of phosphinic acid GABA_B agonists,^[2] which also includes SKF-97,541. It has a binding affinity (pK_i) to the GABA_B receptor of 8.30 (i.e., ~3 nM).^[3]

References

^ "3-APPA". IUPHAR/BPS Guide to Pharmacology. Retrieved March 23, 2021.
^ Lacey G, Curtis DR (1994). "Phosphinic acid derivatives as baclofen agonists and antagonists in the mammalian spinal cord: an in vivo study". Experimental Brain Research. 101 (1): 59–72. doi:10.1007/BF00243217. PMID 7843303. S2CID 19055950.
^ Froestl W, Mickel SJ, von Sprecher G, Diel PJ, Hall RG, Maier L, et al. (August 1995). "Phosphinic acid analogues of GABA. 2. Selective, orally active GABA_B antagonists". Journal of Medicinal Chemistry. 38 (17): 3313–31. doi:10.1021/jm00017a016. PMID 7650685.

[1] "3-APPA". IUPHAR/BPS Guide to Pharmacology. Retrieved March 23, 2021.

[2] Lacey G, Curtis DR (1994). "Phosphinic acid derivatives as baclofen agonists and antagonists in the mammalian spinal cord: an in vivo study". Experimental Brain Research. 101 (1): 59–72. doi:10.1007/BF00243217. PMID 7843303. S2CID 19055950.

[3] Froestl W, Mickel SJ, von Sprecher G, Diel PJ, Hall RG, Maier L, et al. (August 1995). "Phosphinic acid analogues of GABA. 2. Selective, orally active GABA_B antagonists". Journal of Medicinal Chemistry. 38 (17): 3313–31. doi:10.1021/jm00017a016. PMID 7650685.

[1]

[2]

[3]

Identifiers

IUPAC name 3-aminopropylphosphinic acid
CAS Number	103680-47-3^Y
PubChem CID	121956
IUPHAR/BPS	1081
ChemSpider	10462431
UNII	QMT5SS3QRE
ChEMBL	ChEMBL112203
CompTox Dashboard (EPA)	DTXSID201336775
Chemical and physical data
Formula	C₃H₁₀NO₂P
Molar mass	123.092 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C(CN)CP(=O)O
InChI InChI=1S/C3H10NO2P/c4-2-1-3-7(5)6/h7H,1-4H2,(H,5,6) Key:ZTHNRNOOZGJLRR-UHFFFAOYSA-N