Chemistry:Tolibut

Tolibut
Clinical data
ATC code	None;
Identifiers
	IUPAC name 4-Amino-3-(4-methylphenyl)butanoic acid;
CAS Number	28311-38-8 ; 28311-37-7 (HCl);
PubChem CID	49344;
ChemSpider	44852;
UNII	UJ5N9SJ9NL;
Chemical and physical data
Formula	C11H15NO2
Molar mass	193.246 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1=CC=C(C=C1)C(CC(=O)O)CN;
	InChI InChI=1S/C11H15NO2/c1-8-2-4-9(5-3-8)10(7-12)6-11(13)14/h2-5,10H,6-7,12H2,1H3,(H,13,14); Key:MSZRPURXKHMSFF-UHFFFAOYSA-N;

Short description: Chemical compound

Tolibut, also known as 3-(p-tolyl)-4-aminobutyric acid (or β-(4-methylphenyl)-GABA), is drug that was developed in Russia . It is an analogue of γ-aminobutyric acid (GABA) (that is, a GABA analogue) and is the 4-methyl analogue of phenibut, and is also an analogue of baclofen where the 4-chloro substitution has been replaced with a 4-methyl substitution. Tolibut has been described as possessing analgesic, tranquilizing, and neuroprotective properties. It is not fully clear as to whether the drug was ever approved or used medically in Russia.^[1]^[2]^[3]^[4]

References

↑ "Functional aspects of neuroprotective effects of new salts and compositions of baclofen in the convulsive syndrome caused by electroshock". Bulletin of Experimental Biology and Medicine 153 (5): 710–713. September 2012. doi:10.1007/s10517-012-1806-5. PMID 23113265.
↑ "Effect of analogs of γ -aminobutyric acid on the uptake of [3H]-γ -aminobutyric acid by synaptosomes of the rat brain". Pharmaceutical Chemistry Journal 11 (1): 10–12. January 1977. doi:10.1007/BF00779108.
↑ "[The spectrum of analgesic activity of baclofen and tolibut]" (in ru). Farmakologiia I Toksikologiia 50 (1): 24–27. 1987. PMID 3556547.
↑ "[A hypothesis of the possible mechanism of the action of analgesic agents at the neuronal level]" (in ru). Eksperimental'naia i Klinicheskaia Farmakologiia 55 (1): 16–18. 1992. PMID 1363942.

{{Navbox | name = GABA receptor modulators | title = GABA receptor modulators | state = collapsed | bodyclass = hlist | groupstyle = text-align:center;

 | group1 = Ionotropic
 |  list1 = {{Navbox|subgroup
 | groupstyle = text-align:center
 | groupwidth = 5em

   | group1 = GABA_A
   | list1  =

Agonists: (+)-Catechin
Bamaluzole
Barbiturates (e.g., phenobarbital)
BL-1020
DAVA
Dihydromuscimol
GABA
Gabamide
GABOB
Gaboxadol (THIP)
Homotaurine (tramiprosate, 3-APS)
Ibotenic acid
iso-THAZ
iso-THIP
Isoguvacine
Isomuscimol
Isonipecotic acid
Kojic amine
Lignans (e.g., honokiol)
Methylglyoxal
Monastrol
Muscimol
Nefiracetam
Neuroactive steroids (e.g., allopregnanolone)
Org 20599
PF-6372865
Phenibut
Picamilon
P4S
Progabide
Propofol
Quisqualamine
SL-75102
TACA
TAMP
Terpenoids (e.g., borneol)
Thiomuscimol
Tolgabide
ZAPA

Positive modulators (abridged; see here for a full list): α-EMTBL
Alcohols (e.g., ethanol)
Anabolic steroids
Avermectins (e.g., ivermectin)
Barbiturates (e.g., phenobarbital)
Benzodiazepines (e.g., diazepam)
Bromide compounds (e.g., potassium bromide)
Carbamates (e.g., meprobamate)
Carbamazepine
Chloralose
Chlormezanone
Clomethiazole
Dihydroergolines (e.g., ergoloid (dihydroergotoxine))
Etazepine
Etifoxine
Fenamates (e.g., mefenamic acid)
Flavonoids (e.g., apigenin, hispidulin)
Fluoxetine
Flupirtine
Imidazoles (e.g., etomidate)
Kava constituents (e.g., kavain)
Lanthanum
Loreclezole
Monastrol
Neuroactive steroids (e.g., allopregnanolone, [[Chemistry:Cholecholesterol]], THDOC)
Niacin
Nicotinamide (niacinamide)
Nonbenzodiazepines (e.g., β-carbolines (e.g., [[abecarnil), cyclopyrrolones (e.g., zopiclone), imidazopyridines (e.g., zolpidem), pyrazolopyrimidines (e.g., zaleplon))
Norfluoxetine
Petrichloral
Phenols (e.g., propofol)
Phenytoin
Piperidinediones (e.g., glutethimide)
Propanidid
Pyrazolopyridines (e.g., etazolate)
Quinazolinones (e.g., methaqualone)
Retigabine (ezogabine)
ROD-188
Skullcap constituents (e.g., baicalin)
Stiripentol
Sulfonylalkanes (e.g., sulfonmethane (sulfonal))
Topiramate
Valerian constituents (e.g., valerenic acid)
Volatiles/gases (e.g., chloral hydrate, chloroform, [[Chemistry:Diethyl diethyl ether, Par paraldehyde]], sevoflurane)

Negative modulators: 1,3M1B
3M2B
11-Ketoprogesterone
17-Phenylandrostenol
α5IA (LS-193,268)
β-CCB
β-CCE
β-CCM
β-CCP
β-EMGBL
Anabolic steroids
Amiloride
Anisatin
β-Lactams (e.g., penicillins, cephalosporins, carbapenems)
Basmisanil
Bemegride
Bicyclic phosphates (TBPS, TBPO, IPTBO)
BIDN
Bilobalide
Bupropion
CHEB
Chlorophenylsilatrane
Cicutoxin
Cloflubicyne
Cyclothiazide
DHEA
DHEA-S
Dieldrin
(+)-DMBB
DMCM
DMPC
EBOB
Etbicyphat
FG-7142 (ZK-31906)
Fiproles (e.g., fipronil)
Flavonoids (e.g., amentoflavone, oroxylin A)
Flumazenil
Fluoroquinolones (e.g., ciprofloxacin)
Flurothyl
Furosemide
Golexanolone
Iomazenil (¹²³I)
IPTBO
Isopregnanolone (sepranolone)
L-655,708
Laudanosine
Leptazol
Lindane
MaxiPost
Morphine
Morphine-3-glucuronide
MRK-016
Naloxone
Naltrexone
Nicardipine
Nonsteroidal antiandrogens (e.g., [[apalutamide, [[Chemistry:Bicalutbicalutamide, Enzalut enzalutamide, Chemistry:Flutamide|flut]]amide]], nilutamide)
Oenanthotoxin
Pentylenetetrazol (pentetrazol)
Phenylsilatrane
Picrotoxin (i.e., picrotin, picrotoxinin and dihydropicrotoxinin)
Pregnenolone sulfate
Propybicyphat
PWZ-029
Radequinil
Ro 15-4513
Ro 19-4603
RO4882224
RO4938581
Sarmazenil
SCS
Suritozole
TB-21007
TBOB
TBPS
TCS-1105
Terbequinil
TETS
Thujone
U-93631
Zinc
ZK-93426

   | group2 = GABA_A-ρ
   | list2  =

Negative modulators: 5α-Dihydroprogesterone
Bilobalide
Loreclezole
Picrotoxin (picrotin, picrotoxinin)
Pregnanolone
ROD-188
THDOC
Zinc

}}

 | group2 = Metabotropic

| list2 =

 | below =

See also: Receptor/signaling modulators; GABA_A receptor positive modulators; GABA metabolism/transport modulators

}}

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Original source: https://en.wikipedia.org/wiki/Tolibut. Read more

[TyurenkovBorodkina2012-1] "Functional aspects of neuroprotective effects of new salts and compositions of baclofen in the convulsive syndrome caused by electroshock". Bulletin of Experimental Biology and Medicine 153 (5): 710–713. September 2012. doi:10.1007/s10517-012-1806-5. PMID 23113265.

[Morozov1977-2] "Effect of analogs of γ -aminobutyric acid on the uptake of [3H]-γ -aminobutyric acid by synaptosomes of the rat brain". Pharmaceutical Chemistry Journal 11 (1): 10–12. January 1977. doi:10.1007/BF00779108.

[pmid3556547-3] "[The spectrum of analgesic activity of baclofen and tolibut]" (in ru). Farmakologiia I Toksikologiia 50 (1): 24–27. 1987. PMID 3556547.

[pmid1363942-4] "[A hypothesis of the possible mechanism of the action of analgesic agents at the neuronal level]" (in ru). Eksperimental'naia i Klinicheskaia Farmakologiia 55 (1): 16–18. 1992. PMID 1363942.

[1]

[2]

[3]

[4]

v t e Anxiolytics (N05B)
5-HT_1AR agonists	Buspirone Gepirone^† Tandospirone
GABA_AR PAMs	Benzodiazepines: Adinazolam Alprazolam Bromazepam Camazepam Chlordiazepoxide Clobazam Clonazepam Clorazepate Clotiazepam Cloxazolam Diazepam^# Ethyl loflazepate Etizolam Fludiazepam Halazepam Ketazolam Lorazepam^# Medazepam Nordazepam Oxazepam Pinazepam Prazepam; Others: Alpidem^‡ Barbiturates (e.g., phenobarbital) Carbamates (e.g., meprobamate) Chlormezanone^‡ Ethanol (alcohol) Etifoxine Imepitoin; Herbs: Kava Skullcap Valerian
Gabapentinoids (α₂δ VDCC blockers)	Gabapentin Gabapentin enacarbil Phenibut Pregabalin
Antidepressants	SSRIs (e.g., escitalopram) SNRIs (e.g., duloxetine) SARIs (e.g., trazodone) TCAs (e.g., clomipramine^#) TeCAs (e.g., mirtazapine) MAOIs (e.g., phenelzine); Others: Agomelatine Bupropion Tianeptine Vilazodone Vortioxetine
Sympatholytics (Antiadrenergics)	Alpha-1 blockers (e.g., prazosin) Alpha-2 agonists (e.g., clonidine, dexmedetomidine, guanfacine) Beta blockers (e.g., propranolol)
Others	Benzoctamine Cannabidiol Cycloserine Fabomotizole Hydroxyzine Kanna Lavender Lorpiprazole Mebicar Mepiprazole Nicotine Opipramol Oxaflozane^‡ Phenaglycodol Phenibut Picamilon Selank Tiagabine Tofisopam Validolum
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

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Clinical data

ATC code	None
Identifiers
IUPAC name 4-Amino-3-(4-methylphenyl)butanoic acid
CAS Number	28311-38-8 28311-37-7 (HCl)
PubChem CID	49344
ChemSpider	44852
UNII	UJ5N9SJ9NL
Chemical and physical data
Formula	C₁₁H₁₅NO₂
Molar mass	193.246 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC1=CC=C(C=C1)C(CC(=O)O)CN
InChI InChI=1S/C11H15NO2/c1-8-2-4-9(5-3-8)10(7-12)6-11(13)14/h2-5,10H,6-7,12H2,1H3,(H,13,14) Key:MSZRPURXKHMSFF-UHFFFAOYSA-N

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