Nipecotic acid

Names

[ CAS No. ]:
498-95-3

[ Name ]:
Nipecotic acid

[Synonym ]:
hexahydronicotinic acid
MFCD00005992
(±)-Nipecotic acid
(±)-Piperidine-3-carboxylic acid
Nipecotic acid
UNII:1U1QTN40SY
Piperidine-3-carboxylic acid
EINECS 207-873-9
(±)-3-Piperidine carboxylic acid
3-Piperidinecarboxylic acid
H-DL-Nip-OH

Biological Activity

[Description]:

Nipecotic acid ((±)-β-Homoproline) is a potent inhibitor of neuronal and glial-aminobutyric acid (GABA) uptake in vitro. Nipecotic acid can also directly activate GABAA-like chloride channels, with an EC50 of approximately 300 μM[1][2].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> GABA Receptor

Research Areas >> Neurological Disease

Signaling Pathways >> Neuronal Signaling >> GABA Receptor

[Target]

GABA Receptor[1]

[In Vitro]

Nipecotic acid (1 mM) activated inward unitary currents when applied to outside-out patches of paraventricular neurones[1].

[In Vivo]

Nipecotic acid does not readily cross the blood-brain barrier (BBB)[2].

[References]

[1]. Barrett-Jolley R, et, al. Nipecotic acid directly activates GABA(A)-like ion channels. Br J Pharmacol. 2001 Jul;133(5):673-8.

[2]. Dhanawat M, et, al. Design, Synthesis and Enhanced BBB Penetration Studies of L-serine-Tethered Nipecotic Acid-Prodrug. Drug Res (Stuttg). 2021 Feb;71(2):94-103.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
265.8±33.0 °C at 760 mmHg

[ Melting Point ]:
261ºC (dec.)

[ Molecular Formula ]:
C₆H₁₁NO₂

[ Molecular Weight ]:
129.157

[ Flash Point ]:
114.5±25.4 °C

[ Exact Mass ]:
129.078979

[ PSA ]:
49.33000

[ LogP ]:
-0.04

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.479

[ Storage condition ]:
Store at 0-5°C

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi:Irritant

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S37/39

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
TM6125380

[ HS Code ]:
2933399090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933399090

[ Summary ]:
2933399090. other compounds containing an unfused pyridine ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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