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148553-50-8

Basic Information
CAS No.: 148553-50-8
Name: Pregabalin
Article Data: 135
Molecular Structure:
Molecular Structure of 148553-50-8 (Pregabalin)
Formula: C8H17NO2
Molecular Weight: 159.228
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;
EINECS: 200-659-6
Density: 0.997 g/cm3
Melting Point: 194-196 °C
Boiling Point: 274 °C at 760 mmHg
Flash Point: 119.5 °C
Appearance: off-white solid
Hazard Symbols: Xn,T,F
Risk Codes: 63-48/22-39/23/24/25-23/24/25-11
Safety: 22-36/37-45-16-7
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
ConditionsYield
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
ConditionsYield
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 ether59%
palladium on activated charcoal In tert-butyl methyl ether59%
951792-40-8

(S)-3-azidomethyl-5-methyl-hexanoic acid ethyl ester

148553-50-8

pregabilin

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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 methanol35%
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With hydrogen In methanol at 20℃; under 760.051 Torr; for 6h; Reagent/catalyst;95%
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    pregabalin CAS: 148553-50-8 Molecular Formula: C8H17NO2 Home Product Category other other 148553-50-8 148553-50-8 - Names and Identifiers Name pregabalin Synonyms CI 1008 CI-1008 PD 144723 Pregablin PD-

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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.

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.