Picamilon Chemical Properties

Melting point:

211.0 to 215.0 °C

Boiling point:

522.4±30.0 °C(Predicted)

Density 

1.245

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO (Slightly, Heated), Methanol (Slightly)

form 

Solid

pka

4.60±0.10(Predicted)

color 

White to Off-White

InChI

InChI=1S/C10H12N2O3/c13-9(14)4-2-6-12-10(15)8-3-1-5-11-7-8/h1,3,5,7H,2,4,6H2,(H,12,15)(H,13,14)

InChIKey

NAJVRARAUNYNDX-UHFFFAOYSA-N

SMILES

C(O)(=O)CCCNC(C1=CC=CN=C1)=O

CAS DataBase Reference

34562-97-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2933599590

Picamilon Usage And Synthesis

Description

Pikamilone is a drug having a central (vegetotropic and vascular) and peripheral (vasodilating) mechanisms of action.

Clinical Use

Pikamilone treatment of benign prostatic hyperplasia
Pikamilone is an original drug of Russian produce having a central (vegetotropic and vascular) and peripheral (vasodilating) mechanisms of action. The drug was tried as monotherapy in elderly patients with benign prostatic hyperplasia who had symptoms of the lower urinary tracts to estimate its effect on local and general mechanisms of nervous and vascular regulation of detruzor function in infravesical obstruction.
https://pubmed.ncbi.nlm.nih.gov/11150159/

Description

Picamilon: an analogue of the neurotransmitter γ-aminobutyric acid (GABA)
Picamilon is a derivative of γ-aminobutyric acid (GABA) and nicotinic acid developed in 1970 by the All-Union Vitamin Research Institute to increase central nervous system (CNS) levels of γ-aminobutyric acid (GABA). Drugs that can mimic or increase GABA activity in the brain have the potential to provide anti-anxiety and anti-convulsive effects. GABA itself, when consumed orally, does not cross the blood-brain barrier. Much research has, therefore, been devoted to developing orally active agents that have GABA-like effects. Both gabapentin (a GABA analogue) and picamilon were designed to be orally administered drugs that cross the blood-brain barrier and provide inhibitory CNS effects. Picamilon, prescribed in dosages from 50 mg to 200 mg, can cross the blood-brain barrier in animal models and, once in the CNS, is hydrolyzed into GABA and nicotinic acid. The released GABA could potentially have inhibitory properties, including anti-anxiety and anti-convulsant effects. Nicotinic acid would also be released, potentially leading to dilation of CNS blood vessels. The FDA has never approved picamilon for use in the USA, but picamilon is used in Russia to treat various neurological conditions[1].

Uses

anti-cancer agent

Uses

Nicotinoyl-γ-aminobutyric Acid is a pro-drug of γ-Aminobutyric Acid (A602920). Studies show that Nicotinoyl-γ-aminobutyric Acid is involved in the regulation of the processes in the brain of streptozotocin-induced diabetic rats.

Pharmacokinetics

Because Picamilon can dramatically increase blood flow and circulation within the brain, picamilon is used as a nootropic. Also used for the treatment of depression, anxiety, and migraine, picamilon works by crossing the blood-brain barrier, after which it is hydrolyzed into GABA and nicotinic acid. In addition, picamilon has extremely low toxicity and no allergenic or carcinogenic properties. An animal study has shown that picamilon is rapidly absorbed (Tmax = 0.23 h) and penetrates well through the blood-brain barrier in mice. At oral administration, the drug bioavailability in mice was 21.9% and in rats between 53% and 78.9%[2].

Synthesis

General procedure for the synthesis of 3-((3-carboxypropyl)carbamoyl)pyridine from compound (CAS: 121667-28-5): 10% palladium charcoal (10 mmol) and dry methanol (10 v/v) were added to a 50 mL flask, followed by the addition of compound-2 (10 mmol) under stirring. The atmosphere in the flask was replaced with nitrogen and then hydrogen. The reaction mixture was stirred vigorously in hydrogen atmosphere for 2.0 hours at room temperature. After completion of the reaction, the reaction mixture was filtered through diatomaceous earth and washed with methanol. The organic layer was evaporated and the residue was dissolved in ethyl acetate and washed with water. The organic layer was dried with sodium sulfate, filtered and the solvent was evaporated to give compound-3 (yield: 90%).

in vivo

References

[1] Bharathi Avula. “Identification and quantification of vinpocetine and picamilon in dietary supplements sold in the United States.” Drug Testing and Analysis 8 3–4 (2015): 334–343.
[2] Wenqi Cui . “Determination of picamilon concentration in human plasma by liquid chromatography–tandem mass spectrometry.” Journal of Chromatography B 878 15 (2010): Pages 1181-1184.

Picamilon (34562-97-5)Related Product Information

• Pyridine
• Glycine
• CARBONYL SULFIDE
• PYRAZOPHOS
• L(+)-2-Aminobutyric acid
• 3-Aminopyridine
• 4-Aminobutyric acid
• DL-3-Aminobutyric acid
• 6-Aminocaproic acid
• DL-2-Aminobutyric acid
• D-2-Aminobutyric acid
• r-Amino Butryric Acid
• Pikamilone sodium
• N-(5-hydroxynicotinoyl)-L-glutamic acid
• Glutamic acid, N-(2-chloronicotinoyl)-
• Pikamilone
• DL-2,4-Diaminobutanoic acid
• 1-[(2-hydroxypyridin-3-yl)carbonyl]piperidine-4-carboxylic acid