GABAPENTIN (CAS 60142-96-3) — formula C9H17NO2, molecular weight 171.24.
| CAS Number | 60142-96-3 |
|---|---|
| Molecular Formula | C9H17NO2 |
| Molecular Weight | 171.24 |
| Melting Point | 162-166 °C; also reported as 165-167 °C |
| LogP | 1.25 |
| Applications | Uses: MEDICATION (VET), MEDICATION, Analgesics, Anti-Anxiety Agents, Anticonvulsants, Antimanic Agents, Antiparkinson Agents, Calcium Channel Blockers, Excitatory Amino Acid Antagonists, Use (kg) in Switzerland (2009): >2500, Use (kg, approx.) in Germany (2009): >50000, exact) in Germany (2009): 70059, Use (kg) in USA (2002): 433000, Consumption (g per capita) in Switzerland (2009): 0.32, Consumption (g per capita, approx.) in Germany (2009): 0.61, exact) in Germany (2009): 0.86, Consumption (g per capita) in the USA (2002): 1.5, Excretion rate: 1, Calculated removal (%): 92.1, It was originally developed for the treatment of epilepsy, and currently, gabapentin is widely used to relieve pain, especially neuropathic pain. [wikipedia]. 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., Use Classification: Pharmaceuticals, Pharmaceuticals -> Nervous System -> Antiepileptics, Methods of Manufacturing: In the original synthesis (Goedecke) cyclohexenone is reacted with ethyl cyanoacetate in the presence of ammonia to yield the Guareschi salt, which is hydrolyzed and decarboxylated to give 1, 1-cyclohexanediacetic acid which is transformed to the corresponding anhydride with acetic anhydride. This anhydride is treated with methanol to yield the half ester 2-[1-(methoxycarbonyl)cyclohexyl]acetic acid, which is subjected to a Curtius type rearrangement to give the isocyanate 2-[1-(isocyanatomethyl)cyclohexyl]acetic acid. The desired compound is obtained by hydrolysis of 2-[1-(isocyanatomethyl)cyclohexyl]acetic acid with HCl, followed by hydrochloric salt removal via anion exchange., Cyclohexane-1, 1-diacetic acid is monoesterified with methanol and the ester reacted with ethyl chloroformate in the presence of triethylamine followed by reaction with sodium azide to yield the 1-isocyanatomethyl derivative of the monoester. This latter compound is converted to the 1-(aminomethyl) product and the lactam, through the cyclization of the ester and the free amine. The mixture is refluxed with dilute HCl to give the product., Preparation: G. Satzinger et al., German patent 2460891 (1976 to Godecke), eidem, United States of America patent 4024175 (1977 to Warner-Lambert)., Formulations, Preparations: Table: Gabapentin Preparations [Table#6936], Table: Gabapentin Enacarbil Preparations [Table#6937] |
Documented applications: Uses: MEDICATION (VET), MEDICATION, Analgesics, Anti-Anxiety Agents, Anticonvulsants, Antimanic Agents, Antiparkinson Agents, Calcium Channel Blockers, Excitatory Amino Acid Antagonists, Use (kg) in Switzerland (2009): >2500, Use (kg, approx.) in Germany (2009): >50000, exact) in Germany (2009): 70059, Use (kg) in USA (2002): 433000, Consumption (g per capita) in Switzerland (2009): 0.32, Consumption (g per capita, approx.) in Germany (2009): 0.61, exact) in Germany (2009): 0.86, Consumption (g per capita) in the USA (2002): 1.5, Excretion rate: 1, Calculated removal (%): 92.1, It was originally developed for the treatment of epilepsy, and currently, gabapentin is widely used to relieve pain, especially neuropathic pain. [wikipedia]. 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., Use Classification: Pharmaceuticals, Pharmaceuticals -> Nervous System -> Antiepileptics, Methods of Manufacturing: In the original synthesis (Goedecke) cyclohexenone is reacted with ethyl cyanoacetate in the presence of ammonia to yield the Guareschi salt, which is hydrolyzed and decarboxylated to give 1, 1-cyclohexanediacetic acid which is transformed to the corresponding anhydride with acetic anhydride. This anhydride is treated with methanol to yield the half ester 2-[1-(methoxycarbonyl)cyclohexyl]acetic acid, which is subjected to a Curtius type rearrangement to give the isocyanate 2-[1-(isocyanatomethyl)cyclohexyl]acetic acid. The desired compound is obtained by hydrolysis of 2-[1-(isocyanatomethyl)cyclohexyl]acetic acid with HCl, followed by hydrochloric salt removal via anion exchange., Cyclohexane-1, 1-diacetic acid is monoesterified with methanol and the ester reacted with ethyl chloroformate in the presence of triethylamine followed by reaction with sodium azide to yield the 1-isocyanatomethyl derivative of the monoester. This latter compound is converted to the 1-(aminomethyl) product and the lactam, through the cyclization of the ester and the free amine. The mixture is refluxed with dilute HCl to give the product., Preparation: G. Satzinger et al., German patent 2460891 (1976 to Godecke), eidem, United States of America patent 4024175 (1977 to Warner-Lambert)., Formulations, Preparations: Table: Gabapentin Preparations [Table#6936], Table: Gabapentin Enacarbil Preparations [Table#6937].
GABAPENTIN is a chemical compound with CAS registry number 60142-96-3 and molecular formula C9H17NO2 (molecular weight 171.24).
CAS number: 60142-96-3
Its molecular formula C9H17NO2 comprises 9 C, 17 H, 1 N, 2 O atoms.
Also known as: GABAPENTIN · 加巴喷丁
The CAS registry number of GABAPENTIN is 60142-96-3.
Molecular formula C9H17NO2, molecular weight 171.24.
It is also registered under: GABAPENTIN, 加巴喷丁.
Recorded applications: Uses: MEDICATION (VET), MEDICATION, Analgesics, Anti-Anxiety Agents, Anticonvulsants, Antimanic Agents, Antiparkinson Agents, Calcium Channel Blockers, Excitatory Amino Acid Antagonists, Use (kg) in Switzerland (2009): >2500, Use (kg, approx.) in Germany (2009): >50000, exact) in Germany (2009): 70059, Use (kg) in USA (2002): 433000, Consumption (g per capita) in Switzerland (2009): 0.32, Consumption (g per capita, approx.) in Germany (2009): 0.61, exact) in Germany (2009): 0.86, Consumption (g per capita) in the USA (2002): 1.5, Excretion rate: 1, Calculated removal (%): 92.1, It was originally developed for the treatment of epilepsy, and currently, gabapentin is widely used to relieve pain, especially neuropathic pain. [wikipedia]. 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., Use Classification: Pharmaceuticals, Pharmaceuticals -> Nervous System -> Antiepileptics, Methods of Manufacturing: In the original synthesis (Goedecke) cyclohexenone is reacted with ethyl cyanoacetate in the presence of ammonia to yield the Guareschi salt, which is hydrolyzed and decarboxylated to give 1, 1-cyclohexanediacetic acid which is transformed to the corresponding anhydride with acetic anhydride. This anhydride is treated with methanol to yield the half ester 2-[1-(methoxycarbonyl)cyclohexyl]acetic acid, which is subjected to a Curtius type rearrangement to give the isocyanate 2-[1-(isocyanatomethyl)cyclohexyl]acetic acid. The desired compound is obtained by hydrolysis of 2-[1-(isocyanatomethyl)cyclohexyl]acetic acid with HCl, followed by hydrochloric salt removal via anion exchange., Cyclohexane-1, 1-diacetic acid is monoesterified with methanol and the ester reacted with ethyl chloroformate in the presence of triethylamine followed by reaction with sodium azide to yield the 1-isocyanatomethyl derivative of the monoester. This latter compound is converted to the 1-(aminomethyl) product and the lactam, through the cyclization of the ester and the free amine. The mixture is refluxed with dilute HCl to give the product., Preparation: G. Satzinger et al., German patent 2460891 (1976 to Godecke), eidem, United States of America patent 4024175 (1977 to Warner-Lambert)., Formulations, Preparations: Table: Gabapentin Preparations [Table#6936], Table: Gabapentin Enacarbil Preparations [Table#6937].
Independent reference data for GABAPENTIN (CAS 60142-96-3), compiled from public chemistry databases.
| CAS Registry Number | 60142-96-3 |
|---|---|
| PubChem CID | 3446 |
| Molecular formula | C9H17NO2 |
| IUPAC name | 2-[1-(aminomethyl)cyclohexyl]acetic acid |
| UNII (FDA) | 6CW7F3G59X |
| Molecular Weight | 171.24 |
|---|---|
| XLogP3 | -1.1 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 3 |
| Exact Mass | 171.125928785 |
| Monoisotopic Mass | 171.125928785 |
| Topological Polar Surface Area | 63.3 |
| Heavy Atom Count | 12 |
| Melting Point | 162-166 °C; also reported as 165-167 °C |
|---|---|
| Melting Point | 165 - 167 °C |
| Solubility | >100mg/mL |
| Solubility | In water, 4.49X10+3 mg/L at 25 °C |
| LogP | 1.25 |
| LogP | log Kow = -1.10 |
| LogP | -1.10 |
| Dissociation Constants | 3.7 |
| Collision Cross Section | 139.7 Ų [M+H]+ |
gabapentin; 60142-96-3; Neurontin; 1-(Aminomethyl)cyclohexaneacetic acid; Gabapentine; 2-[1-(aminomethyl)cyclohexyl]acetic acid; Aclonium; Gabapetin; Gabapentinum; gabapentina; Gabapentino; Gralise; Cyclohexaneacetic acid, 1-(aminomethyl)-; Goe-3450; Fanatrex; 2-(1-(aminomethyl)cyclohexyl)acetic acid
| GHS notification summary | 30.8% (32 / 104) |
|---|
| GHS notification summary | 30.8% (32 / 104) |
|---|---|
| Reported hazard statements | H315 (57.7%), H319 (66.3%), H335 (59.6%), H360 (54.8%) |
This chemical does not meet GHS hazard criteria for 30.8% (32 of 104) of reports.
H315 (57.7%): Causes skin irritation [Warning Skin corrosion/irritation]
GABAPENTIN · CAS 60142-96-3 · C9H17NO2. UNII 6CW7F3G59X. Melting Point: 162-166 °C; also reported as 165-167 °C; Melting Point: 165 - 167 °C; Solubility: >100mg/mL.
Source: PubChem / Wikidata; the batch COA governs where values differ.
Supplier: Jinan Shenghe Chemical Co., Ltd.
中文页面: 加巴喷丁