Home > Compound List > Compound details
60142-96-3 molecular structure
click picture or here to close

2-[1-(aminomethyl)cyclohexyl]acetic acid

ChemBase ID: 869
Molecular Formular: C9H17NO2
Molecular Mass: 171.23678
Monoisotopic Mass: 171.12592879
SMILES and InChIs

SMILES:
OC(=O)CC1(CCCCC1)CN
Canonical SMILES:
NCC1(CCCCC1)CC(=O)O
InChI:
InChI=1S/C9H17NO2/c10-7-9(6-8(11)12)4-2-1-3-5-9/h1-7,10H2,(H,11,12)
InChIKey:
UGJMXCAKCUNAIE-UHFFFAOYSA-N

Cite this record

CBID:869 http://www.chembase.cn/molecule-869.html

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2-[1-(aminomethyl)cyclohexyl]acetic acid
IUPAC Traditional name
gabapentin
2-[1-(aminomethyl)cyclohexyl]acetic acid
Brand Name
Aclonium
Neurontin
Novo-Gabapentin
Synonyms
1-(Aminomethyl)cyclohexaneacetic Acid, Neurontin, GOE-3450
Fanatrex
Gabarone
Neurontin
1-(Aminomethyl)-cyclohexaneacetic acid
Gabapentin
Gabapentine [INN-French]
Gabapentino [INN-Spanish]
Gabapentino [Spanish]
Gabapentinum [INN-Latin]
Gabapetin
Gabapentin GR
gabapentin
Gabapentin
2-(1-(aminomethyl)cyclohexyl)acetic acid
(1-Aminomethyl-cyclohexyl)-acetic acid
Aclonium
2-[1-(aminomethyl)cyclohexyl]acetic acid
CAS Number
60142-96-3
EC Number
262-076-3
MDL Number
MFCD00865286
Beilstein Number
2359739
PubChem SID
160964332
46506529
24278159
PubChem CID
3446

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 4.6313047  H Acceptors
H Donor LogD (pH = 5.5) -1.3162769 
LogD (pH = 7.4) -1.2728618  Log P -1.273033 
Molar Refractivity 46.3283 cm3 Polarizability 18.621471 Å3
Polar Surface Area 63.32 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -1.88  LOG S -1.6 
Solubility (Water) 4.34e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
4490 mg/L expand Show data source
H2O: soluble10 mg/mL expand Show data source
Methanol expand Show data source
Water expand Show data source
Apperance
off-white solid expand Show data source
White to Off-White Solid expand Show data source
Melting Point
162-166°C expand Show data source
169 - 171°C expand Show data source
Hydrophobicity(logP)
-0.66 expand Show data source
1.4 expand Show data source
Storage Condition
-20°C expand Show data source
Refrigerator expand Show data source
Storage Warning
IRRITANT expand Show data source
RTECS
GU6496000 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
61-36/37/38 expand Show data source
Safety Statements
26-36/37/39-45 expand Show data source
TSCA Listed
false expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H315-H319-H335-H360 expand Show data source
GHS Precautionary statements
P201-P261-P305 + P351 + P338-P308 + P313 expand Show data source
Personal Protective Equipment
Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand Show data source
Gene Information
human ... ADORA1(134), CACNA2D1(781)rat ... Cacna1a(25398) expand Show data source
Mechanism of Action
GABA-like amino acid which penetrates the blood-brain barrier expand Show data source
regulator expand Show data source
Voltage-gated N-type calcium ion channels expand Show data source
Purity
>98. expand Show data source
95% expand Show data source
97% expand Show data source
98% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Application(s)
Anticonvulsant expand Show data source
CNS depressant expand Show data source
Pharmacopeia Traceability
traceable to USP 1287303 expand Show data source
Empirical Formula (Hill Notation)
C9H17NO2 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00996 external link
Item Information
Drug Groups approved; investigational
Description Gabapentin (brand name Neurontin) is a medication originally developed for the treatment of epilepsy. Presently, gabapentin is widely used to relieve pain, especially neuropathic pain. Gabapentin is well tolerated in most patients, has a relatively mild side-effect profile, and passes through the body unmetabolized.
Indication For the management of postherpetic neuralgia in adults and as adjunctive therapy in the treatment of partial seizures with and without secondary generalization in patients over 12 years of age with epilepsy.
Pharmacology Gabapentin, an analog of GABA, is used as an anticonvulsant to treat partial seizures, amyotrophic lateral sclerosis (ALS), and painful neuropathies. Potential uses include monotherapy of refractory partial seizure disorders, and treatment of spasticity in multiple sclerosis, tremor. mood disorders, and attenuation of disruptive behaviors in dementia. Gabapentin has high lipid solubility, is not metabolized by the liver, has no protein binding, and doesn't possess the usual drug interactions.
Toxicity Symptoms of overdose include ataxia, labored breathing, ptosis, sedation, hypoactivity, and excitation.
Affected Organisms
Humans and other mammals
Biotransformation All pharmacological actions following gabapentin administration are due to the activity of the parent compound; gabapentin is not appreciably metabolized in humans.
Absorption Rapid. Absorbed in part by the L-amino acid transport system, which is a carrier-mediated, saturable transport system; as the dose increases, bioavailability decreases. Bioavailability ranges from approximately 60% for a 900 mg dose per day to approximately 27% for a 4800 milligram dose per day. Food has a slight effect on the rate and extent of absorption of gabapentin (14% increase in AUC).
Half Life 5-7 hours
Protein Binding Less than 3% of gabapentin circulates bound to plasma protein.
Elimination Gabapentin is eliminated from the systemic circulation by renal excretion as unchanged drug.
Gabapentin is not appreciably metabolized in humans.
Distribution * 58±6 L
Clearance * 190 mL/min
References
Mathew NT, Rapoport A, Saper J, Magnus L, Klapper J, Ramadan N, Stacey B, Tepper S: Efficacy of gabapentin in migraine prophylaxis. Headache. 2001 Feb;41(2):119-28. [Pubmed]
Backonja MM, Serra J: Pharmacologic management part 1: better-studied neuropathic pain diseases. Pain Med. 2004 Mar;5 Suppl 1:S28-47. [Pubmed]
Choudhuri I, Sarvananthan N, Gottlob I: Survey of management of acquired nystagmus in the United Kingdom. Eye. 2007 Sep;21(9):1194-7. Epub 2006 May 26. [Pubmed]
Pande AC, Crockatt JG, Janney CA, Werth JL, Tsaroucha G: Gabapentin in bipolar disorder: a placebo-controlled trial of adjunctive therapy. Gabapentin Bipolar Disorder Study Group. Bipolar Disord. 2000 Sep;2(3 Pt 2):249-55. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Selleck Chemicals - S2133 external link
Research Area: Neurological Disease
Biological Activity:
Gabapentin (Neurontin) is a pharmaceutical agent, specifically a GABA analogue. Gabapentin (Neurontin) was originally developed for the treatment of epilepsy, and currently, gabapentin is widely used to relieve pain, especially neuropathic pain. Its therapeutic action on neuropathic pain is thought to involve voltage-gated N-type calcium ion channels. It is thought to bind to the α2δ subunit (1 and 2) of the voltage-dependent calcium channel in the central nervous system. [1][2]
Sigma Aldrich - G154 external link
Biochem/physiol Actions
Anticonvulsant with unknown mechanism of action; crosses the blood brain barrier; increases GABA concentrations in the brain and reduces excitatory amino acid neurotransmission, perhaps through its effects on voltage-gated calcium channels; exhibits antinociceptive, anxiolytic, neuroprotective and anti-epileptic effects.
Toronto Research Chemicals - G117250 external link
Amino acid structurally related to γ-Aminobutyric Acid (GABA), designed to cross the blood brain barrier. Used as an anticonvulsant.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Mathew NT, Rapoport A, Saper J, Magnus L, Klapper J, Ramadan N, Stacey B, Tepper S: Efficacy of gabapentin in migraine prophylaxis. Headache. 2001 Feb;41(2):119-28. Pubmed
  • • Backonja MM, Serra J: Pharmacologic management part 1: better-studied neuropathic pain diseases. Pain Med. 2004 Mar;5 Suppl 1:S28-47. Pubmed
  • • Choudhuri I, Sarvananthan N, Gottlob I: Survey of management of acquired nystagmus in the United Kingdom. Eye. 2007 Sep;21(9):1194-7. Epub 2006 May 26. Pubmed
  • • Pande AC, Crockatt JG, Janney CA, Werth JL, Tsaroucha G: Gabapentin in bipolar disorder: a placebo-controlled trial of adjunctive therapy. Gabapentin Bipolar Disorder Study Group. Bipolar Disord. 2000 Sep;2(3 Pt 2):249-55. Pubmed
  • •  http://en.wikipedia.org/wiki/Gabapentin
  • • Vollmer, K.-O. et al.: Arzneimittel-Forshc., 36, 830 (1986)
  • • Saletu, B., et al.: Int. J. Clin. Pharmacol. Ther. Toxicol., 24, 362 (1986)
  • • Ger. Pat., 1976, Goedecke, 2 460 891; CA, 85, 94679h, (synth)
  • • Hengy, H. et al., J. Chromatogr., 1985, 341; 473, (hplc)
  • • Vollmer, K.O. et al., Arzneim.-Forsch., 1986, 36, 830, (metab)
  • • Bartoszyk, G.D. et al., Curr. Probl. Epilepsy, 1986, 4, 147, (rev, pharmacol)
  • • Griffiths, G. et al., Helv. Chim. Acta, 1991, 74, 309, (synth, bibl)
  • • Goa, K.L. et al., Drugs, 1993, 46, 409, (rev)
  • • Antiepileptic Drugs, 4th edn., (eds., Levy, R.H. et al), Raven Press, 1995
  • • Pellock, J.M., Drugs of Today (Barcelona), 1998, 34, 31-35, (rev, pharmacol)
  • • Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 346
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle