Gabapentin

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Gabapentin are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Gabapentin?

The molecule Gabapentin presents a molecular formula of C9H17NO2 and its IUPAC name is 2-[1-(aminomethyl)cyclohexyl]acetic acid.

Gabapentin is a medication used to treat epilepsy and nerve pain. It is also used to relieve hot flashes and other symptoms of menopause. Gabapentin is an anti-epileptic drug, also called an anticonvulsant. It works by decreasing abnormal activity in the brain. Gabapentin is used to treat seizures and to relieve pain after shingles. Gabapentin is sometimes used to treat restless legs syndrome (RLS)..

3D structure

Cartesian coordinates

Geometry of Gabapentin in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Gabapentin UGJMXCAKCUNAIE-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Gabapentin

 

Molecule descriptors

 
IUPAC name2-[1-(aminomethyl)cyclohexyl]acetic acid
InChI codeInChI=1S/C9H17NO2/c10-7-9(6-8(11)12)4-2-1-3-5-9/h1-7,10H2,(H,11,12)
InChI KeyUGJMXCAKCUNAIE-UHFFFAOYSA-N
SMILESNCC1(CC(=O)O)CCCCC1

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (1-Aminomethyl-cyclohexyl)-acetic acid
  • 1-(Aminomethyl)-cyclohexaneacetic acid
  • 1-(Aminomethyl)cyclohexaneacetic acid
  • 1-(Aminomethyl)cyclohexaneaceticAcid
  • 1-(aminomethyl)cyclohexanacetic acid
  • 1-(aminomethyl)cyclohexyl-acetic Acid
  • 1-Aminomethyl-1cyclohexane-acetic acid
  • 1-amino methyl cyclohexane-acetic acid
  • 1-aminomethyl cyclohexaneacetic acid
  • 1-aminomethyl-1-cyclohexane-acetic acid
  • 1-aminomethylcyclohexane acetic acid
  • 2-(1-(aminomethyl)cyclohexyl)acetic acid
  • 2-[1-(aminomethyl)cyclohexyl]acetic acid
  • 42G963
  • 60142-96-3
  • 6CW7F3G59X
  • AB07485
  • AC-1485
  • ACT03340
  • AM20070538
  • Aclonium
  • BBL010794
  • BCP25698
  • BDBM50080153
  • BIDD:GT0656
  • BPBio1_000993
  • BRN 2359739
  • BSPBio_000901
  • C07018
  • C9H17NO2
  • CARBATIN
  • CCG-204671
  • CCRIS 7210
  • CI 945
  • CI-945
  • CS-1545
  • Cyclohexaneacetic acid, 1-(aminomethyl)-
  • D00332
  • DB00996
  • DDS-2003
  • DM-1796
  • DM-5689
  • DSSTox_CID_74
  • DSSTox_GSID_20074
  • DSSTox_RID_75350
  • EN300-52516
  • EU-0100582
  • FT-0626586
  • FT-0668920
  • Fanatrex
  • G-154
  • G0318
  • GABAPENTIN; NEURONTIN
  • GABAPETINE
  • GBN
  • GOE 2450
  • GOE 3450
  • GTPL5483
  • Gabapen
  • Gabapentin
  • Gabapentin (JAN/USP/INN)
  • Gabapentin GR
  • Gabapentin solution
  • Gabapentin, solid
  • Gabapentin-ER
  • Gabapentine
  • Gabapentino
  • Gabapentinum
  • Gabapetin
  • Gabarone
  • Go 3450
  • Goe-3450
  • Gralise
  • HMS1570N03
  • HMS2089J03
  • HMS2097N03
  • HMS2236O03
  • HMS3261F06
  • HMS3650A20
  • HMS3714N03
  • HSDB 7364
  • HY-A0057
  • KS-1064
  • L000733
  • LP00582
  • Lopac-G-154
  • Lopac0_000582
  • MFCD00865286
  • MLS000069358
  • NCGC00015466-01
  • NCGC00015466-02
  • NCGC00015466-03
  • NCGC00015466-04
  • NCGC00015466-05
  • NCGC00015466-06
  • NCGC00015466-07
  • NCGC00015466-08
  • NCGC00015466-09
  • NCGC00015466-11
  • NCGC00015466-27
  • NCGC00016891-01
  • NCGC00021545-02
  • NCGC00021545-04
  • NCGC00021545-05
  • NCGC00261267-01
  • NSC 742194
  • NSC 759254
  • NSC-742194
  • NSC-759254
  • NSC742194
  • Neuontin
  • Neurentin
  • Neurontin
  • Novo-Gabapentine
  • Prestwick0_000861
  • Prestwick1_000861
  • Prestwick2_000861
  • Prestwick3_000861
  • Prestwick_151
  • Q410352
  • SBI-0206904.P001
  • SDCCGSBI-0050564.P002
  • SMR000058311
  • SR-01000000019
  • SR-01000000019-11
  • SR-01000000019-2
  • SR-01000000019-6
  • STK598009
  • Sefelsa
  • Serada
  • Therapentin-90
  • Tocris-0806
  • Vultin
  • Z1258578343
  • [1-(AMINOMETHYL)CYCLOHEXYL]ACETIC ACID
  • gabapentin
  • gabapentin (Neurontin)
  • gabapentina
  • gabapentinium
  • s2133

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC4949
  • CAS-60142-96-3
  • UNII-6CW7F3G59X
  • AKOS000280865
  • DTXSID0020074
  • CHEMBL940
  • CHEBI:42797
  • Tox21_110157
  • Tox21_500582
  • Tox21_110157_1
  • EINECS 262-076-3
  • SPBio_002822
  • SCHEMBL8343

Physico-Chemical properties

IUPAC name2-[1-(aminomethyl)cyclohexyl]acetic acid
Molecular formulaC9H17NO2
Molecular weight171.237
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity47.48
LogP2.1
Topological polar surface area63.3

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.