picamilon

{{short description|Chemical compound}}

{{cs1 config|name-list-style=vanc|display-authors=6}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 464206196

| IUPAC_name = 4-(Pyridine-3-carbonylamino)butanoic acid

| image = Picamilon2d.png

| image2 = Picamilon3d.png

| tradename = НПК ЭХО

| pregnancy_AU =

| pregnancy_US =

| legal_US = Unapproved drug; use in dietary supplements, food, or medicine is unlawful.{{Cite web |date=November 29, 2017 |title=Picamilon in Dietary Supplements |url=https://www.fda.gov/food/dietary-supplement-ingredient-directory/picamilon-dietary-supplements |archive-url=https://web.archive.org/web/20230324212002/https://www.fda.gov/food/dietary-supplement-ingredient-directory/picamilon-dietary-supplements |url-status=dead |archive-date=March 24, 2023 |access-date=June 9, 2023 |website=FDA}}

| legal_status = RU: OTC

| routes_of_administration = Oral

| bioavailability = 50%–88%

| metabolism =

| elimination_half-life = 1.5 hours

| excretion = Renal

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 34562-97-5

| ATC_prefix = N

| ATC_suffix = 02CX

| ATC_supplemental =

| PubChem = 60608

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = 0S5N9SEK4N

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 54634

| C = 10

| H = 12

| N = 2

| O = 3

| smiles = O=C(NCCCC(=O)O)c1cccnc1

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = NAJVRARAUNYNDX-UHFFFAOYSA-N

| synonyms = nicotinoyl-GABA

}}

Picamilon (also known as N-nicotinoyl-GABA, pycamilon, and pikamilon) is a drug formed by a synthetic combination of niacin and γ-aminobutyric acid (GABA). It was developed in the Soviet Union in 1969{{cite journal | vauthors = Kopelevich VM, Gunar VI | title = Some approaches to the directed search for new drugs based on nicotinic acid | journal = Pharmaceutical Chemistry Journal | volume = 33 | issue = 4 | pages = 177–187 |date=April 1999 | doi = 10.1007/BF02509934 | s2cid = 36930437 }} and further studied in both Russia{{cite journal | vauthors = Mirzoian RS, Gan'shina TS | title = [The new cerebrovascular preparation pikamilon] | language = ru | journal = Farmakologiia i Toksikologiia | volume = 52 | issue = 1 | pages = 23–6 | year = 1989 | pmid = 2707413 }} and Japan as a prodrug of GABA.{{cite journal | vauthors = Matsuyama K, Yamashita C, Noda A, Goto S, Noda H, Ichimaru Y, Gomita Y | title = Evaluation of isonicotinoyl-gamma-aminobutyric acid (GABA) and nicotinoyl-GABA as pro-drugs of GABA | journal = Chemical & Pharmaceutical Bulletin | volume = 32 | issue = 10 | pages = 4089–95 | date = October 1984 | pmid = 6529802 | doi = 10.1248/cpb.32.4089 | doi-access = free }}

In Russia, picamilon is sold as a prescription drug. The rights to the drug belong to the Russian pharmaceutical company NPK ECHO ("НПК ЭХО"). It is not approved for sale in the United States and has been deemed an adulterating agent in dietary supplements,{{cite journal | vauthors = Avula B, Chittiboyina AG, Sagi S, Wang YH, Wang M, Khan IA, Cohen PA | title = Identification and quantification of vinpocetine and picamilon in dietary supplements sold in the United States | journal = Drug Testing and Analysis | volume = 8 | issue = 3–4 | pages = 334–43 | date = March 2016 | pmid = 26426301 | doi = 10.1002/dta.1853 | doi-access = free }} with five American companies required to remove their picamilon products from the market in November 2015.{{cite web | url = http://www.nutraingredients-usa.com/Regulation/FDA-sends-five-warning-letters-over-supplements-containing-picamilon/?c=7InNqGv0AjdjxWpyk%2BfGQw%3D%3D&p2= | title = FDA sends five warning letters over supplements containing picamilon | date = 2 December 2015 | publisher = NutraIngredients-USA.com, William Reed Business Media|access-date=3 December 2015}} However, as recently as 2020, picamilon has been found in pharmaceutical dosages in over-the-counter supplements in the US.{{cite journal | vauthors = Cohen PA, Avula B, Wang YH, Zakharevich I, Khan I | title = Five Unapproved Drugs Found in Cognitive Enhancement Supplements | journal = Neurology. Clinical Practice | volume = 11 | issue = 3 | pages = e303–e307 | date = June 2021 | pmid = 34484905 | pmc = 8382366 | doi = 10.1212/CPJ.0000000000000960 }}