{"id":3910,"date":"2025-09-02T02:24:50","date_gmt":"2025-09-02T02:24:50","guid":{"rendered":"https:\/\/modafinil.pl\/?post_type=product&p=3910"},"modified":"2026-10-03T05:51:54","modified_gmt":"2026-10-03T05:51:54","slug":"pregabalin-pregabalina","status":"publish","type":"product","link":"https:\/\/modafinil.pl\/en\/sklep\/pregabalin-pregabalina\/","title":{"rendered":"Pregabalin \/ Pregabalina (CAS 148553-50-8) \u2014 Chemical Reagent, 1000 mg, Purity \u2265 99%"},"content":{"rendered":"

(3S)-3-(aminomethyl)-5-methylhexanoic acid<\/strong>, crystalline powder, 1000 mg package. Material intended exclusively for laboratory and analytical research use in vitro<\/strong>. The product is not intended for consumption by humans or animals<\/strong>, is not a medicinal product, a dietary supplement, a food product, or a cosmetic.<\/p>\n

Three different entities that must not be confused<\/h2>\n

Pregabalin is one of the most extensively studied molecules among GABA analogues, which is why separating the layers matters here in particular. The same chemical name simultaneously functions as the active ingredient of a prescription-only medicinal product<\/strong> marketed under more than a dozen trade names. Three contexts, three entirely different legal statuses:<\/p>\n\n\n\n\n\n\n\n
Separating the layers: substance \u2014 medicinal product \u2014 reagent<\/caption>\n
Entity<\/th>\nWhat it is<\/th>\nWhat it concerns<\/th>\n<\/tr>\n<\/thead>\n
Chemical substance
pregabalin, CAS 148553-50-8<\/th>\n		A chemical concept \u2014 a molecule of defined structure, an analogue of gamma-aminobutyric acid (GABA). In itself it is neither a drug nor a reagent; its status is conferred by the form in which it was manufactured and approved.<\/td>\nchemistry, substance registries<\/td>\n<\/tr>\n
Medicinal product
including Lyrica and generic equivalents (Pregabalin Sandoz, Pregabalin Zentiva, Vronogabic)<\/th>\n		A pharmaceutical preparation: a defined pharmaceutical form, manufacturing under GMP, registration documentation, safety oversight. In Poland dispensed only on a doctor’s prescription.<\/strong><\/td>\nthis entity is the subject of clinical trials involving humans<\/strong><\/td>\n<\/tr>\n
Chemical reagent
the material offered here<\/th>\n		Material for laboratory and analytical work. It does not have and cannot have approval for use in humans or animals<\/strong> \u2014 it has no pharmaceutical form or medicinal product documentation.<\/td>\nanalytics, chemistry, reference standards<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

The consequence is unambiguous.<\/strong> The study results cited further on this page were obtained either using the registered medicinal product<\/strong> (clinical trials involving humans), or using the substance administered to laboratory animals or animal tissue under controlled experimental conditions<\/strong> (preclinical studies). None of these studies was conducted using the analytical reagent<\/strong>, and none of these results carries over to the material offered here. The reagent is not the form in which the substance has ever been studied in humans, and it cannot be used in that way.<\/p>\n

Reagent identification card<\/h2>\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n
Registry data and identifiers \u2014 pregabalin<\/caption>\n
Systematic name (IUPAC)<\/th>\n(3S)-3-(aminomethyl)-5-methylhexanoic acid<\/td>\n<\/tr>\n
Common name<\/th>\npregabalin (pregabalina, pregabaline)<\/td>\n<\/tr>\n
Development code<\/th>\nCI-1008<\/td>\n<\/tr>\n
CAS Number<\/th>\n148553-50-8<\/td>\n<\/tr>\n
Molecular formula<\/th>\nC8<\/sub>H17<\/sub>NO2<\/sub><\/td>\n<\/tr>\n
Molar mass<\/th>\n159.23 g\u00b7mol\u22121<\/sup><\/td>\n<\/tr>\n
Monoisotopic mass<\/th>\n159.1259 Da<\/td>\n<\/tr>\n
InChIKey<\/th>\nAYXYPKUFHZROOJ-ZETCQYMHSA-N<\/td>\n<\/tr>\n
SMILES<\/th>\nCC(C)C[C@@H](CC(=O)O)CN<\/td>\n<\/tr>\n
PubChem CID<\/th>\n5486971<\/a><\/td>\n<\/tr>\n
ChEMBL ID<\/th>\nCHEMBL3978768<\/td>\n<\/tr>\n
Melting point<\/th>\n187\u00b0C<\/td>\n<\/tr>\n
Form<\/th>\ncrystalline powder, white to off-white<\/td>\n<\/tr>\n
Purity<\/th>\n\u2265 99%<\/td>\n<\/tr>\n
Intended use<\/th>\nresearch reagent \u2014 not for consumption by humans or animals<\/strong><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

Molecular lineage: from gabapentin to a single enantiomer<\/h2>\n

Anticonvulsant drug discovery program<\/h3>\n

Pregabalin was not a chance discovery but the product of a deliberate, multi-year research program. The starting point was gabapentin<\/strong> \u2014 a compound registered as a medicinal product in 1993, the first success of the research line of gamma-aminobutyric acid (GABA) analogues. Chemist Richard B. Silverman (Northwestern University), working with Parke-Davis (later Warner-Lambert, part of Pfizer since 2000), built a series of branched GABA analogues<\/strong> and tested them for affinity to the same molecular target as gabapentin, searching for a molecule with stronger binding. Silverman himself described the discovery history in the first person in a retrospective article from 2008 [1<\/a>].<\/p>\n

Among the compounds tested, the best results were obtained for the isomer designated by the internal development code CI-1008<\/strong> \u2014 numbering originating from Parke-Davis’s internal system. It was this very molecule that, after years of further research, went on to registration as a medicinal product \u2014 trade names are listed in the table above.<\/p>\n

The synthesis challenge: obtaining a single enantiomer<\/h3>\n

The molecule has one stereogenic center \u2014 the carbon atom at position 3 \u2014 and only the (S)<\/em> form was selected for further development. The industrial challenge became developing an efficient, selective synthesis of this single enantiomer at production scale, without costly after-the-fact separation of a racemic mixture. The solution turned out to be asymmetric hydrogenation<\/strong> catalyzed by rhodium complexes with chiral bisphosphine ligands. Hoge and coworkers described this synthetic route in two papers from 2003\u20132004: the first names CI-1008 (pregabalin) directly in the title as the reaction product [2<\/a>], the second describes the design of the catalyst ligand itself [3<\/a>].<\/p>\n

Timeline<\/h2>\n\n\n\n\n\n\n\n\n\n\n\n\n
Timeline: origin and spread of the molecule<\/caption>\n
1993<\/th>\nregistration of gabapentin \u2014 the parent compound of the GABA analogue research line \u2014 as a medicinal product<\/td>\n<\/tr>\n
1990s<\/th>\nR. Silverman’s program seeking more strongly binding, branched GABA analogues; the compound coded CI-1008 is created [1<\/a>]<\/td>\n<\/tr>\n
2003\u20132004<\/th>\ndevelopment of an industrial asymmetric synthesis of the single (S) enantiomer [2<\/a>][3<\/a>]<\/td>\n<\/tr>\n
2004<\/th>\nregistration as a medicinal product in the European Union and the United States (trade names \u2014 table above)<\/td>\n<\/tr>\n
2006\u20132011<\/th>\nstudies of binding to the \u03b12\u03b4 subunit of calcium channels on animal tissue ex vivo [6<\/a>][7<\/a>][8<\/a>]<\/td>\n<\/tr>\n
2016<\/th>\npublication of a method for direct enantiomer separation on a chiral column with MS and UV detection [12<\/a>]<\/td>\n<\/tr>\n
2015\u20132017<\/th>\nLC-MS\/MS methods in environmental monitoring [15<\/a>] and post-mortem toxicology [16<\/a>]<\/td>\n<\/tr>\n
1 April 2019<\/th>\nthe United Kingdom classifies pregabalin as a Class C controlled substance \u2014 a regulatory fact concerning another country and another legal entity, not applicable to the offered reagent<\/td>\n<\/tr>\n
2019<\/th>\nchiral GC-MS method for enantiomer identification in forensic toxicology [13<\/a>]<\/td>\n<\/tr>\n
2023<\/th>\ncrystal engineering and co-crystals of pregabalin [14<\/a>]<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

Three research strands that shaped knowledge of the molecule<\/h2>\n

The literature on pregabalin is dispersed thematically more than geographically. For clarity it is worth separating it into three strands, each corresponding to a different research question.<\/p>\n

The synthetic strand: producing a pure enantiomer at industrial scale<\/h3>\n

Process chemists (Hoge and coworkers) focused on asymmetric catalysis \u2014 a purely synthetic question, independent of any biological application [2<\/a>][3<\/a>].<\/p>\n

The receptor pharmacology strand: a molecular target on animal tissue<\/h3>\n

The second strand covers studies of binding to the \u03b12\u03b4 subunit of calcium channels \u2014 carried out on rodent brain tissue ex vivo<\/em> and in synaptic models, not in humans. A review of the mechanism was published by Taylor and coworkers [5<\/a>]; an autoradiographic study in genetically modified mice showed that the \u03b12\u03b4 type 1 subunit is the main pregabalin-binding protein in the cortex, hippocampus, amygdala and spinal cord [6<\/a>]; a synaptic model in mice showed a reduction in neurotransmission after binding to the presynaptic \u03b12\u03b4 subunit [7<\/a>]; and a selectivity analysis showed binding to both the \u03b12\u03b4-1 and \u03b12\u03b4-2 subunits [8<\/a>]. A general review of the molecule’s development was published by Kavoussi [4<\/a>]. All of these studies were conducted on animal tissue or in model systems, not in humans, and none of them describes any application of the analytical reagent.<\/strong><\/p>\n

The analytical-forensic strand: detection in various matrices<\/h3>\n

The third strand is the work of forensic and environmental toxicology laboratories, developing methods for detecting pregabalin in successive matrices: human plasma [9<\/a>], municipal wastewater [15<\/a>], post-mortem blood [16<\/a>], and samples secured in drug-facilitated sexual assault cases [17<\/a>].<\/p>\n

Chemistry: a GABA analogue without an aromatic ring<\/h2>\n

Why the absence of a chromophore complicates detection<\/h3>\n

The structure of pregabalin \u2014 a branched aliphatic chain terminated by a carboxyl group and a primary amino group \u2014 contains no aromatic ring or other strong chromophore<\/strong>. This clearly distinguishes it from the other reagents in our catalog, such as modafinil<\/a> or bromantane<\/a>, whose phenyl rings give strong UV absorption. Standard UV detection is therefore made more difficult, which explains why some analytical methods rely on fluorescence detection after derivatization<\/strong>, validated for human plasma [9<\/a>]. For the same reason, GC-MS methods require prior derivatization of polar groups.<\/p>\n

The absence of a chromophore also carries a practical pitfall during HPLC sample preparation: Lin and coworkers described an artifactual degradation product<\/strong> formed by the addition of acetonitrile to pregabalin, catalyzed by alkaline impurities during sample preparation [10<\/a>]. A validated “green” HPLC-DAD and HPTLC method was described by Naguib and coworkers [11<\/a>].<\/p>\n

Stereogenic center at carbon C3<\/h3>\n

Unlike bromantane (a symmetric adamantane cage, no stereogenic center) and modafinil (a stereogenic center on the sulfur atom), pregabalin has one stereogenic center on a carbon atom<\/strong>, at position 3 of the chain. Only the (S)<\/em> form was selected for development \u2014 exactly the one encoded by this molecule’s canonical SMILES string. Separating the enantiomers requires chiral methods: direct separation on a chiral column with MS and UV detection was described by Chennuru and coworkers [12<\/a>], and a method based on derivatization with the chiral reagent S-TPC for GC-MS was described by Hitchcock and Marginean [13<\/a>].<\/p>\n

Physicochemical characterization<\/h3>\n\n\n\n\n\n\n\n\n\n\n\n
Computational descriptors and their analytical significance<\/caption>\n
Parameter<\/th>\nValue<\/th>\nWhat this means<\/th>\n<\/tr>\n<\/thead>\n
Partition coefficient (logP)<\/th>\n\u22121.6<\/td>\nvery low lipophilicity \u2014 high water solubility, poor retention in standard RP-HPLC<\/td>\n<\/tr>\n
Topological polar surface area<\/th>\n63.3 \u00c52<\/sup><\/td>\na moderately polar molecule despite its small mass<\/td>\n<\/tr>\n
Hydrogen bond donors<\/th>\n2<\/td>\nthe amino group and the acid hydroxyl group \u2014 favors co-crystal formation<\/td>\n<\/tr>\n
Hydrogen bond acceptors<\/th>\n3<\/td>\ncarbonyl oxygen, hydroxyl oxygen, and amino nitrogen<\/td>\n<\/tr>\n
Rotatable bonds<\/th>\n5<\/td>\na flexible aliphatic chain \u2014 no rigid ring core<\/td>\n<\/tr>\n
Melting point<\/th>\n187\u00b0C<\/td>\nhigh for such a small molecule \u2014 indicates an ionized (zwitterionic) form in the crystal, typical of free amino acids<\/td>\n<\/tr>\n
Solubility<\/th>\nvery good in water and aqueous buffers; poor in nonpolar solvents<\/td>\nthe inverse of the modafinil and bromantane profile \u2014 prepare stock solutions in water or buffer, not in DMSO<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

The simultaneous presence of a carboxyl group and a primary amino group means that in the solid state pregabalin, like most free amino acids, adopts the form of a zwitterion<\/strong>. This accounts for both its relatively high melting point and its ability to form co-crystals with dicarboxylic acids \u2014 using maleic acid as a coformer, this was described by Komisarek and coworkers, comparing mechanochemistry with crystallization from solution [14<\/a>].<\/p>\n

Nomenclature and synonyms<\/h2>\n

Behind the same molecule bearing CAS number 148553-50-8 lie several names and codes used in the literature and chemical databases \u2014 apart from the trade names of medicinal products, which we discuss solely in the “Three different entities” table above:<\/p>\n