Pregabalin supplier | CasNO.148553-50-8

Name
Pregabalin
EINECS 200-659-6
CAS No. 148553-50-8
Article Data135
CAS DataBase
Density 0.997 g/cm³
Solubility
Melting Point 194-196 °C
Formula C₈H₁₇NO₂
Boiling Point 274 °C at 760 mmHg
Molecular Weight 159.228
Flash Point 119.5 °C
Transport Information
Appearance off-white solid
Safety 22-36/37-45-16-7
Risk Codes 63-48/22-39/23/24/25-23/24/25-11
Molecular Structure
Hazard Symbols Xn,T,F
Synonyms Hexanoic acid, 3-(aminomethyl)-5-methyl-, (S)-;3-isobutyl GABA;(R-)-3-isobutyl GABA;CI 1008;PD 144723;CI-1008;Hexanoic acid, 3-(aminomethyl)-5-methyl-, (3S)-;Lyrica;Pregablin;(3S)-3-(aminomethyl)-5-methylhexanoic acid;(S)-(+)-3-Aminomethyl-5-methylhexanoic acid;
PSA 63.32000
LogP 1.78240

Synthetic route

: 1021167-91-8
(R)-3-((tert-butoxycarbonylamino)methyl)-5-methylhex-4-enoic acid

: 148553-50-8
pregabilin

Conditions

Conditions	Yield
With hydrogenchloride; hydrogen; palladium dihydroxide In methanol at 20℃; under 4560.31 Torr;	100%

: 157422-27-0
(S)-3-azidomethyl-5-methylhexanoic acid

: 148553-50-8
pregabilin

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol for 3h;	99%
With hydrogen; palladium 10% on activated carbon In methanol for 3h;	99%
palladium on activated charcoal In tert-butyl methyl ether	59%
palladium on activated charcoal In tert-butyl methyl ether	59%

: 951792-40-8
(S)-3-azidomethyl-5-methyl-hexanoic acid ethyl ester

: 148553-50-8
pregabilin

Conditions

Conditions	Yield
With hydrogen; palladium 10% on activated carbon In methanol for 3h;	99%
Multi-step reaction with 2 steps 1: 90.9 percent / LiOH*H2O / tetrahydrofuran; methanol; H2O / 0.25 h / Heating 2: 99 percent / H2 / Pd/C / methanol / 3 h View Scheme

: 1253690-87-7
C23H29NO4

: 148553-50-8
pregabilin

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 7500.75 Torr; for 15h;	99%

: 181289-33-8
(3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid

: 148553-50-8
pregabilin

Conditions

Conditions	Yield
Stage #1: (3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid With sodium hydroxide In water at 0 - 10℃; for 0.166667h; Hofmann Rearrangement; Large scale; Stage #2: With sodium hypochlorite In water at 0 - 75℃; for 1h; Temperature; Hofmann Rearrangement; Large scale;	97.7%
Stage #1: (3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid With sodium hypochlorite; sodium hydroxide In water at -15 - -10℃; for 3h; Industrial scale; Stage #2: With sodium sulfite at -10 - 40℃; for 5h; Reagent/catalyst; Temperature; Industrial scale; Further stages;	85%
With sodium hypochlorite; sodium hydroxide In water at 10 - 47℃; Temperature;	83%

: 181289-21-4
5-methyl-3-(nitromethyl)hexanoic acid

: 148553-50-8
pregabilin

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 24h; Reagent/catalyst; Solvent; Time; Temperature;	96%
With palladium on activated charcoal; hydrogen In methanol; water at 20℃; under 2660.18 - 3040.2 Torr; for 16h;

: 181289-45-2
(S)-(+)-5-methyl-3-(nitromethyl)hexanoic acid

: 148553-50-8
pregabilin

Conditions

Conditions	Yield
With hydrogen In methanol; water at 18℃;	95%
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; Solvent;	77%
With hydrogen; 5%-palladium/activated carbon In methanol for 5 - 8h;	35%
With hydrogen; 5% Pd(II)/C(eggshell) In methanol	35%
With hydrogen; palladium on activated charcoal In methanol at 20℃; for 48h;

: 1310495-04-5
(S)-3-(aminomethyl)-5-methyl-N-((S)-1-phenylethyl)hexanamide

: 148553-50-8
pregabilin

Conditions

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water at 65℃; for 6h; Reagent/catalyst;	95%
Stage #1: (S)-3-(aminomethyl)-5-methyl-N-((S)-1-phenylethyl)hexanamide With water; hydrogen bromide at 100 - 110℃; for 5h; Stage #2: With sodium hydroxide In water	83%

: C10H17NO3

: 148553-50-8
pregabilin

Conditions

Conditions	Yield
Stage #1: C10H17NO3 With hydrogenchloride In water for 24h; Reflux; Stage #2: With sodium hydroxide In water pH=7.2;	95%

: sodium 5-methyl-3-nitromethyl-hexanoate

: 148553-50-8
pregabilin

Conditions

Conditions	Yield
With hydrogen In methanol at 20℃; under 760.051 Torr; for 6h; Reagent/catalyst;	95%

: 181289-23-6
(S)-4-isobutyl-pyrrolidin-2-one

: 148553-50-8
pregabilin

Conditions

Conditions	Yield
With ethanol; sodium hydroxide at 40℃; for 5h; Green chemistry;	94.1%
With lipase from Rhizopus delemar; sodium carbonate In water at 35℃; for 5h; pH=9 - 10; Reagent/catalyst; Solvent; Temperature; Enzymatic reaction;	93.2%
With hydrogenchloride In water at 100 - 106℃; for 10h;	88%

: 1078737-39-9
(S)-pregabalin-(-)-O,O'-dibenzoyl-L-tartrate

: 148553-50-8
pregabilin

Conditions

Conditions	Yield
With ammonia In methanol; water at 0℃;	93%

: 930280-44-7
{(S)-4-methyl-2-[((S)-1-phenylethylcarbamoyl)methyl]pentyl}carbamic acid methyl ester

: 148553-50-8
pregabilin

Conditions

Conditions	Yield
Stage #1: {(S)-4-methyl-2-[((S)-1-phenylethylcarbamoyl)methyl]pentyl}carbamic acid methyl ester With hydrogen bromide In water for 3h; Heating / reflux; Stage #2: With sodium hydroxide In water at 20℃; pH=3; Stage #3: With tributyl-amine In 2-methyl-propan-1-ol at 2℃; for 1h; Product distribution / selectivity;	90%
Stage #1: {(S)-4-methyl-2-[((S)-1-phenylethylcarbamoyl)methyl]pentyl}carbamic acid methyl ester With sulfuric acid In water at 115 - 120℃; for 5 - 10h; Stage #2: With sodium hydroxide In water at 20 - 25℃; pH=1; Stage #3: With tributyl-amine In 2-methyl-propan-1-ol pH=4; Product distribution / selectivity;	40.4%
Stage #1: {(S)-4-methyl-2-[((S)-1-phenylethylcarbamoyl)methyl]pentyl}carbamic acid methyl ester With hydrogenchloride; sodium chloride; phenol In water at 105 - 110℃; for 15 - 24h; Stage #2: With sodium hydroxide In water at 20 - 25℃; pH=1; Stage #3: With tributyl-amine In 2-methyl-propan-1-ol pH=4 - 4.5; Product distribution / selectivity;
Stage #1: {(S)-4-methyl-2-[((S)-1-phenylethylcarbamoyl)methyl]pentyl}carbamic acid methyl ester With hydrogenchloride; sodium chloride; phenol In methanol; water at 105 - 110℃; for 15 - 24h; Stage #2: With sodium hydroxide In methanol; water at 20 - 25℃; pH=1; Stage #3: With tributyl-amine In 2-methyl-propan-1-ol pH=4 - 5; Product distribution / selectivity;

: 1082077-26-6
(S)-3-(isopropoxycarbonyl-aminomethyl)-5-methyl-hexanoic acid (S)-(-)-1-phenylethylamine salt

: 148553-50-8
pregabilin

Conditions

Conditions	Yield
Stage #1: (S)-3-(isopropoxycarbonylamino-methyl)-5-methyl-hexanoic acid (S)-(-)-1-phenylethylamine salt With hydrogenchloride In water; toluene for 0.166667 - 0.25h; Stage #2: With hydrogenchloride; water at 90℃; for 24 - 48h; Stage #3: With methylamine In water pH=~ 6;	88%
Stage #1: (S)-3-(isopropoxycarbonylamino-methyl)-5-methyl-hexanoic acid (S)-(-)-1-phenylethylamine salt With hydrogenchloride In water at 90℃; Inert atmosphere; Stage #2: With methylamine In water; toluene at 0 - 90℃; for 1h; pH=6;	88%
Stage #1: (S)-3-(isopropoxycarbonylamino-methyl)-5-methyl-hexanoic acid (S)-(-)-1-phenylethylamine salt With hydrogenchloride; water at 90 - 95℃; for 24h; Stage #2: With sodium hydroxide; water at 0 - 5℃; for 1h; Product distribution / selectivity;	82%

: 1082077-19-7
isopropyl (S)-{4-methyl-2-[(1-methoxycarbonyl)methyl]pentyl}-carbamate

: 148553-50-8
pregabilin

Conditions

Conditions	Yield
Stage #1: isopropyl (S)-{4-methyl-2-[(1-methoxycarbonyl)methyl]pentyl}-carbamate With hydrogenchloride; water at 90℃; for 24 - 48h; Stage #2: With water; methylamine pH=~ 6; Product distribution / selectivity;	88%

: (S)-(+)-pregabalin (2R,3R)-(+)-tartaric acid

: 148553-50-8
pregabilin

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In water; isopropyl alcohol at 20 - 25℃; pH=7.0 - 7.5; Product distribution / selectivity;	88%
With ammonium hydroxide In water at 0 - 65℃; Product distribution / selectivity;	81.1%

: (S)-pregabalin O,O'-di-p-toluoyl-(D)-tartrate

: 148553-50-8
pregabilin

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In water; isopropyl alcohol at 20 - 25℃; pH=7.0 - 7.5;	87%

: 951792-39-5
(S)-3-bromomethyl-5-methyl-hexanoic acid ethyl ester

: 148553-50-8
pregabilin

Conditions

Conditions	Yield
Stage #1: (S)-3-bromomethyl-5-methyl-hexanoic acid ethyl ester With sodium azide In N,N-dimethyl-formamide at 20℃; for 5h; Stage #2: With 5%-palladium/activated carbon; hydrogen at 20℃; for 5h;	84.5%
Multi-step reaction with 3 steps 1: 92.9 percent / NaN3 / dimethylformamide / 4 h / 20 °C 2: 90.9 percent / LiOH*H2O / tetrahydrofuran; methanol; H2O / 0.25 h / Heating 3: 99 percent / H2 / Pd/C / methanol / 3 h View Scheme

: 1026095-29-3
C8H8O3*C8H17NO2

: 148553-50-8
pregabilin

Conditions

Conditions	Yield
In tetrahydrofuran; water at 0 - 55℃; for 5h;	83%

: (S)-3-[(dibenzylamino)methyl]-5-methylhexanoic acid

: 148553-50-8
pregabilin

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 3750.38 Torr; for 24h; Solvent; Pressure;	82.7%

: C13H25NO4

: 148553-50-8
pregabilin

Conditions

Conditions	Yield
With water; sodium hydroxide at 24℃; Reflux;	81%

: (S)-4-isobutyl-2-oxo-pyrrolidine-3-carboxylic acid

: 148553-50-8
pregabilin

Conditions

Conditions	Yield
Stage #1: (S)-4-isobutyl-2-oxo-pyrrolidine-3-carboxylic acid With hydrogenchloride; water In ethyl acetate at 80 - 110℃; for 42 - 44h; Stage #2: With potassium hydroxide In water pH=5.2 - 5.5;	80%

: C13H24N2O2

: 148553-50-8
pregabilin

Conditions

Conditions	Yield
With hydrogenchloride In water for 36h; Reflux;	80%

: C21H26N2O3

: 148553-50-8
pregabilin

Conditions

Conditions	Yield
With perchloric acid; water for 12h; Reflux;	79%

: C16H29NO6

: 148553-50-8
pregabilin

Conditions

Conditions	Yield
With hydrogenchloride In water for 72h; Reflux;	79%

: C17H25NO4

: 148553-50-8
pregabilin

Conditions

Conditions	Yield
With water; potassium hydroxide In water for 20h; Reflux;	78%

: methyl (S)-3-cyano-5-methyl-hexanoate

: 148553-50-8
pregabilin

Conditions

Conditions	Yield
Stage #1: methyl (S)-3-cyano-5-methyl-hexanoate With water; potassium hydroxide In methanol at 20 - 25℃; for 1.5h; Stage #2: With hydrogen In methanol at 30℃; under 7500.75 Torr; for 48h; Reagent/catalyst; Temperature; Time;	74.62%
Multi-step reaction with 2 steps 1: nickel dichloride; sodium tetrahydroborate; methanol 2: hydrogenchloride; water View Scheme

: 949890-75-9
(-)-(S)-3-(benzyloxycarbonylamino-methyl)-5-methyl-hexanoic acid

: 148553-50-8
pregabilin

Conditions

Conditions	Yield
With palladium on activated charcoal; hydrogen In methanol at 40℃; under 11251.1 Torr; for 10h; Solvent;	68%
With hydrogen; palladium on activated charcoal In methanol at 20℃; under 7500.75 Torr; for 15h;	60%
With palladium on activated charcoal; hydrogen In methanol at 20℃; under 11251.1 Torr; for 15h;	60%

: 156048-97-4
3-(azidomethyl)-5-methyl-hexanoic acid phenylmethyl ester

: 148553-50-8
pregabilin

Conditions

Conditions	Yield
With hydrogenchloride; palladium on activated charcoal In tetrahydrofuran; water at 20℃;	65%

: 1174524-47-0
(1R)-1-({[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl}oxy)ethyl 2-methylpropionate

: 148553-50-8
pregabilin

: 1174748-30-1
3-{[(α-(R)-isobutanoyloxyethoxy)carbonyl]aminomethyl}-5-(S)-methylhexanoic acid

Conditions

Conditions	Yield
In water; acetonitrile at 20℃; for 16h;	100%

: 1174524-50-5
(S)-1-(2,5-dioxoazolidinyloxycarbonyloxy)-2-methylpropyl 2-methylpropanate

: 148553-50-8
pregabilin

: 1179336-90-3
3-{[(α-(S)-isobutanoyloxyisobutoxy)carbonyl]aminomethyl}-5-(S)-methylhexanoic acid

Conditions

Conditions	Yield
In water; acetonitrile at 20℃; for 6h;	100%

: 1174524-53-8
{[(1R)-Benzoyloxyethoxy]carbonyloxy}succinimide

: 148553-50-8
pregabilin

: 1174748-47-0
(3S)-{[(1R)-benzoyloxyethoxy]carbonylaminomethyl}-5-methyl-hexanoic acid

Conditions

Conditions	Yield
In water; acetonitrile at 20℃; for 16h;	100%

: 143-07-7
lauric acid

: 148553-50-8
pregabilin

: 1414928-47-4
(S)-3-(aminomethyl)-5-methylhexanoic acid laurate

Conditions

Conditions	Yield
In isopropyl alcohol for 1.5h; Product distribution / selectivity;	100%

: 110-16-7
maleic acid

: 148553-50-8
pregabilin

: 1414928-41-8
(S)-3-(aminomethyl)-5-methylhexanoic acid maleate

Conditions

Conditions	Yield
In 2-methylpropyl acetate for 0.75h; Product distribution / selectivity;	100%

: 65-85-0
benzoic acid

: 148553-50-8
pregabilin

: 1414928-43-0
(S)-3-(aminomethyl)-5-methylhexanoic acid benzoate

Conditions

Conditions	Yield
for 0.75h; Product distribution / selectivity;	100%

: 124-07-2
Octanoic acid

: 148553-50-8
pregabilin

: 1414928-45-2
(S)-3-(aminomethyl)-5-methylhexanoic acid caprylate

Conditions

Conditions	Yield
In tert-butyl methyl ether for 0.75h;	100%

: 334-48-5
1-decanoic acid

: 148553-50-8
pregabilin

: 1414928-46-3
(S)-3-(aminomethyl)-5-methylhexanoic acid caprate

Conditions

Conditions	Yield
In tert-butyl methyl ether for 0.75h;	100%

: 24424-99-5
di-tert-butyl dicarbonate

: 148553-50-8
pregabilin

: 228104-41-4
3-((tert-butoxycarbonylamino)methyl)-5-methylhexanoic acid

Conditions

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; water	98%

: 148553-50-8
pregabilin

: 181289-23-6
(S)-4-isobutyl-pyrrolidin-2-one

Conditions

Conditions	Yield
With acidic kaolin In 5,5-dimethyl-1,3-cyclohexadiene for 6h; Solvent; Reagent/catalyst; Reflux;	97%
With diazomethyl-trimethyl-silane In methanol; hexane for 0.5h;
at 80℃; for 336h; Kinetics; Temperature;

: L-mandelate anion

: 148553-50-8
pregabilin

: 17199-29-0
(S)-Mandelic acid

Conditions

Conditions	Yield
With pyrographite In isopropyl alcohol at 0 - 85℃; for 4h;	95%

: 24424-99-5
di-tert-butyl dicarbonate

: 148553-50-8
pregabilin

: 649748-09-4
(S)-3-(((tert-butoxycarbonyl)amino)methyl)-5-methylhexanoic acid

Conditions

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran; water at 0℃; Inert atmosphere; Schlenk technique;	93%
Stage #1: pregabilin With sodium hydroxide In 1,4-dioxane; water at 20℃; for 0.0833333h; Stage #2: di-tert-butyl dicarbonate In 1,4-dioxane; water at 20℃; for 1.5h;	86%
With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃;	63%

: 7776-34-3
L-proline hydrochloride

: 148553-50-8
pregabilin

: 1414928-44-1
(S)-3-(aminomethyl)-5-methylhexanoic acid L-proline hydrochloride

Conditions

Conditions	Yield
In acetonitrile at 20℃;	93%

: 148553-50-8
pregabilin

: 61312-87-6
4-(2-methylpropyl)pyrrolidin-2-one

Conditions

Conditions	Yield
at 190℃; for 0.166667h;	91%

: 14371-10-9
(E)-3-phenylpropenal

: 148553-50-8
pregabilin

: 5-methyl-3-({(Z)-[(2E)-3-phenylprop-2-en-1-ylidene]amino}methyl)hexanoic acid

Conditions

Conditions	Yield
With acetic acid In ethanol at 40℃; for 6h;	90%

: 87-69-4
L-Tartaric acid

: 148553-50-8
pregabilin

: 1190093-69-6
(S)-3-(aminomethyl)-5-methylhexanoic acid L-(+)-tartrate

Conditions

Conditions	Yield
In water; isopropyl alcohol at 0 - 20℃; Product distribution / selectivity;	89%

Pregabalin History

Pregabalin was first developed by medicinal chemist Richard Bruce Silverman at Northwestern University in the United States. In 2004,The drug was approved in the European Union. Pregabalin received U.S. FDA approval for use in treating epilepsy, diabetic neuropathy pain and post-herpetic neuralgia in December 2004, and appeared on the U.S. market in fall 2005.

Pregabalin Specification

1. Introduction of Pregabalin
Pregabalin is one kind of white or almost white crystalline powder or off-white solid. The IUPAC name of this chemical is (3S)-3-(aminomethyl)-5-methylhexanoic acid. The product's categories are APIs; Miscellaneous Biochemicals; Intermediates & Fine Chemicals; Neurochemicals; Pharmaceuticals; API. Besides, the Classification Code of it is Analgesics; Anticonvulsant; Anticonvulsants; Central Nervous System Agents; Peripheral Nervous System Agents; Sensory System Agents. It is freely soluble in water and both basic and acidic aqueous solutions. The Pregabalin is an organic compound.

2. Properties of Pregabalin
Physical properties about Pregabalin are:
(1)ACD/LogP: 1.12; (2)ACD/LogD (pH 5.5): -1.39; (3)ACD/LogD (pH 7.4): -1.38; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 3; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 6; (11)Polar Surface Area: 29.54 Å²; (12)Index of Refraction: 1.464; (13)Molar Refractivity: 44.12 cm³; (14)Molar Volume: 159.6 cm³; (15)Polarizability: 17.49×10^-24cm³; (16)Surface Tension: 37.8 dyne/cm; (17)Density: 0.997 g/cm³; (18)Flash Point: 119.5 °C; (19)Enthalpy of Vaporization: 56.4 kJ/mol; (20)Boiling Point: 274 °C at 760 mmHg; (21)Vapour Pressure: 0.00153 mmHg at 25°C.

3. Structure Descriptors of Pregabalin
You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)C[C@H](CC(C)C)CN
(2)InChI: InChI=1/C8H17NO2/c1-6(2)3-7(5-9)4-8(10)11/h6-7H,3-5,9H2,1-2H3,(H,10,11)/t7-/m0/s1
(3)InChIKey: AYXYPKUFHZROOJ-ZETCQYMHBI
(4)Std. InChI: InChI=1S/C8H17NO2/c1-6(2)3-7(5-9)4-8(10)11/h6-7H,3-5,9H2,1-2H3,(H,10,11)/t7-/m0/s1
(5)Std. InChIKey: AYXYPKUFHZROOJ-ZETCQYMHSA-N

4. Uses of Pregabalin
Pregabalin is an anticonvulsant drug used for neuropathic pain and as an adjunct therapy for partial seizures with or without secondary generalization in adults. It has also been found effective for generalized anxiety disorder and is approved for this use in the European Union. It was designed as a more potent successor to gabapentin. It is considered to have a dependence liability if misused, and is classified as a Schedule V drug in the U.S. It can be used as anticonvulsion, anti-epileptic drug.

Product Name

Pregabalin

Synthetic route

Pregabalin History

Pregabalin Specification

Related Products

Hot Products